Chris Hutchins Blog

💳 Increased Hotel Card Offers: Marriott & Hilton

Mon, 17 Mar 2025 21:35:32 +0000

Note: American Express is a ChrisHutchins.com advertiser

If you're familiar with any of the hotel programs below and have been thinking about a new card, the offers below might be interesting and valuable as most of them offer free night awards. And always, you can find the full list of best card offers on our Best Cards Page.

Marriott

I've long been a fan of Marriott points because the chain has so many amazing luxury hotels all over the world (e.g. St Regis, Ritz Carlton, Luxury Collection). Despite some recent devaluations, there are plenty of deals to take advantage of across their portfolio, so if you're familiar enough with the program to maximize it, these welcome offers (that are almost double the usual offer) could be of great value.

Marriott Bonvoy Brilliant® American Express® Card
Earn 185k Marriott Bonvoy bonus points after a $6k spend in 6 months. Plus, receive 1 Free Night Award every year and earn 6x points at Marriott, 3x on worldwide restaurants and flights booked directly with airlines, 2x on everything else.
Marriott Bonvoy Bevy™ American Express® Card
Earn 155k Marriott Bonvoy bonus points after a $5k spend in 6 months. You can also earn 1 Free Night Award after spending $15,000 on eligible purchases within a calendar year.
Marriott Bonvoy Business® American Express® Card
Earn 3 Free Night Awards after a $6k spend in 6 months. Each Free Night Award has a redemption level up to 50,000 Marriott Bonvoy® points, for a total potential value of up to 150k points.

Hilton

After Hilton partnered with Small Luxury Hotels, we booked an incredible stay at Cap Rocat on our recent Europe trip with Hilton points that saved us $10k+. Ever since then, we've gotten a lot more excited about earning Hilton cards and Free Night Certificates (which you can earn with the first two cards below). All three offers below end on 4/29/2025.

Hilton Honors American Express Surpass® Card
130k Hilton Honors bonus points, plus a Free Night Reward after a $3k spend in 6 months.
Hilton Honors American Express Card
70k Hilton Honors bonus points, plus a Free Night Reward after a $2k spend in 6 months.
The Hilton Honors American Express Business Card
175k Hilton Honors bonus points after a $8k spend in 6 months.

Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

🤑 My Top Finds, Latest Deals, and Best Recommendations (3/8/25)

Sat, 08 Mar 2025 16:00:04 +0000

This week, we'll cover: the best AI tools, insurance planning for fires & more, how to earn 5x on insurance payments and tax prep in March, free year of Calm mediation app, new Flying Blue Promo Rewards, 5% off gift cards and more.

Advertiser Disclosure

Note: American Express is a ChrisHutchins.com advertiser

🎙 Mailbag: AI Tools, Insurance Planning for Fires & More

My good friend Kevin Rose joined me for another Q&A episode where we talk everything from the best AI tools to takeaways from losing a home in the LA fires to the benefits of rope training and saunas. We also discuss strategies for optimizing home insurance, how to think about where to live, and answer more of your questions. If you want to share a question for a future episode, please share it here.

📺 Watch or 🎧 Listen

🛫 Travel, Points & Miles

🏨 Free Night Anywhere with New Welcome Offers

You can currently earn a Free Night Reward, good at any category property in addition to big welcome bonuses. The offer is available on the Hilton Honors American Express Surpass® Card (which we got last year), but it's also on the no-fee Hilton Honors American Express Card (more on rates and fees here).

💸 5x in March on Insurance Payments and Tax Prep

Chase is offering a surprise bonus of 5% cash back on insurance and tax preparation service payments made on the Chase Freedom Flex® and the Chase Freedom Unlimited® between 3/1 and 3/31. The bonus category is limited to $1,500 in spending, which includes the regular quarterly bonus categories (Q1 categories are grocery stores, fitness clubs, and hair, nails, and spa services). Make sure to register here to qualify.

💺 Flying Blue Promo Rewards for March 2025

Air France-KLM's Flying Blue program's March 2025 Promo Rewards is offering a 25% discount on economy award flights between Europe and Detroit, Mexico City, Seattle, Washington, Austin and Boston. There are also business-class options to Ottawa starting at 45k miles and to Panama City and San Jose (SJO) for 63,750 miles. Book before 3/31 for travel until 8/31.

🛏️ 15% Off Award Nights at New IHG Properties

IHG One Rewards is offering 15% off award nights at new and revamped properties, including the Iberostar properties in Aruba, Malaga, and Tunisia, and Noku Maldives. This offer is valid for stays through 3/31, 4/30, and 5/31, depending on the property.

🛍️ Up to 1k Bonus Points on Southwest Shopping Portal

You can earn up to 1,000 bonus Rapid Rewards points via the Southwest shopping portal until 3/17. Spend $100 to earn 500 or $300 to earn 1,000 bonus Rapid Rewards points.

👑 MGM Rewards Tier Status Match Challenge

MGM Rewards has brought back its Status Match Challenge. Until 7/31, you can get an instant match to MGM Gold or Platinum using a loyalty card from an eligible competitor (list here). Plus, you can extend the status beyond the initial 90 days if you complete the challenge requirements.

🤑 Latest Deals

🎁 5% Off Gift Cards with U.S. Bank Cards

Have a U.S. Bank debit/credit card? You can get a 5% discount when purchasing gift cards for shopping, travel, dining and entertainment on the U.S Bank gift card site. Thanks for sharing this Ford!

⚾ Redeem Capital One Miles for Exclusive MLB Tickets

Capital One cardholders can access exclusive field-level MLB tickets by redeeming only 5,000 miles each via the Capital One Entertainment portal. These tickets will be available for the next two months with limited availability (usually only 4 tickets per game), so it's a good idea to secure them ASAP.

⛷️ 2025-2026 Epic Passes on Sale!

After a successful ski trip with the kids this year, we're thinking seriously about getting an Epic Pass next year. They're now on sale for next season and offering 10 free buddy passes as an early bird deal. The competing Ikon Pass goes on sale next week on 3/12.

💳 Latest Card-Linked Offers

Card-linked offers are a great way to save on shopping you’re already doing and there are a bunch of great ones I've recently found, including getting a free year of the Calm Meditation app.

Calm Meditation App: 100% back (up to $69.99)
Prenuvo Full Body MRI: $600 off $2499+
Lifeforce Biomarker Testing: $300 of $599+
JetBlue: $25 off $250
IKEA: 10% off (up to $27)
Kroger: 10% off (up to $9)
Lululemon: $20 off $100+
Southwest Airlines: 10% off (up to $40)
Office Depot/Max: 5%-15% off
Vail Resorts: 10k Bonus Rewards points on $500
Big Sky Ski Resort: $50 off $250
Select gift cards: 10% off when you redeem Citi points

Note: Not every cardmember might see these offers, but if you want to automate them, try CardPointers Pro with 30% off here.

🕵️ Great Finds

📱 Invite Code for $0/mo Helium Mobile Plan (No CC)

Last month I shared how you can get a free “Zero Plan” (no credit card required) from Helium Mobile including 3GB of data, 300 texts and 100 mins of calls—but you had to join a waitlist. I finally got in and have a referral code to skip the waitlist: 5XNO54A. Note they do require location services turned on to get the free plan.

📺 Show Recommendation: Zero Day

I enjoyed this new Netflix conspiracy mini-series where Robert DeNiro is in charge of investigating a cyberattack in the US. It has mixed reviews from critics, but I love this genre and only being 6 episodes makes it an easy watch!

🛫 Limited Time Welcome Offers: Delta, Southwest, United and Hawaiian

Sat, 08 Feb 2025 15:11:56 +0000

Advertiser Disclosure

Note: American Express is a ChrisHutchins.com advertiser

If you're familiar with any of the airline programs below and have been thinking about a new card, these limited-time welcome offers on these co-branded credit cards might be a great way to earn some extra miles. And always, you can find the full list of best card offers on our Best Cards Page.

Delta

There are currently some big Delta bonuses up to 100k miles. All of these cards come with 15% off Delta award bookings and a free checked bag. The Platinum/Reserve cards also help you earn MQDs towards Delta status. If you fly Delta regularly or have an upcoming trip, these perks could come in handy.

Personal

Delta SkyMiles® Gold American Express Card: 80k miles after $3k spend in 6 months.
Delta SkyMiles® Platinum American Express Card: 90k miles after $4k spend in 6 months.
Delta SkyMiles® Reserve American Express Card: 100k miles after $6k spend in 6 months.

Business

Delta SkyMiles® Gold Business American Express Card: 90k miles after $6k spend in 6 months. Offer Ends 4/2/25.
Delta SkyMiles® Platinum Business American Express Card: 100k miles after $8k spend in 6 months. Offer Ends 4/2/25.
Delta SkyMiles® Reserve Business American Express Card: 110k miles after $12k spend in 6 months. Offer Ends 4/2/25.

United

This card is a good option for business owners who are loyal to United Airlines. It has great perks like a free first checked bag, 2 United Club℠ one-time passes per year, priority boarding privileges and more.

United℠ Business Card: 100k miles after $5k spend in 3 months.

Southwest

Southwest is currently offering 30,000 points and Free Companion Pass through 2/28/26 on it's personal cards after spending $4,000 in the first 3 months. The offer is only available until 3/23/25 for the following cards:

All information about Southwest Cards has been collected independently by Chris Hutchins. The card details on this page have not been reviewed or provided by the card issuer.

Hawaiian

The Hawaiian Airlines® World Elite Mastercard from Barclays is currently offering 70,000 HawaiianMiles after the first purchase, which makes this one of the best offers ever, from an ROI perspective. Since the Hawaiian + Alaska was confirmed, you can convert your HawaiianMiles to Alaska Miles, so this offer is effectively 70,000 Alaska Miles as well.

💸 The 5 Types of Wealth: Redefining What It Means to Be Truly Rich

Sat, 08 Feb 2025 14:20:16 +0000

What comes to mind when you hear the word "wealth"? For most people, it’s money—savings, investments, and material stuff. But what if wealth is about way more than just money? On Ep #213, Sahil Bloom breaks down five different types of wealth: time, social, mental, physical, and financial to help you think differently about what it means to be truly rich.

1. Time Wealth

Time wealth is about realizing how finite it is and taking control over how you spend it. But it’s not just about having free hours on your calendar. It’s about having autonomy over your schedule, being intentional with your commitments, and making space for the people and activities that bring you joy and good energy.

Time wealth isn’t about doing less; it’s about doing more of what matters most to you.

Tactics to Improve Time Wealth

Track activities that energize you versus those that drain you through an energy calendar to make better decisions on where to invest your time.
Limit your focus to just a few key priorities to avoid spreading yourself too thin.
Regularly ask yourself, "Would I say yes to this if it were tomorrow?" to combat overcommitting.

2. Social Wealth

No one dreams of success if it means being alone. Social wealth is about meaningful relationships—both your closest people and your broader community. Sahil suggests relationship mapping to figure out which connections are adding value to your life and which ones might be draining you. Instead of traditional networking, find value-aligned rooms where you can meet people who share your interests.

The strength of your relationships isn’t just important for emotional well-being; it’s also one of the biggest predictors of long-term health. Studies show that strong social connections can improve longevity, reduce stress, and even boost your immune system.

Tactics to Improve Social Wealth

Use a simple two-by-two matrix to map your relationships and identify your strongest connections and areas needing attention.
Maintain a list of friends to call during downtime, like walks or commutes, to maintain connections.
Whenever an old photo of someone pops up on your phone memories, send it to them and start a conversation.

3. Mental Wealth

Mental wealth is all about having a sense of purpose, staying curious, and creating space to think. Remember, your job doesn’t have to be your purpose—it can just be what supports your bigger life goals. We also talk about the "Ambition Paradox"—ambition can drive you, but if it goes unchecked, it can burn you out.

Cultivating mental wealth means making time for reflection, learning new things, and being okay with not having all the answers. It’s about creating mental clarity, managing stress effectively, and engaging in activities that challenge your mind.

Tactics to Improve Mental Wealth

Spend 5 minutes on a daily basis to reflect on what brought you joy, what challenged you, and what you learned.
Reread impactful books or revisit podcasts to gain new insights based on your current life stage.
Identify a higher-order purpose that your daily activities support, even if your job isn't your ultimate passion.

4. Physical Wealth

Sahil poses a powerful question to reflect on your physical health: will you be able to dance at your 80th birthday party? Physical wealth isn’t about being an elite athlete—it’s about feeling good and staying active for as long as possible. Focus on the basics: move your body, eat real food, and get enough sleep.

But beyond the basics, physical wealth is also about understanding your body’s needs and respecting its limits. It’s not just about avoiding illness; it’s about optimizing your energy, mobility, and resilience.

Tactics to Improve Physical Wealth:

Aim for 30 minutes of daily movement, whether it's walking, lifting, or any physical activity you enjoy.
Practice the 80/20 nutrition rule. Focus on whole, unprocessed foods 80% of the time while allowing flexibility.
Prioritize consistent sleep routines to support recovery and overall health.

5. Financial Wealth

We all know what financial wealth is, but Sahil reframes it with the idea of "expectation liability"—basically, the more you expect, the harder it is to feel satisfied. The goal isn’t just to make more money; it’s to define what “enough” looks like for you.

Financial wealth isn’t just about income or net worth; it’s about financial freedom and peace of mind. It’s the ability to make choices without being driven solely by financial constraints.

Tactics to Improve Financial Wealth:

Clearly articulate what financial security and satisfaction mean to you.
Grow your income strategically by focusing on skill development and value creation.
Simplify money management with automated savings and investments to reduce decision fatigue.

Balancing the Five Types of Wealth

Life isn’t perfectly balanced all the time, and that’s okay. Sahil talks about using what he calls "dimmer switches" for each area of wealth. You don’t have to be 100% focused on all of them at once, but you shouldn’t ignore any of them completely either. Think of life as having different seasons. Sometimes your career might take center stage, while other times, your focus might shift to family, health, or personal growth. The key is to stay aware of how you’re doing in each area and make small adjustments when needed.

Sahil has a Wealth Score Quiz to help you assess your current standing in each area. Pro tip if you have a partner: do the quiz on your own and compare the results. My wife Amy and I took this approach and found out there were areas where I thought I was doing great (I'm a bit of an optimist), but Amy’s perspective helped me see blind spots I’d overlooked. I highly recommend doing it this way—it’s like a 360 review for your life, but with someone who knows you best.

Real wealth isn’t just a number in your bank account. It’s about how you spend your time, the people you’re connected to, your mental clarity, your health, and yes, your financial stability. So the next time you think about wealth, ask yourself: How am I doing in these five areas? Because true wealth isn’t just about what you have—it’s about how you live.

🏆 10 Powerful Lessons from 2024 to Transform Your Life, Money, and Travel

Thu, 16 Jan 2025 00:06:11 +0000

Over the past year, I’ve explored strategies, stories, and insights with incredible experts to help you upgrade your life, money, and travel. Here are my 10 most impactful takeaways from 2024, covering essential lessons on investing smarter, making time for what matters, building healthier habits, mastering travel hacks, and much more.

1. There’s No One Right Way to Invest

Investing is personal. What works for one person might not work for another because your risk tolerance, liquidity needs, and goals are unique. Even the most seasoned investors will tell you that there is no perfect investment strategy, so whether you prefer real estate, private credit, or index funds, always choose a strategy you can stick with long-term. Simplicity often beats complexity, and consistency is key.

Episodes mentioned

2. Deals Can Be a Lucrative Side Hustle

A side hustle doesn’t have to mean starting a business (which is how I used to view them). It can be as simple as leveraging deals to save or earn extra money. From credit card bonuses to buying groups to reselling gift cards or gold, these strategies can add up significantly. I'll continue to do episodes on new areas I'm exploring but if you want to see the latest deals I'm finding, so make sure to sign up for my weekly newsletter here.

Episodes mentioned

3. Move Beyond Checklist Travel

Transform your travel experiences by focusing on immersion rather than ticking off destinations. Leave room for flexibility, revisit favorite places, and prioritize meaningful moments. I spoke to a few travel experts last year who also inspired this shift and all seemed to agree that your second or third visit to a destination often feels richer and more rewarding than the first.

Episodes mentioned

4. Award Travel is Still the Best Deal in Travel

Points and miles remain a powerful way to save thousands on travel. Flexibility is key—whether in dates, destinations, or booking windows. And thankfully, there are so many different tools and award booking services that make it easier than ever to maximize your value. For example, last year, we saved over $20,000 on a single trip to Europe.

Episodes mentioned

5. Cash Back Can Be Better Than Points

2024 was the year that I really processed and understood that you can disassociate earning points from redeeming points because 1) points and miles are constantly on sale, and 2) there are newer cash back cards that earn up to 4%, and you can use that cash back to buy points (and often to buy more points than you would have earned with a points card). If you want to go deeper, check out this card optimizer tool I built that will help you maximize your rewards and/or cash back by helping you find the ideal mix of credit cards, personalized for your spending patterns.

Episode mentioned

#170: Cash Back vs. Points: Are We Playing the Wrong Credit Card Game?

6. Spend Time with the Right People in the Right Way

Time is a limited resource, so it’s so important to spend it with people who uplift you and bring positivity to your life. My friend Sahil put together these charts that show how time with family and friends diminishes as we age, making it even more important to be intentional with how and with whom you spend your time. Prioritize relationships that energize you, distance yourself from negativity, and focus on meaningful connections.

Episode mentioned

#190: Why High-Performers Focus on Energy, Not Time with Sahil Bloom

7. You Can Make Time in Your Life

Delegation, automation, and outsourcing can free up time for what truly matters. From hiring assistants (I hired mine from Oceans ← you can get $1000 off for mentioning ATH) to leveraging AI tools, there are endless ways to offload tasks and create space, which can transform both your work and life. Use the time you’ve gained to be present, reduce distractions, and build more meaningful relationships.

Episodes mentioned

8. Prioritizing Your Health is Easier Than You Think

Your health is the foundation for everything else in life, and prioritizing it is easier than you think. Start by taking inventory—whether it’s through a blood panel, a DEXA scan, or VO2 max testing—and focus on the area that matters most to you. Simple changes in sleep, diet, or exercise can have a big impact on your well-being

Episodes mentioned

9. The Key to Good Communication is Listening

Ironically, great communication starts with listening, not speaking. Listening fosters deeper connections, builds trust, and creates better outcomes in almost every conversation. Whether it’s adopting a “learn it all” mindset, practicing the three levels of listening (me, you, and us), or asking open-ended questions, active listening can transform your relationships.

Episodes mentioned

10. Building Good Habits Takes Time, But It’s Worth It

Building good habits is challenging at first but brings lasting benefits. Shifting to an early wake-up routine gave me an extra hour of focused morning time for exercise, work, and more. The key was creating consistency with cues, routines, and rewards. Focus on keystone habits that spark positive ripple effects, and try an approach that works for you, like the 30 for 30 method: 30 minutes a day for 30 days to build momentum.

Episode mentioned

#159: Masterclass on Habits and Becoming a Super Communicator with Charles Duhigg

These 10 takeaways are more than just insights—they’re practical strategies to help you thrive in every aspect of your life. My hope is that they inspire and empower you as much as they’ve transformed my own perspective. Start with just one actionable step today to live better, travel smarter, and achieve your financial goals. Make 2025 the year you turn these lessons into lasting success!

🧠 5 Resets to Rewire Your Brain for Less Stress and Burnout

Fri, 10 Jan 2025 22:53:59 +0000

Stress is the modern epidemic. Today, 70% of people report experiencing significant stress, and burnout is at an all-time high. Unlike our ancestors, who faced brief bursts of acute stress from physical dangers, modern life keeps us in a constant state of “fight-or-flight.” Deadlines, financial pressures, relationship issues, and endless digital distractions prevent our brains from ever fully relaxing. This chronic stress overwhelms both the mind and body, causing widespread physical, mental, and emotional symptoms.

To better understand how stress impacts us—and what we can do to manage it—I spoke with Harvard physician Dr. Aditi Nerurkar (Ep #209). Dr. Nerurkar has spent her career studying the science of stress and resilience. Here’s what I learned from her.

💡 The Effects of Stress on Your Body and Mind

Before you can effectively manage stress, it’s important to identify how it shows up in your life. Physically, stress can cause headaches, neck and back pain, digestive issues, dizziness, and disrupted sleep. Mentally, it may lead to anxiety, irritability, hypervigilance, trouble focusing, and brain fog. Emotionally, it can result in low energy, a quick temper, and a persistent feeling that something bad is about to happen.

However, it’s essential to recognize that not all stress is harmful. Healthy stress (adaptive) motivates you, pushes you forward, and helps you grow—like preparing for a big presentation or starting a new job. In contrast, unhealthy stress (maladaptive) is chronic and unrelenting, leading to mental and physical health issues that can feel draining and overwhelming.

The goal isn’t to eliminate stress but to keep it manageable and healthy. Below are five practical, science-backed resets Dr. Aditi recommends to help you rewire your brain for calm, resilience, and focus.

🎯 Reset 1: Get Clear on What Matters MOST

When stress takes over, your brain shifts into survival mode, governed by the amygdala—the part responsible for your fight-or-flight response. To move from this reactive state to a more strategic, forward-thinking mindset, create a MOST goal:

Motivating: A goal that excites and inspires you.
Objective: Clear, measurable progress you can track.
Small: Break it down into small, achievable steps.
Timely: Focus on goals you can work toward over the next 2-3 months.

For example, instead of saying, “I want more energy,” your MOST goal could be, “I will take a 10-minute walk every evening.” By starting small, you create measurable progress, which builds momentum and confidence to tackle larger challenges.

📱 Reset 2: Create Digital Boundaries

Digital overload is a significant driver of chronic stress. From endless notifications to mindless scrolling, technology overstimulates your brain, leading to what experts call “popcorn brain”—a scattered, hyperactive mental state. To restore balance, set intentional digital boundaries:

Switch your phone to grayscale mode to make it less enticing.
Remove devices from your nightstand to improve sleep.
Create screen-free buffer times—5-10 minutes in the morning and before bed.

Small changes like these can significantly reduce overstimulation, allowing your brain to rest, recharge, and focus.

🏃 Reset 3: Sync Your Brain and Body

Stress disconnects us from our physical selves, but the mind-body connection allows us to regulate stress intentionally. Simple practices can help you feel grounded and calm:

Stop, Breathe, Be: Pause, take a deep breath, and “just be” for three seconds before jumping into stressful tasks like checking emails or joining meetings.
Daily Movement: Even 5-10 minutes of mindful walking reduces stress and strengthens mental resilience. Focus on the sensation of your feet on the ground and take slow, intentional breaths.

By syncing your brain and body, you reduce physical stress symptoms like headaches, tension, and fatigue while restoring balance to your nervous system.

😮‍💨 Reset 4: Come Up for Air

Multitasking feels productive, but it actually weakens focus and drains mental energy. Instead, adopt monotasking—focusing on one task at a time to preserve mental bandwidth.

Use time blocking: Dedicate 10-15 minutes to a single task, take a short break, and then move on. Gradually increase your focus periods over time.

Monotasking preserves productivity, strengthens the prefrontal cortex (the part of the brain responsible for focus and problem-solving), and helps you approach tasks with clarity instead of overwhelm.

🧘 Reset 5: Bring Your Best Self Forward

The final reset builds emotional resilience through two powerful tools:

Therapeutic Writing: Spend 20-25 minutes writing about a stressful or emotionally charged experience for four consecutive days. This simple, science-backed exercise releases mental tension and promotes healing.
Self-Compassion: Treat yourself with kindness, grace, and understanding—just as you would a close friend. Practicing self-compassion reduces the amygdala’s stress response, quiets the inner critic, and strengthens emotional resilience.

By silencing negative self-talk and processing emotions, you’ll feel more empowered to face challenges with strength and clarity.

🚀 The Best Approach: Start Small and Build Momentum

One of the most critical insights Dr. Aditi shares is that your brain can only handle two new changes at a time. Trying to do too much at once will overwhelm your system, leading to failure. Instead, pick two small resets to implement over the next eight weeks. Once these habits feel automatic, add two more.

This gradual, intentional approach ensures long-term, sustainable progress toward reducing stress and building resilience. Remember, small steps create big changes over time.

🗓️ 7 Questions to Reflect, Reset, and Make 2025 Your Best Year Yet

Wed, 01 Jan 2025 16:00:54 +0000

As the year winds down, there’s no better time to reflect on where you’ve been and where you’re headed. Inspired by a conversation I had with Sahil Bloom on Ep #99 about the art of conducting a personal annual review, I’ve found that asking these 7 questions can become the key to uncovering insights and setting a purposeful course for the year ahead. This practice helps me understand my growth, pinpoint areas for improvement, and ensure I’m aligned with what truly matters and I hope it helps you plan for your best year yet.

1. What Did I Change My Mind On This Year?

This question is about embracing change and updating your “mental software.” If you’re not changing your mind about something each year, you’re probably not growing.

For me, one of the biggest shifts this year was learning to let go of my frugality in small decisions. I realized that obsessing over minor costs was draining unnecessary energy. By reframing my mindset to focus on the bigger picture, I’ve experienced a significant boost in my happiness and reduced stress levels.

How to Approach This

Reflect on conversations, books, or experiences that shifted your perspective.
Use tools like photo albums or calendars to jog your memory and avoid recency bias.

2. What Created Energy for Me This Year?

Think about the activities, people, and projects that made you feel alive. For me, spending time on adventures with my kids was a huge source of energy. Whether it was taking my daughter on a bike-and-train trip to get donuts or building a fort in the living room, these moments were pure joy.

Another surprising energy boost came from primary research for my podcast. I love diving into the details—like testing credit card perks, experimenting with loyalty programs, or trying new travel hacks.

Your Turn

Look back at your calendar or journal and identify patterns in what made you feel energized.
Ask yourself: Did I spend enough time on these things?

3. What Drained My Energy This Year?

On the flip side, it’s equally important to identify the activities and habits that sapped your energy. For me, one big drain was trying to fit our kids into our “old life” by planning vacations the way we did pre-kids.

Another culprit was social media. Feeling the pressure to post content for every platform was exhausting. I realized I was spreading myself too thin and decided to focus on what I enjoy most: creating podcast episodes and writing my newsletter.

Take Action

Look at your patterns. Are there recurring meetings, habits, or even relationships that drain you?
Strategize on how to reduce or eliminate these from your life.

4. Who or What Were the Boat Anchors in My Life?

Sahil calls these “boat anchors”—people or habits that hold you back. These might be relationships where negativity or lack of support creates drag on your progress.

For me, one “boat anchor” I uncovered wasn’t a person, but a mindset: my fear of not making enough money. It’s a self-limiting belief that occasionally distracts me from bigger opportunities. By recognizing it, I’ve started working on reframing that fear and focusing on what truly matters.

How to Navigate This

Identify the anchors in your life and plan to reduce their impact.
You don’t need to cut ties entirely—sometimes just limiting engagement is enough.

5. What Did I Avoid Because of Fear?

This question helps uncover opportunities missed because of hesitation or anxiety. For years, I avoided going full-time on my podcast because I was afraid it might not work. This year, Amy and I faced a similar decision about her joining the podcast full-time. I’m proud we pushed past that fear and took the leap—it’s been one of the best decisions we’ve made.

How to Push Past Fear

Use “fear-setting,” a concept from Tim Ferriss, to deconstruct your fears and evaluate the real risks.
Ask yourself: What’s the worst that could happen, and can I handle it?

6. What Were My Greatest Hits and Worst Misses?

This is where you reflect on your wins and losses to balance optimism with self-critique.

My Greatest Hits:

Watching my daughter walk to school with her backpack on—it’s a small, everyday moment, but it fills me with pride.
Our first group trip to Iceland was a huge success, and I’m thrilled to do more in the future.
Maintaining consistency: We didn’t miss a single week of the podcast, and the newsletter hit a weekly cadence.

My Worst Misses:

Everything felt too last-minute. Whether it was planning episodes or personal trips, I want to be more intentional next year.

Pro Tip

Writing down both hits and misses gives you a clearer, balanced view of your year.

7. What Did I Learn This Year?

This question ties everything together. It’s about extracting the lessons from the entire review process and using them to guide your future decisions.

For me, the overarching theme was intentionality. I want to be more deliberate about how I spend my time, energy, and money. Whether it’s planning a vacation or making a business decision, I’m aiming for alignment between my goals and actions.

Final Thought

Use this question to synthesize your reflections and chart your course for the next year.

How to Track Progress and Improve Next Year’s Review

To make this process smoother next year, Sahil proposes adapting the 1-1-1 Journaling Method. This straightforward approach encourages daily reflection by focusing on three key elements: one win, one point of tension, and one point of gratitude.

One Win: Identify a moment from your day that you feel proud of, no matter how small. Acknowledging these wins helps build a positive mindset and reinforces your progress.
One Point of Tension: Write down any stressors or challenges you faced. This allows you to process these feelings and find solutions, reducing their impact on your well-being.
One Point of Gratitude: End your reflection by noting something you appreciate, whether it’s a supportive friend or a beautiful moment. Cultivating gratitude improves mental health and increases happiness.

Additionally, you can commit to monthly reviews to stay aligned with your goals and track progress throughout the year.

Reflecting on the past year is one of the most valuable investments you can make in yourself. I hope these questions and examples inspire you to conduct your own annual review and set the stage for a purposeful and fulfilling year ahead.

Here’s to an incredible year ahead!

🎁 2024 Holiday Gift Guide

Wed, 20 Nov 2024 05:02:27 +0000

The holidays are here and I’ve rounded up over 80 gift ideas across a variety of categories to help you find the perfect gift for everyone on your list. I'll also share some tips on how I save 5–25% on almost all my shopping.

🧑‍🔧 Personal Tech
🍳 Kitchen, Food and Drink
👕 Clothing & Gear
💪🏼 Health & Fitness
🧩 Games
👨‍👩‍👧‍👦 Kids
📖 Learning & Books
💰 Apps To Save On Shopping

I’ve included links to all the products and services along with current discounts. Please note that some are affiliate links and I’d be grateful if you use them to support the podcast, unless you find a better deal elsewhere!

Every product and service on this list is something I personally love and use (unless stated otherwise). None have paid to be included, though you’ll see a few sponsors of the podcast mentioned because I only partner with brands I trust and can recommend.

If you enjoy this guide, I’d be so grateful if you share this gift guide with a friend or family member.

Happy Holidays!

🧑‍🔧 Personal Tech

MOFT iPhone Wallet (← 25% off): I use this every day—it’s a slim, magnetic wallet that sticks to your iPhone and holds a few cards and some cash. It even flips into a stand, which is perfect for propping up your phone while working or watching videos.
Anker Wireless Charging Stand: We’ve got these everywhere—my desk, the kitchen, and even the bedroom. It’s perfect for charging your phone, AirPods, or Apple Watch, and honestly, having one in the kitchen keeps me more present during family time since I can leave my phone to charge.
Airpods 4 (← 8% off): My old AirPods were dying way too fast, so I upgraded, and the noise cancellation is a game changer, especially on planes! I also love that I can charge them with a USB-C cable now.
AirTags (← 29% off): These are a must for travel, I toss them in all our bags for peace of mind. It looks like airlines are also now using AirTags to find lost luggage.
Anker GaNPrime Power Bank (← 20% off): This little power bank is like a power brick with a built-in battery. I bring it everywhere to charge my phone and computer.
Synology 4-Bay NAS DiskStation: This is definitely for the techies, but I needed a better way to back up all of my content locally, and this has been a perfect solution to keep my data safe and even syncing with the cloud.
Raspberry Pi: If you’re into tech projects, this tiny computer is a game-changer. I’ve used it for everything from home automation to little coding experiments.
Sonos Speakers: These speakers are all over the house, and they’re hands-down my favorite for seamless, high-quality sound. The portable Sonos Move is a standout for its waterproof design.
Eight Sleep (← up to $400 off): This might be one of the best investments I’ve made for better sleep. My wife and I have completely different ideas of what a comfortable sleep temperature is, and this has been a life saver. It even adjusts the temperature throughout the night so we both sleep better.
Oura Ring: I've been using an Oura Ring for years, and I love how it tracks everything from sleep to fitness. The new version even monitors heart rate during workouts.
Sleep is a Skill Store: Mollie Eastman from Ep #151 is the founder of Sleep is a Skill and she’s put together an incredible collection of products for better sleep. If you’re serious about improving your rest, check it out.
DeleteMe (← 20% off): It might not be the flashiest gift, but it’s one of the most practical and thoughtful ones. With scams and AI-driven risks on the rise, DeleteMe removes your personal info—like your name, email, and phone number—from hundreds of data broker sites.
Cameo Video: I've never actually given a Cameo, but my wife and I have received a few. You can hire a celebrity—usually not A-list but still recognizable—to record a personalized video message. They can be a really fun, unique gift, especially if you don't know what else to get someone.
Funko Action Figures: This is another one I haven't personally gifted, but Funko lets you “pop yourself” by designing your own action figure-style character. You can customize everything from skin tone and hairstyle to clothes and accessories, making it a playful and creative gift.

🍳 Kitchen, Food & Drink

COSORI Air Fryer (← 27% off): We got this as a gift, and I was surprised at how much we use it. From reheating leftovers to making fries, chicken and even pizzas.
Maui Nui Venison (← 20% off): We love eating this healthy red meat and the snack sticks would make great stocking stuffers!
Ninja CREAMi (← 12% off): This is my favorite way to make incredible protein ice cream (recipe here) at home. It’s easy, customizable, and even makes delicious sorbets with just frozen fruit—thanks, Sahil Bloom, for turning me onto this!
Breville: I’m a huge fan of Breville’s products, especially the tea maker and immersion blender.
Waring Double Belgian Waffle Maker: Weekend breakfasts wouldn’t be the same without this. We make protein-packed waffles almost every week, and it’s a hit with the whole family. Please note that we bought this when it was only sale for $75 and the price has increased a lot since.
Cuisinart Smashed Burger Kit (← 10% off): I’m obsessed with making smash burgers at home and this kit has everything you need.
Ooni Pizza Oven: We gifted this to a family member a few years ago, and it’s been such a hit.
DASH Rapid Egg Cooker (← 5% off): This is such a fun and quirky gadget. It’s foolproof for making hard-boiled eggs, and the kids love the little song it plays when the eggs are done.
Anyday Cookware (← up to 40% off): My episode with David Chang changed my perspective on microwave cooking and I love this cookware.
Umami App: I used to recommend the Paprika App for recipe management, but I'm excited to switch to the Umami App, which is much less expensive.
- Recipe Book Idea: Create a family recipe book by digitizing handwritten recipes from your parents or grandparents. It's a thoughtful, practically free gift that preserves cherished traditions.
Coravin Wine Preserver (← up to 40% off): This is perfect for those nights when you don't want to drink an entire bottle of wine. You can pour a glass without opening the whole bottle, and it preserves the rest of the wine with argon gas.
Ember Mug (← 19% off): My wife Amy swears by this for keeping her coffee hot, and I love the travel version too.
Ratio Coffee Machines (← $10 off): I've heard amazing things about these pour-over coffee machines.
Trade Coffee (← 30% off) and Atlas Coffee Club® (← 50% off): Subscriptions for incredible coffees from around the world.
The Pathfinder: One of the better non-alcoholic spirits I've found.
Hot Ones Challenge: This makes for such a fun holiday activity!

👕 Clothing & Gear

Vuori Activewear (← 20% off): I literally live in Vuori gear. Their joggers, hoodies, and shirts are so soft and comfortable!
Bonobos (← 25% off): I love their dress shirts, especially the Riviera Short Sleeve.
goodr sunglasses (← $10 off): These are my go-to for sunglasses, they’re affordable, durable, and perfect for any activity.
Quince: Quality clothes with sustainable practices and good prices. My wife got me a cashmere sweater and it’s now one of my favorites.
Waterproof Birkenstocks: My wife and daughters love these. They’re lightweight, easy to clean, and perfect for everything from the beach to casual outings.
Crocs: These are a hit with the kids, especially with all the fun jibbitz charms you can customize them with (which make good stocking stuffers).
Arcade Jewelry: My wife loves their jewelry, and the pieces are so unique.
Stance Socks (← up to 30% off): These socks make the perfect stocking stuffers.
Hanna Andersson® Pajamas (← up to 40% off): Matching family pajamas have become one of our favorite holiday traditions!
Tortuga (← 20% off): I love the daypack for short trips, and the full backpack is my go-to for longer travel.
Away and Monos: I have and love both these roller-boards for travel.
Fifty Fifty Gear (← 10% off): A listener started this company and they make the best diaper bags ever.
Cuyana Travel Case Set: My wife has gifted these to so many people, and they’re always a hit. The option to monogram them adds a personal touch.

💪🏼 Health & Fitness

SHOKZ OpenRun Pro Headphones (← 11% off): I love these for running because they’re open-ear, so I can stay aware of my surroundings while still enjoying music or podcasts.
Nike RN8050 Slim Waist Pack: I wasn’t sure about switching from an arm band, but I'm really enjoying this alternative.
Nike Vaporfly 3: These shoes are amazing for race days. They’re built for speed, and I’ve noticed a real difference in my times when I wear them.
Nike Pegasus 41: For everyday runs, these are my favorite. I even customized mine, which makes them feel like a truly personal gift.
Paddle Boards: We got these as gifts and didn’t realize how much fun they would be. We use them regularly in warmer months, and they’re great for relaxing on the water or getting a little exercise.
JadeYoga Harmony Mat: I didn’t realize how much a good yoga mat could matter until I borrowed my wife’s JadeYoga mat.
Bowflex SelectTech 552 Adjustable Dumbbells (← 22% off): These are great if you're limited on space and don't want a whole rack of dumbbells.
Hydroflask (← 25% off): These are our go-to water bottles.
DexaFit: A DEXA scan is a unique gift for anyone interested in their health.
Instalab Longevity Panel, Function Health (← code: ALLHACKS100) and InsideTracker (← 10% off): All three offer a similar set of biomarkers focused on longevity.

🧩 Games

Box One | Box Two: Box One was one of the best games I've played and I can’t wait to try out (or gift) Box Two this year!
Theory 11 Cards: The most beautiful playing cards out there. Perfect for stocking stuffers.
Monopoly Deal: We play this all the time—it’s fast-paced, portable, and way more fun than traditional Monopoly.
Coup: This game of deception and strategy is a favorite for game nights.
Illimat Card Game (← 5% off): I bought this after hearing great reviews, and I’m excited to dive into it.
Games Magazine Subscription: I look forward to this every month—it’s packed with puzzles and challenges that keep your brain sharp.
Hinomaru: The Japanese Flag Puzzle: This seemingly simple puzzle is deceptively difficult.
Tesla Puzzle from Puzzle Potato: I loved solving this! It’s an escape-room-style puzzle in a compact package, and it’s great for anyone who loves a challenge.
Lockpicking Kit: This is such a fascinating skill to learn. The kits often include clear locks so you can see how everything works.

👨‍👩‍👧‍👦 Kids

Ookkie Kids Learner Skateboard: I love watching my daughters learn to balance and lean on their Ookie.
Melissa and Doug Pizza Play Set: Out of all the play sets we have, the pizza one gets the most use!
Toniebox: This audio player is a lifesaver for screen-free entertainment. (Also check out the Yoto Player)
Nugget: These modular cushions are endlessly versatile—our kids use them to build forts, seating areas, and even makeshift beds.
KidKraft Building Bricks Play N Store Mega Table: Just saw this amazing Lego table at Costco that I kind of want for the kids.
Jellycat Stuffed Animals: These are our kids' favorite stuffed animals.
Coloring Books and Kit: We love this compact kit for travel. It keeps everything organized, which is a win for parents.
Lovevery (← $20 off): These Montessori-inspired toys are incredible. Each kit is tailored to a specific age range and packed with educational fun.
Swedish Ladder with Rope Accessories: This indoor gym setup is amazing to keep your kids active and I wish we had the space to get one.
Monkey Around: This simple, silly game is one of the few games that works well with very young kids.

📖 Learning & Books

Internet Pipes (← $200 off with ALLTHEHACKS): Steph Smith (from Ep #198) created this great course.
MasterClass (← 15% off): I’ve gifted this so many times—it’s perfect for anyone who loves learning new skills, from cooking to business to photography.
Credit Card Optimization Tool: I created this tool to help people maximize their credit card rewards and/or cash back.
Storyworth (← $10 off): This great gift compiles a year’s worth of family stories into a beautiful book, preserving memories for generations.
All the Hacks: If anyone in your family loves learning, you should obviously send them our podcast or newsletter :)

Here are some books of guests that were on the show this year:

Limitless by Jim Kwik (Ep #158)
Supercommunicators by Charles Duhigg (Ep #159)
To Sell is Human by Daniel Pink (Ep #163)
Radical Candor by Kim Scott (Ep #169)
10x Is Easier Than 2x by Benjamin Hardy (Ep #171)
Breath by James Nestor (Ep #178)
Expecting Better | Cribsheet | The Family Firm by Emily Oster (Ep #183)
Make Time by Jake Knapp and John Zeratsky (Ep #185)
5 Types of Wealth by Sahil Bloom (Ep #190)
Hope for Cynics by Jamil Zaki (Ep #193)
The Simple Path to Wealth by JL Collins (Ep #194)
Good Energy by Casey Means (Ep #196)

💰 Apps To Save On Shopping

Keepa: Browser extension that tracks historical Amazon prices and sales.
Savewise: Compares cash-back and points earning across all the different shopping portals.
Rakuten (← free $40): My default shopping portal that also lets you convert cash back to Amex points.
Pepper App (← $20 back with 612342): Regular discounts on major brand gift cards (e.g. Amazon, Sam's Club, Nike, Lowes).
CardPointers Pro (← 30% off or 50% off for ATH members): Automatically activates card-linked offers on all your credit cards.

💸 How Money Shapes Our Lives: 10 Lessons on Wealth, Happiness, and Family

Thu, 31 Oct 2024 03:44:47 +0000

We all strive for a happier and wealthier life, but the path to achieving these goals is often unclear. Recently, I attended a retreat for high-net-worth individuals hosted by Long Angle, where investors and financial experts shared insights on the intersection of wealth, happiness, and family.

Tad Fallows and I decided to share a recap of our top ten takeaways from these impactful discussions (which you can listen to in Ep 199 or watch here), offering a fresh perspective on how money shapes our lives in ways both expected and surprising.

1. Wealth Amplifies What’s Already There

Money tends to amplify what’s already present. If you’re happy, money can increase that sense of joy; if you’re dealing with personal or professional issues, wealth can actually make those struggles feel heavier. As Morgan Housel says, “Money is a financial asset, but a psychological liability.” It’s like a magnifying glass, intensifying both the good and the bad. The pursuit of “just a little bit more” can easily turn into a lifelong chase, and if happiness isn’t there to begin with, money alone won’t change that.

2. There’s No “Right” Way to Invest

Investing is like picking your favorite food—there’s no “right” answer. Just as some people love Mexican food while others swear by Italian, investing depends on personal preferences. Some people can tolerate more risk or less liquidity, while others want something stable and predictable. The key is understanding your own financial comfort zone and crafting an investment strategy that fits, rather than trying to follow a “perfect” method.

3. Understanding Trade-Offs Can Unlock Hidden Opportunities

While markets are generally efficient, they're also incredibly complex, operating across a multitude of variables. We heard from a real estate investor who accepts less liquidity in exchange for higher returns, embracing what’s called a “liquidity premium.” Every decision has a trade-off, whether it’s prioritizing growth, stability, or accessibility. Recognizing these nuances can help you make choices that work for your specific financial goals, revealing opportunities that might otherwise go unnoticed.

4. Building Resilience Is More Valuable Than Chasing Perfection

When it comes to investing, resilience often pays off more than perfection. Building a strong foundation and sticking with a plan allows your wealth to grow without constant disruption. As Charlie Munger famously said, “The first rule of compounding is to never interrupt it unnecessarily.” I'm at a point in my life where I'm able to fight the urge to react to daily market fluctuations, allowing my investments to work in the background without additional stress or anxiety.

5. Flexibility Is Essential in an Unpredictable World

Life is unpredictable, and the best financial plans are adaptable. We heard a story about an entrepreneur who invested heavily in a farmland trust, aiming for tax benefits, only to realize years later that he couldn’t access those funds when his family needed support. This example highlights the importance of flexibility in wealth management. As the saying goes, “The best-laid plans of mice and men often go awry.” Keeping room for adjustments in your plan allows you to navigate life’s curveballs with ease.

6. Everyone Can Benefit From Seeking Advice

No one has all the answers—not even seasoned investors. Talking through financial decisions with a trusted friend, spouse, or advisor can offer insights that you might overlook on your own. One story that stood out was about an attorney who chose to handle his own estate planning, only to accidentally leave one grandchild out of the will. The family fallout that followed underscored the value of consulting experts. The lesson? Having a sound advice network is essential, even if you think you can handle everything yourself.

7. Recognize That You’re Not at the End of History

Our values and priorities shift as we grow, and understanding that you’re constantly evolving can make a huge difference in financial planning. It’s much easier to look back and see how much you’ve changed than to imagine how much you’ll continue to change in the future. We heard so many examples from people further along in their journeys who had seen their priorities shift, and the message was clear: your financial plan should be flexible enough to adapt as you grow.

8. Happiness Requires a Purpose Beyond Just Accumulating Wealth

While financial success is important, it's not the sole key to happiness. Many individuals find that their happiness actually dips after achieving financial goals, particularly if their sense of identity was solely tied to their career or wealth accumulation. Cultivating passions outside of work—whether it's through philanthropy, hobbies, or meaningful relationships—is essential for creating a life of true fulfillment. In Ep #47, behavioral social scientist Arthur Brooks dives deep into how purpose is a greater driver of happiness than money alone, and this sentiment echoed throughout the retreat.

9. Teaching Kids About Money Is Complicated

Even the most experienced financial experts struggle with finding the correct way to teach children about money. Every child is different, and their relationship with money can be influenced by various factors, including their personality and the family's financial background. From my personal experience, here’s what you can do: model good behavior, have open conversations, and give your kids a hands-on experience with money. Whether it’s a modest allowance or encouraging a summer job, showing them the value of money can make a lasting impact.

10. Optimization Isn’t Binary

This key takeaway is very near and dear to my heart because it took me a while to understand that optimization doesn’t have to be an all-or-nothing game. Whether it’s with travel points, credit cards, or financial returns, you can reap the benefits without going overboard. Chasing every last point or dollar isn’t necessary to make meaningful progress, so find the level of optimization that works and brings you the most value, allowing yourself the freedom to enjoy the journey.

Ultimately, the biggest takeaway from the retreat was that financial decisions—and really, all life decisions—are inherently personal. There’s no universal answer to building wealth or happiness, so make choices that align with your values and goals. Surround yourself with a community of trusted people, seek advice when needed, and allow your plans to adapt as you grow. Embracing this freedom of choice means you can chart your own path to a happier, more fulfilling life.

🛬 Shortcuts to Southwest Companion Pass

Thu, 12 Sep 2024 20:58:38 +0000

Advertiser Disclosure

All information about Southwest Cards has been collected independently by Chris Hutchins. The card details on this page have not been reviewed or provided by the card issuer.

The coveted Southwest Companion Pass lets you bring a companion on any Southwest flight, whether booked with cash or points, for just the cost of taxes and fees. Companion Pass holders can also switch their designated companion up to three times per calendar year, making the pass incredibly flexible. So if you had two kids, both parents could get one of these cards, and both kids could travel free all year.

The usual way to earn a Companion Pass is to fly 100 qualifying one-way flights or accumulate 135,000 qualifying Southwest points in a calendar year. As a Southwest cardholder, that requirement is dropped to 125,000, and even better, points earned through credit cards and their welcome bonuses count.

To make things even easier, Southwest is currently offering 30,000 points and a Free Companion Pass through 2/28/26 on it's personal cards after spending $4,000 in the first 3 months.

Personal Cards: Free Companion Pass + 30k after spending $4k in 3 months.

Business Cards

Southwest® Rapid Rewards® Premier Business Credit Card: 60k points after spending $3k in 3 months.
Southwest® Rapid Rewards® Performance Business Credit Card: 80k points after spending $5k in 3 months.

Tip to Extend the Companion Pass for 2 Years

When you earn Companion Pass, you get it for the remainder of that year and the following year, so timing is absolutely crucial. The goal is to earn your Companion Pass in early in the year, so you have it for that entire year AND the next year. Now points and welcome bonuses post when the statement closes, so my strategy is to wait to hit any spending requirements for a welcome bonus until I'm spending on a statement that closes in January.

For example, if your statement closes on the 7th of the month, you'd want to avoid spending enough to trigger the welcome bonus until after December 7th, so your spending is all on the statement that closes January 7th. If you're approved for the card sometime in mid-to-late September and end up with a statement closing date towards the end of the month, you can request a new closing date towards the beginning of the month, which should give you a window to meet your minimum spend for the welcome bonus within the 3 month requirement that still falls during a statement window that won't close until January. That said, if you hold off on getting the card until a few days into October, it'd be much easier.

Quick Reminder: The Chase 5/24 Rule

Before applying, remember Chase’s "5/24 Rule," which limits approvals if you’ve opened 5 or more personal credit cards from any bank in the last 24 months. Most business cards you already have (including Southwest's) don't count, but certain business cards from TD Bank, Discover, and Capital One do count toward this 5/24 limit.

⌛ 9 Ways High-Achievers Use Their Time

Sat, 31 Aug 2024 04:48:14 +0000

Time is your most precious asset, and how you use it can significantly impact the quality of your life. According to Sahil Bloom, being intentional with your time isn’t about finding more hours in the day; it’s about making the most of the time you already have. Whether you’re focusing on productive work, creating meaningful solitude, or deepening relationships, purposeful time management ensures you invest in activities that bring the highest returns.

And while time is fixed—everyone has the same 24 hours each day—your energy fluctuates, and understanding this can be a game-changer. Instead of just scheduling tasks, it’s about aligning them with your energy levels to maximize productivity. Similarly, being present with others isn’t just about being there physically; it’s about dedicating your full attention and energy, making even a few minutes of undistracted time more impactful than hours spent distracted.

Sahil and I dive deep into this topic on Ep 190, but today, I’m going to share 9 key strategies to be more intentional with your time so you can achieve better outcomes and live a more fulfilled life.

First, let’s explore how to be intentional with your time when you’re alone, ensuring it aligns with your goals and well-being.

1. Create an "Anti-To-Do" List

Sahil suggests creating an "Anti-To-Do" list as a proactive way to avoid bad habits and distractions that can derail your productivity and focus, like checking your phone during family time or getting sidetracked by low-priority tasks at work. This list serves as a daily reminder to steer clear of activities that don’t serve your long-term goals.

Here's a simple way to create your own Anti-To-Do list:

Write down the personal and professional challenges you’re struggling with.
Start small, with 3-5 high-priority items.
Keep your Anti-To-Do list visible throughout the day, just like your To-Do list.
Check off items as you build a habit to successfully avoid them.

2. Believe in the Law of Reversed Effort

The law of reversed effort suggests that sometimes, the harder you try, the less successful you are. Intense effort can create tension and anxiety, ultimately hindering performance. For example, sprinters often run faster at 80% effort than at 100% because they are more relaxed. This principle applies not just in athletics but in any area where overexertion might be counterproductive—like struggling to fall asleep when you try too hard.

3. Schedule a Think Day

Inspired by Bill Gates' "Think Week," Sahil proposes a "Think Day"—a day set aside from daily tasks to focus on big-picture thinking. It’s a time to step back from the grind, reflect on your goals, and consider broader life strategies. Even if you can’t take a full week, dedicating one day a month or quarter to deep thinking can provide clarity and direction in both your personal and professional life.

Here are six prompts to help your thinking:

What are your strongest beliefs? What would it take for you to change your mind?
What do you know now that you wish you knew 5 years ago?
How can you do less, but better?
Are you hunting antelope (big important problems) or field mice (small urgent problems)?
What actions from 5 years ago make you cringe today? What are you doing now that might make you cringe in 5 years?
What would your 80-year-old self say about your decisions today?

4. Go on a Walk

Walking isn’t just good for your health; it’s also a powerful tool for boosting creativity. A Stanford study showed that walking increases creative output by 60%, making it a simple yet effective way to solve problems and generate new ideas. Incorporating a daily walk into your routine can help you break out of mental blocks and approach challenges with fresh perspectives.

5. Build Better Habits Using the 30 for 30 Approach

The "30 for 30" approach is about committing to 30 minutes of focused work every day for 30 days. This strategy is particularly effective for building new habits or improving a specific skill because it’s manageable and sustainable. By the end of 30 days, the cumulative 900 minutes of effort can lead to significant progress, all without the intimidation of a larger time commitment.

If you’re struggling to stick with a new habit, Sahil encourages you to focus on making just one good decision at a time. Don’t get overwhelmed by the big picture—just concentrate on the next step that will improve your situation tomorrow. This will help keep you on track and make progress easier.

Now, let’s focus on being intentional with your time spent with others, especially your loved ones, to strengthen relationships and create meaningful connections.

6. Disconnect from Your Phone

A study found that merely having your phone visible during a conversation significantly reduces the sense of connection between people, even if you’re not using it. The presence of the phone acts as a distraction, subtly signaling that your attention could be diverted at any moment. By keeping your phone out of sight—like placing it face down or in another room—you can enhance the quality of your interactions and be more present with those around you.

Phones are designed to be addictive, with features and apps that constantly demand your attention. To reclaim your focus, Sahil suggests simple yet powerful tactics like using grayscale mode to make your phone less visually appealing, setting up focus modes to hide distracting apps, or physically separating yourself from your phone during important tasks or family time. These small changes can drastically reduce screen time and improve your ability to concentrate.

Grayscale mode: Enable grayscale mode on your phone to make it less visually appealing and reduce the urge to check it frequently.
No distractions mode: Set up a custom focus mode on your phone that hides all app screens and only allows essential notifications, like texts and calls. I created a custom phone setting called "No Distractions" to help minimize interruptions and stay focused. In this mode, all app screens are hidden, leaving my home screen completely blank. I set it up so that from 5 AM to 9 PM, my phone only allows notifications for texts and phone calls—everything else is silenced.

Physical separation: Leave your phone in another room during important activities, like family dinners, to prevent mindless checking and ensure you're fully present.
Kale vs. cocaine phone: Use a “kale phone” (a phone without apps or internet access) for essential communication, and keep your regular phone (the “cocaine phone”) out of reach when you need to focus.
App deletion: Delete distracting apps, like social media and browsers, from your phone to minimize temptation and reduce screen time.

7. Learn the Skill of Listening

Sahil believes that listening is a skill with different levels of depth:

Level 1 (me listening): You listen to relate everything to yourself.
Level 2 (you listening): You listen to truly understand the other person.
Level 3 (us listening): You listen with a broader context in mind, considering the other person’s world and how their words fit into it.

Moving from Level 1 to Levels 2 and 3 can enhance your relationships, making you a better communicator and more charismatic, as people feel genuinely heard and understood.

In romantic relationships, really listening to understand instead of just waiting to talk can make a huge difference. A great way to figure out what they need is to ask, “Do you want to be helped, heard, or hugged?” This simple question can clear things up and help you give the right kind of support.

Sometimes your partner just wants to be heard, not have their problems fixed. This video pretty much sums up what I mean by that:

8. Surround Yourself with the Right People

The people you spend time with have a profound impact on your life. The Pygmalion effect is the phenomenon where people tend to rise or fall to meet the expectations others have of them, meaning that higher expectations often lead to better performance. Positive, growth-oriented individuals can inspire and uplift you, while negative people can drain your energy and hold you back.

Here are some ways to find communities that align with your values and support your growth:

Find microcommunities: Look for small, focused communities where people genuinely support each other, such as fitness and wellness groups, where members often have a growth mindset and positive energy.
Engage in fitness and wellness activities: Joining groups centered around health, like running clubs or gyms, can help you connect with others who share a commitment to personal growth and optimism.
Seek out environments with aligned values: Put yourself in spaces where people have similar values to yours, like delayed gratification or optimism, which naturally filters for high-energy, positive individuals.
Join professional groups: Participate in groups like YPO (Young Presidents' Organization) or Sam Parr’s Hampton, where people invest time and money to be around others with similar professional ambitions and growth-oriented mindsets.

9. Don’t Complain (About Anything)

This is Sahil’s #1 rule in life. Complaining gives power to the things that frustrate you, wasting energy on issues you often can’t change. Instead, focus on what you can control. If something is within your power to change, take action. If not, let it go and move on to something more productive. Adopting a no-complaint mindset can reduce stress and help you focus your energy on positive, constructive activities.

Since hearing this, I’ve tried to adopt it and catch myself whenever I complain. I ask myself, "Can I fix this?" If I can't, there’s no point in complaining. I also follow a sub-rule that I learned from Hristo (from The Tim Ferriss Show): don’t ask for help until you’ve spent at least 15 minutes trying to solve the problem yourself. If we all followed these simple rules, I'm sure the world would be a much better place.

🧑‍💻 Stuff I Use for Life, Work, Health, Home and Beyond!

Fri, 16 Aug 2024 07:23:23 +0000

Advertiser Disclosure

When it comes to my day-to-day life, both personally and professionally, there are a few key products, services and gadgets that I rely on heavily. These are the things that keep me productive, organized, entertained (and sometimes, sane). So I’ve shared a breakdown of what I use and why I can’t imagine going without them across these categories:

🧑‍💻Tech Essentials
💻 Computer & Mobile Apps
💸 Money & Subscriptions
🏋🏽 Health, Fitness & Clothing
🧳 Travel Tools & Apps
🏠 Home, Kitchen & Auto
👶 Kids & Dog
💼 Business & Podcasting

Just to clarify, none of the brands I’m mentioning below have paid to be included—they’re all genuinely my favorites. If some happen to be sponsors, it’s because I only work with advertisers whose products I already love. Wherever possible, I’ve added affiliate links and discount codes and I’d really appreciate if you use them, but ONLY if it’s the best deal you can find!

🧑‍💻Tech Essentials

Personal Devices

iPhone 15 Pro: This is my core device. I tried Android a couple of times but the iMessage integration makes it indispensable.
MacBook Air with M2 Chip: I do a lot of my work on this machine and I’ve almost never had any issues on it.
Mac mini: My primary computer.
Magic Keyboard + Magic Trackpad: I love this combo but I’ve been eyeing the Magic Keyboard with Touch ID!
Apple AirPods: I lost my 3rd Generation AirPods so I went back to the 2nd Generation - they’re reliable and the sound quality is great. I tried the AirPods Pro andAirPods Max and I must say, I’m not a fan.
MOFT iPhone Wallet: This was a gift, and I love it. It’s a MagSafe charger and a phone stand all in one. Super handy!

Power Banks

Anker Prime Power Bank: Anker makes the best charging products, hands down.
Anker PowerWave Charging Stand: I use this magnetic charger on my desk to keep my devices charged throughout the day.

Desk Setup

Bose Companion 2 Speakers: I like having high-quality sound and these are perfect for it.
UPLIFT **Standing Desk:** A really solid desk that lets me switch between sitting and standing effortlessly.
Steelcase Gesture Office Chair: If you’re going to spend hours at a desk, you need a good chair. This one is incredibly comfortable and supports good posture.
Elgato Stream Deck MK.2: Originally designed for gamers, I use this to control everything from my records to switching cameras to muting myself on video meetings to pausing my Spotify and the list goes on. It’s a game-changer.

Storage

For cloud, I used to use Dropbox but we ran out of space after recording videos for the pod, but now I’ve switched to Google Drive for the extra space. iCloud handles all my personal backups, including photos and messages.
Synology DiskStation DS923+: This little device is my local storage solution. It’s like a personal cloud that syncs with my network and the actual cloud. It’s perfect for backing up large files and keeping everything in sync.

💻 Computer & Mobile Apps

Productivity Apps

Alfred: A replacement for Spotlight Search with way more functionality.
Superhuman (←Free month with code ALLTHEHACKS): The fastest email I’ve ever used. With AI features that save me hours every week, it’s easily one of the tools I’d be lost without.
Loom: I use this to record quick videos for work. It’s cross platform, making it a great way to communicate asynchronously and avoid unnecessary meetings.
Rectangle: A free app that lets you move and manipulate windows on my screen with ease.
Arc: I’ve fully switched to Arc as my browser on all my devices. The layout is unique, and it’s incredibly intuitive once you get used to it. I absolutely cannot imagine living without it.

Privacy and Security

Code Piper: This app lets you autofill two-factor authentication codes on the computer, making it easier to stay secure without the hassle.
1Password (← Free 2-week trial): I’ve been using this password manager for so many years and I’ve made everyone in my family switch over. It’s super reliable and keeps all my passwords, two-factor codes, and passkeys in one secure place.
NordVPN (← Discount + 4 months free): You can use NordVPN to connect to almost any country quickly. It’s a great hack for accessing different versions of the Olympics i.e. head over to the UK to use BBC. It’s also useful for taking advantage of referral programs with multiple email addresses.

Chrome Extensions

Library Extension: When browsing books on Amazon, this extension shows me if my local library has it available for checkout or as an eBook. Super handy!
Points Path: This one’s great for travelers. It shows the points cost for flights directly in Google Flights.
Rakuten (← Free $30): Earn cash back on almost every online purchase, and if you link your American Express card to your account, you can earn Membership Rewards® Points instead of dollars.
Keepa: An Amazon price tracker that provides historical price graphs to help monitor price changes and make informed purchasing decisions.
Don't F*** With Paste: This extension allows you to paste text on websites that try to block it. A small but mighty tool.
Eno from Capital One: Lets you create virtual cards for online shopping, adding an extra layer of security to my purchases.

Mobile Apps

BestParking: If you’re ever in a city and need to find parking, this app is a lifesaver. It’s basically a map of the prices of nearby parking garages and lots.
TV Time App: It tracks your favorite shows, shares recommendations, and keeps up with upcoming schedules, but the app isn’t the most reliable because it crashes often (but it’s still the best I’ve found).
ChatGPT: I use this for app for everything its actually my shortcut button.
Morty: Amy and I love escape rooms, and this app is our go-to directory to find the best-rated escape rooms escape rooms around the world.
Infatuation: When it comes to food reviews, I love the editorial content on this app. It’s like having a trusted friend recommend the best spots in town.
Podcasts: I used to use Spotify, but it didn't support my private RSS feeds from Patreon. I tried Apple Podcasts but it caps playback at 2x speed, and I prefer 2.1x. Lately, I've been using Overcast— it's not perfect, but I really like it.

💸 Money

Bank Accounts

If you haven’t already, make sure to listen to episode #177 on the best accounts to replace your checking account and maximize interest earning but here are my top 3:

Wealthfront: I used to work at Wealthfront. Get $5k managed free and/or a 0.5% APY boost.
Mercury
Fidelity

Personal Finance Tools

Kubera (← 1st year free for ATH members): This is one of the best ways to track and monitor your net worth.
ProjectionLab (← 10% off with code ATH-10): When it comes to more detailed financial modeling, I really like ProjectionLab. It allows you to build and simulate your own financial plan.
Copilot (← 2 months free with code HACKS2): One of the simplest ways to categorize your spending and create a budget retrospectively.
Daffy (← Free $25 for charity): Our go-to platform for charitable giving. We use it to donate to a donor-advised fund, making the process efficient and tax-friendly.
Carry: Since we run our own company, we've consolidated all our old 401(k)s into a solo 401(k) with Carry. It’s the most effective way we've found to manage both our 401(k)s and self-directed IRAs.
Gelt (← Skip the waitlist): The best CPAs. This is how we handle everything from personal taxes to business finances.
Trustworthy: A digital vault that securely stores your tax returns, IDs, and other critical information. If anything were to happen to you, it ensures that someone can easily access your estate details, account information, and essential documents like passports and insurance cards.

I also did a deep dive on tracking your spending on episode #133 covering why you should do it, as well as top apps/services, setting up budgets, managing recurring expenses, picking categories and more.

Subscriptions

MasterClass (← 15% off): I’ve learned so much from the experts on this platform. Whether it’s cooking tips from Gordon Ramsay or leadership advice from business leaders, MasterClass is a go-to resource for expanding my knowledge.
Stable (← 50% off): I use this virtual mailbox service to handle all my business mail. They receive your mail, scan it, or ship it to you, making it easy to manage plus, keeps my home address private.
DeleteMe (← 20% off): Your personal information often gets sold to data brokers and ends up online. I use DeleteMe to remove this data, and they regularly review and remove listings, keeping my info private. It’s been so effective that I’ve signed up my entire family.
Paramount Plus (Free with Walmart+): I’m not even sure I watch it, but since The Platinum Card® by American Express gives me free Walmart+, I get Paramount Plus at no extra cost.
ChatGPT Plus: The new 4.0 version is great and while there are other faster, free models out there, once you start using ChatGPT, it’s hard to switch. I do wish they had an easier way to search.

🏋🏽 Health, Fitness & Clothing

Health & Fitness

Peloton Bike: I’ve had it for years and still love it, though I admit that I’ve been eyeing a Tonal for strength training (but I’m not sure we have the space for it).
Bowflex SelectTech 552 Adjustable Dumbbells: Space-saving and versatile for at-home workouts.
Oura Ring: My go-to sleep tracker. It helps me monitor and improve my sleep quality.
SHOKZ OpenRun Pro Headphones: These open-ear headphones are perfect for runs. I can stay aware of my surroundings while still enjoying my music or podcasts or even talk to Amy.
Nike Vaporfly 3: If you’re serious about running, these shoes are game-changers. They’re a bit pricey, but the performance boost is undeniable. They almost got banned from the Olympics because they're just THAT amazing.
Cold Plunge (← $150 off): I love their Plunge products!
Haven Sauna: They haven’t officially launched yet, but you can sign up for their waitlist here.
One Medical: We use it for the whole family. It’s pretty convenient for scheduling last-minute doctors appointments and virtual calls.
Peter Attia Membership: I’ve subscribed to his membership which gives me access to premium podcast content and premium show notes. I highly recommend it if you want to dial into your health (and you can also check out his recent book Outlive).

Clothing

Vuori Activewear (← 20% off): These are my all-time favorite clothing items, even beyond active wear. I wear them at least once or twice a week—they’re just that comfortable and versatile. If I HAD to pick my favorites, it’d be the Sunday Performance Jogger, the Strato Tech Tee and the Kore Short.
Bonobos (← 25% off): The Riviera Short Sleeve Shirt has become my go-to shirt. I probably have 6-7 of them because they’re incredible!
Indochino (← 10% off with code ALLTHEHACKS): I got a couple of suits from them for our wedding which was 12 years ago, and they’re still wear them! The custom tailoring has held up well, and they still look fantastic.
goodr sunglasses (← $10 off): I probably own five or six pairs of goodr sunglasses. They’re affordable, stylish, and great for working out or just everyday use.
Mack Weldon Underwear (← $20 off): I use The Platinum Card® by American Express’s Saks credit every six months to stock up on Mack Weldon underwear. I think they’re a bit pricey, but they’re worth every penny for the comfort and quality.

🧳 Travel Tools and Apps

Flighty: This app keeps me updated on all my flights with real-time alerts.
Portable Mini Travel Router: I love this product because it solves the common issue of hotel Wi-Fi requiring room number authentication, which many devices can’t handle. This affordable, compact travel router creates its own Wi-Fi network, allowing all your devices to connect seamlessly while you authenticate through your phone or laptop.

Suitcases and Bags

Away (← $40 off): I love their The Weekender bag.
Monos: Also love their Weekender bag.
Tortuga Backpacks: My favorite travel backpack.

Points and Miles

I’ve covered a lot of content around this topic which you can check out on episode #155 to find out which credit cards are in my wallet for 2024, and #166 to learn about the best tools to book flights and #167 for hotels.

CardPointers Pro (← 30% off): Automatically loads card-linked offers into your Amex or Chase account and suggests the best card to use while shopping.
Award Wallet: Tracking points and miles can be tricky since many airlines block access to balance information, but Award Wallet is the best solution available.
My Credit Card Optimization Tool: I spent dozens of hours building out a robust credit card optimizer tool, so you could maximize your earnings from credit cards. If you're an ATH member, (or want to be), you’ll get free access to the tool and so much more!

🏠 Home, Kitchen & Auto

Smart Home Tech

Ubiquiti Wifi + Cameras: Ubiquiti is my favorite brand for Wi-Fi and security cameras. Professional-grade gear that just works and no rebooting needed but it is a bit technical to use.
Ring: For all our home security alarms.
August: Smart home locks to keep the house secure.
Samsung Frame TV: Absolutely love this TV, it has enough services hooked up to don't even need an Apple TV.
Sonos: Love the sound quality, though I’m not a fan of their new app.
Tesla Powerwall + Solar Roof: There were there when we got the house.
Sense: Monitors electricity usage, identifies devices, and helps me optimize energy consumption.
SPAN Smart Panel: I don’t have this yet but it’s a smart home energy panel that replaces circuit breakers and lets you to monitor and control your home’s energy usage directly from your phone.
Eight Sleep (← $150 off): Amy loves the bed warm but I love it cool so their products have been a game changer for our sleep.

If you want to learn how to save money and time with a smarter and more energy efficient home, tech enthusiast Matt Ferrell and I dive deep into this topic on episode #135.

Food & Kitchen

Green Chef (← 50% off with code ALLTHEHACKS50): We’ve probably had 100+from Green Chef and love them. The meals are healthier, tastier, and offer more variety than other meal kits we’ve tried.
DRAM (← 20% off): This sparkling beverage with natural flavors and ingredients has completely replaced all the soda and soft drinks in our house.
June Oven: We use this almost every day but unfortunately they’re all currently sold out.
Ninja CREAMi: Shout out to Sahil for recommending this amazing kitchen gadget. It’s perfect for making my favorite protein ice cream (recipe) in just a fews mins but you can make so many different things.
Breville: This tea maker and immersion blender has been going strong for 14 years, delivering perfect tea every time.
Waring Double Belgian Waffle Maker: It cooks two waffles at once, making breakfast quick and easy, especially on busy mornings (was only $75 when I bought it)
DASH Rapid Egg Cooker: This tiny machine cooks the perfect hard-boiled eggs with just one button. A must-have for egg lovers.
Hydro Flask: If Amy could be sponsored by any company, it would be Hydro Flask. She loves them.
Coravin Wine Preserver: Lets you pour a glass without ruining the bottle, using a needle that goes through the cork, so you don’t have to commit to the whole bottle.
Paprika Recipe Manager: Our go-to app for recipe storage, meal planning, and grocery tracking. Amy and I both use it to save and rate recipes, create grocery lists, and plan meals for the week, all synced across our phones.

Games

Monopoly Deal: It's one of the games we love to play at home.
Coup: A quick game that involves a bit of deception, similar to Mafia or Werewolves.
Games Magazine: I subscribed to Games Magazine after someone recommended it, and it’s been great. It’s packed with puzzles, perfect for trips, and I love diving into them during downtime.

Auto

TeslaFi (← 2 Weeks Free): If you have a Tesla, this is a fantastic tool for logging drives, tracking business vs. personal miles, and accessing detailed stats about your vehicle.

If you want to dive deep into insurance, listen to episode #104 where I break down how to optimize your insurance policies.

👶 Kids & Dog

Kids Stuff

Hatch Rest+: It’s a light and sound machine that helps keep us regulate the kids’ bedtime. Ex: Red light means stay in bed, green light means it’s okay to get up, and white light is for those mornings when they just won’t budge.
nanit (← 15% off with CHRISH15): These cameras are awesome for keeping an eye on them, even when we’re traveling with the portable stands.
Lovevery (← $20 off): They have subscription boxes filled with well-crafted, Montessori-inspired toys for kids. They arrive every few months with a little guide on how to use them, and they’ve been a hit from the baby to toddler stage!
Clek Fllo + Foonf: Huge shoutout to our neighbors, Shannon and Joe, for these car seats. They’re safe, sturdy, and have been perfect for our kids.
RideSafer Travel Vest: A game-changer for keeping the kids safe without having to haul around a bulky car seat everywhere we go.
tonies Toniebox: A favorite in our house. It’s a little box where you place different character figures on it using RFID, and it plays various stories related to those characters. We’ve managed to create personalized stories for our kids that uses our voices to narrate.
Cultural Care (← $175 off): We’ve had a great experience with Cultural Care for finding au pairs. They make it easy to filter, interview, and handle all the logistics, so we’ve been really happy with the process.

For the Dog

Sundays (← 50% off): The dog food that solved all of our pup’s stomach problems. We’ve never considered switching.
RadDog All-In-One Collar + Leash: Perfect for off-leash dog parks; it’s a collar with a leash attached.

💼 Business & Podcasting

Business Services

Brex + Mercury: For all things banking related.
Oceans (← $1000 off for mentioning ATH): They offer the most incredible virtual assistants. You can also refer to my delegation guide if you want to explore delegation and hiring an assistant.
Kick: Our awesome new bookkeeping software.
Stripe: We do a lot of our payment processing and invoicing on Stripe.
ConverKit: How we send out our newsletter and emails to members.
Notion (Try Notion AI free here): I run most of my life on Notion, that includes most of the business as well.
Calendly: For automated scheduling.
Zapier: I absolutely love Zapier—it's a dream for anyone who loves optimizing workflows. With Zapier, you can connect just about anything and create rules to automate tasks. The possibilities are endless, and I could easily get lost building automations all day.

Podcasting Services & Equipment

Riverside: I use this for recording high-quality remote interview recordings.
Descript: I do most of the video and audio editing from my end on this fantastic tool.
Upfire Digital: An amazing podcast production company. Shoot me an email at podcast@allthehacks.com if you want an intro.
Shure SM7B: My main microphone but I use the Shure MV7 when I’m traveling. The ATR2100X is my old microphone that was used to record the first 50 episodes.
Sony Alpha 7C: My main camera which is connected to the computer through a Elgato Cam Link 4K.
Sony a6400 4K + Sony ZV-1: My back up cameras that I bought off Facebook marketplace.
Audio-Technica ATH-M50X: Fantastic over the ear headphones.
Elgato Ring Light + Godox VL150: For lighting.
Rodecaster Pro 2: This audio interface makes recording and mixing audio super easy.
ATEM Mini Pro ISO: I use this multitrack video recording for extra redundancy. It records all camera feeds separately onto a solid-state drive, ensuring I don't lose an episode recording if an SD card fails.
Megaphone: Hosting platform I’ve been using (though I’ve been considering Transistor lately).
Chartable: For tracking podcast performance and gaining insights.

Chris Hutchins is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon.com.

Chase Ink Business Preferred® Credit Card

Fri, 26 Jul 2024 21:07:58 +0000

Advertiser Disclosure

I've had the Chase Ink Business Preferred for many years and it's been a favorite for so many small business owners who want to earn Chase Ultimate Rewards points on their regular business expenses. Right now, new cardmembers can get a welcome offer of 90,000 points.

But it doesn't stop there, the Ink Business Preferred Card earns 3x Chase points on up to $150,000 in spending per cardmember year (then 1x) in the following categories:

Travel
Internet, cable and phone services
Shipping purchases
Advertising purchases through social media sites and search engines

This card also offers 5x points on Lyft rides through March 2025 and 1x points on all other purchases.

So if you've been thinking about getting the Ink Business Preferred, now is a fantastic time to do so.

Welcome Bonus Details

The current 90,000 Chase point welcome bonus is only available to new cardmembers after spending $8,000 on the card within the first 3 months of account opening.

So what can you do with 90,000 Chase points? When using points to book travel through Chase Travel℠, each point is worth 1.25¢, which make this bonus worth $1,125. But my favorite way to use Chase points is by transferring them to one of Chase’s 14 airline and hotel partners, which can offer an even outsized redemption value, which I recently discussed on this episode of my podcast.

My Takeaway

The Ink Business Preferred is my longest standing business card and one of my favorite to recommend. It not only offers great spending bonuses and benefits for a reasonable annual fee, but it also unlocks the ability to transfer points to all 14 of Chase's transfer partners. So when you add the welcome bonus of 90,000 points, I think this a great card to add to your wallet.

💬 Excel in Spontaneous Conversations

Thu, 15 Feb 2024 13:16:25 +0000

Turns out the majority of our communication is spontaneous.

It is rarely planned except for our formal presentations, pitches, or meetings. In the spur-of-the-moment we often feel anxiety because the urgency, desire for precision, and need to adapt to the situation converge simultaneously.

Good news! Successful spontaneous speaking, whether it's answering questions, providing feedback, or engaging in small talk, is a skill everyone can refine.

I recently spoke with Stanford Professor Matt Abrahams (🎧 Ep. 139), who has dedicated his life to enhancing people’s communication skills. He's also the bestselling author of Think Faster, Talk Smarter and hosts the Think Fast, Talk Smart Podcast.

In our conversation, he shared with me his six steps that, when practiced over time, can elevate anyone's spontaneous communication:

Step 1: Address anxiety
Step 2: Prioritize connection over perfection
Step 3: View these moments as opportunities, not threats
Step 4: Listen for the bottom line of what the person is saying
Step 5: Establish a structure for effective speaking
Step 6: Apply the 'F-word' (focus)

Let's dive into each one.

😰 Step 1: Address anxiety

To effectively address anxiety, a two-pronged approach is necessary to consider symptoms and sources.

Symptoms of anxiety manifest physically in your body (a direct response to the fight or flight reaction):

Sweating or blushing
Speaking too fast

Sources of anxiety are the instigators and intensifiers, primarily the internal dialogue that hijacks your cognitive focus:

Overthinking your words
Judging (yourself) while speaking

Personally, my anxiety is more source-related. During a recent presentation at NasSummit, despite my comfort with the microphone and audience, I couldn't help but fixate on the two slides I didn't know with 100% certainty. Over and over again. And just moments before going on stage, I remember thinking:

"Can I just feel good about the thing I feel worse about?"

I wish I had talked to Matt before the presentation.

It's crucial to recognize that everyone's anxiety is unique; what unsettles you may differ from mine. And while it’s probably obvious, there's no one-size-fits-all solution (except for some deep breathing).

Here are some practical techniques you can explore:

If you experience sweating or blushing, cool down your body by holding something cold
If you speak too quickly, take a deep belly breath before you begin
If you get caught up in your thoughts, focus on the value you bring to the audience, reminding yourself that you're the only one who knows what to say

Check out Speaking Up without Freaking Out, which shares 50 techniques for managing anxiety.

🌐 Step 2: Prioritize connection over perfection

Trying to be perfect messes with your cognitive bandwidth.

Instead of worrying about what you're trying to say, consider what's relevant and essential to the person you're speaking to.

Small talk is a perfect example of this. Often, we feel pressured to be super interesting and insightful when we should be focused on being interested. We might make it feel like a competition (trying to say just the right things) when we should be making it a collaboration (trying for the back and forth).

When you're curious and connect with others, it becomes easier, and you don't have to worry about being perfect. That said, small talk carries much nuance, so I asked Matt for some tactics.

Ways to Kick Off Small Talk

You want to avoid the usual suspects: "How are you?" or "What do you do?"

Instead, start by highlighting things in the environment and context around you. If you were at a speaking event, you could mention something that happened before the keynote. For example, if everyone at an event wore blue shirts, you could say,

"Did I miss the memo? Why is everyone in blue?"

Avoiding the typical doom loops (standard greetings and surface-level questions) can enable a better start.

Tactics for Exiting with Grace

Ending a conversation is as important as starting one.

Most of us default to biology, "I have to go to the bathroom, or I'm hungry, or I'm thirsty."

Two problems with these:

It's too transparent and obvious
Sometimes, the person has to/wants to do the same – and now you're walking and talking more.

Instead, try the "white flag" approach. In auto racing, the white flag signals to the drivers that this is the final lap.

“Hey, there are some people over there I want to speak with, but before I go, I'm really curious for you to tell me more about your last job because we started talking about it.”

They share more. At the end of that, wrap it up with:

“That's really fascinating. Thank you so much for the conversation. I'm going to head over there to introduce myself before it's too late.”

You can do the same in your conversations. You can signal about something they mentioned, talk more, politely say thank you, and go on your way.

It's an excellent, polite way to exit.

Tactics for Chatty People

A conversation is the process of turn-taking. There are two types: support turns and shifting turns.

A supporting turn is when you get someone to tell you more about what they're saying. A shifting turn when you move the topic to something you're interested in.

Imagine someone saying, "I just went to Hawaii." A supporting turn would ask, "Which island did you go to?" A shifting turn would be saying, "Oh, I just went to Costa Rica."

Supporting responses get people to keep talking
Shifting responses stop people from talking

You want to do more supporting turns (about three-quarters) and fewer shifting turns (about one-quarter) to keep the conversation going smoothly.

When faced with chatty people, first make sure you’re not accidentally encouraging it (sometimes the person talks a lot because you're encouraging it without realizing it). If that's not the case, the single best thing to use is to paraphrase to redirect the dialogue.

Highlight something of value the person has said. Name it. And then move on to something else.

Back to the Hawaii example -- If the person is going on and on, you can paraphrase,

"Yeah, it sounds like you were able to relax a lot. In fact, I love relaxing by reading a book. I'm curious: what other things do you do to relax?"

This method is particularly effective for moderators or facilitators in work settings seeking to maintain a productive conversation flow.

Three Important Words

"Tell me more."

When used sincerely, this phrase communicates genuine interest and invites the other person to share further. The simplicity of "tell me more" disarms any sense of threat, fostering a space for open and authentic dialogue.

🔭 Step 3: View these moments as opportunities, not threats

If somebody asks a question or any situation where you're caught off guard, you inherently feel threatened.

When this happens, it is crucial to give yourself time to turn it into an opportunity. Here are three practical ways to give yourself time:

Pause: Feeling pressured to respond instantly is common, but taking a beat is okay. A short pause allows you to gather your thoughts before responding. Time is on your side; don't rush.
Ask a clarifying question: Buying yourself time and ensuring a thoughtful response is possible by asking a clarifying question. It provides a momentary buffer and helps you understand the situation better, leading to a more relevant reply.
Reply with a paraphrase: Paraphrasing is a valuable tool (not to be confused with repeating verbatim like a five-year-old). Instead, it involves highlighting critical aspects of the question or request. This technique buys you time and allows for multitasking since paraphrasing requires lower-order cognitive skills.

Buying time through these methods enables you to gather your thoughts and respond more effectively, turning unexpected moments into opportunities for thoughtful interaction.

The power of "I don't know."

Admitting uncertainty is a powerful move.

If you don't know the answer, be honest about it. Saying, "I don't know, but I'll find out and get back to you," even boosts credibility more than providing a correct answer.

One, you're being honest. Two, you're demonstrating tenacity and going to find the answer. And three, you're showing you can think beyond what you know by saying my hunch or inkling is.

👂 Step 4: Listen for the bottom line of what the person is saying

Most of us could be better listeners.

We grasp the basics of what someone is saying and then dive into judgment, evaluation, rehearsal, or planning. To truly connect, we must enhance our listening skills, a journey we can all embark on.

When listening, focus on uncovering the bottom line, the core of what someone is expressing. Remember the trio: Pace, Space, and Grace.

Pace: Listening requires slowing down. Rushing around impedes effective listening, so take a moment to ease the pace. Deliberate, unhurried listening allows for a deeper understanding.
Space: Create both physical and mental space for effective listening. Find a quiet spot where you can genuinely hear the person. Clearing mental clutter is crucial—shed judgments, evaluations, and thoughts about what comes next. Be present and mentally attentive.
Grace: Grant yourself permission not only to absorb the words but also to discern the context and observe how the person interacts. Listening involves not just what is said but also tuning into your intuition.

We can avoid misinterpreting nuances and missing the mark with attentive listening. It's a skill worth honing for more meaningful connections and accurate comprehension.

🪜 Step 5: Establish a structure for effective speaking

Our brains crave structure—a well-defined beginning, middle, and end with a logical flow of ideas.

Without structure, communication can feel chaotic and stress-inducing, leaving listeners bewildered. The benefit of structure is freedom.

Consider the analogy of budgeting. While some view budgets as restrictive, I see them as tools that make life more freeing. A budget allows for planned spending and the freedom to spend with pre-determined permission.

Creating a structure gives your audience freedom from confusion to ensure your ideas are conveyed smoothly, enhancing understanding and engagement.

Matt shared three structures to use:

Problem-Solution-Benefit (for pitches and problem-solving)

Think about every pitch you've encountered — it was likely initiated by identifying an issue, proposing a solution or improvement, and concluding with the benefits of embracing the proposed changes.

PSB establishes a logical flow of ideas, ensuring a seamless connection between points. Whether addressing a problem or seizing an opportunity, this structure is not just a formula; it's a tool that enhances clarity and impact in your communication.

What-So-What-Now What (for everything)

This is the Swiss army knife of structures:

'What' is the foundation. It represents your idea, product, service, or any offering you're presenting. It's the core content, the substance that you want to convey to your audience.
'So What' involves explaining why your idea is relevant or essential to your audience. Here, you're answering the question, "Why should they care?" This step elevates your message from mere information to meaningful significance.
Now What is the process of guiding your audience on the next steps. Whether you're seeking feedback, suggesting actions, or outlining plans, 'Now What' propels the conversation forward.

Imagine a scenario where someone asks you for feedback – Praising someone's performance in a meeting ('What'), explaining that clarity is crucial for effective communication ('So What'), and suggesting they slow down for better articulation in the future ('Now What').

I might say, "You did a great job, except when you talked about the implementation plan. You babbled, and you didn't go into as much depth as you did the other parts. People think you're not as prepared when you speak quickly without giving depth. Next time, I'd like you to slow down and include these two specific examples.”

This structure extends beyond verbal communication. Apply it to email correspondence—use the subject line for the 'Now What,' making your intention clear, while the body of the email houses the 'What' and 'So What.'

This versatile framework ensures your messages are heard, understood, and acted upon.

W.H.A.T. (for toasts or tributes)

Toasts (and tributes), while common, can sometimes become cringe-worthy experiences. Try this

Why are we all here: When initiating a toast, clarify the purpose. In some settings, it's obvious (like a wedding), but where it is a bit fuzzier, specify why this particular tribute is significant. For example, acknowledging a team's recent product release as a noteworthy achievement.
How are you connected: Establishing your connection to the event is crucial. Whether it's 20 years of friendship or a professional collaboration, providing context ensures your audience understands your perspective.
Anecdote (or two): Ensure they are clear, concise, and relevant to everyone present. Avoid lengthy or overly personal stories, keeping them appropriate for the occasion. These anecdotes help create a connection and make your tribute memorable.
Thank you (or toast): Conclude your speech with gratitude or an actual toast. It might be a cheerful "Cheers!" at a wedding accompanied by a clink of glasses. In a work setting, express gratitude to the team and anticipate future successes. This final step wraps up your tribute neatly.

🤬 Step 6: Apply the 'F-word' (focus)

Matt's mother had this saying, "Tell me the time, don't build me the clock."

The problem is that most of us are clock builders – we say more than we need to. Either because we want to rationalize and demonstrate the thought process we went through or just show off how smart we are.

The thing is, people just want to know the time.

Even in spontaneous situations, consider your goal to address what you want people to know, how you want them to feel, and what you want them to do. Without it, you're more likely to ramble. Focus on the audience's needs and establish a clear goal to streamline your message.

Prioritize your words; opt for simplicity over complexity
Avoid unnecessary repetition and choose efficient language
Paraphrase to help you articulate your thoughts

It takes practice

The unconventional insight is that you have to practice and prepare to be spontaneous.

Initially, this notion might sound peculiar. However, consider other aspects of life; in sports, players engage in drills and practice to enhance flexibility and agility during the actual game.

Similarly, in communication, practicing specific techniques and preparing for various scenarios can significantly improve your spontaneity. This awareness liberates you from constraints, allowing you to easily navigate interactions. As you become attuned to these practices, you'll observe patterns, discover what works best for you, and ultimately enhance your spontaneous communication skills.

💳 What’s in My Wallet for 2024

Thu, 25 Jan 2024 16:00:00 +0000

Advertiser Disclosure

Note: American Express is a ChrisHutchins.com advertiser, but all information about The Platinum Card® by American Express, American Express® Green Card and Hilton Honors American Express Aspire Card have been collected independently by Chris Hutchins. The card details on this page have not been reviewed or provided by the card issuer.

I’ve said it many times, but credit cards are valuable financial tools for strategic spenders. And for me, there are three main reasons to have a card: spending, perks, and bonuses.

Spending: Many cards offer bonus points tailored to specific spending categories. If you frequently spend in a particular category, aligning your card with that spending can maximize your rewards.
Perks: Some cards have perks good enough to justify the high annual fees (even if you rarely use the card). For example, we rarely spend on the Hilton Honors American Express Aspire Card, but the perks (free night, diamond status, airline/hotel credits) definitely outweigh the cost.
Bonuses: While some cards may not be a long-term fit, an enticing welcome bonus may be worth considering. I typically look for a minimum of 75,000 to 100,000 points, but sometimes you can go even higher).

That said, tailoring your choices to your goals and priorities is crucial, so this post is merely a glimpse into how I’m thinking about what I’m doing this year. I’ll break it down into the four steps I use to have the right set of cards, focusing on personal cards. If there’s any interest, I may write something later about business cards.

Also, one important callout for this post: I’ll be 100% focused on earning points, so with a few exceptions, I’m not going to talk about Cash Back cards. However, I am including a few cards that are marketed as cash back cards (e.g., Citi Custom Cash℠ Card or Chase Freedom Flex®), but when paired with a points earning card from the same program (e.g., Citi Premier® Card or Chase Sapphire Reserve®) will either earn transferable points or can convert the cash back earned to transferable points.

Step 1: Align spending patterns with your existing cards

I ask myself, “What are my big spending categories, and what cards have I used for them?”

To figure out my spend, I use the Copilot app — it's been a game-changer for me. Since I used it to track everything in 2023, I know exactly how much I spend in each category, which I can plug into this tool I built to optimize many of the most popular cards. It breaks down the earning potential of many top points cards, making it easy for you to input your spending and see how adding a specific card can boost your points.

If you end up going through this process yourself, please keep in mind that just because you might find a card that earns more points per dollar in a given category, you may not spend enough in that category to make it worth it or even justify the annual fee. For example, I could get a card that earns 4x on streaming services, but given my spending habits (and the streaming credits I get from The Platinum Card® by American Express), it’d probably only result in an extra 1,000 points a year, so it’s not worth it for me.

Below, I’ll walk through all my major spending categories, my card pick for each, and some backup suggestions if I didn’t have my #1 pick.

Restaurants

For dining, I use the American Express® Gold Card, which earns 4x Membership Rewards® Points at restaurants worldwide on up to $50,000 in purchases per calendar year, then 1x, including Takeout and Delivery in the U.S. But some other compelling options are:

Capital One Savor Cash Rewards Credit Card (4% cash back)
Chase Sapphire Preferred® Card, Chase Sapphire Reserve (3x points on restaurants)
Chase Freedom Flex and Chase Freedom Unlimited® (3% cash back on dining at restaurants, including takeout and eligible delivery services)
Bilt Mastercard® (3x points on dining if you use the card 5 times each statement period to earn points - more on rewards & benefits here)
Citi Custom Cash (5% cash back on the first $500 spent in the top category each month, and 1% after that)

Grocery Stores & Supermarkets

I also use the Amex Gold at U.S. supermarkets since I can earn 4x points on up to $25,000 per calendar year in purchases (but we don’t hit that limit, so we’re good here), then 1x thereafter. If I weren’t using the Amex Gold, here are some other options:

Capital One Savor (3% cash back at grocery stores)
Citi Premier (3x at supermarkets)

Travel

I’m currently using Amex Platinum for 5x on flights booked directly with airlines or through American Express Travel^®(on up to $500,000 per calendar year, which we never come close to, and 1x thereafter).

For all my non-flight travel, I'm using my Chase Sapphire Reserve for 3x points, but here are some backup travel cards:

American Express® Green Card (3x on travel)
Citi Premier (3x on air travel and hotels)

Also, here are some other options that give big bonuses when you spend in their travel portals:

Capital One Venture X Rewards Credit Card (10x on hotels and rental cars, and 5x on flights booked through Capital One Travel)
Chase Sapphire Reserve (10x on hotels and car rentals and 5x on air travel booked through Chase Travel℠)
Chase Sapphire Preferred (5x points on travel booked through the Chase Travel℠)
Amex Platinum (5x on flights and prepaid hotels booked through AmexTravel.com)

The reason I call out the travel portal is because there are some considerations.

When you book through a travel portal, you’re usually booking through an agency, meaning you have to deal with that agency to make changes. And if you're booking hotels in the portal, some hotel rates don't always accrue points. I’ve had some success, but the portal can create a few added problems if things go wrong that I often find isn’t worth the hassle.

However, I learned (via this article on The Points Guy) that while sometimes travel portals had a markup, there were almost as many times when the travel portal was 10%-20% cheaper (at least for Citi, Capital One, and Amex). So I’ll probably start checking their portals more frequently for expensive flights.

Amazon

We use the Prime Visa Card (5% cash back), even if it means earning cash back instead of points.

Cell Phone Services

This category is mostly focused on business cards, so for most people, I would choose the card that gives you the best phone insurance. However, if you’re eligible for a business card, my picks are the Ink Business Cash® Credit Card (5x on the first $25,000 each year) and Ink Business Preferred® Credit Card (3x on the first $150,000 each year).

Gas

I don’t personally worry about this category (since we have 2 EVs), but for those who do, the two best options are:

Citi Premier (3x points)
Citi Custom Cash (5% cash back on the first $500 in your top category)

The Wyndham Business Earner® Card will earn 8x points on qualifying gas purchases, which might be the best option if you’re willing/able to get a business card for gas.

Costco

There isn't a card that earns more than 2x points at Costco, so we use our Capital One Venture X However, in a future post (and episode) on cash back, I’ll be talking about the U.S. Bank Altitude Reserve, which can earn up to 4.5% cash back on Apple Pay and other mobile wallet purchases, which Costco accepts.

Other

For any other purchases, we use our Capital One Venture X to earn 2x points.

If you have a Citi Premier, then you can use the Citi® Double Cash Card to earn 2% back that can be converted to 2x points.

If you prefer Amex points, there isn’t a great personal option, but The Blue Business® Plus Credit Card from American Express earns 2x on all business purchases, up to $50,000 in spend per year (1x thereafter).

Finally, if you want to stick within the Chase ecosystem, the Chase Freedom Unlimited is your best bet, earning 1.5x transferable points on everything, as long as you have the Chase Sapphire Preferred, Sapphire Reserve or Ink Business Preferred.

Step 2: Audit my current cards to see if they still make sense

I ask myself, “What are all the cards in my wallet, and what is the reason I should keep using them?”

One major factor in this process is the annual fee for each card, which for some cards can be high enough to give you a lot of pause. One tool I love to help out here is the Premium Card Worksheet from the Frequent Miler team. It itemizes all the perks of most premium cards, giving their estimate of the value, and letting you adjust as needed to see if you’re getting a positive ROI.

So, here is every card we have and our takeaways:

Chase Sapphire Reserve: Keeping it for 3x points on non-flight travel (and for the excellent rental car coverage).
Chase Freedom Unlimited: Keeping this because it has no annual fee and I’ve had it forever, so it’s giving my credit score a boost.
Chase Freedom Flex: This quarter, I’m using it for 5% on groceries, but since it has no annual fee, we’re keeping it and adapting its use to fit the quarterly bonuses.
Prime Visa Card: Keeping it for 5% on Amazon and Whole Foods.
United Gateway℠ Card: We downgraded a previous United card to this no annual fee version, because it’s Amy’s longest-standing card and we want to maintain its long credit history.
Amex Gold: This is the primary card we use for dining and grocery stores.
Amex Platinum: While it has a high annual fee, we’re able to get enough value from the perks that it’s worth keeping. We use this to get 5x on all flights.
Marriott Bonvoy American Express® Card: I didn’t mention this above, but I’m going to keep it because it earns 15 elite nights each year and I get enough value from the free night certificate to cover the annual fee. It’s also no longer available for new signups, but it’s pretty similar to the Marriott Bonvoy Boundless® Credit Card.
Hilton Honors Aspire: With a free night certificate at any Hilton worldwide, Diamond status and the resort/airline credits, this card pays for itself.
Blue Cash Everyday® Card from American Express: I haven’t used this card in years, but I’ve had it open since 2003, so I’m keeping it for the credit history.
Capital One Venture X: This is our everything card and it gets a ton of usage. The $300 travel credit, plus the 10,000 points a year, make it a break-even on the annual fee, so it’s definitely staying in my wallet.
Target RedCard™: I know it’s not technically a credit card, but we’re going to keep it for 5% off at Target.

Step 3: Adjust card portfolio

For any cards that didn’t make sense in Step 2, I ask myself, “What should I do with the card?”

Here are four options:

Do nothing. If there is no annual fee, consider keeping it because it helps with your credit score (length of credit history).
See if you can get a retention offer to offset the annual fee. In the past I’ve gotten everything from 30,000 points to a $550 annual fee waived. For some issuers you can use the live chat to ask for retention offers and for others you have to call in.
Downgrade the card. Many cards can be downgraded to a no annual fee option in their card family, which lets you keep the positive impact on your credit score without the cost.
Cancel the card. This is a good last resort, but know that most card issuers really frown on canceling within the first year, so I suggest you let the annual fee post and then cancel in the 13th month. Most issuers give you 30 days after posting to get a refund.

Step 4: Look ahead to opportunities

Finally, I ask myself, “What cards might I want to add to my roster this year?”

This should go without saying, but anytime there is an exciting welcome bonus, I pay attention to it and assess it within the portfolio of cards. Aside from that, here are some cards I’m excited about for 2024:

Bilt Mastercard®

I regretted not having this card earlier, but it was the first new card I got this year, so let me tell you why.

First off, if I were a renter, I would have already had the Bilt Mastercard®, because you can earn up to 100,000 points a year paying rent, even if your landlord requires a check or a specific payment portal. The card also offers 3x dining and 2x travel if you use the card 5 times each statement period to earn points, but I had those categories covered at higher earning rates. You can read more about Bilt Rewards & Benefits here.

Now I’ve talked about how I think Bilt Rewards is one of the highest value point currencies, because they have the best transfer partners, including American Airlines (unique to Bilt), United, Air Canada, Air France/KLM, Hyatt, Turkish and more. But if I can earn more points on my spend elsewhere, then how much does that matter?

Well once I saw what Bilt kept doing every month last year on Rent Day (the 1st the month), I decided I needed to get a Bilt Mastercard®. First, every Rent Day, points are doubled (up to 10,000 bonus points each month), which means you get 6x on dining, 4x on travel, and 2x on everything else. If I could time some major purchases and date nights right, that could help increase my earning. But the real reason I finally signed up was because they kept doing so many ridiculous Rent Day Promotions.

For example, on January 1st, they offered 75-150% transfer bonuses to Air France, Virgin Atlantic, and IHG. That means that if you wanted to move 50k points to Air France, any Bilt member would end up with 87.5k Air France miles (75% bonus), but Bilt Platinum members would get the full 150% bonus and end up with 125k Air France miles. If I could optimize these bonuses where I end up getting 2.5x as many points, that’d make the earning rates on the Bilt Mastercard® the best in the market.

Now there’s no guarantee they’ll keep these insane transfer bonuses all year, but they’ve done at least half a dozen of them already and just yesterday Bilt announced that they raised $200m, so I want to take advantage of it while I can. My 2024 goal is to make sure I manage to spend enough to get Bilt Platinum status, so the next time they have a monster bonus, I can participate.

If you want to join me on that goal, this is my personal referral link for the Bilt Card.

Delta SkyMiles® Platinum American Express Card

The next card I’m looking at this year is the Delta SkyMiles Platinum.

This card offers a few enticing perks, including a big welcome bonus (through a target mailing offer), free checked bags, a companion certificate, and a 15% discount on award bookings.

While Delta points might not top the charts in terms of value, the combination of these benefits and a few already planned Delta trips this year is why I’m considering the card. However, please note you only start receiving the annual companion certificate after your first cardmember year.

Capital One Savor

Every time I research cards, I can't help but think that the Capital One Savor is such a great card and find myself wanting it.

While marketed as a cash-back card, its true potential shines when paired with the Venture or Venture X because it can earn 4% cash back on dining, entertainment & popular streaming services, 3% back at grocery stores and for most of this year 10% on Uber and Uber Eats.

That said, I have most of those categories covered and just don’t spend enough on Uber to make that perk worth it (not to mention it’s set to expire towards the end of the year). However, if you have the Venture or Venture X and like the simplicity of earning points in one program I think it’s a fantastic card.

Marriott Bonvoy Brilliant® American Express® Card

I didn’t requalify for Marriott Platinum this year, so the Marriott Bonvoy Brilliant is on my radar, because it includes Platinum status as a perk. It has a high annual fee, but if we end up having a longer stay at a Marriott this year, the free breakfast perk (combined with the free night certificate) might make up for the annual fee. Also, I can lock in Bonvoy Platinum for life with 3 more years of Platinum, so that could help justify the cost as well.

Citi

While I talk about Citi a lot, I don’t have any Citi cards. It’s not that they don’t have a good lineup. In fact you could have a stellar 3-card Citi lineup:

Citi Strata Premier: 3% cash back on restaurants, supermarkets, gas stations, air travel and hotels
Citi Custom Cash: 5% cash back on the first $500 spent in your top spending category
Citi Double Cash: 2% cash back on everything else

That trifecta is a powerful combination, but I just happen to have cards to cover all those categories except Gas and we only have EVs. Not to mention, Citi doesn’t currently have any unique transfer partners except Thai Airways, which doesn’t have a compelling award chart.

So I’ll keep tabs on Citi and could change my mind if they introduce a new card to take the spot of the now-retired Citi Prestige or launch some new transfer partners.

Wells Fargo Autograph℠ Card

Wells Fargo might not be on your radar, but the Wells Fargo Autograph has piqued my interest, solely because they’ve announced that they’ll be adding transfer partners this year. They’ve shared no specifics, but if they have a compelling list of partners that transfer 1:1, this could quickly become one of the top cards, given that it currently earns 3x on dining, travel, gas, transit, streaming, and cell phone services.

There are also whispers of another new and more premium card, rumored to be the Autograph Journey. If it comes with better earnings than the regular autograph and/or offers a huge welcome bonus (like the Venture X and Sapphire Reserve did when they launched), it could be a great new option for 2024.

💭 Parting Thoughts

Preparing for this post was a really great way to force myself to go through this process and even left me considering a few new options. Whether this is your first time thinking about your credit card portfolio or you’re a seasoned pro, I hope it was valuable to you.

If you want to support the show when you’re looking at new cards this year, I’d really appreciate you using the links above or the ones you can find on our Cards Page. That said if you find a better bonus somewhere else, please go there and get the most points you can. Also, if you click some of the links above and they don’t look like they’re any type of partner or referral link, don’t worry, many of them aren’t. I am sharing all the cards that were top of mind, including many that we have no affiliation with. I’ll always try to do my best to share whatever I think is best, whether they help my business or not.

Finally, we want to hear from you. If you have any unique strategies or insights, please share them with us. Send your thoughts to podcast@chrishutchins.com.

🎉 My Top 10 Takeaways from 2023

Thu, 04 Jan 2024 15:56:08 +0000

Happy New Year!

I just wanted to take a moment to say how much I appreciate you being part of our journey. Thank you so much for your support! I'm incredibly excited about what lies ahead in 2024 and I couldn't do it without you.

This past year I had so many invaluable insights and after revisiting everything from 2023, excited to share my top 10 takeaways.

- Chris

P.S. Thanks to everyone who supported our Daffy Campaign to raise money to build water projects with charity: water. Thanks to your generosity, we're actually so close to funding two projects and will be closing the campaign this week to ensure funds get deployed asap.

🩷 Kindness is so important

In episode 118 with Gary Vaynerchuk, a profound realization emerged — kindness is paramount in pursuing success.

We debunked the conventional notion of "nice guys finish last," given that there’s an overwhelming abundance of resources and opportunities in the world. Jealousy may be the culprit of this behavior, but when you zoom out, you realize that success is not a finite resource and that others' achievements don't diminish your potential.

The difficulty in embracing kindness often stems from fear — fear of failure, fear of vulnerability, and fear of being taken advantage of. However, I strongly feel that when you ditch fear for kindness and accountability, it can become a catalyst for personal and collective growth. One step you can take is getting super clear on understanding the motivations behind your pursuits — whether it's for personal happiness, parental approval, or peer validation. Ultimately, it’s going to lead you to what makes you happy most.

A nuanced insight from episode 123 with Nuseir Yassin highlighted the distinction between being nice and kind. Sometimes, we may believe we’re being kind, but we’re just being nice by not sharing words that will help someone (even if it’s difficult to deliver). When delivering challenging news, sincerity is key.

In my personal experiences, providing candid but constructive feedback has proved super helpful. For example, when I chose not to invest in certain startups, I’d approach these situations with a genuine desire to help, sharing specific concerns to prompt reflection and potential course correction.

Focusing on kindness can reshape our perspectives on success, foster personal growth, and create a supportive environment where feedback, even if critical, becomes a catalyst for improvement.

⏳ Value your time

In episode 98, my conversation with Dan Martell highlighted the critical importance of valuing time and optimizing productivity through outsourcing, delegation, and selective task-dropping.

We discussed calculating your buyback rate, which is key to figuring out what your time is worth. The math may be simple, but actually applying it is much more challenging, especially for more frugal-minded individuals (like me). But the more I take steps to protect my time, the easier it gets (because I start to see the things that have happened in my life with extra time to be creative and think).

Take this podcast as an example. Transitioning to full-time allowed me to do much more:

Greater consistency in managing the newsletter
Engaging with the membership
Conducting extensive research for solo episodes

I even (finally) hired an assistant through Oceans, Pasini, who’s been amazing, and I’m super grateful for her.

A simple strategy for you to start with is a time audit, where you scrutinize tasks on your calendar and identify areas for potential outsourcing. Focus on tasks that drain energy, lack enjoyment, or hinder creativity can often be delegated to free up time for more meaningful pursuits. But your most powerful weapon in all of this is saying “no.” So when you get a phone call, you can say no. When you get an email, you can just archive it.

Don't forget that you need to be more protective of your own time.

💪 Everyone can build more confidence

In episode 130, my conversation with Aziz Gazipura shed light on how confidence isn't an inherent trait but a skill everyone can refine.

A key insight from the episode emphasized that being confident about something differs from asking for it. The often-scary act of asking actually leads to more than you can imagine. Part of the answer to this is getting more comfortable with rejection. I understand that is not a simple feat. I’m not a fan of rejection by any means, but I have learned that a bit of exposure therapy (asking people for things even though you know you’ll probably get rejected) is a great way to understand the feeling of discomfort better.

That fear we all have is directly tied to uncertainty in situations. Explored in episode 139 with Matt Abrahams, we talk about how preparation can play a pivotal role in relieving that pressure of uncertainty (especially in spontaneous conversations). Matt offered valuable tactics to navigate spontaneous conversations, emphasizing the power of well-timed pauses, asking for clarification, paraphrasing what someone said, and notably, admitting when you don't know—an act of humility that can enhance credibility.

He also offered a few ways to handle uncertainty by using structured conversation frameworks like:

What, So What, Now What: It’s a 3-part framework for thinking about “what happened, why it is important, and what action you are taking next."
Problem-Solution-Benefit: It’s a blueprint for delivering concise and impactful messages by framing your responses or questions by stating the problem, what you will do, and why it matters.
WHAT: It’s a structure when giving unexpected toasts or tributes. Why you're here, How you're connected, some Anecdotes, and wrap up with a Tribute or Toast.

💳 Learn the skill of spending

We talk about saving, investing, and spending less all the time – but we can’t overlook intentional spending as a part of your personal finance plan.

This process comes with two steps.

The first step is gaining clarity on your spending. In solo episode 133, I explored the best tools for keeping us organized and facilitating decision-making. But the process of finding the right tool actually gave me more clarity on our spending in my entire life. We ended up using Copilot — a tool that tracks expenses and excels in categorizing them, setting it apart from other apps (and for all Mint users and Android web users, some important Copilot upgrades are coming soon).

The second step is being intentional about spending. The hard part for me was steering away from a frugal mindset and dialing up investments in what genuinely matters. I heard this idea that a “budget being is more freeing than restricting” because when you predetermine an amount beforehand, it permits you to spend without worry. This year, we intentionally dialed up our travel spend. It wasn’t just because Amy and I love to travel, but we wanted to make it more comfortable with two kids. That meant getting bigger spaces and spending 2-3x more. But we did so by cutting back on less important areas.

In episode 141, I talked about the skill of spending with Brad Barrett, and even in episode 9 with Ramit Sethi, we discussed the concept of money dials. Both episodes emphasize the idea of spending on what matters and cutting back unapologetically on what doesn't.

🧭 There are so many paths to happiness and success

In episode 119, my conversation with Codie Sanchez tipped the scale in rethinking what it means to have a successful and happy career path.

For 10 years, Amy and I have been deeply embedded in tech and startups and the Silicon Valley success mindset. Even though I went full-time last year, it still felt like a less exciting path because it wasn't successful in how the last decade has trained me.

Codie’s “boring business” empire made me rethink all the possible things we could do to achieve success and happiness with our career choices. More specifically, they don’t need to conform to predefined notions but instead align with our interests and passions (even if they seem less glamorous).

I really encourage you to explore unconventional avenues to fulfillment and success beyond the traditionally celebrated ones.

🩺 Be in charge of your health

Personal health is an individual responsibility.

For most of my life, my cholesterol levels have been high. For years, the conventional advice I received centered on exercise, a healthy diet, and periodic check-ins. The numbers didn’t get better, but the advice remained the same.

In episode 97, I discussed with Dr. Jordan Schlain the importance of being in charge of our health. The best doctors in the world don't have the time (or ability) to care about your health as much as you do. Many have to tailor advice to what patients can do, what’s covered by insurance, and what information they have been given (which can be outdated).

So I took my cholesterol situation into my own hands. I got my calcium score, revealing a small amount of calcium in my arteries, and I took things more seriously. I sought a doctor to listen to some of these results and offer a course of action that has reduced my cholesterol levels and made me feel so much better (thanks, statins!).

I encourage you to explore diagnostic tests beyond an annual physical, especially since they are becoming more accessible (e.g., blood/biomarker tests, DEXA scans, VO2 max, whole-body MRIs, and more). But please don’t get caught up in everything because you could go down too many rabbit holes and spend a fortune. As I’ve often been reminded, none of this extra stuff probably matters if you’re not eating healthily or exercising.

🥗 Eating well can be much easier than you think

Eating healthy has often felt like a challenging task.

However, this year, we've realized we've been overcomplicating it. So, let me share some valuable tips we've discovered and implemented to simplify the process.

Meal plan: We use the Paprika app for meal organization, but you can try ChatGPT or your favorite AI to create tailored plans based on preferences and dietary requirements. Consider meal prep for added convenience.
Subscribe to meal kit services: Three of our weekly meals come from Green Chef for delicious, health-focused options. I’m such a fan that I got them to offer 60% off your first order here.
Repeat meals: We remove the friction from the planning process by repeating some of our favorite recipes or assigning specific meals to certain days of the week.
Outsourced grocery shopping: We use services like Amazon Fresh or Whole Foods Delivery to save time. Or, if you hire an assistant, consider delegating meal planning and grocery ordering.
Meal prep assistance: Before Green Chef, we found someone on Craigslist to cook meals and prep for the week. This can be a cost-effective alternative to meal deliveries, providing freshly cooked meals for several days.
Use the microwave (more): You can find a handful of tactics to cook at home from Chef David Chang in episode 122. But the biggest by far is using the microwave for quick, nutrient-dense meals. We now use our Anyday cookware all the time (and you can get 15% off here).

🎮 You’re in control of your life

In episode 140, my conversation with Robin Arzón made this cliché come to life because she helped me realize taking charge doesn't always require massive changes; even small, intentional steps can lead to significant transformations.

You don’t need the best outcome to make change happen. You can just get started as the first step without worrying about perfection. And then, later, you can fine-tune and make it better, adjusting it to what truly works for you.

Meditation is a great example of this. There is a misconception that meditation demands significant time and specific conditions can hinder progress, but in episode 126, Light Watkins highlighted that meditating for a few minutes from anywhere still brings tangible benefits.

Shifting your perspective on commitment can be a powerful motivator. Robin pushed me to run/move 3 miles a day for 31 days despite it being the hardest time of the year (we had both sets of parents visiting two kids, all the holidays, and everything we were trying to get done for the end of year work, taxes, and everything). Being someone who follows through on personal promises, especially in health and exercise, becomes a defining aspect of your identity.

I still can't believe that happened! #3for31

Amy and I also went through a “billionaire life exercise,” which explored what life would be like without time or money constraints. Surprisingly, the gap between an ideal "billionaire" life and the current reality might not require a fortune and instead just need some intentional, subtle changes. Identifying even the smallest adjustments (like us replacing our loud garage door opener) could significantly enhance your daily life. The cost of these improvements might be minimal compared to the immense satisfaction and happiness they bring. By intentionally reframing commitments, you can shape your life in ways that align with your aspirations and values.

👋 Ditch Plan B

In episode 105, I learned from Matt Higgins about the power of getting rid of Plan B and how contemplating backup plans can hinder success.

My inclination as an optimizer leads me to ponder options and have contingency plans. However, there’s proof out there that demonstrates how having backup plans makes it less likely for Plan A to be successful. The key is to commit fully without looking back.

Quitting my job and focusing entirely on the podcast alongside Amy showcased the power of unwavering commitment. In episode 116, Sahil Bloom shared a valuable lesson he referred to as the Optimist Razor, and it holds the key to manifesting this commitment in your life. The Optimist Razor advocates prioritizing time with optimists over pessimists.

As I navigate 2024, I aim to intentionally surround myself with individuals who inspire me to embrace commitment, burn the boats, stay dedicated to Plan A, and resist the temptation of fallback plans.

🪞 Take Time to Reflect

Reflecting on personal experiences, lessons, and energy-draining activities catalyzes growth and intentional living.

In episode 99, I spoke with Sahil Bloom about his personal annual review framework. I was so focused on having it for the podcast that I failed to reflect on my life. So, this year, I’m making sure to carve out time to reflect using his template:

What did I change my mind about this year?
What created energy for me?
What drained my energy?
What (or who) were the boat anchors in my life?
What did I not do because of fear?
What are my greatest hits and worst misses from the year?
What did I learn this year?

One tactic for me to accomplish this is a calendar audit (as I mentioned above). It involves looking back at a few weeks and evaluating everything based on whether they created or drained energy. Then, use this information to set goals to take control of your life.

I’ve also adopted Derek Sivers' 'hell yeah or no' philosophy regarding personal goals. In episode 108, we talked more about living a happier life and leveraging the word “no” more often. I say yes only to what genuinely excites me and aligns with my goals, even if it means declining hard-to-turn-down invitations.

Finally, Amy and I adopted Codie Sanchez's TEAM framework to take inventory of our relationship. It can be a short 10-minute structured discussion that serves as a proactive approach, preventing impromptu, heat-of-the-moment conversations.

'T' for touch: an opportunity to hold hands or sit close.
'E' for education: a chance to share intriguing discoveries from the day.
'A' for appreciation: sharing something you appreciate about the other person (without recycling the same appreciative gesture).
'M' for metric: delving into aspects that you or your partner wish to alter within the relationship.

It presents a practical method to incorporate regular relationship evaluations, ensuring they aren't overshadowed by individual goals and personal reflections.

💭 Parting Thoughts

2023 was a remarkable year for us, and I hope it was just as amazing for you. If you haven’t done so, I encourage you to take some time to reflect on the past so you can be clear on what to achieve in 2024.

We also want to hear from you. If you have any key takeaways from 2023, please share them with us at podcast@chrishutchins.com.

💰 How to Save on Taxes in 2023

Thu, 21 Dec 2023 14:02:29 +0000

This is the third year of the end-of-year tax post (feel free to check out the past ones from 2021 and 2022).

This year, I not only want to help you think about saving on taxes in 2023 but also introduce a number of other ways to save on taxes that you might want to bring into 2024 as well. And if you want to keep going on the topic, you can check out my recent discussion on Taxes with Ankur Nagpal (🎧 Ep. 147).

By the end of this post, you’ll learn more about:

Mental frameworks for approaching taxes
Standard vs. itemized deductions
Charitable contributions
Capital gains, losses, and (tax loss) harvesting
Energy and solar tax benefits
Non-qualified deferred compensation plans
Real estate tax advantages
Tax savings for startup investing
Benefits for business owners

Now before we get started, I want you to know that I fully believe in paying taxes; they are important and fund many aspects of society.

However, I also believe in democratizing the information that a small number of people know about taxes and giving you all the knowledge to make informed decisions about lowering your tax liability. That said, this is not tax advice, so please talk with your tax professional for more details. And if you need a recommendation, I am so happy with my personal and business tax firm Gelt (who, after saving me a ton fixing my prior CPAs mistakes, became a partner of ours).

I hope you all have an incredible holiday season!

Chris

🚰 Support our Clean Water Campaign

I recently had an incredible conversation with the founder/CEO of charity: water, Scott Harrison (🎧 Ep. 148), and learned so many things, but today I want to share three quick things about water:

1 in 10 people around the world don't have access to clean water
Diseases from dirty water kill more people every year than all forms of violence, including war.
Every day, women and girls (who are responsible for water collection 8 out of 10 households around the world) spend an estimated 200 million hours collecting water. That's time taken away from education, work, and community development.

For all these reasons and more, Amy and I have created a Daffy Campaign to build an entire water project with charity: water and bring clean water to a community in need. To help hit our $10,000 goal to fund an entire water project, we're going to be matching the first $5,000 donated (and if we hit that goal, we'll keep going for as much water as we can). If you want to consider supporting the campaign, you can learn more here:

ATH 2023 Clean Water Campaign

Note: you don't need to set up a donor-advised fund with Daffy to contribute to the campaign, but if you want to set one up and use this link, you'll get an extra $25 to donate to this or any other cause once you make your first contribution.

👫 Tax Tips for Everyone

I'll start with the tactics that are most applicable to everyone and end with more tips for business owners.

🪜 Mental Frameworks

Before we dive into specific topics, I want to share a few essential frameworks for approaching your taxes to add context to the tactics covered in this post.

Let’s start with my approach to taxes.

First, I try to avoid taxes
Second, I try to defer taxes
Third, I try to minimize taxes

…all while 100% following the rules of law.

My strategy is to continuously expand my tax knowledge while finding the best professionals to partner with (to further educate and execute on my behalf).

Here are three other frameworks Ankur shared with me:

Don’t let the tax tail wag the dog – which means you don’t want tax advantages to dictate how you live. Instead, live the life you want to live and figure out a tax strategy in response to that.
Understand your return on hassle – which means focus your energy on the few things that make a huge difference versus trying to do everything and burning yourself out.
Think about your lifetime tax rate – which means it might make sense to front-load taxes to pay substantially less later in life (e.g., Roth IRA)

🧮 Standard vs. Itemized Deduction

The government gives most people an automatic discount, known as the standard deduction, which is about $27,700 for married couples and $13,850 for single filers.

Surprisingly, almost 9 out of 10 people choose the standard option. However, itemized deductions open the door to extra discounts for charitable contributions, student loan interest, investment interest, state and local taxes (up to $10,000), mortgage payments, medical bills (over 7.5% of adjusted gross income), and even losses from gambling.

If the total deductions you can list are more than the standard deduction in a particular year, it's a good idea to go with the itemized deductions, even if you switch back and forth each year. And if it's close, you might want to bring together all your deductions in a single year. This could mean paying your mortgage or property taxes in advance or allocating extra charitable contributions to a year.

📈 Charitable Contributions

Charitable donations provide a unique chance to do good while also getting a reward in return.

When you donate a dollar to charity, the government is quite generous; your taxable income goes down by a dollar. But if you want to get even more benefit, you can donate appreciated assets (like stocks), where you get a double tax break, because you also avoid any capital gains tax you'd pay if you sold the asset and contributed the cash, while still getting the deduction on the full amount.

For example, if you give a charity $1000 cash they get $1000, and you get a $1000 deduction on your taxes. However, if you give $1000 of a stock that you bought for $100, that stock might only be worth $700 to you after you factor in the taxes you'd owe on capital gains, but the charity gets the full $1000, and you get to deduct $1000 too.

There is also no wash sale rule on charitable donations. If you hold any stock worth more than you paid, you donate it to save on capital gains. Then, immediately buy the same stock you donated, and then you can step-up your cost basis for free.

Donating Items

Charitable giving isn't just about money; you can donate things at home, like electronics or clothes. This way, you can support causes you care about while getting a tax benefit. Donating items becomes an attractive option, especially if you have many things you no longer need at the end of the year.

Donor Advised Funds

Donor Advised Funds (DAFs) offer a simple way to manage charitable contributions without unnecessary complications. These funds provide a centralized platform where you can organize and streamline your charitable giving efforts. It lets you front-load your entire donation and give from that fund whenever you want. Moreover, the money you put into a DAF can be invested, so it grows over time, which means you get a tax break, and the charity benefits more in the future. This avoids the hassle of coordinating stock transfers and dealing with minimums that some charities might have. I use Daffy, and you can get a free $25 to give to a charity of your choice. You can also check out my episode with Daffy co-founder Adam Nash (🎧 Ep. 50) for more on DAFs.

💸 Capital Gains, Losses and Tax Loss Harvesting

Not all income is taxed equally, and capital gains (profits from the sale of investments or assets) often enjoy more favorable treatment.

In the United States

Long-term capital gains held for over a year are subject to lower tax rates (mostly 15%), with the highest tier capped at 20%.
Short-term gains held for less than a year are typically taxed at ordinary income rates.

The tax code has a provision allowing you to utilize capital losses to counterbalance capital gains. However, if you lack capital gains, there's a silver lining – you can deduct up to $3,000 of losses annually against your income, carrying forward any remaining losses.

This opens up an opportunity for harvesting losses but requires you to understand the wash-sale rule first. According to this rule, you cannot repurchase the same security (or one that is "substantially identical") for 30 days to claim a loss. The good news is that various ETFs and index funds have similar yet not "substantially identical" pairings. This allows you to sell one for a loss and purchase the other without violating the wash-sale rule.

While you can manage this process independently (and probably should before the end of the year), using robo-advisors (I use Wealthfront) is much easier. I wrote more about tax loss harvesting in All About Investing Part 2.

🏦 Tax-Advantaged Accounts

I really wanted to get to the topic of tax-advantaged accounts in this post, which would include 401ks, IRAs, Solo 401ks, HSAs/FSAs, DAFs, and more. But there was already so much to cover that it's going to have to come in the future. However, last month I published an awesome episode on this topic with Katie Gatti Tassin (🎧 Ep. 144). So if you want to go deeper on that topic, check it out.

🎧 Ep. 144 on Tax-Advantaged Accounts

🪫 Energy Efficiencies

The Inflation Reduction Act made energy improvements even more appealing.

The lifetime cap on tax benefits for improvements like installing heat pumps and upgrading windows, insulation, and furnaces now stands at $1,200, allowing homeowners to make eco-friendly changes and receive tax benefits. However, it's crucial to note that specific stipulations and conditions may apply to different items, so homeowners should investigate the details before making these upgrades.

Additionally, if you're considering a clean vehicle (electric, hybrid, fuel cell), the tax credit offers a $7,500 benefit. It's important to remember that this credit has an income cap, meaning your income may impact the amount you're eligible to receive.

While December 31st might seem like a deadline for some energy efficiency improvements, some benefits extend beyond a single year. The Act extends tax benefits for specific improvements until 2033. This gives homeowners flexibility, making it clear that tax planning for energy efficiency is not a one-time opportunity.

To learn more about saving money with energy efficiency and solar, check out my conversation with Matt Ferrell (🎧Ep. 135)

☀️ Solar Investing

If you’re a high W2 earner or a business owner with a lot of income, I have not seen a better strategy for reducing your taxes than solar investing.

Unlike traditional real estate, commercial solar ventures can offer tax credits up to 40% of the initial investment. These tax credits, different from deductions, directly reduce the taxes you owe. When you combine the credits with depreciation and the potential income (typically with commercial solar), you can immediately see 70% to 80% of the investment.

But to maximize the taxes and offset some active income, you must be classified as a “solar professional,” which requires you to dedicate 100 hours per year to solar-related activities (though 100 hours across an entire year is a lot less than it seems).

Discovering and participating in solar projects can be facilitated through partnerships and platforms with reputable entities, such as Valur and similar platforms. These platforms simplify the investment process and allow investors to diversify their portfolios by exploring various solar opportunities.

💰 NQDC for High W2 Earners

One option for high W2 earners is to participate in a Non-Qualified Deferred Compensation Plan (NQDC). These plans enable individuals to divide their income into immediate and deferred portions. The deferred income is then paid out a specified number of years later (and invested pre-tax until that time).

Your employer does need to offer a NQDC, but if they don't already they might consider doing it as an employee perk. However, one downside is in the non-qualified aspect, meaning the plan may lack the same level of protection as a 401k in case of bankruptcy or creditor issues. Definitely consider the employer's stability before participating.

I did this at Google. After leaving the company and starting my startup (at a much lower salary), I finally got paid my deferred compensation when I had a much lower tax bracket.

Many Fortune 500 companies, especially in the tech sector, frequently employ these strategies as a recruiting incentive and strategic tax optimization tool despite potential administrative efforts.

🏘️ Real Estate Tax Advantages

The government offers lots of tax benefits for real estate. One of the most common is that homeowners can deduct mortgage interest payments up to $750,000, providing a significant tax advantage (though I wrote about some tax tactics to deduct the interest on $1m+ homes in this post). Additionally, when selling a primary residence, individuals can enjoy tax-free gains of up to half a million dollars, fostering a favorable environment for homeownership.

Decoding the Opportunity Zones Advantage

Opportunity Zones provide a distinctive opportunity to defer capital gains taxes while potentially realizing tax-free profits in the long run.

These zones were created to encourage investments in underdeveloped areas, offering investors a chance to contribute to community growth. Investors can defer taxes until 2026 and receive an automatic step-up basis if the investment is held for ten years.

This strategic alignment can lead to short-term and long-term tax advantages, making it a worthwhile consideration for individuals seeking tax-efficient wealth-building strategies.

Commercial Real Estate Tax Benefits

There are countless tax benefits for real estate investors, like being able to generate massive "expenses" through depreciation or using 1031 exchanges to reinvest the proceeds after selling a property and deferring taxes owed.

I'm not going to go deep into real estate in this post, but I did in last week's episode with Ankur (🎧Ep. 147) and with real estate investor Brandon Turner (🎧Ep. 80).

However, one note for high W2 earners is that if you or your spouse are able to achieve the status of “real estate professional” (which requires 750 hours per year) you can use all the real estate losses you generate from depreciation to offset all your other income.

🧑‍💻 Qualified Small Business Stock (QSBS)

Qualified Small Business Stock (QSBS) offers the potential for huge tax benefits if you start, invest in or work at small businesses or startups.

After holding shares for at least five years, the IRS (and many states) give you the greater of 10x your basis or $10 million in tax-free gains.

The company needs to be a C corporation with assets under $50 million when you become a shareholder. Also, the tax-free exemption is “per company per taxpayer,” so if you invest in multiple businesses or give shares to family members, those all have separate exemptions. Finally, if you realize the gains before the five-year window is finished, you can roll your gains into another company for the remaining time.

Employees can benefit from this tax incentive through the startup's stock options as long as they are exercised while the company's assets (not valuation) is under $50 million. However, keep in mind that exercising options may be expensive and have tax consequences.

🧑‍💼 Tax Benefits for Business Owners

If there's a group the IRS seems to want to give the most tax breaks to its business owners. Here are a few of the tax advantages you get as a business owner:

Solo 401k's
Qualified Business Income (QBI) benefit
Elective state taxes (to bypass the $10,000 limits on state and local tax deductions)
S-Corporation election
Hiring your children

Solo 401k's

This was one of my biggest optimizations for 2023. The Solo 401k is a retirement account for small business owners who don't have any non-spouse W2 employees and it's amazing. When set up properly, you (and your spouse if they're an employee) can contribute up to $66,000 into your Solo 401k, through employee and employer contributions. And if your plan allows for it, you can make after-tax contributions and roll them over to a Roth IRA (commonly known as the mega backdoor Roth IRA).

The options for Solo 401k's weren't great when I looked at them last year and I almost ended up going with mysolo401k.net, but fortunately I came across Carry (formerly Ocho) and decided to open my account there and it's been amazing. We've since consolidated all of our past 401k's from previous employers into our Carry Solo 401k, which has made managing our retirement accounts so much easier. I'm a huge fan of Carry and they're offering our subscribers 50% off the Pro Plan at: chrishutchins.com/carry

QBI Deduction

The Qualified Business Income (QBI) deduction grants business owners an automatic deduction of up to 20%.

The QBI benefits are subject to limitations tied to the wages paid, so finding the right equilibrium is crucial to minimizing overall tax liability. While online resources may offer general guidance, the complexity of QBI calculations underscores the importance of seeking professional advice.

Elective State Taxes

Business owners in high-income states (e.g., California) can benefit significantly from their company electing to pay their state taxes, which has the effect of going around the $10,000 limit on state and local tax deductions. There are a lot of rules here, so I'd recommend seeking out professional guidance to make sure you're eligible and doing it right.

S Corporation Election

When you opt for S Corp status, you can split your net income into salary and owner distribution.

This division is beneficial because only the salary portion is subject to self-employment taxes (e.g., Social Security and Medicare). Typically, the S Corp becomes more advantageous when your net income reaches around $100,000 (but for some states like New York, this number could be higher).

The downside is that reducing your salary through an S Corp can affect your social security benefits (since they're based on your top 35 earning years), but I ran the numbers and for me, the benefits far outweighed the cost.

Also, the amount you pay yourself in W2 salary as an S Corp directly influences the contributions you can make to your Solo 401k account, so if you want to maximize your Solo 401k contributions, you'll want to make sure to pay yourself at least the contribution maximum ($66k) or more (if you want to make all your contributions pre-tax).

Hiring Your Children

Business owners have a legitimate way to involve their children in the family business (while fostering financial responsibility).

Hiring children for genuine tasks (e.g., social media assistance or office work) is legal. It allows children to earn income (no taxes below the standard deduction) and makes them eligible to start a Roth IRA. This move initiates the compounding process earlier and sets the stage for long-term financial growth.

Consider having your children invest every dollar in the Roth and give them spending money to maximize contributions.

The compounding effect of starting a Roth IRA at a young age can significantly impact their financial future.

💭 Parting Thoughts

I hope this post gives you valuable insights to optimize your taxes. Exploring these strategies further (and talking with your tax professional) can lead to significant financial benefits and smarter decision-making in managing your tax liabilities.

Thanks to Ankur for sharing insights and information to help you lower your tax liability. You can learn more about Carry and check out their free resources.

Your input matters! We invite you to contribute to our community's knowledge base if you have tips for maximizing tax savings. Together, let's build a resourceful space for effective tax-saving strategies.

Feel free to send your thoughts to podcast@chrishutchins.com. Thanks!

Chris

Feel free to send your thoughts to podcast@chrishutchins.com.

🤷‍♂️ 10 Ways to Improve Your Decision-Making

Fri, 01 Dec 2023 15:00:05 +0000

We've all made our fair share of poor decisions (I know I have), so I want to talk about improving our decision-making.

I had the chance to interview Annie Duke (🎧Ep 81) at the end of 2022 about changing how you approach your choices. Annie is the author of bestsellers Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts and Quit: The Power of Knowing When to Walk Away.

Today, we’ll get actionable and uncover 10 ways to improve decisions and understand why quitting might be a good option in some scenarios.

Let's dive in!

Chris

🧠 10 Ways to Improve Decision-Making

The outcomes of your decisions are shaped by luck and beliefs.

Luck may be out of your control, but that doesn’t mean you can't do anything about it. To increase luck, get better at forecasting how luck influences outcomes – and then put yourself in better positions for luck to happen.

Beliefs are essential in making decisions because much of your needed information is hidden. That's why a choice might seem different in hindsight – because that hindsight is the hidden information you didn't have when deciding. To make better decisions, focus energy on improving the quality of your beliefs.

Let’s talk about 10 ways to improve your luck and beliefs to increase the quality of your decisions.

1. Get Independent Perspectives

Improve the quality of information you are getting by gathering independent viewpoints.

Find a team of people that would add value to a decision and offer a variety of perspectives. This can be in a professional context (e.g., hiring a position) and even a personal one (e.g., buying a house). Your goal is to construct a well-rounded view of the decision.

The key here is to facilitate an independent perspective – that means two things:

Share just the facts, not your opinion, to avoid a biased viewpoint
Ask individually, not in a group setting, to prevent an echo chamber

How many people do you ask? It depends.

Everyone’s desire for independent advice is different; however, I’ll say this – if the goal is to get a variety of perspectives, ask enough people until you’ve accomplished it. That said, factor in the importance of the decision. Asking 5-7 people for their advice on your new job opportunity may be perfectly reasonable.

2. Document Thoughts for Clarity

A straightforward yet powerful decision-making tool is writing things down.

By transferring information from your mind to paper, you remove mental clutter. This process enables a comprehensive understanding of options. Whether outlining pros and cons or crafting possible outcomes, putting pen to paper facilitates a visualized decision-making landscape.

It will lead to a more thoughtful and informed choice.

3. Think in Advance

Decision quality often falters in the heat of the moment.

Thinking through the decision in advance can add objectivity to the process. This proactive approach minimizes the risk of making emotional choices and ensures more accurate forecasts.

Doing so can create a buffer against the influences of immediate desires. One way I love to implement this is by deciding what to order at a restaurant in advance. I'm much more likely to pick a salad or something healthier than a burger if I decide on the spot.

4. Establish Kill Criteria

Proactive decision-making involves setting clear kill criteria – observable signals indicating when killing is necessary.

For example, when considering leaving your job or selling a stock, ask yourself, “What would need to happen over the next three months to indicate I shouldn’t leave (or sell)?”

Committing to specific actions if predetermined criteria are met removes the emotion and propensity to make last-second changes.

5. Use Base Rates (To Forecast)

A base rate provides a starting point to estimate the likelihood of an outcome of a specific event.

It’s an anchor used to counter the biases of our perspectives. Base rates can be applied to a variety of factors, from widespread to local (and even personal):

Rate of divorce
Likelihood of a small business failing
The probability you’ll beat the stock market
Typical high-traffic times in your local area
Average time it takes you to get the kids ready for school

According to Annie's research, understanding base rates is essential for improving decision quality because you start with the correct objective anchor and modify it with your internal view of the world.

Base rates will prevent you from starting your forecast on a poor foundation.

6. Judge A Decision On Inputs, Not Outputs

Not every decision turns out how you wanted, but that doesn’t necessarily mean you made a poor decision. Anytime I’m evaluating my past decisions, I have to remind myself to focus on judging the quality of my decisions by the information I had at the time, not by the outcome.

I use this approach every time I have regrets about making a poorly-timed investment and try to think whether I would have done anything differently if I only had the information I had at the time of the decision (and usually, I wouldn’t have).

This approach allows us to appreciate the complexity of decision-making and prevents us from misattributing post-decision emotions. After all, there are so many other external factors that affect a decision, including luck.

7. Segment and Simplify

While we like having more choices, we can get overwhelmed with the decision (i.e., the paradox of choice). Breaking it down into segments can reduce feeling overwhelmed.

Take something as small as a restaurant menu or determining which movie to watch on Netflix. Instead of deciding what you want, cut out the options you don’t. Ultimately, if the decision is insignificant, you can simplify the final decision-making process by flipping a coin or delegating it to someone else.

This can apply to more impactful decisions like which fund to invest in your 401k retirement account. The key is to be willing to abandon a choice if it doesn't meet expectations, making decision-making more efficient and freeing individuals from unnecessary overthinking.

8. Let Quitting Be An Option

Our ability to make decisions in the face of uncertainty hinges on the option to quit.

Even though quitting contradicts common opinion, sometimes it is the best option.

Exiting a job with a toxic boss
Ending a harmful relationship
Recognizing the impracticality of a dangerous hike

Quitting at the right time can propel you forward faster – it liberates you from investing time and resources in pursuits that hinder your goals, opening avenues for more promising opportunities.

9. Hire a “Quitting Coach”

Consider a quitting coach for decisions about changing the status quo.

They should be a trusted ally who prioritizes your success over short-term discomfort. It’s their job to provide honest feedback and prevent individuals from veering off course. People often avoid sharing truths for fear of hurting others' feelings – but withholding this honest feedback may cause more harm.

Uncomfortable truths pave the way for necessary course corrections, ensuring decisions align with broader goals.

10. Prioritize Challenging Tasks Over Easy Ones

The Monkeys and Pedestals mental model serves as a powerful guide for decision-makers, urging you to assess the value and impact of your pursuits.

Imagine training a monkey to juggle flaming torches on a pedestal in a town square, a potentially lucrative venture.

Should one invest resources in building the pedestal first or attempt to train the monkey?

Pedestals symbolize easy tasks – achievable but not necessarily transformative
Monkeys represent challenging tasks – uncertain but pivotal for project success

The critical bottleneck lies in training the monkey, not constructing the pedestal.

By prioritizing the challenging aspects of a project over easily achievable tasks, you can swiftly assess feasibility, reduce sunk costs, and make better decisions.

🎙️ Podcast: Fitness and Mental Strength

Yesterday, I talked with renowned fitness instructor Robin Arzón about ways to achieve your fitness goals, master your motivation, and live the life you want.

We cover the fundamentals of fitness training, recovery, the role of nutrition, and the importance of building mental strength to stay motivated and committed to your life goals.

🎧 Listen Now

💭 Parting Thoughts

I hope this blog post equips you with valuable tips for enhancing your decision-making skills. Investing time in understanding these frameworks can yield substantial benefits to work and life.

We also want to hear from you! If you have any unique tips for navigating decision-making, we encourage you to share them with us. Your insights can enrich our community's collective knowledge.

Feel free to send your thoughts to podcast@chrishutchins.com.

🎁 2023 Holiday Gift Guide

Tue, 21 Nov 2023 05:02:23 +0000

Last year's gift guide was a huge hit, so I put together this list of 50+ of my favorite products, gifts, past purchases and more. Hopefully some of them might make good ideas for gifts this holiday season. I've broken everything into the following sections:

🏡 Home & Food
🧑‍🔧 Tech & Gear
👕 Clothes & Bags
🏃 Health & Fitness
👨‍👩‍👧‍👦 Family & Kids
📖 Books & Learning
💰 Saving Money When You Shop

Please know that none of the products or services I included below have paid to be included in the list, however some of them are sponsors of our podcast (probably because most of my sponsors were a result of me reaching out to them after loving their products).

Additionally, some of the links below are my affiliate links, so if you don’t find a better price elsewhere, I’d obviously appreciate you clicking them.

Finally, If you’re in the spirit of giving, the best gift I could ask for is simply sharing this email or the podcast with someone you think might enjoy it. Thanks so much and happy holidays!

🏡 Home & Food

Coravin (← 30-40%): There are plenty of nights we want a glass of wine, but we don’t really want to finish a bottle and thanks to the Coravin we can do that! It’s a device with a small, hollow needle that pierces through the cork and let’s you pour out wine, replacing the space it took up with Argon gas, which keeps your wine fresh for a future day.
Anyday Cookware (← 15% off): After interviewing Chef David Chang (ep 122), I was convinced to start cooking more in the microwave and haven’t look back. We’ve made David's Salmon Rice countless times and it’s great every time. I’m also a big fan of David’s book Cooking at Home, which would also make a great gift. Our subscribers can get 15% off Anyday here (or you can get 20% if you're a member).
OXO Bench Scraper: We use this all the time in our kitchen (thanks to Lenny Rachitsky for the recommendation) and even have a non-metal one too, which is a bit more delicate when scraping kids messes off our wood dining room table.
Ember Mug (← 17% off): I think we’ve gifted an ember mug half a dozen times now and have two in our kitchen. They’re fantastic at keeping a coffee warm all morning and their customer service is fantastic.
Zalto Denk'Art Universal Wine Glass: These aren’t cheap, but we were gifted a set of them a few years ago and we absolutely love them. It seems crazy, but just like this skeptical Bon Appetit writer, I think wine does taste better out of them.
Trade Coffee (← 30% off): Based on the smile that shows up on Amy’s face every time she opens up our Trade Coffee subscription, I feel confident saying that this would make an amazing gift for any coffee lover. Each delivery they’ll get a new curated bag of coffee beans from the top independent roasters around the country. You can get your first bag free AND up to 30% off here.
Paprika App (← 40% off): I’ve mentioned this app multiple times, because I think it’s the best way to organize recipes and family meal planning. However, it’s a bit pricy, so it could make a great gift. Not to mention you could curate all your favorite recipes and share the export so whoever you gift it to starts off with a whole list of amazing recipes loaded in.
Death & Co Cocktail Books: If you know someone who likes cocktails and books that look great on a coffee table, then any of the Death & Co. books would make a fantastic gift. My favorite is Cocktail Codex, which focuses on six “root cocktails” you can master that give you the knowledge you need to make so many more.

🧑‍🔧 Tech & Gear

Standing Desk: With so many of us working from home, it’s such a nice luxury to have a standing desk in my home office. They used to be so expensive, but Uplift Desk (which I have) is a reasonably priced option that feels very well built. However, last weekend Amy picked up a Tresanti standing desk from Costco and it’s fantastic too.
Sense Energy Monitor (← 20% off): After doing an episode on Home Energy (ep 135), I was so excited to dive into the data from our Sense and figure out how we can be more efficient. While it might not be as great as the Span electrical panel, the Sense is about 1% of the price, so I’m still happy.
Lutron Caséta Dimmers: I’ve played around with a lot of smart home devices over the years, but none have worked more consistently or stood the test of time than our Lutron Caseta lights switch/dimmers. Despite not being on sale, I still highly recommend them!
Samsung Frame TV (← 20% off): I’m not one for fancy TVs and the last 3-4 we’ve bought have all been inexpensive TCL Roku TVs, but last week we bought a Samsung Frame TV and we love it. With the matte display and a teak bezel, it really does look like Art instead of a TV, which is a welcome change for our living room. The Black Friday deals on Samsung’s website right now are great, but they’re even better when you stack them with an “employee discount”, which you can get if you find someone with access to PerksAtWork or PerkSpot. Even better, you can stack the discount with: Rakuten for 5% cash back and if you Live Chat with Samsung they’ll offer you a free 2 year warranty OR free mounting (my choice).
Shokz Headphones (← 15-30% Off): These are my new favorite wireless headphones for running or any other time where I actually want to be a little more aware. That’s because they’re open-ear, so you can hear what’s going on around you or in my case, actually have a conversation with Amy when we’re on a run together. We’ve been using the OpenRun Pro and OpenFit for almost 6 months and love both of them.
AirTags (← 20% off): Now that we have kids and end up checking bags on every trip, I always make sure to keep an AirTag in every checked bag. I haven’t had to use them to locate a lost bag yet (and I hope I never have to), but it’s so comforting to be able to see that your bags made it on the plane or to your destination before they come off the carousel.

👕 Clothes & Bags

Vuori (← 20% off): They make the most amazing performance apparel that’s ridiculously comfortable (seriously Amy and I are basically wearing it every single day). My favorites are the Sunday Performance Joggers, Kore Shorts and Strato Tech Tee, but you really can’t go wrong with anything they make. Also, you can get 20% off your first order here.
Patagonia Nano Puff: This is a go-to jacket for our family. It’s incredibly warm, not bulky and packs down to nothing – so it’s easy to take everywhere. They’re also easy to wash which comes in handy with two little kids.
Arizona Waterproof Birkenstocks: Amy has several pairs of these and their wearability is super versatile. I’ve seen her wear them to the park, beach, brunch, pool, gardening, and running errands. They’re waterproof, easy to clean, super comfortable, and budget friendly. She’s a huge fan and we also have a pair for the kids as well.
Stance Socks (← 40% off): We’ve tried so many sock brands and Stance socks are incredible. So many other brands wear out quick, but these are durable, ultra comfy, and come in a lot of great colors/patterns. Perfect stocking stuffers.
Fifty Fifty Gear (← 10% off): Their bags are amazing and are what we use whenever we’re going out with the kids. But the backstory here is amazing: one of the founders heard about unclaimed money from our podcast and discovered he was owed $5,000 that ended up using to help fund this company. So as a thanks, he set up the promo code ALLTHEHACKS so you can get 10% off.
Dagne Dover Bags (← $20 off): I think Amy’s given Dagne Dover bags as a gift more than anything else. Her favorites are the Landon Carryall and the Dakota Backpack. There’s no sale (yet) but this is Amy’s referral link for $20 off. Update: 25% off for Black Friday

🏃 Health & Fitness

Oura Ring (← up to $100 off): I’ve mentioned my Oura ring a lot, but it’s the one thing I wear every day to track sleep, workouts, heart rate and HRV (the Gen3 also tracks blood oxygen levels). They're not a sponsor (yet!), but they did send me this link for up to $100 off. Update: you can now use your FSA money for an Oura ring.
Outlive: The Science and Art of Longevity: I’m a huge fan of Peter Attia’s podcast and I had this book preordered the moment it was announced. It long, but I’m guessing we can all agree that time is one of our most valuable resources, so a book about getting more time is well worth the read!
Henson Razor (← 100 Free Blades): After spending a few weeks shaving with a Henson Razor on one side of my face and a regular cartridge razor on the other I was a total convert. Not to mention it’s a gorgeous razor with blades that costs only $3-5/year, but you can get 100 free blades with this link (just don’t forget to add them to your cart).
Levels (← $100 off): I learned so much about my metabolic health by wearing a continuous glucose monitor and tracking how my blood sugar reacted to different foods. Thankfully for me, it seems like cinnamon really limits blood sugar spikes from sugar, so I’ll be partaking in my fair share of pumpkin cinnamon roll pancakes this week.
Hydroflask: We have an entire shelf dedicated to our growing supply of these water bottles and use them daily (especially the 32oz Wide Mouth). In fact, we just got rid of all other water bottles in the house that aren’t Hydroflask. They also have great kids options too!
Goodr Sunglasses: I love these sunglasses and somehow between Amy and I we must have at least 10 pairs. They’re polarized, stay on during a run and best of all, they’re only $25. My favorites are the OGs, but they have a few different styles and a seemingly unlimited selection of colors.

👨‍👩‍👧‍👦 Family & Kids

Family

StoryWorth (← $10 off): If you’ve ever wanted to capture all the stories and memories from your loved ones, this is a great gift. Every week for a year, StoryWorth will email your loved one a single life-related question like: “What’s the bravest thing you've ever done?” or “What’s the farthest you’ve traveled?” Then they compile it all into a hard-cover book that you can pass down for generations to come. Get $10 off your first purchase here.
Aura Photo Frame (← up to 22% off): Digital photo frames have been around for years, but I haven’t found one that works as seamlessly as Aura. It’s so easy for you and anyone else in the family to share pictures (or videos) with the frame you give someone. At this point everyone in our family now has an Aura frame and we’re constantly passing photos of the kids around to everyone.
Escape Rooms: Ok, I love escape rooms. Amy and I have probably done at least 50 together and try to do the best room we can find in every city we visit. So if you’re looking for a fun activity for the family or a good gift, I highly recommend an escape room. And if you’re looking to find one, check out the Morty app, which let’s you search over 40,000 of them (thanks Drew and Carrie for sharing Morty)!
Box One (← 20% off): A good friend of mine worked with Neal Patrick Harris to develop an amazing game called Box One. It’s a solo, one-player board game and I don’t really know how to explain it, but anyone you know likes puzzles or escape rooms they will love this (I know I did). The company behind it (Theory11) also sells the most amazing and beautiful playing cards in the world with collections ranging from Harry Potter to James Bond to Notorious B.I.G., there’s something for everyone, including this amazing Star Wars Box Set. If you want Box One or the Star Wars set you can use the code allthehacks23 for 20% off.
Board Games: With two young ones, I haven’t gotten much time to play board games the past year, but I’m looking forward to playing some Coup and Codenames and Bohnanza with family during the holidays!
DeleteMe: We’ve now gifted this to all of our parents, because it’s crazy how many sites are sharing your personal data (e.g. phone #, home address, relatives, email). It’s a huge pain to get them to take it all down, but DeleteMe will remove your info from hundreds of data broker sites. It might not be the most exciting gift, but I think it’s an amazing one for just about anyone. Get 20% off all DeleteMe plans here.

Kids

Toniebox (← 30% off): Our girls wake up in the morning and immediately turn on stories from their Tonies box. They love this thing and it keeps them entertained for hours. The best part… it doesn’t involve a screen. If you get one, check out this episode to see how I used AI to make personalized Tonies stories about our family.
Jellycat Stuffed Animals: Our girls’ favorite “friends” are their Jellycat plushies. They’re high quality, very soft and super huggable for any kid. They also have a great assortment of animals, foods, and more.
Little Sleepies Jammies (← 30% off): These pjs are our girls favorite. They’re made from bamboo viscose so they’re super soft, breathable, and stretchy - lasting much longer than standard pjs. They also come in fun prints and colors that our girls love.
Ookkie Kids Learner Skateboard (← 10% off): As a long-time skateboarder, it was so awesome to come across this skateboard and then watch our girls get excited to be skateboarding (including our 1-year old). I try to get them out on it as often as I can!
Lovevery (← $20 off): We’ve had a subscription to Lovevery since our first daughter was born. Every few months they send award-winning, montessori-inspired toys to your home with a guide for exactly how to use them to help your child learn & grow. All their toys are designed by child development experts, well built and sustainably-made. Here’s my referral link for $20 off your subscription.
Babyzen Yoyo: We love our Yoyo and have actually now bought it twice (we left the first one on the sidewalk and drove off by accident). It’s such a great travel stroller because it’s so durable and folds small enough to fit in the overhead bin.
Nanit Baby Monitor (← 30% off): You probably need to know someone very well (or be married to them) to get them a Baby monitor as a gift, but the Nanit is such a great product that I feel like I need to include it on this list. Also, it’s an FSA eligible expense, so it’s great if you have FSA dollars to spend before year-end.

📖 Books & Learning

If anyone in your family loves learning, you should obviously send them our podcast or newsletter :)
Die with Zero: This book (and my subsequent interview with author Bill Perkins) had such a big impact on the way I think about life and money, that it had to be on the list. Highly recommend!
Masterclass (← 2 for 1): I could spend hours watching all the amazing classes they have and I’m confident a membership makes a good gift, because I gave one to my dad and he loved it! There’s definitely something for everyone and you can get two memberships for the price of one here.
Bucket List Journal: I had Ben Nemtin join me (ep 36) to talk about bucket lists, audacious goals and living the life you truly want. To help people actually achieve those goals, Ben wrote this awesome book to help you track your list, take tangible steps toward your goals, and ultimately achieve them.

I haven’t read these yet, but they’ve come highly recommended so I’m including them:

When Breath Becomes Air: Sahil Bloom (a 3-time guest) told me this is his most gifted book and I’m really excited to read it.
Same as Ever: A Guide to What Never Changes: I’m a huge fan of Morgan Housel (loved Psychology of Money) and can’t wait to read his latest book that came out this month.
Four Thousand Week: Time Management for Mortals: In a recent member event we discussed living a more fulfilling life and a top recommendation was this book, so it’s on my list to read soon too.

💰 Saving Money When You Shop

Cash Back Portals: I always like to check CashBackMonitor to see the best way to earn cash back or points when shopping online, but more often than not I end up just using Rakuten, because it’s easier and you can earn Amex points. Even better, if you haven’t signed up for Rakuten yet, you can get $40 free after your first purchase here.
Promo Codes and Offers: I feel like it’s gotten so hard to find a working promo code to use online. RetailMeNot used to be my go to, but it seems like every time I try to find a working promo code it fails. The tactic that seems to work much more often is using the live chat on a site to ask for a discount, so give that a try! Also, make sure to regularly check your Chase, Amex and Capital One offers, because there might be some deals on purchases you were already going to make. Also check out CardPointers Pro (← 30% off) to quickly register you for all the offers on all your cards).
Gift Cards: Most online retailers don’t qualify for bonus points on credit cards, so while I could always earn 2x points on the Venture X (← 90k welcome bonus), I usually try to see if I can buy a gift card for the retailer somewhere I earn more points. My two go-to’s are buying them at the grocery store (for 4x points with the Amex Gold) or on Amazon (for 5% back with the Amazon Prime Visa).

💰 Spending & Cash Flow: Apps, Tools, Tips and Tricks

Thu, 09 Nov 2023 17:24:10 +0000

It’s no secret I've been on this journey to optimize my finances, seeking ways to save money while still enjoying the things that matter most.

Today, we're diving into one aspect of financial optimization: spending and cash flow.

It's not about frugality; it's about making informed choices, understanding where your money flows, and ultimately having more control over your financial destiny.

By the end of this post, you'll learn:

The importance of budgets and tracking
The best software tools to simplify the process
Proven tactics to set up your financial system
Tips and tricks to deal with some (likely) challenges
The two questions you need to ask yourself for success

This is a timely post because this week Intuit announced their budgeting tool Mint will be no more – it’s big news impacting over 3 million users. If you’re one of them, I have some advice for you below :)

🤑 Why Tracking Your Spend Matters?

Most people I know monitor and track their account balances and net worth, but I find only a handful of them actually know how much they spend each month.

Tracking your spending allows you to be more deliberate in your decisions and better understand your future financial picture. And the simple act of tracking can enable you to make changes and save more money.

Budgeting vs. Spending Tracking

While “budgeting and spending tracking” may seem synonymous, the two have an important difference.

Budgeting involves establishing specific spending targets and ensuring your spending aligns with those targets.
Spending tracking is a more passive/reactive approach where you focus more on tracking what you’re doing and making adjustments later.

Amy and I focus much more on spending tracking, but we do make a budget, just not for the typical reason. For us, the budgets act as a monthly or annual target for spending that we can compare to reality each month/year. It helps us gauge whether we are spending more than we were planning.

💵 Spending Tracking Tools

When tracking your spending, there are so many tools at your disposal (plus new ones keep popping up regularly). I first started with Mint, but categorizing transactions was so frustrating. Then I tried a manual spreadsheet, but that became too time-consuming, so I restarted the Mint account again with fresh eyes, but it wasn’t “easy” enough to keep it up.

However, as the podcast transformed into a permanent endeavor and Amy and I left our jobs, we decided it was time to try again. So we invested A LOT of time finding the right tool that required the least effort to get good data, and I’m so glad we did.

How These Tools Work

While many apps for budgeting and spending tracking allow you to enter everything manually, I think that’s way too much work and would be near-impossible to maintain. Instead, I prefer an automated tool that connects with my bank accounts and credit cards to pull in all my transactions.

Most of these tools rely on data aggregators like Plaid, Yodlee, or MX to collect your financial data. Typically, you share the login credentials for your financial institution to the aggregator, who regularly pulls your transaction data and shares it with the app you’re using. Recently, some institutions have adopted Open Banking, which allows you to authorize read-only access to your data without needing to share your login credentials, but right now, there are only a few of the major institutions that support this.

Personally, I trust using these aggregators to connect my accounts with all the finance apps I use. However, if I’m ever using an app that asks for my credentials directly instead of through a popup operated by an aggregator like Plaid, I would stop using the app immediately.

I’m telling you this because security is paramount. If you’re ever prompted to enter your credentials to link accounts, make sure it’s a trusted aggregator or the financial institution itself.

Tools Experimentation

So, as I said, I was committed to finding the best tool for myself (and to help you all), so I decided to open an account with each of the following tools earlier this year and even synced all my financial transactions from 2022 from all my accounts.

Copilot
Monarch Money
Mint
Rocket Money
TIllerHQ
YNAB (You Need A Budget)
SimpliFi (Quicken product)

The tl;dr of that process was that I found Copilot to be the clear winner and have been using it almost every day for the past six months. Naturally, once I decided it was the best product for me, I decided to reach out to them to see if they would partner with us, which they did, so you all can get 2 months free with the code HACKS2. However, just to be clear, they are not paying me to produce this post, and they had no input into the content or the highlights from all my testing:

Copilot ($95/year, but 2 months free with HACKS2) has speed, user-friendly design, versatile functionality, and automatic categorization (using a personal AI/LLM model from your date). Even better, they built a few features to help manage some common issues, like tracking Amazon purchases, Venmo transactions, and variable monthly budgets. All this made it the best option for us; however, it is only available on iOS and Mac devices.
Monarch Money ($99/year) was another option that worked on more platforms (Android and web), but once I had a lot of transactions imported, the web interface felt slow. I also had a strong preference for the Copilot UI/UX. That said, it might be a good option if you’re an Android user or want to manage budgets and track spending from a Windows computer.
Mint (free) was a popular choice for years until it announced that it would be shutting down and transitioning its functionality to its sister product, Credit Karma. The good news is that Copilot and Monarch will soon both have tools to import any of your previous Mint transactions.
Rocket Money (free) was already an app I had used to cancel subscriptions and automate bill negotiations, but it wasn’t until this process that I decided to really put its tracking functionality to the test. I was pretty impressed with the product, but it lacked some of the customization features I was looking for and was impossibly slow to manage a large amount of historical transactions. That said, it was the best free tool I found.
TillerHQ ($79/year) is designed for the spreadsheet lover and basically sits as a technology interface to the aggregators and pulls all your transactions directly into Google Sheets or Excel. It has a steep learning curve, but if you want everything in a spreadsheet, you should check it out.
SimpliFi ($48/yr) earned recognition as Wirecutter's top pick, but many of the apps above weren’t even tested, so I’m not sure how much to read into it. Personally, I found it way too complicated to use. For example, transactions don’t link to any budget or tracking until you manually create a separate spending plan (requiring you to then add them again one by one). I even watched every SimpleFi video I could find on YouTube, but I couldn’t find anyone that made it look easy to use or worth spending more time on.
YNAB ($99/year) uses a zero-balance budgeting approach, which isn’t for everyone. It means that instead of just tracking what’s happening, you need to assign every dollar of income to a specific purpose (e.g., expense, saving, debt payment). It’s great for those who want to budget like that, but it’s not for me. To learn more about YNAB's philosophy, check out 🎧Ep 16 with their CEO.

✅ Setting Categories

Regardless of the tool you use, categorizing your spending is vital to managing your finances effectively, and the setup for most tools is quite similar. The primary goal is to ensure that every expense you have is tied to a particular category so that you can analyze your spending later.

Most tools provide a default set of categories you tweak as much as you’d like. The level of detail you require is a personal decision. For instance, you might not need to differentiate between various dining expenses, such as coffee shops, bars, restaurants, or fast food. You may simply want to know the total spent on “dining.”

It's essential to remember that making things too complicated might make the whole process unsustainable. So, I’d suggest erring on the side of simplicity when starting and deciding later if you require more categories.

Our Categories (and subcategories)

In case it’s helpful, here’s the set of categories we ended up with:

Then, for each category, I have a specific budget set. Most of them default to a monthly basis – but some give you the flexibility to go in and set different budgets for each month. This matters for expenses like property taxes that I have to pay semi-annually.

Note on fees: This is almost entirely credit card annual fees, but any time I get a credit for purchases, I put the credits in “Fees” as well to offset the annual fees.

🧮 Tips & Tricks for Categorizing & Tracking

After all the setup is complete, the monthly task is to categorize transactions. Most apps do a decent job of auto-categorizing to their default categories, but you can usually set up your own rules that will auto-categorize specific merchants/amounts to a specific category and save you time in the future.

Once you have the process down, this only takes a few minutes to complete each week.

However, some other issues might come up along the way, so here are a few I went through and how you might deal with them.

Multi-Category Retailers

Some retailers (e.g., Target and Amazon) sell everything from clothing to groceries to electronics and may not fit perfectly in one category.

You can take the simple approach where you lump an entire retailer into its category or spend more time diving into the itemized transactions and categorizing them correctly.

For Target, we’ve opted for a straightforward approach. We use the category "Shops" and place all expenses related to this store there. We took this approach because much of what we spend at Target is relatively similar, and to be honest, "Shops" could probably just be “Target.”

That is different, however, when it comes to Amazon. We buy a wide range of items that we’d like to keep separate. Fortunately, there are two good options for making it easy to categorize Amazon purchases:

Go to the transactions page, where everything is sorted by credit card charges instead of orders: Go to “Account & Lists” => “Account” => “Your Payments” => “Transactions”
If you use Copilot, they have an Amazon integration where you can sync your Amazon account with the Copilot app, and they’ll show the individual items within the transaction, making it really easy to categorize.

Handling Refunds

Refunds sometimes pose a challenge when it comes to accurate expense tracking when the timing is spread across multiple months (e.g., purchasing a holiday gift in December but returning it in January). This means you’ll still have that expense in one month and a negative transaction the next month. I try to manually backdate the refund charge to be in the same month as the original transaction, ensuring that the expenses cancel each other out in the same month.

ATM and Spending Cash

You all know I love points, so I rarely spend cash, but sometimes when traveling abroad, it’s necessary. The most common advice would be to categorize the ATM withdrawal as a “transfer” and then manually enter every cash transaction with the right category. That seems like too much work for me, so if I’m withdrawing cash on a trip and most of it was used for food, I’ll just categorize it all as “Dining and Drinks” and not worry about some of it being spent in another category. While this isn’t perfect, it's far more convenient than manually logging each cash transaction.

Venmo

Venmo and other P2P payment app transactions can also be a source of confusion because they often maintain their own balance, so if you receive $50, send $30, receive $20, and then cash out, you’ll just see a $40 deposit. I’ve had limited success with using aggregators to sync with Venmo, so here are two options:

Be diligent about always cashing out your balance so it’s always at $0, and every payment (sent or received) ends up hitting your checking account.
If you use Copilot, they’ll create an email address; you can use email filters to auto-forward your Venmo transaction receipts so they can add them all as transactions to your account.

Rollover Budgets

One challenge with most tools I’ve used is that they require monthly budgets. That works well for many things, but there are some categories, like Travel, where the bulk of the spending happens in a few months of the year that aren’t always the same. The simplest way I’ve found to solve this is to enable rollover budgets (assuming the tool you pick allows it), which just roll over any leftover money in the budget to the next month.

Some tools even let you selectively choose which categories utilize rollover budgets and which do not, providing you with the flexibility to manage variability in your expenses each month effectively.

Non-Monthly Recurring Payments

One category of transaction that always tripped me up was larger semi-annual or annual expenses, like Car Insurance or Property Tax. While you could use rollover budgets for this, I didn’t think it was a perfect solution. However, the advice I frequently found online was to take a payment like semi-annual insurance and split the transaction into six transactions (then change the dates to spread them out over six months). This seemed like a lot of administrative work, so here are two easier alternatives:

Some insurance companies (thanks, USAA!) let you pay monthly for no additional fee, so you can do that and not worry about it.
Some tracking tools will let you change your budgets every month. So I have my Property Tax budget in Copilot set up to be $0/month for 10 months of the year and then much higher the two months I have to make our semi-annual payments.

🏆 Why Spend The Time Tracking? (Benefits!)

The real value in all of this is in the insights that come from doing the tracking.

You can understand your spending patterns comprehensively – and examine your expenses on both a category and subcategory level, revealing where your money goes each month. This information empowers you to assess whether your current spending aligns with your financial goals and priorities.

For Amy and me, it enables us to think about two very important questions:

If we were going to spend more money, where would we put it (i.e., is there a category where we feel like we're too restrained)?
If we were to cut from our current spending, where would we cut?

It allows us to think about where we would spend more or less – and make the adjustments to align with the lifestyle we want to embrace.

While budgeting and expense tracking may require time and effort, their many advantages can significantly enhance your financial well-being and decision-making.

Finding a balance that works for you and your unique financial goals is important.

🎙️ Want More on Optimizing Your Finances?

If you enjoyed this post, I suggest diving deeper down the rabbit hole:

Listen to this podcast – (🎧 Ep. 9) How to Live Your Rich Life
Read this newsletter post – 📰 5 Ways to Optimize Your Money

And if you want even more ways to save money in each category, listen to (🎧Ep.133) Mastering Cash Flow: Tracking Spending to Boost Savings and 10+ Ways to Spend Less

🧳 6 Tips to Travel Like A Local

Thu, 02 Nov 2023 15:21:14 +0000

Throughout my travels to over 60 countries, I've had the most incredible experience when I ditched my tourist hat and immersed myself in the local way of life.

Today, we're diving into the art of traveling like a local. It's all about breaking free from typical experiences and fully embracing the culture of the places you visit. Whether you're a seasoned traveler or just starting your journey, these insights and tricks will enhance your travel experiences and leave you with unforgettable memories.

Having had the chance to engage with experienced travelers on the podcast, I've compiled six tips for you to travel like a local:

Plan with local sites or journalists
Walk until your day becomes interesting
Use public transportation whenever possible
Dive into culture at local markets
Embrace and (engineer) serendipity
Travel as you live

Let’s dive into each one.

🧭 Plan with local sites or journalists

Here's a pro tip when plotting your next adventure: skip the mainstream travel sources.

Local websites, blogs, and advice from residents or savvy journalists offer the real treasures you won't find in your typical travel guide. Platforms like TripAdvisor can be a jumble of opinions, making it challenging to uncover genuine hotspots. So, if you're on the hunt to feel like a local, trust content from locals.

Let’s take food, for example.

Focus your planning on reliable local sources like Le Fooding (for France), Gambero Rosso (for Italy), and Tabelog (for Japan). These sources expertly combine quality and atmosphere, providing you with curated and insider insights.

Social media can also be your unexpected ally. I love following local journalists or city/country-specific channels (like Food Story Highlight from @paris.explore). Sometimes, I’ll search Instagram or Twitter to see if I can find some fresh insights on where to explore.

The key takeaway is prioritizing quality recommendations from sources with genuine local knowledge – ensuring you're tapping into the most authentic and insider information.

🚶 Walk until your day becomes interesting

Instead of being bound by a tight schedule, put on your most comfortable shoes and step outside.

Your mission is to soak in the location's pace, rhythm, and soul. You're not chasing famous landmarks or ticking items off your checklist; you're simply strolling until the place unfolds its secrets. This approach encourages you to slow down and savor the everyday elements that make a place truly unique.

Take 7-Eleven in Japan. While there, I stumbled upon the most delicious premade pancakes in the world. Another time in Kenya, I decided to get a local haircut. Both experiences were unexpectedly amazing.

This doesn't mean traditional sightseeing is off-limits, just that you should be allocating a decent amount of unplanned time to explore.

For the anxious bunch, you can wander aimlessly without worry and easily find your way back using Google Maps (you can even download maps to use offline if you don’t want to use int’l data).

So next time you travel, give yourself the luxury of just "being" in the moment, and I bet you’ll find yourself forging an even deeper connection with that place.

🚌 Use public transportation whenever possible

Remember your backpacking days when every penny counted? Back then, choosing public transportation was a no-brainer. Even with more resources now, there's immense value in those thrifty adventures. Public transportation isn't just a money-saver; it's the key to unlocking the city's essence.

Public transportation isn't solely about getting from point A to point B; it's about the experience and exploring the places in between. As you ride, you'll start to understand a city through the people getting on and off at each stop. You might even get a unique perspective on the city's layout through its transit maps.

And don't fret about navigating unfamiliar systems. You'd be surprised by how helpful locals can be when you're lost. I’ve been helped many times – these small yet unforgettable interactions make your journey memorable.

So, on your next trip, make it a challenge to try public transportation. It will save you money, deepen your understanding of the place, and open doors to meaningful encounters with locals.

🥖 Dive into culture at local markets

When you step into a new place, make it a ritual to start with a visit to a food market – they are often the heart and soul of many cities.

And it's not just about the food; it's an immersion into local culture, traditions, and everyday life. As you navigate a market, think of it as though you're gathering stories. It's like a crash course in understanding the people, their eating habits, and even their haggling styles. You can learn a lot by simply watching and engaging in this lively atmosphere.

One way to level up this experience is with a guided tour. An experienced local can help you navigate the market, provide some background and history, introduce you to some of the best foods, and answer any questions you have. It's like a fast track to understanding the local way of life.

Another option to level up the experience is to join a cooking class that shows you how to cook with the local ingredients (and often starts with a trip to the market). It's these unexpected moments, like discovering a unique fruit or tasting a local delicacy, that truly define your journey.

And it's not limited to food markets; market squares in various places offer intriguing glimpses into daily life. You might chance upon a friendly vendor or even a soccer match out front.

In the end, remember that the locals aren't usually queuing up for the most famous tourist spots, but immersing yourself in these experiences can help you create unique memories and connections to the daily rhythm of a place.

🎉 Embrace and (engineer) serendipity

Here's some travel advice that's both simple and life-changing: put your phone away.

This simple act will allow you to position yourself in the present moment and open yourself up for serendipitous encounters. Some of the most unforgettable moments begin with being present.

For example, a simple "hello" to a stranger could lead to engaging conversations and unexpected experiences. In my experience, people are naturally curious and eager to share their perspectives and steer you clear of overly touristy paths. That being said, think of it as a two-way exchange. You're not just there to take but to give as well. Consider how you can be generous to the people and places you visit. This mindset of reciprocity can lead to goodwill, leaving a positive mark wherever you go.

I know it's not always easy – social situations like this can be daunting, but a little push outside your comfort zone can go a long way.

There's one more tip – a mindset shift that can truly transform your travel experience. It's about admitting your own ignorance and embracing it. There's a tendency among well-traveled folks to make travel a competition.

It's easy to say, "I know this place inside out; I don't need help getting around." But the truth is, you'll never know as much as someone who lives there, who grew up there.

To put yourself in a position to capitalize on serendipity, remember these three keys:

Put the phone away
Step outside your comfort zone
Embrace your own ignorance

By doing so, you'll have incredible travel experiences and create lasting memories that stay with you long after your journey ends.

This especially happens when you travel solo.

🏠 Travel as you live

While you're traveling, imagine you're simply living your everyday life.

At home, you cook your meals, right? Well, instead of always dining at pricey restaurants when you're abroad, try cooking local foods with fresh local ingredients (maybe from the market you went to). It's a fantastic way to taste the true flavors of the place you're visiting.

Or, rather than booking a hotel near the usual tourist spots, consider staying in residential neighborhoods. They offer a sneak peek into daily life beyond the touristy façade. Some of the local restaurants we’ve found in residential neighborhoods have been our favorite meals in a new place.

If you're all about budget-friendly activities, then apply that principle to your travels. Walk around, use public transportation, and find a cozy spot to chill. Sometimes, the best part of a trip is simply existing in that place and feeling its unique vibes.

Think about your hometown – people there follow a routine: work, take the bus, shop for groceries, and maybe relax in a park. Guess what? It's not so different in other parts of the world. If you have kids, I suggest taking them to the local playground. Not only is it a good glimpse into local life, but it can help take your kids out of their language comfort zone and expose them to a new culture as well.

So, the next time you're on a trip, take a day or two and just imagine you're living as you do at home. Cook some of your meals, explore residential areas, and engage in the daily rhythms of the locals.

You'll discover what's special about the place and connect with the universal aspects of life that unite us all.

🎙️ More on travel? Check out these episodes

These five podcast episodes inspired this blog – listen here for more travel tips from these experts.

🦸‍♂️ The Art of Confidence

Thu, 12 Oct 2023 15:25:21 +0000

Confidence isn't just a feeling; it's a potent force you can harness to transform your life. Last month, we talked about the secret language of charismatic communication. While charisma might be the signal you externally communicate, confidence acts as the inner foundation.

Yet so often we're caught in the trap of validation dictating our confidence, whether it is good job performance, social approval, or positive feedback. While these validations can make us feel confident, real confidence is internal.

Today, I want to share everything I learned recently from Dr. Aziz Gazipura (🎧Ep. 130) on the subject.

By the end of this post, you’ll learn how to:

Unlock confidence
Defeat your inner critic
Prepare without overthinking
Conquer the fear of rejection
Create a personal bill of rights
Navigate social obligations authentically

💪 Unlock Confidence

Confidence is a dynamic force that can significantly impact your life.

It's not just about feeling good; it's about believing in yourself and what you can achieve. Consider how it empowers you in various aspects of your life:

Excel at your job: Confidence is your secret weapon at work. When you believe in your abilities, you're more likely to take on new challenges, speak up in meetings, and pursue career opportunities. Your self-assured demeanor can be a game-changer in achieving professional success.
Connect with others: Confidence plays a vital role in building relationships. It enables you to approach people with openness and authenticity. This authenticity fosters trust and meaningful connections, making it easier to connect with others on a deeper level.
Strengthen relationships: Beyond connecting, confidence allows you to express your thoughts, feelings, and concerns in your relationships. Believing in yourself makes you more likely to communicate effectively and resolve conflicts constructively.
Shape your future: Confidence is your ticket to creating your desired future. It empowers you to take the necessary steps to achieve your goals and dreams. Confidence makes you more likely to embark on new projects, seek opportunities, and push beyond your comfort zone.

To harness the power of confidence, consider cultivating two fundamental habits:

Be on your own side – meaning you learn to treat yourself with kindness, change your inner self-talk, and build a positive relationship with yourself.
Take bold actions – meaning you learn to take risks and grow through discomfort.

Unfortunately, we often avoid bold actions because we fear pain, rejection, or disapproval. We procrastinate and fall into a loop of negative self-talk.

🥊 Defeat Your Inner Critic

The inner critic is your biggest threat to your confidence.

It's like a voice that makes you feel bad and unsure about yourself. Learn to stand up to this inner critic with three steps.

Recognize it: The first step to overcoming the inner critic is recognizing when it's at play. Understand that the critical thoughts you experience are not a reflection of reality but a product of your inner critic.
Name it: Give your inner critic a name. This simple act separates its voice from your true thoughts, making it easier to recognize when it's trying to undermine your confidence.
Take control: Dr. Aziz emphasizes the need to stand up to your inner critic with strength and determination. When that critical voice starts criticizing you, and you believe it, you might think, "I've identified it, but what's next?" The key is to ignite a revolution within. You must dethrone the power of your inner critic and take charge of your inner self, becoming the captain of your own ship. This decision stems from reaching a turning point where you truly observe and recognize the damaging impact of your self-criticism. It's about reaching a moment of intense outrage or profound dissatisfaction with how you've been treating yourself. It's the point where you declare, "Enough is enough. I'm taking control from now on."

This applies even if you're already somewhat confident. There can still be a little bit of fear that holds you back.

⚖️ Prepare Without Overthinking

Sometimes, it's hard to tell if we're getting ready for something bad or just thinking something bad will happen. The inner critic likes to think about all the bad things that could happen, like "What if everything goes wrong?" and "What if the worst happens?"

This can make us really scared and anxious.

To find the right balance between being prepared and being worried, you need to know how much risk you can handle. When you start imagining the worst-case scenarios, take a break and consider whether things are as bad as they seem. Just taking a moment to think can make those scary thoughts less powerful.

Ultimately, you might need to practice not always being super prepared. It doesn't mean you should stop preparing altogether but try to be more open-minded. Remember, you can't control everything and don't have to worry about every bad thing that might happen. Odds are, everything will be okay.

One way I put this in practice is when I'm doing public speaking. While I do try to rehearse, I prefer to go into a talk without note and accept that I'll probably miss 10-20% of my talking points. However, by not needing to rely on those talking points I can take a lot more ownership in the delivery, which, so far, has lead to a better overall outcome.

💸 Conquer the Fear of Rejection

Conquering the fear of rejection is a big part of gaining confidence.

One good way to do this is by practicing getting rejected and doing things that make you uncomfortable. This helps you step out of your comfort zone, face your fear, and realize rejection isn't as painful as you think. It's a strong way to overcome the fear of rejection and become more socially confident.

Try this exercise: Ask someone for something you're sure they'll say no to. For example, go up to a stranger and ask for $100 without begging or giving a reason. It's designed to help you face the discomfort. And sometimes, surprisingly, you might get a "yes."

Before you read more, listen to some crazy examples of things you'd expect people to say "no" to, but they actually say "yes."

The Art of Confidence: Find It, Grow It and Use It to Your Advantage

The rejection practice exercise is about developing social freedom.

📃 Craft a Personal Bill of Rights

A "Personal Bill of Rights" is a key to being authentically yourself in social situations. It's like a list of permissions you give yourself to counter feelings of guilt or obligation. When you acknowledge these rights, it helps you navigate social interactions without unnecessary stress.

Here are some examples from Dr. Aziz:

I have the right to say no to people's requests.
I have the right to ask for what I want.
I have the right to approach anyone.
I have the right to ask for any fee I want for my services.

Creating these rights can be a powerful way to discover more about yourself.

Guilt often comes from a conflict between what society expects and what you truly desire. Your Bill of Rights challenges the idea that you must always please others, allowing you to focus on your well-being. When you really believe in these rights, you won't feel pressured to meet others' expectations.

Your Bill of Rights can apply to different parts of your life:

In relationships: You have the right to express your feelings and concerns.
In your career and work: You have the right to question, disagree, and seek clarity.
In conversations: You have the right to change the subject or interrupt politely.

Identify areas where you feel uncomfortable or hesitant, and then create rights that counter those feelings. Your Bill of Rights acts as a guide, making decisions easier and reducing inner conflicts. Writing them down and practicing them reinforces your commitment to being true to yourself.

Your Bill of Rights is the foundation for prioritizing your needs and values without unnecessary guilt.

🧭 Navigate Social Obligations Authentically

It can be tough to navigate social commitments while staying true to yourself. Sometimes, you might end up in situations you'd rather skip.

Here's the challenge: How do you honor your own desires (like not wanting to be there) without coming across as impolite?

Instead of going to every event out of a sense of duty, focus on the relationships that mean the most to you. Identify the connections that bring you happiness and enrich your life. Realize that nurturing these meaningful relationships might require you to decline certain gatherings so you can save your time and energy for what truly matters.

When you say "no," there's no need to give a long explanation. A simple and honest response is enough. Express your gratitude and politely explain that you won't be able to attend. This straightforward approach sets clear boundaries without offending.

While it might seem hard at first, learning to "say no" more feels like a superpower and actually frees up your time, letting you "say yes" more as well.

🎙️ Podcast: Science-Backed Tactics to Level Up Your Health, Happiness, Relationships & Success

Yesterday, I talked with health and wellness expert Liz Moody, discussing her science-backed strategies to improve your life. Our conversation centered on practical steps for achieving more success, tricks to boost gut health, ways to nurture deeper relationships, and methods for reshaping your mindset to boost happiness.

🎧 Listen Now

💭 Parting Thoughts

Building and harnessing confidence is a challenge we all face, but these valuable insights we've shared will be the key to unlocking your true potential.

If you have any unique tips for building confidence, please reply to this email or send me a note at podcast@chrishutchins.com!

If you like this post, you’ll love my posts on charismatic communication.

💰🧠 The Psychology of Money

Wed, 27 Sep 2023 15:03:33 +0000

Money is much more about human behavior than logic and data.

It offers valuable clues into the intricate web of emotions, biases, and instincts that shape our relationship with money. When we understand this, we can manage our money better.

One of my favorite writers on this topic is Morgan Housel, the author of The Psychology of Money, who joined me for one of the most popular podcast episodes I’ve ever done (🎧Ep 6).

So let’s dive into what I learned from Morgan so you can learn how to leverage the behavioral side of finance to get smarter about money and investing.

💰 Money is Behavioral

When Morgan started writing during the market crash of 2008, he was very curious as to why people made strange money decisions.

To figure this out, he didn’t just study finance; he also looked at psychology, sociology, biology, and other areas to understand how people respond to fear, greed, risk, and uncertainty in the context of money.

While it may seem obvious to you, teaching from the lens of behavior is contrary to how finance has historically been taught. Schools typically focus on formulas, data, and charts, not the softer, behavioral side.

But money is emotional.

Educating people about how to respond to greed and fear is much closer to learning how to be a good spouse - essential but not easily summarized into a formula or tested on a midterm.

This was the catalyst for his book – to help people learn about money in a way that aligns with how it works in real life.

🪙 The Ultimate Wealth

The highest form of wealth isn’t measured in material possessions or luxurious experiences.

It’s the ability to wake up every morning and decide how to spend your day on your terms. The power to choose when, where, and how you work, with a sense of independence and autonomy, permeates every aspect of your life.

It’s the kind of freedom that brings lasting happiness (or at least less misery). While cars and homes may initially bring joy, this fades over time, and they become part of the norm.

Imagine having the security to pursue your dream job instead of seeking the first opportunity. Or the peace of mind that comes with a financial safety net for unexpected emergencies.

Every small step toward greater control is one step closer to the ultimate wealth.

💵 Cash Offers Freedom

One powerful tool for achieving freedom is having cash on hand when you need it most.

While having cash readily available may not be as thrilling as the stock market, it's a bit like a superpower. It empowers you to do things like turn down undesirable job offers, raise your insurance deductibles, or prevent you from panicking in market downturns.

People often underestimate the value of cash until they find themselves in a situation where they desperately need it. In those moments, it becomes evident that cash is the oxygen of independence, enabling you to breathe freely when life’s circumstances take an unexpected turn.

Fortunately, with high interest rates right now, keeping money in cash is not just tolerable but a pretty compelling place to get a return. However, when rates eventually drop again, don't forget the value of keeping some cash on hand.

📈 The Allure of More

The desire for more is deeply ingrained in human nature.

It's entirely natural to aspire to improve our lives and attain higher levels of comfort and security. This aspiration often extends to wanting to impress those around us—friends, coworkers, and potential romantic partners—by showcasing our possessions or achievements. We seek validation and recognition, and it's tempting to believe that acquiring more will earn us that approval.

Yet, this pursuit can quickly become a double-edged sword. No matter how much we earn or accumulate, someone else always seems to have more. And it becomes a game of comparison.

And this never-ending game of “keeping up with the Joneses” can lead to a sense of dissatisfaction and anxiety. I've seen countless friends aspire to hit a certain wealth or net worth target only to raise the bar every time they hit it and setting their sights higher on vacations, homes, cars and more.

From all my experience, it seems like the allure of more can sometimes lead to less overall happiness and contentment. It can divert our focus from what truly matters; things like meaningful relationships, personal growth, and experiences that can bring genuine fulfillment.

⚖️ Saving vs. Earning

It’s hard for many to save more and spend less.

Most people focus on earning more to build wealth, but the ability to lower expenses and save is something you can directly control. One is not more important than the other; it’s simply realizing that changing spending habits can move the needle more for most people.

That said, going to extremes with frugality isn’t healthy (believe me, I know from experience haha). Even if you can survive spending so much less, your friends and family may struggle to relate or even reject that lifestyle. While saving more might accelerate your path to financial independence, it’s also crucial to remember the value of life experiences and relationships. I covered this topic in depth in my post on Net Fulfillment Over Net Worth.

A balanced approach to financial freedom ensures you don’t miss out on enjoying life while securing your financial future.

📉 Trying to Beat the Market

Some people are drawn to active investing (e.g. picking stocks) because they think they can beat the odds.

But luck plays a much bigger role than talent. Over the last 10 years, the number of active managers outperforming the market is less than 7%. How can an individual who doesn’t spend all their time actively researching the market be successful in the long term?

The market is the market - it’s tough to beat.

My former boss and legendary investor, Andy Rachleff (🎧Ep. 19), always preached, "Good investing should be boring." I wrote about this in a past newsletter, All About Investing Part 1.

That said, boring is still boring. It’s perfectly natural to want to scratch the itch of active investing. So it's reasonable to play with a tiny portion of your portfolio, but I always try to keep it at ~5%-10% of a portfolio.

📚 Experiencing Risk & Learning from History

Assessing your risk tolerance is challenging until you've truly experienced a big drop in your portfolio. These major financial events and market crashes (e.g., 2008 crisis and COVID-19) can trigger unexpected emotions. For example, it’s easy to say you'd be buying more as the market drops on a questionnaire, but pulling the trigger after consecutive days of big declines is much harder at the moment.

I got to see this first hand during the Covid-19 market crash. Many friends of mine who previously said they'd buy more during a a big drop found themselves selling out of fear of an even bigger correction and then really struggled to get back in when the market quickly recovered.

But assuming you can learn the right lessons from history might not always work as you planned. As Morgan put it, “Investors don’t learn from history; it’s that they’ve learned too precise a lesson from history.” Precise lessons will not teach you much about the future because the biggest events that will shift the rest of our lives are surprises no one else can predict.

Instead, we should be focusing on broader insights about human behavior when looking back in time and if there's one big takeaway, it's just that the world is always surprising.

🏆 Characteristics of a Successful Investor

Even successful investors make wrong choices sometimes.

Renowned investor Benjamin Graham knew you only need a few outsized returns to make all the difference. Consistent success doesn’t always rely on being right but on managing risks effectively and avoiding catastrophic failures.

Making the “right” decision is not based on the outcome of the action.

I think the smartest thinkers are totally comfortable looking at their historical experiences and how they prepared for them. Even if, in hindsight, it looks like it wasn’t the best decision with the information that you had at the time, it may have actually been a great decision.

Morgan Housel

Here are three characteristics he shared about successful investors

Patience: Successful investors must be patient and willing to endure short-term fluctuations. Compound interest (with time) is how to grow wealth.
Make enough bets: Some investments are big winners, so having exposure to multiple opportunities and staying in the game increases the likelihood of finding investments that yield significant returns.
Accept imperfection: Don’t be too harsh on yourself. We only know one version of history—the one that happened—and the future is full of uncertainties and surprises.

Making the “right” decision based on the information available at the time should be appreciated, even if outcomes differ from expectations.

🪞 The Most Essential Part of Finance

Morgan believes the most essential part of behavioral finance (maybe one of the most overlooked) is to know yourself.

Become introspective about who you are.

Everyone is different, so you have to be honest about your skills, weaknesses, how you deal with risk, and what you want in life – and not just read about other people or other people’s situations. Knowing yourself is the only way you can understand and master the behavioral side of finance.

📚 Read more of Morgan’s Work

I’d be remiss if I didn’t share some of Morgan’s amazing work.

Check out his book The Psychology of Money
Read his work on the Collab Fund blog
Follow him on Twitter/X

🎙️ Energy Savings and Home Automation

Today, I released a podcast episode on saving money and time with a smarter and more energy efficient home.

I spoke with Matt Ferrell, a lifelong tech enthusiast and one of the most knowledgeable people I've ever met on the topic. He produces incredible content for his show Undecided, where he explores how smart and sustainable technology can impact our lives for the better. He also hosts the Still To Be Determined podcast.

If you want to learn to make your home smarter and more efficient, ultimately saving you time and money, then you’ll love this episode.

🎧 Listen to Episode 135

💭 Parting Thoughts

I hope this helps you reframe money in a new light. Seeing it as behavioral will help you understand how it works and enable you to trick your mind to be a more rational, reasonable investor, saver, earner, and spender.

If you have any unique tips you use for investing, saving, or finance in general, please let me know by emailing podcast@chrishutchins.com!

And if you enjoyed this, two requests:

Please share this blog post with a friend, colleague, or family member who might find it valuable
Check out these two posts on investing: Part 1 and Part 2.

🕵️ The Secret Language Of Charismatic Communication

Wed, 06 Sep 2023 19:00:00 +0000

Some people have that “it” factor. When they speak, people hang on to every word. It's that perfect balance of “warmth “ and “confidence” that makes you feel this person knows exactly what they are talking about.

Today, we’re talking about charisma.

In 2022, I had a remarkable conversation with Vanessa Van Edwards (🎧Ep.46), bestselling author of Captivate: The Science of Succeeding with People and Cues: Master the Secret Language of Charismatic Communication. Over 50 million people have watched her YouTube tutorials and TEDx Talk.

I want to share with you everything I learned from her so that you can unlock your most charismatic self. By the end of this post, you’ll learn how to:

Master the formula of charisma
Better use your vocal power, nonverbal cues, and words
Have more effective meetings
Write with warmth and competence
put a bunch of rapid-fire tips into use

🧪 Master the Formula

Would it surprise you to know that charisma is a simple formula?

It’s not just for those born with it. Research shows that charisma can be cultivated and learned over time. And it all relies on a series of cues.

Cues are the social signals we send to others through nonverbal body language, vocal tone, words, and even imagery, such as colors and props. In her research, Vanessa discovered that charismatic people rank off the charts in two specific traits: warmth and competence.

Warmth reflects someone who is collaborative, a team player, patient, and compassionate
Competence reflects someone impressive, powerful, efficient, and memorable

To become trustworthy, friendly, and likable while being seen as capable, powerful, and smart relies on balance.

Too much warmth and you’re viewed as:

Sweet, but not smart
Compassionate, but not competent
Relatable, but not impressive

Too much competence and you’re viewed as:

Smart, but not approachable
Dependable, but not collaborative
Important, but not kind

So, if you don’t feel like you possess warmth or competence, it doesn’t mean you aren’t charismatic; it means you haven’t mastered the formula to communicate it effectively.

So, let’s move into the three attributes: vocal power, nonverbal cues, and the words you use.

📣 Vocal Power

The first 10 words spoken during an interaction will set the tone for warmth and competence.

You can use vocal range, pace, and tempo to influence behavior. Here’s an example Vanessa shared with me of that vocal power in action:

Participants were asked to rate the warmth and competence of some doctors based only on a 10-second voice recording. The catch was that the doctor’s words were garbled in the recording…so the participants could only hear the volume, pace, and tempo, but not the words. Imagine the intercom system from high school, but all distorted.

The purpose of the study was to isolate vocal power to assess the doctor’s levels of warmth and competence. The participants were asked questions like “How smart is this person or how friendly is this person?”

They found the doctors with the lowest ratings for warmth and competence had the highest number of malpractice lawsuits. It indicates that people didn’t just sue doctors based on their skills and our perception of their skills through their vocal power.

This is just one example of how your words can influence behavior.

Actionable Tip

You can apply vocal power to improve your video calls.

Vanessa points out that one way to use vocal power to your advantage is to start the conversation in the low range instead of the high one because the low range signals competence. It’s natural for many of us to hold our breath just as we’re about to start. By doing so, the “hello” comes out on your highest note.

So, to communicate with competence, speak on the out-breath instead of holding it in.

🙊 Nonverbal Cues

Nonverbal cues such as tone of voice, body language, and facial expressions play a crucial role.

In the 1970s, Dr. Albert Mehrabian's research developed the 7-38-55 communication framework. It suggests that only 7% of your communication is verbal, while tone of voice and body language make up 38% and 55%, respectively.

While experts have pointed out some limitations of this framework, it still suggests that nonverbal communication is more important than the words themselves.

Actionable Tip

You can signal your charismatic nonverbal cues through something as simple as your video call background

To start, Vanessa suggests using your real background instead of a virtual or blurred background. She says they often confuse the other person's brain, since they wants to see what’s behind the person on the other side of the screen. And doing so can divert attention from the conversation. So, instead, use your real background to foster a more engaging and focused interaction.

Then, you can set up the space behind you to convey your warmth and competence.

Books, awards, or degrees can signal competence
Family photos, games, or personal items signal warmth
And a mix of both ensures a well-rounded perception of the communicator's personality.

This was very important to me since most of my interviews are virtual, so I connected with Kevin Shen at dreamstudiocourse.com to help me rethink my studio setup.

I think it came out great!

📢 Words Matter

It’s no secret that words are important – but what most people might overlook is that words are cues for behavior.

Our brains constantly seek cues to determine how to act, think, and feel. In another study Vanessa shared, participants were brought into a dark room and were asked to eat a bowl of strawberry yogurt and rate it on its strawberry flavor.

The study aimed to determine if words could change a person’s perception.

59% of participants rated the yogurt as having a “nice strawberry flavor.” The problem was the yogurt was chocolate.

Words have the power to prime people and influence behavior.

Actionable Tip

Use predictive rapport to improve your video calls.

Productive rapport is the process of priming people for excitement by starting the meeting with positive words. Words can change behavior, so negative words like “stress, busy, complicated, and wait” can trigger people to think about these words.

You want to spark positive engagement through your words.

🏁 End your meetings right

I think the most awkward time is the end of a video call.

You can have a great meeting, but if it has this slow, awkward death, you will leave a poor lasting impression. And just like first impressions, lasting impressions matter. Here are two tips that, when used together, create a great ending.

The first is to use a “future” mention because mentioning future actions or plans subtly signals that the conversation is winding down. Examples include:

“I’ll follow up on XYZ that we just talked about.”
“I hope you have a great weekend.”
“Thanks so much for your time; I hope you have a really nice rest of your day.”

The second is to wrap up in an "end” tone of voice to convey that the conversation is coming to a close. Check out how Vanessa describes it here in the video (at 23:11):

✏️ Written Communication

While written communication lacks nonverbal or vocal cues, it still offers opportunities for impactful interactions.

You can include "verbal charisma" in written form by strategically incorporating specific words and phrases to trigger desired attitudes and behaviors. Use purposeful language choices that align with warmth or competence goals by tailoring email subjects, greetings, and sign-offs to match charisma objectives.

For those new to the concept, assess your online profiles and introductory lines for the balance between warm and competent words.

Warm words evoke an emotional connection, including "collaborate, cheers, excited, together, and happy."
Competent words convey expertise and include terms like "efficient, lead, productive, streamline, and knowledge."
Warm symbols are emojis and exclamation points.
Competent symbols are data and charts.

Striving for equal representation of both types of words helps create a balanced and approachable impression.

For individuals aiming to enhance charisma on a deeper level, Vanessa suggests you adjust your warmth and competence levels to mirror the language and demeanor of the receiver. You demonstrate respect and understanding by adapting your warmth and competence cues to match theirs.

Auditing your recent emails is an excellent way to improve your written charisma.

🔥 Rapid Fire Tactics:

Smiles change how your voice sounds – an authentic smile can audibly alter one's tone, infusing it with warmth.
Use social media to get a sense of whether a person is warm or competent – match your tone to theirs so your message resonates more.
Use hand gestures as visual highlighters – underline or emphasize certain words because we give 12.5x more weight to gestures than words.
In meetings, where you sit should match your intentions
- Leadership Position: Face the door
- Influence Position: Choose seats to the right or left of the leader
- Challenging Position: Sit directly opposite the leader or the key influencer
- Low Visibility Position: Sit along the sides of the table
Start an email with “Hi friend or team” - this will help signal warmth and collaboration to the recipient.
Title a meeting "goal session" or "2023 wins" - this can help signal competence or productivity.

🎙️ Podcast: Essential Practices for Finding Success and Joy in Everything You Do

Today, I have Suneel Gupta back again to talk about the ancient wisdom of Dharma and ways to incorporate simple and effective daily habits into your life so that you can find success and joy in everything you do without sacrificing your professional ambition.

🎧 Listen to Episode 132

💸 5 Ways to Optimize Your Money

Thu, 31 Aug 2023 15:26:00 +0000

I’ve been interested in personal finance for as long as I can remember and back in 2016 I took that passion to launch a financial planning company (Grove) that didn’t work out as well as I had hoped. Fortunately, we found a home at Wealthfront, where I continued to work on building products to help make it easier to save and invest for the future. Then in 2021 I launched the podcast with a goal to have ~1/3 of the content be focused on money, investing and personal finance. Well, today I want to share five ways to optimize your personal finances.

Here’s what we’ll talk about:

Emergency savings
Options for High Yield Cash
Putting finances on autopilot
Paying down your mortgage or investing
Finding professionals to help with money

💰 Right-size Your Emergency Savings

I’ve long believed that everyone needs to have some type of emergency savings, but a few events in the past year have evolved my perspective even more and made me rethink my stance on emergency funds.

But first, I want to emphasize how important I think it is to have an emergency fund. It helps you deal with unexpected life events, bills, or costs without worrying how you will pay for them. It makes life less stressful when you have a cushion of savings and don’t have to borrow at a high interest rate when things don’t go according to plan.

A good rule of thumb is to aim to build an emergency fund that covers 6 months of your monthly spending, including housing costs, but that number may vary depending on a lot of factors. For example, I love Brian Feroldi’s (🎧Ep 38) formula for sizing your emergency savings:

As for what caused this recent change in my opinion on emergency funds… well, the first event was when interest rates started rising. Previously, we didn’t have much emergency savings, because low interest rates made it easy to rely on Wealthfront’s PLOC, which lets you borrow against your portfolio (but limiting those loans to 30% of the portfolio value, so it’s very unlikely you’d ever face a margin call and need to immediately repay the loan). However, those borrowing rates are now 7.65% – 8.90%, which makes it a much less appealing option for emergencies (though it’s still comforting to know it’s a backup option).

Then, a few months later, our primary bank (Silicon Valley Bank) collapsed over the course of a couple of days, leaving us unable to access our money. It was definitely a stressful weekend, and even though the FDIC ultimately quickly helped the bank open up withdrawals, I learned that you might want to keep some emergency funds at a separate financial institution from your primary bank.

Next, in the past six months, my wife Amy and I both transitioned from being employees to being self-employed. As employees, we had a predictable paycheck and a lot more job security than we do now, where our income varies drastically from month to month. Given that fluctuation, we’re keeping a lot more in our emergency fund than we used to. All that said, we’re both so happy to have burned the boats.

Finally, it was only a few years ago that cash was only earning 1% or less, which made it tough to have a proper-sized emergency fund, because it felt like you were missing out on so much earning potential. However, with rates on most cash savings at ~5%, it feels so much easier to leave money in cash.

🏃 Tap into High-Yield Cash Opportunities

So where do we put all our cash? Finally, we get to talk about the upside of these high interest rates, which is being able to earn meaningful interest on your cash. But where do you put all that cash? And does it make sense to hold any money in cash outside of your emergency savings?

My rule of thumb is this:

Any money I believe I’ll need in the next three to five years, that I can fund with my regular savings, is money I keep out of the market and in cash or cash-like investments, where I’m not taking much risk that it will lose value.

So where do I keep my cash? Right now, I think there are a few good options, which I discussed in much more detail in yesterday’s podcast episode (Ep 131):

High Yield Savings

This option is probably the easiest, because it’s easy to transfer money in and out, and if you use an account like the Wealthfront Cash account, you can even earn interest from an account with all the standard checking functionality like direct deposit, bill pay, etc. All of my High Yield Savings cash is in my Wealthfront Cash account earning 5.3%, which is 0.5% higher than advertised, because I used a referral link (← this link randomly cycles through our Member referral links, so in addition to getting an extra 0.5% yourself, you'll also be helping fellow subscribers earn more interest too). Aside from Wealthfront, this Doctor of Credit article has a massive list of the top-earning High Yield Savings accounts.

US Treasury Bills

It seems like everyone is talking about investing in US Treasury Bills, which makes sense when today’s rates are from 5.29% - 5.54% for a 4 to 52 week investment. Not to mention they’re state-tax free, which means that in a state like NY or CA, the effective rate could be greater than 6%. You can buy them directly from the US Government at TreasuryDirect, you can buy them on the secondary market from your brokerage firm or you can invest in them through a short-term treasury ETF like SGOV.

CDs (Certificates of Deposit)

If you’re confident you won’t need access to your funds for a specific period of time, it could be worth looking into CDs, which you’ll get through your financial institution. When I checked recently, it looked like for terms of 1 to 5 years, the rates for CDs were sometimes more attractive than US Government securities, but rates change daily so definitely do your research first. Also, make sure you really don’t need the funds for the duration of the CD, because you might face fees, penalties or lost interest if you need to withdraw your funds early.

Rate Chasing

As much as it might seem exciting to jump between High Yield savings accounts to try and get the best rates, it might not work out in your favor. Typically interest is paid daily in cash, savings, and money market accounts. So, when your money is in transit from one account to the next, you don’t accrue the interest during the transfer time, which means you’re reducing your overall yield.

Plus, transferring your funds for a higher interest rate only works in your favor if the new bank continues to offer that higher rate. If it goes down, not only did you get a lower rate, but you also got 0% interest during the time of transfer.

So my advice is to find an institution that has a history of competitive high rates and not worry about chasing higher rates. And if you want a deeper dive on the topic, definitely check out this article.

💸 Pay Off Mortgage or Invest?

In so many of the personal finances, real estate, and Q&A podcasts, a common question resurfaces:

Should I accelerate my mortgage payments to reduce my debt faster?

There are a lot of emotions at play in this question and the benefit of being “debt-free” might outweigh any financial math, but personally, I’ve never made an extra mortgage payment.

Firstly, mortgage interest is tax-deductible in the U.S. for mortgages up to $750,000 when itemizing taxes. Depending on the state and tax bracket, this deduction can lower effective interest rates by as much as 30% to 50%. So a 5% mortgage could have an effective cost of as little as 2.5%. And if you really want to go down the rabbit hole here, I previously wrote about a trick to deduct interest even if your mortgage is greater than $750,000.

In contrast, average long-term equity portfolio returns range from 6% to 10%, which for me is where I’d prefer to put my long-term savings to work. Not to mention that no matter how much of your mortgage you pay down, you still get 100% of the appreciation of your home (or depreciation if the value goes down). So paying down your mortgage won’t offer you any financial upside, except for saving on interest.

That said, I’d prefer to pay down debt with interest rates over 5% before investing. So with some mortgage rates over 7% right now, if you weren’t able to get any tax-deductibility on that mortgage, it might make a lot more sense to pay down your balance before investing.

Finally, let me add a deeper, more contrarian take on the topic of mortgages and interest. I love interest-only mortgages (I recently discussed it in the Ultimate Home Buying Guide newsletter). While I didn’t get one for my recent home, the reason why I love them is the same as why I wouldn’t pay down my mortgage faster. I’d instead save or invest my money somewhere that’ll generate a return rather than lower the loan because I benefit from the appreciation of my house whether I pay down the mortgage more or not. And with interest-only, you typically pay a lower payment in the first 5-10 years (and a higher one later on), which means I’m investing the difference in the early years and planning to make principal payments and/or refinance in the later years.

🤖 Put Finances on Autopilot

Back in February, we released the 100th episode of the podcast, where I reflected on a few topics with Brad Barrett. One was this funny little paradox that the people who care (and talk) most about finances often spend little time actively managing their money.

It’s often overlooked, but putting your finances on autopilot is one of my key operating principles for optimizing your finances (and once implemented, you’d be surprised how little time you really need to spend managing your money). The key is to optimize for stress reduction, enabling financial processes to occur seamlessly, with minimal active management.

It’s a strategy supported by decision rules, automation, and consolidation.

Here is an example of our decision rules:

Ensure we always have $10k in Checking (Chase)
Maintain 6-months of expenses in our Emergency Fund (Wealthfront Cash)
Max out retirement account contributions (Ocho Solo 401k and Wealthfront Roth IRA)
Contribute to our kids’ college savings accounts (Wealthfront 529s)
Invest the rest (Wealthfront Investment)

I’m actually such a big fan of rules-based automation for your money that when I was working at Wealthfront I helped build a service called Autopilot that would automate this entire process for users. Here’s what the rules above look like within Autopilot (though sadly there’s no way to support 401k contributions):

On top of decision rules, we also have all our bills (credit cards, cell phones, utilities, etc.) set to autopay on a credit card (usually the Capital One Venture X Rewards Credit Card) or from our checking account. Instead of reviewing each bill before it gets paid, we just review every transaction in Copilot, where we can get a clear picture of how we spend all our money. And after using almost every app for tracking spending, I feel confident saying Copilot is the best (if you’re an iOS/Mac user).

After being a HUGE Copilot fan for years, I was able to partner with them to offer you a 2 month free trial when you download Copilot here and use the code HACKS2.

Now it hasn’t always been this easy. I used to open a lot of bank and investment accounts to test them out, but unfortunately that meant that our money was spread across so many places that it felt chaotic and unnecessarily stressful. Over the last year, we’ve really focused on consolidating to just 1 checking account, 1 high-yield savings account, 2 investment accounts and 4 retirement accounts.

I can’t tell you how much peace of mind this simplicity has brought.

🔎 Hiring a Professional

Finally, I know that many people really love having some support when it comes to their finances and investments. So when it comes to getting help with your money, I think there are two types of professionals to focus on:

Financial Planner

If you’re looking for someone to help review your entire financial situation and help create a comprehensive financial plan to align your goals, savings and investments, then a financial planner is exactly what you want. But there’s one important question to ask when evaluating any financial planner (or investment advisor if that’s what you’re looking for).

Are you a fiduciary?

This matters because a fiduciary is a person (or organization) that is legally required to put clients’ interests ahead of their own, with a duty to preserve good faith and trust. If the answer to that question is a yes, great. However if you get anything other than a direct “yes” (e.g., “I always look out for my customers”), you should be concerned. My recommendation is to focus on looking for a Certified Financial Planner (CFP), not only because they’re all held to the fiduciary standard, but also because they’ve also gone through rigorous educational and ethical qualifications.

If you didn’t already know, I actually started a financial planning firm called Grove back in 2016, which is part of the reason I’m so passionate about the industry and helping people get good financial advice. Unfortunately we ended up shutting the company down in 2019, but when we had to decide where to direct all our clients, we ended up partnering with another online financial planning firm Facet, because they held themselves and all their financial planners to the same fiduciary standard and similarly built out a lot of technology to make their service much more accessible and affordable.

That said, if you’d prefer to find a local advisor you can meet with in person, I’d recommend checking out Wealthramp or the XY Planning Network.

Accountant

As soon as your financial life starts to get complicated, a good tax professional can add a lot of value to your life and be a great partner to your financial planning/investing strategies. This is even more true if you have your own business, have complicated company stock/option grants, have dual-citizenship or any other complicated financial situations. I had previously worked with a larger accounting firm, but switched after a new accounting firm (Gelt) found a mistake they made that almost cost me >$10,000. Thankfully they helped me re-file and get back the full amount. So if you have your own business income or other complicated tax situation, I definitely recommend you check them out here (they still have a waiting list, but have promised to give priority to anyone that signs up with that link).

🎙️ Podcast: Maximize Earnings on Cash, CD Ladders, Bank Bonuses, Bulk Buying, and Automating Returns

Yesterday, I released another mailbag episode where I discussed the best places to earn interest on cash, including high yield savings, US Treasuries, CDs and bank bonuses. I also covered lots of listener questions and tips, like when to sell your I Bonds, saving money on meat, protecting your identity online, automating returns and a lot more.

🎧 Listen to Ep131 w/ Chris

🎧 Recent Podcast Appearances

I've been fortunate to be a guest on a few great podcasts recently, so I wanted to share those episodes in case you're interested:

Millennial Investing (Being a VC, building and selling companies, and my favorite personal finance tools)
Side Hustle Nation (Why I chose podcasting, how I grew the audience and becoming a full-time creator)
Inside Out Money (Top financial tipcs and the importance of automation and simplifying your finances)
Danny Miranda Show (Building a world-class network and finding work that you actually love)
Where it Happens (The best reasons to start a podcast and how to grow it way beyond sponsorship revenue)
Mile High Fi (Favorite tips and tricks, life optimization, and key takeaways/changes from “Die with Zero”)
The Fort Podcast (My filter for finding tips and tricks, credit card points, travel tips and the business of podcasting)

🧘‍♀️ Reduce Stress with Effortless Meditation

Wed, 16 Aug 2023 16:54:00 +0000

Why is it that meditation seems to have so many amazing benefits, yet it's so hard for many of us to make it a habit? Why does it appear so effortless for some, yet so challenging for others? I’m excited to answer those questions and share some insights and practical tips on meditation that I gathered from my interview with Light Watkins (🎧Ep 126).

Light is a meditation coach with 15+ years of experience, known for his unique approach to mindfulness and making meditation easy and accessible to people from all walks of life.

So today, I’m going to break down my key learnings from him, which include:

Body and mind benefits
The power of gratitude, presence, happiness, and fulfillment
Common misconceptions
Steps to get started (and to make it effortless)
Finding purpose using curiosity
And, of course, some rapid-fire tactics

💡 Just Start

I’ll share how to start your meditation journey in a few sections. But there is no better way to start than to...just start.

So here is a short video of Light’s calming meditation technique. He walks you through his process and gives you a 3-minute window of silence to practice.

3 minutes.

Just start…then come back 😁.

If you took action before reading on…excellent.

If you’re back after reading the rest of the newsletter…wonderful.

😩 Stress & Meditation

Science has shown that meditation can profoundly affect well-being. Dr. Herbert Benson, a Harvard cardiologist, pioneered research on the relaxation response triggered by meditation, which counters the stress of the “fight or flight” survival response.

Stress often sabotages our efforts to exercise, eat well, be kind, and sleep peacefully. By incorporating meditation into your routine, you can reduce stress to foster a genuine desire to pursue other positive habits.

🙏 Gratitude & Presence

Being more present daily can also be a powerful source of joy.

One effective trick to enhance your presence is to practice radical gratitude. This means intentionally recognizing and appreciating the blessings surrounding your every moment.

Consider a thought exercise aimed at the practice of radical gratitude:

How would you feel if someone gifted you $10 million?

Seriously, $10 million.

Excitement and appreciation for such a gift would be undeniable.

However, the catch is in exchange for the $10 million; you can’t wake up tomorrow.

I’m guessing you’ve changed your feeling toward it. This means simply waking up each day is more valuable than receiving $10 million.

This exercise is designed to reframe the value of waking up each day and is, in essence, a gift worth millions. It’s unlikely you ever feel the exhilaration of $10 million because waking up each morning is taken for granted.

Here's the video of this exercise from Brad Lea.

This exemplifies how you can reframe the present moment and be more grateful.

Gratitude amplifies the present moment. And surrendering to the present moment lets you see opportunities and solutions previously obscured by the noise of “woulda coulda shoulda.”

Meditation helps you find your presence with practice.

🙂 Happiness & Fulfillment

The spiritual perspective on happiness greatly differs from the common belief that happiness comes from achievement.

This means there are two ways to think about happiness.

Happiness is the prize of accomplishments
Happiness is the prize of the process

Prize of Accomplishments

Most of us believe that happiness is on the other side of achievement.

Finishing that project, getting that new job, earning enough to buy that new car... each of these events have a spike in dopamine and joy, but the level of happiness doesn't last forever. With time, you always seem to settle back into the level you had before.

You know where I’m going with this…happiness as the prize of accomplishments leads to adverse consequences, impacting health and straining relationships. It’s a paradox of pursuits and commonly ends in dissatisfaction.

Bill Perkins (🎧Ep 91) taught me a similar lesson about the pitfalls of focusing on net worth over net fulfillment.

Prize of Process

A meditation practice can help you solve this paradox. You can build a stable foundation of fulfillment, peace, and happiness through meditation. It’s a way to increase the baseline gradually, not the spikes. It means that you need less and less to feel content over time.

Taking this path opens up the opportunity to lean into work that fills you, possibly reshaping career choices, relationships, and personal projects you undertake.

For instance, leaving a high-paying, soul-sucking job in favor of a lower-paying, highly-engaging role. What may seem crazy to most could offer you a renewed sense of purpose and joy. Besides, who knows…such shifts in perspective may create unforeseen paths.

Like Bill, Light reminded me that happiness is not based on achievement. And leaning into your heart will take you out of your comfort zone and into your growth zone.

Meditation helps you cultivate your inner fulfillment.

✖️ Misconceptions

Starting meditation doesn’t have to be complicated or stressful.

But it is easy to overcomplicate the process by thinking you must follow a laundry list of instructions like “let go, focus on your breathing, or witness your thoughts.”

Light clarified that you don’t need to do any of that, and doing less means more delightful meditation experiences.

“…you have more delightful experiences if you do less, and then if you do least, and ultimately if you can do nothing and just practice pure being, that’s when it works the best. So I learned how to operate in concert with my thinking mind, and that was a big game changer for me. It literally made me an enthusiastic daily meditator within a couple of days.

And before that, I was probably one of the most reluctant meditators because I just felt like my mind was all over the place. I was sitting there with my eyes closed, waiting for the time to pass. My body was writhing in pain; it just felt like torture.

And then it [transformed] to feel like dessert, and it was amazing. And I recognized that I wanted to be on this mission to help introduce as many people as possible to this feeling.”

-Light Watkins

🧘 Begin Your Meditation Journey

There are many variations of meditation and even more ways to start. Here’s one process you can use to help you get started on this transformative journey today.

Sit Comfortably: Find a quiet and comfortable spot to sit. Leaning back against something is okay because, as Light shared, it’s more important to be supported and comfortable than to have a perfect posture.

Set a Timer: Have a timing device nearby to track the duration of your meditation. Start with a manageable time frame, such as 10 minutes. During this time, let go of your attachment to time passing quickly or slowly – it’s all part of the experience.

Embrace Your Thoughts: As you close your eyes, you’ll likely be hit by a wave of thoughts. While we’ve been conditioned to fight the thoughts – they are natural and not something to fight.

Anchor with Breath: You can gently bring your attention back to your breath.

Shift to the Present: Shift your focus from controlling your thoughts to simply being present. Like swimming with the water’s flow, move with the rhythm of your thoughts without trying to stop or analyze them. And cultivate a nonchalant attitude toward your thoughts. Learn to see them without judgment or expectations.

Do Less: Ease into the experience by releasing the tendency to force a particular outcome. There’s no need to anticipate results or set expectations.

Embrace the Heart Voice: Meditation helps you connect with your heart voice – your internal GPS. Listen to it without resistance, as you would follow directions from a GPS.

Embrace the Drop off: As you indulge your thoughts, you might suddenly lose awareness of them – akin to how you sometimes drift off while reading a book. This transition to deeper understanding can’t be forced; it happens naturally when you embrace your mind’s flow.

Are you going to succeed right away? No

But consistency matters in meditation, just like in physical exercise.

🏋️ Building the Habit

Meditating sporadically won’t yield the same results as a daily practice.

We all know that stress is a constant factor in our day-to-day lives, so counterbalance it with daily routine. It will take some work (and discipline) to build the habit.

Conventional wisdom has said it takes 21 days to form the habit. But on average, it takes 66 days for a new behavior to become automatic (depending on the person).

Ready to start?

🧘‍♂️ Effortless Meditation

I know I just ended the last paragraph talking about daily practice and suggesting 66 days of work. That can seem like a daunting commitment, but the trick is to learn how to do it enjoyably.

Think about meditation the same way you do your other habits that you effortlessly engage in. Brewing your morning coffee or going for a midday walk…similarly, meditation can become a natural part of your routine when you create a sense of authentic enjoyment.

It will help to shift your mind from “have to meditate” to “get to meditate.” It’s removing the feeling of obligation and substituting it with opportunity.

Attitude matters.

By adopting a renewed attitude, you’ll find that your thoughts gradually settle effortlessly, and your ability to prioritize daily meditation will become easier.

😸 Find Purpose with Curiosity

Light suggests you learn to tune into your “heart voice.” That’s the one telling you to do the right thing for you. The problem is that it’s soft and often overshadowed by the voices of your social circles, family, teachers, and coaches...and what you "should" be doing.

I learned that trusting and acting on your heart voice aligns curiosity with purpose and the opportunity to create remarkable stories in your life.

Light shared a story on the power of his heart voice and how it told him to buy a Rubik’s cube, which became a catalyst for transformation.

I urge you to listen to the episode for the full story around the 43-minute mark (🎧Ep 126), but here’s a short version:

Light had this inexplicable urge after a meditation class one evening to find and buy a Rubik’s cube. It was 9:45 pm. He was tired and just wanted to go home. But his inner work and commitment to listening to his heart voice led him to act.

Why? He’d soon find out.

When Light gets home, his friend calls, and he’s dumbfounded as to why Light is spending time learning how to solve a Rubik’s cube. And why Light should be spending time on more productive things.

Instead of listening to his friend, Light started researching how to solve a Rubik’s cube. While he had assumed you had to be a genius to solve one, he discovered it was a simple step-by-step process. And so, in a few days, he could solve the cube in 3 minutes. What was once a seemingly impossible task became this structured process.

It turned into this neat little party trick…people on the train are amazed he’s solving it so fast. And then it dawns on him one day the process of solving the cube (row by row) parallels the levels of meditation.

He made a YouTube video to share his insights (mind you, this was 2006). Unexpectedly, the video went viral, spreading across the meditation community, driving more and more people to learn how to meditate.

This was what he ultimately wanted…to help people see the value of meditation. And through his heart voice was this excellent, adventurous path to get that result.

Curiosity is the gateway to purpose. You never know where it will lead, but you must trust and follow it; it will lead you to the place you’ve always envisioned for yourself but in the most unpredictable way possible.

If you don’t know what to do, follow your curiosity.

🔥 Rapid Fire Tactics

Today’s post is deep but intentionally so, but I wouldn’t be Chris without a series of tactics. So here are 5 simple tactics you can use to stay consistent with your meditation practice.

Find an accountability partner: Connect with a coach, close friend, or someone else online looking for an accountability partner too
Gamify the process: Use apps like Headspace or Waking Up to guide you and tap into the power of gamification
Focus on 10-minute increments: Keep it simple and eliminate the burden of promising yourself long periods
Remind yourself often: Use any means necessary to remind yourself every day to meditate (phone alarms, calendar invites, sticky notes)
Create an excuse book: If you are considering skipping a day, write down your excuse…because the moment you finish writing it, you’ll realize you really should just meditate

🏠 The Ultimate Home Buying Guide

Fri, 04 Aug 2023 16:05:00 +0000

Buying a home is the biggest purchase that most of us make. And while real estate can be a great investment, today I want to focus on the actual home-buying process and all the strategies and tactics you need to do it well.

This topic was inspired by a conversation I had for the podcast with real estate professionals David Greene and Rob Abasolo from the BiggerPockets Real Estate podcast (🎧Ep.121). We covered everything from finding deals and picking an agent to inspections and insurance.

So today, I'll share everything I can so you’re well-equipped to be a seasoned pro for your next home purchase.

🏠 Why buy a home?

Before diving into the home-buying process, knowing why you want to make this significant investment is essential. The type of investment (primary residence, an investment property, or a vacation home) changes the home you might seek and how you treat, manage, or run the property.

Fortunately, while there are a few exceptions, the home-buying process remains fairly standard, so this post be helpful for all of you. However, if you're looking for a vacation home, you'll love my post on the topic.

🤝 Finding the right real estate agent

Enlisting the help of a skilled real estate agent can make all the difference. A knowledgeable agent can guide you through each step, answer your questions, handle paperwork, and protect your interests. The best part? As the buyer, you don’t have to pay the agent, as the seller covers the deal’s commission (typically split between the buyer's agent and the seller's agent).

What to Look for

The first thing to look for in an agent is someone with a track record of selling many houses. Repetition does develop mastery.

The second thing is to look for an agent who owns real estate. Agents with personal investment experience have a unique perspective and can offer valuable insights others might overlook, like spotting bad neighborhoods, possible tenant problems, and poor floor plans.

The third thing is finding an agent that understands the financial aspect of real estate. Agents will typically lead with personality and likability. But being the nicest or friendliest does not mean they are the smartest. Agents who prioritize financial considerations can help you make intelligent decisions that align with your long-term goals. You want them to tell you about the important town considerations, how insurance might change in certain zones, tax aspects, and if the property could be a rental if you were to leave.

Finally, a great agent will make sure you have access to the right resources even after the home-buying transaction. Find an agent with a well-curated list of reliable vendors, such as trusted contractors, cleaners, landscapers, and other service providers, to help manage properties for personal use or investment.

Dual Agency

One tactic I've used for our past two home purchases is asking the sellers agent to represent me as well, something called dual agency. I don't recommend it for anyone who isn't very confident with the process and leading negotiations, but the advantage I've seen is that because the agent will get both commissions if you buy the property, they're definitely motivated to help you get the home.

So let's say the seller agreed to paying a 6% total commission split between two agents, meaning the sellers agent would get 3%. You could propose a dual agency deal, where the sellers agent reduces the 6% total commission to 5% and credits 1% back to you. That means you and the seller both get 1% back AND the agent makes 1% more – a win for everyone!

Note: dual agency isn’t allowed in all states.

📈 Finding value

Understanding your leverage is crucial. In a hot market with limited inventory and numerous buyers vying for properties, getting a discount may not be feasible. However, in less competitive markets, you can deploy various tactics to improve your chances of getting a better deal.

One approach is to target properties that have been on the market for longer. Sellers tend to have the leverage early on in the process. But this fades when houses are on the market for longer periods. Sellers may become more open to accepting offers they might have rejected when it was first put on the market.

A second approach is to look for properties with poor photos, need light renovations, or even have features that other buyers might overlook. David and Rob believe the best deals are homes with bad smells, ugly floor plans, or dated interiors that you can easily improve with a little effort.

Dealing with Hot Markets

In hot real estate markets with high demand, finding a suitable property before it becomes popular can be challenging but possible.

Building a solid network of realtors can help you stay informed about off-market or upcoming listings. However, you want to be strategic because contacting multiple agents and expressing interest in buying a home without a clear commitment can backfire. Agents may see such behavior as lacking loyalty, reducing their motivation to prioritize their interests. You don’t want to send the vibe of an “open relationship.” That said, it might work better in a cold market where agents do more work for a sale.

🔍 Due diligence process

The “window shopping” stage might be fun and exciting, but when it comes down to the offer stage, many people get stuck dragging their feet.

They need time to think about it.

It’s important to understand that submitting an offer is not a commitment to purchase the property. Most offers come with contingencies, allowing buyers to back out if they discover any issues during the inspection, appraisal, or loan process. It’s a perfectly reasonable strategy (with the right agent) to move fast on the contract, then slow down to do your inspections.

In competitive markets, some sellers may not accept offers with contingencies, but don’t let that deter you. There are strategies you can use to stay ahead.

For instance, California law grants buyers seven days to review property disclosures once received, giving them time to decide without penalty. If the listing agent fails to provide the disclosures upfront, you get extra time to complete your due diligence - and you can back out without penalty.
Another strategy involves earnest money deposit. David said there is no recourse for the seller to demand the money if the earnest money is not deposited and you back out of a deal. So if you’re a buyer, negotiate a longer period to put up your earnest money and use that time to do your own diligence/inspections. Or, if you have a seller that is a stickler with contingencies, try to negotiate for low earnest money. Put up the money, and if you change your mind, the worst-case scenario is just losing that lower amount. It sounds unfavorable, but it's better than buying a home you don’t want.

Inspections

A home inspection is a safety assessment of a listed property. It’s important to note that the inspector is an objective party to provide a professional evaluation.

As the buyer, use the inspection to negotiate changes to the offer based on the property’s condition. Sellers generally don’t want to make concessions, but buyers can always negotiate. Even with an “as is” listing, because it turns out “as-is” is a pretty flexible term.

As the seller, sometimes paying for a home inspection is a smart strategy before listing it. The report upfront can help persuade buyers to waive inspection contingencies, streamlining the process and making the sale more attractive. If you’re a buyer and encounter this strategy, you don’t have to hire your own because home inspectors are almost always neutral professionals. However, David and Rob suggest calling the seller’s home inspector to get additional information or perspectives on specific items, like:

Is a stated issue common for homes like this or in this area?
Does the issue concern you?
When you looked at the house, what stood out most from the inspection?

Another thing David shared was paying attention to the sewer lateral connection in inspections. Older homes may have sewer lines running through the front yard that can become infiltrated by tree roots over time. This can lead to clogs and expensive repairs. Getting the sewer line scoped by a plumber before finalizing the purchase is crucial to avoid unforeseen expenses.

💰 Financing

When going through the financing process and getting pre-qualified for a mortgage, paying attention to your debt-to-income ratio (DTI) is crucial.

Lenders typically look at your DTI, the percentage of your monthly income that goes toward paying off debts. The preferred range varies depending on the lender, but a rule of thumb is a DTI below 36%, with 43% historically being the cap.

To calculate your DTI, add all your monthly debt payments, including credit cards, student loans, car payments, etc., and divide that by your gross monthly income. If your DTI is too high, it might affect the amount you qualify for when buying a home.

Hold off on opening new lines of credit for at least six months before purchasing a home to maintain a clean credit profile during the mortgage application process. Being mindful of your DTI can ensure a smoother loan approval and increase your chances of getting your mortgage’s best terms.

Mortgage Brokers

When securing a mortgage, you have two options: working directly with financial institutions or collaborating with a mortgage broker.

While institutions like Wells Fargo or Chase are popular, mortgage brokers offer distinct advantages.

Brokers can access the same lenders but often receive better pricing because they compare multiple options.
They can save you time by shopping for various loan products and negotiating on your behalf.

Their expertise and experience in navigating complex deals can be invaluable during financing.

Conforming vs. Jumbo

Conforming loans adhere to guidelines set by government-sponsored enterprises like Fannie Mae and Freddie Mac. They meet the loan limits established for specific areas and have more flexible qualification criteria.

In contrast, jumbo loans exceed these limits and are used for high-value properties in expensive real estate markets. Jumbo loans have stricter qualification requirements, higher interest rates, and larger down payment demands.

Fixed Rate vs. Adjustable Rate

Fixed rate mortgage are fairly standard and it means your interest rate and payment amount won't change over the 10-30 year timeframe of the mortgage. However, given high mortgage rates right now, some individuals might consider exploring adjustable mortgages (ARM) where you can lock in a lower rate for a shorter period of time (1-10 years) and then the rate adjusts a new market-based rate after that.

It's a great option to get a lower rate if you don't think you'll be in the home for more than the fixed rate period (though if you're not going to be in the home too long, I'd argue it might make more sense to rent). However, the most common argument I hear from people getting an ARM is that their plan is to refinance the home to a fixed rate mortgage before their adjustable period expires.

However, weighing the risks and historical experiences with ARMs is essential. During the 2007-2008 financial crisis, many people with ARMs at the end of their fixed period experienced substantial rate increases, leading to unaffordable mortgage payments and foreclosure. Regulations now limit how much ARMs can adjust, but borrowers must still assess their risk tolerance and financial goals before choosing between a fixed-rate mortgage and an ARM.

Finally, while it might seem like current mortgage rates are high relative to the past few years, keep in mind that rates didn't drop below 5% from 1971 to 2008, so we might just be looking at the new normal.

Interest Only Mortgages

Another mortgage feature you could consider is an Interest Only mortgage, where you only pay interest the first ~5-10 years of the loan. After that period, you then start making payments for interest and principal. The upside is that you have a lower payment for the interest only period, but after that your payment goes up to something higher than if you had paid principal and interest from the beginning.

Now I probably have a contrarian take here, but I love interest only mortgages. Why? Because I wouldn't adjust my spending/savings based on my mortgage payment. Meaning that if choosing an interest-only mortgage meant a $500/mo lower payment, I'm not spending that money, I'm still saving it (it'd likely just go into my Wealthfront account). And because I benefit from the appreciation of my house at the same rate, whether I pay down the mortgage more or not, I'd rather save my money somewhere that it'll actually generate a return (aside from lowering my monthly interest payments, because I'm paying down the loan).

However, for as much as I'd prefer an interest only mortgage so I can invest in the market instead of into equity in a home I already own, there's two reasons we didn't get one (we have a 30 year fixed):

The bank we got our mortgage from charged a much higher rate for an interest-only mortgage, such that it was no longer worth it.
I couldn't find a 30 year interest only mortgage where it was interest only the whole time. I know I could have just refinanced after 10 years to another interest only mortgage, but we bought in 2020 and I wanted to lock in those rates for 30 years.

Down Payment

The down payment decision depends on your situation. For primary residences, FHA loans allow a low down payment of 3.5%, making them attractive for first-time buyers or those with limited funds. However, conventional loans usually require a 20% down payment to avoid private mortgage insurance (PMI).

Consider the opportunity cost of tying up more cash in a down payment. As interest rates fluctuate, the cost savings from a larger down payment may be less significant. If interest rates are high, a larger down payment could lead to substantial savings on your monthly payments.

📃 Home Insurance

I also recently hosted a podcast deep dive on optimizing your insurance policies, which was partially based on my newsletter post on insurance tips last year. Check them both out for more insurance information and to hopefully save some money.

I’m keeping a running list of hoe much money I've helped people save by repricing their policies, so I'd love to hear from you if you save some money. Just yesterday someone told me that episode is now saving them $15,000/year!

That said, here are a few actionable tips to navigate the world of home insurance:

Assess your coverage needs: Before selecting an insurance policy, carefully evaluate the coverage provided and consider the potential cost of rebuilding your home in case of a disaster. Some lenders and insurance companies may have minimum coverage requirements, but it’s vital to ensure you have enough coverage based on the cost of rebuilding your home.

Extended reconstruction coverage: To safeguard against rising building material costs or unexpected circumstances, consider adding extended reconstruction coverage to your policy. This add-on offers extra protection beyond the policy’s face value, ensuring you can rebuild your home without unexpected expenses.

Insurance in high-risk areas: Obtaining insurance can be more challenging and expensive in regions prone to natural disasters like wildfires or hurricanes. Before closing on a property, ensure you can obtain insurance at a reasonable cost and that it adequately covers potential risks associated with the property’s location.

Don’t assume bundling is best: While bundling home insurance with other policies may seem convenient, it’s essential to research and obtain quotes from multiple carriers to find the most cost-effective coverage for your specific needs.

Know your homeowner's insurance: Homeowners insurance covers damage or destruction to your home, loss or theft of possessions, personal liability for accidents on your property, and additional living expenses if your home becomes uninhabitable. Understand the coverage labels like Coverage A (main dwelling), Coverage B (other structures), Coverage C (personal property), Coverage D (loss of use), Coverage E (liability), and Coverage F (medical payments).

Documenting everything: Take a video on your phone, walking through every room and showcasing your possessions. Having this documentation will help ensure proper reimbursement if a covered incident occurs.

💵 Ways to save on insurance

Regarding saving on homeowners insurance, here are several to consider:

Consider your deductibles: Opting for a higher deductible can lower your premium, but remember that you’ll need to cover small expenses out of pocket. Reserve this approach if you only want to cover the significant/catastrophic issues, but you’ll also need to ensure you have sufficient funds in your emergency fund to handle any smaller incidents.

Explore discounts: Many insurers offer discounts for installing security systems, fire sprinklers, security cameras, and alarms that report to local fire and police stations. These safety features can reduce your policy costs by 15% to 20%. Additionally, some insurers offer affinity discounts for members of specific organizations or credit unions, so it’s worth checking if you qualify for such programs.

Comparison shop: Do your own research. Some insurers have quizzes about your home’s characteristics to streamline the comparison shopping process.

Remember, your home is more than just a physical space—it’s a valuable asset, and having the right insurance coverage ensures its protection.

✒️ The closing process

Lastly, I wanted to touch on the closing process. While we didn’t talk about this, it is an important part. And thanks to David and Rob, they covered this topic on another Bigger Pockets episode in January.

Here are some of the highlights:

In some states, using an attorney for the closing is standard, while others may opt for a title company. With modern technology, remote notary services have allowed investors to sign closing documents from anywhere, even while on vacation or at a restaurant. COVID-19 has also brought changes, allowing some transactions to involve the pre-signing of documents, with funds held in escrow until the official closing date. This flexibility has expedited the process and provided a smoother experience.

Before closing, conducting a final inspection or walkthrough of the property is essential, even if it has been vacant during the contract period. This inspection verifies that the property is in the same condition as when the contract was initiated, ensuring no unexpected issues have arisen.

During the actual closing, buyers should carefully review the closing statement. A reputable title company or attorney should provide the closing statement beforehand for review. The statement includes important details, such as proration of rental income and property taxes or rental income, if the property has tenants in place. Prorating ensures that both parties are fairly compensated for their respective periods of ownership and tenancy.

Familiarize yourself with all the fees involved in the closing process, such as filing fees, title fees, survey fees, and any other charges. Review the closing statement carefully to avoid surprises.

Another important consideration is that closing costs negotiated during the transaction might not be included in the initial paperwork submitted to the title company. Buyers must communicate these details clearly and confirm that the closing statement accurately reflects the agreed-upon credits and adjustments, whether they are lender credits, seller credits, or other adjustments made during the negotiation process.

To avoid last-minute issues, scheduling the signing of paperwork early in the day is advisable, allowing time to address any discrepancies and prevent delays. Human error can occur during the closing process, so vigilance on the part of the buyer is crucial to ensure accuracy and successful closing. If any discrepancies are identified, delaying the closing to address and rectify the issues is acceptable.

🔥 Rapid fire Tactics

Here are a few tactics I’ve learned from my experience buying two homes and a fractional vacation home with Pacaso:

Get a second opinion - If an inspection raises concerns or reveals a costly concern, consider getting a second opinion to safeguard your investment.
Find the priority - Whether the seller wants a quick sale, a nice family to live in their home, or the highest price, understanding their motivation allows you to leverage that one crucial lever.
Ask about the items in the house you want to keep - Small wins can add up during negotiations. You might score free furniture or appliances they planned to replace, saving you money on new purchases. Or, in my case, a huge TV and five lime trees.
Protect your privacy - Put in the contract that the seller should remove photos of your new home from online listings after the sale. Also, if privacy is an even bigger concern, consider purchasing the home through an LLC to prevent your identity from being in public records. If you want more tips on protecting yourself and your identity, check out my newsletter and podcast on the topic.
Raise the price + add seller credits - If the seller doesn’t budge on credit for repairs, propose raising the price and having the seller provide a credit for the same amount. This spreads the cost over the mortgage term, easing your immediate financial burden, especially if you’re tight on capital.
Keep all documents and property information in one place - A Google Drive folder is a simple yet efficient way to organize everything. Gather essential documents like pay stubs, tax information, and bank statements before applying for a mortgage. Having them readily accessible will streamline the pre-approval process with different lenders. Don’t forget to log all property improvements. This accurate record can lead to tax deductions when you sell.

👨‍🍳 Cooking at Home - What I Learned from David Chang

Thu, 27 Jul 2023 18:22:00 +0000

I’m not claiming to be a chef by any means, but now, with two kids, I’ve learned a thing or two. It also helps that I spoke with David Chang (🎧Ep.122) in a recent podcast on how you can become a master of your kitchen. David is a 6x James Beard winner, owner of Momofuku and 3x NYT bestselling author.

So today, I‘m going to share the lessons I learned from him (and a few more of my own):

Why the microwave is your key to better home cooking
Why you should consider more frozen food
Which ingredients to use more often
How to get your kids to eat more
Simple kitchen tricks
My favorite recipes

🔪 Professional cooking vs. home cooking

Let’s cut through the complexities and highlight why professional cooking doesn’t always fit the bill for home cooks.

Cooking at home and in restaurants is worlds apart, and there are some misconceptions when trying to replicate restaurant recipes. About half of what you see in home cooking is inspired by fine dining concepts, but the rest is just practical, whatever-works-best kind of stuff.

Professional kitchen cooking doesn’t always translate to your home kitchen because of the focus on high volume, knife cuts, and using specific, sometimes rare, ingredients. That level of detail isn’t always useful for home cooks.

So embrace that home and restaurant cooking are not the same. Cooking at home is about simplicity, efficiency, and making delicious meals without unnecessary stress.

🪄 Microwave is a magical tool

The microwave is culinary arbitrage… you press a button, and things get hot. It’s arguably the most underutilized tool in your kitchen and the one that will make home cooking so much easier.

How it works

Inside a microwave is a generator called a magnetron which converts electricity into electromagnetic waves (i.e., microwaves). The microwaves penetrate your food which causes the food molecules to vibrate and generate heat.

The microwaves are not harmful. Here’s a snippet from a GoodRx article that relies on primary sources such as medical organizations, governmental agencies, academic institutions, and peer-reviewed scientific journals:

The microwaves were found to be safe and not cause cancer… radiation produced by microwave ovens is electromagnetic radiation, also known as non-ionizing radiation. This type of radiation is different from ionizing radiation, the kind found in X-rays.

What is dangerous is plastics in the microwave. Stick with silicone, heat-proof glass, ceramic (depending on the glaze), and paper products like plates, napkins, or parchment paper.

Benefits

Besides being the tool that makes home cooking easier, using a microwave has benefits over ovens and stovetops.

Energy-efficient way to cook: It will cook in less time and with less water
Keeps food nutrient dense: Less water means less transfer of nutrients
Cooks cleaner: You don’t have to add oils or fats to cook
Uses less dishware: The dishware used to cook in the microwave (like Anyday cookware) can be the same for storage and serving

Wattage and power level

Understanding your wattage is the key to getting to know your microwave.

The problem is that every microwave will be different, and you can screw up a recipe if you don’t dial it in. Here’s a way you can test to determine the wattage of your microwave oven, regardless of what it says in the owner’s manual: the time to boil test.

The second thing people don’t use correctly is the power levels.

Power levels change the time of cooking, not the strength.

By default, the microwave cooks at the maximum level, which means the microwaves are applied the entire time it's on. Also, microwaves penetrate only 1 inch of any food. So when the power level is high, the outside of your food can get overcooked while the inside is not.

For example, “power level 30” means for every minute, only 30% of the time microwaves are being used. So use this as a rule of thumb for power levels.

High power is best used for liquids and foods less than ½ inch thick
Medium power is best for items that cannot be stirred, like chicken or lasagna (melt butter at this power, too)
Low power is best for dairy, grains, delicate sauces, and defrosting

Food that works well in the microwave

Foods that use steam or water for cooking are good options (so long as they don’t require hours of cooking).

Some of David’s recommendations include:

Lobster 🦞
Vegetables 🥦
Pasta 🍝
Gravy 🧉
Fish 🐟

Cookware designed for the microwave

In my conversation with David, we talked a bit about Anyday, the company he partnered with to create the best microwave cookware. In fact, I’ve been using it for the past month, and I’m thoroughly impressed. It’s a bit surreal to be able to cook entire meals for 5 in one dish in the microwave, but we’ve now made Dave Chang’s Salmon Rice on three occasions, and it’s so easy to make, tastes so good, and with only one dish, it’s so easy to clean up!

Even better, I reached out to the Anyday team to set up a 15% off discount for our subscribers, so if you want to check it out, you can use this link.

Even better, if you’re a member, you can get 20% off with the code on the member site. Or if you’re not a member and want to join, you can do that here.

🥶 Quality matters – try frozen

Let’s start with fish.

Three factors can impact the quality.

When it was caught
How it was handled
How it was stored

Unless the person selling the fish is the one that caught, handled, and stored it, it’s hard to be certain. Human error happens in transfers. It’s why David suggests you consider frozen fish over fresh fish at the supermarket (or wherever you buy your fish).

Frozen fish can be a better option because it’s typically flash-frozen at its peak freshness, and you don’t have to worry about human error in handling and storage as much.

Does that mean frozen is always better? No.

But as he put it, fresh fish has a higher upside but a lower downside than frozen fish. If you are going the fresh fish route, he suggests buying it from places you trust how it’s handled.

The same can be true for some fruits and vegetables, like berries and peas, as they are harvested at their sweetest and quickly frozen to preserve flavor and nutrients.

🍱 Impactful ingredients

Olive oil is a smart (and healthy) meal addition

Olive oil comes in various flavors and smoke points, making it a versatile addition to your kitchen.

David always has three olive oils on hand, using lower quality olive oils for cooking because the fragile compounds that make it delicious get destroyed in the violent heating process. He reserves the more delicate, fragrant, or fruity ones for drizzling dressing and other non-heated uses.

Besides, olive oil has excellent health benefits, including healthy fats, antioxidants, and anti-inflammatory properties.

Spices are essential to home cooking

When was the last time you replaced the spices on your spice rack?

Five years?
Ten years?
Did you keep the spices from the previous homeowner?

The flavor of spices degrades over time.

Instead of purchasing bulk quantities for everything, buy small amounts of certain spices to avoid waste and ensure freshness. Spices are an amazing way to unlock flavor for home cooking.

MSG is misunderstood

One of the interesting things I learned from David is that MSG is often misunderstood and unfairly criticized (he has yet to find solid scientific evidence proving it’s harmful).

Per the FDA, “MSG (monosodium glutamate) is the sodium salt of the common amino acid glutamic acid. Glutamic acid is naturally present in our bodies and in many foods and food additives.”

The artificial form is what people think about, but MSG is also natural. Take dry-aged beef; dry-aging produces and harnesses glutamic acid as a key part of its aging process.

Whether you realize it or not, many delicious snacks and dishes contain MSG, including Chick-Fil-A chicken sandwiches, your favorite bag of Doritos, and even the chicken bouillon cubes used for cooking.

While some people might be sensitive to MSG, embracing it in moderation can unlock umami flavors and enrich your cooking.

🧑‍🍳 Unleash your inner foodie

While this newsletter is about cooking from home, I’d miss a huge opportunity not to ask a world-renowned chef about restaurants.

Here are two things David recommended when finding a place to eat out:

Look for the places people love or hate - The hidden gems are the restaurants where the Yelp rating doesn't reflect the restaurant. David suggests you look for places with an average of rating of 3 but comprised of all 1s and 5s (not just all 3s). These are the places that could be amazing or absolutely terrible...Roll the dice...you never know.
Trust the foodie influencers - Instagram is a great curation tool. You have these influencers and creators where all they do is research and deep dive into where to eat. This means you have instant information, and someone is doing your homework. All you need to do is to find the right people to trust and follow their lead.

🍽️ Simple kitchen tricks

I asked David for a few kitchen tricks to save time and frustration:

Skip peeling carrots – wash them thoroughly with a clean sponge for easy prep (also there's good flavor in the skin)
Peel ginger with a spoon – and if those tight crevices and knobs start to anger you, wash it instead
Treat the fat as a friend – don’t assume you need to trim the fat off a chicken breast or thighs
Use the freezer more often – it’s the best way to preserve and ensure quality

Here are some of the ones Amy and I have learned along the way:

Use distilled white vinegar for berries – bathe berries for 30 seconds to 1 minute in a distilled white vinegar and water mix (1:4 parts ratio vinegar to water), then let them dry and store in the fridge for longer freshness
Keep cookies chewy by storing them with a slice of bread – it will keep them softer for longer
Get a good pair of kitchen scissors - it makes cutting food so much easier (especially with kids)
Keep a sharpie next to the fridge – write dates on everything and eliminate the guesswork if your food is still good or not
Make extra and freeze in portions – for things like pasta sauce or chicken broth, you can freeze in portioned sizes and save yourself time in the future

I’ll share one more from a podcast subscriber:

Buy bulk meat from local farmers - Every year, Maxine fills a 9 cu ft chest freezer with various whole animal meat purchases. It saves time and money and adds a layer of convenience and quality assurance. Then she just "shops her freezer.” She even wrote the book on how you can do this yourself!

👨‍👩‍👧‍👧 Get your kids to eat more

All you want to do as a parent is seeing your kid eat.

The trick is to prevent boredom.

If they see the same food the same way, at some point, they are going to push it away. So, find a way to make the same food differently.

For David, it’s the crepe. He says, “It’s the only thing left in my pitching arsenal that [my kids] still can’t hit.”

The beauty of the crepe is its dynamic. Add an egg, fold it over, make it crunchier, mix it with fruit, add bacon, or chop it up. If it’s not the crepe for you – find the versatile foods you can use to do the trick.

Here’s how you can make the crepes:

Use the ratio of 1 egg to 1 cup of milk to 1 cup of flour
Mix it in a blender with a bit of olive oil (or some kind of butter)
Pour into a nonstick pan on medium heat (try to get it as thin as possible – but don’t worry about being perfect)
Then do what you want with it…

🥘 Favorite Recipes

Since this is a newsletter all about food, I thought I’d also share some of our favorite recipes to cook at home (though with Green Chef covering 3 of our meals each week, we’re planning meals a lot less). Also, if you’re wondering how I keep all these recipes organized, we do all our recipe organization and meal planning with the Paprika app.

💳 6 Lessons to Optimize Your Miles & Points

Wed, 19 Jul 2023 18:13:00 +0000

Advertiser Disclosure

Note: American Express is a ChrisHutchins.com advertiser

I could talk for days about points and miles. I’ve earned over 12 million of them, have traveled to 60+ countries (mostly for free), and I want to help you do the same. So today, I’m sharing some of the most important lessons and tips I’ve learned to help you optimize your points (and save some money along the way).

Here’s what you can expect to take away today:

Best two-card combos
Hitting your minimum spend
Maximizing points with your partner
Preventing points from expiring
Canceling your cards
Best ways to track points

💳 The best two-card combos

I recently presented all about credit cards to a wealth management firm’s clients, and one of the most interesting takeaways was the impact of certain two-card combos.

During my prep work, I built a model to determine how many points you could get in a year with different card combinations. It also included point valuations so you could see the value of what you earned too.

I played around with many combos but found that these four pairings had the highest ROI (using BLS average household spending data) for each issuer:

2.41pts/$: Capital One Venture X Rewards Credit Card and Capital One Savor Cash Rewards Credit Card
2.35pts/$: Citi Strata Premier℠ and Citi® Double Cash Card
1.95pt/$: American Express® Gold Card and American Express® Green Card
1.90pts/$: Chase Sapphire Reserve® and Chase Freedom Unlimited®

Note: If you'd like to support me when you sign up for your next card, I'd really appreciate you using the links at https://chrishutchins.com/cards

A few takeaways, but I’ll share a few:

Having a 2x everything else card adds so much value.
When I added all of the 10+ cards I have, the earning only jumped to 2.65pts/$, so there might not be THAT much value going past 2-3 cards.
All of this is very dependent on your own spending patterns, so you can't draw too many conclusions for yourself just from this.
While I prefer transferring points to airlines, the Chase combo gets you 1.5¢/pt in the portal (while all the others only get 1¢/pt), so if that's how you like to redeem, it quickly takes the #1 spot.

What if you don't stick to one issuer?

While the Capital One combo is very strong, the best two card combo is actually the Capital One Venture X and the American Express® Gold, which would earn 2.49pts/$ by getting (4x dining/groceries, 3x flights, 2x everything else). With my personal spending, the gap widens even more, with this combo jumping to 2.71pts/$.

Where is this credit card optimization tool?

If you want to use the tool I made to model your own spending and card choices, I decided to put it up on this site. I think it’s an incredibly valuable tool that can help you maximize your points, but I'd really love your feedback if you decide to check it out.

$48.00

Card Optimizer Spreadsheet
The video below will give you an overview of credit card optimizer spreadsheet.

Get it now!

Or if you're already a member, you can access this tool for free, as well as get all the exclusive member deals we have and a lot more. If you're not a member, you can join here.

♟️ Strategies for hitting the minimum spend

I spend a lot of time talking about the cards I use daily to maximize points, but if you ask me how I get most of them, it’s from welcome bonuses.

I rarely sign up for a new credit card without a big bonus. And when I see a great opportunity, it’s the best time to strike.

The most critical thing to remember is to make sure you meet the minimum spend. I only missed hitting the minimum spend (and thus missed the bonus) once, and I'll never make that mistake again.

So before we get into four strategies you can use to hit your welcome bonus, let me say this:

Please don’t make any purchases you can’t afford to pay for when the statement comes due – points are never worth paying credit card fees and interest. Also, please don’t spend money to buy things you don’t need to meet the bonus – that’s not worth it either.

#1: Open new cards around planned spending

The ideal time to hit your minimum spend is when you have planned upcoming spending, like a wedding, renovation, or large purchase.

Just be sure to double-check with the vendors that they accept credit cards. Some won’t.

#2: Spend money for your friends and get reimbursed

I have often played travel agent for my friend's bachelor/bachelorette parties or other trips. I would book everyone’s flights in hotels, and they would reimburse me.

It was a big benefit to me, but most of my friends thought it was a huge benefit to them since no one wanted to organize all that information. I was putting 10 or 15 flights on a card earning three points per dollar on travel, plus hotels, meals, etc.

I think I won the deal.

#3: Pay your taxes or send money

Even though I usually say it's not worth it to pay fees to use a credit card just to earn points with welcome bonuses, sometimes the math works in your favor.

For example, if you’re at risk of missing an 80,000 welcome bonus because you’re $1,000 short on the minimum spend, paying the $30 in fees is probably worth it for a bonus that's worth over $1,500.

Two ways I've done this before are paying my taxes by credit card and sending money to my wife or a friend on a platform like Paypal or Venmo. Even with fees as low as 1.85%, I think of this option as the last line of defense for making sure you get a bonus and never use it as a way to earn points on spending.

👫 Maximizing points with a Player 2

You can maximize your credit card points game by playing with your partner, who is often called "player 2" in the credit card world.

The strategies for maximizing points can vary depending on your household needs and your partner’s level of engagement. But if you've been playing the game for a few years and feel like you're no longer eligible for some of the bonuses or maybe you're over your 5/24 limit, then adding a Player 2 can be a great option.

Or, if there's a huge welcome bonus, like when Venture X was 100k, Amy and I will both open the same card to take advantage of it. However, over the long term, we try to eliminate having the same card twice unless the perks, credits, and benefits far outweigh the fee.

Aside from welcome offers, there are a few other strategies to consider for earning points/benefits with a partner:

Complementary programs: you can each choose different loyalty programs to focus on. For example, I have a Marriott card and earn all the Bonvoy points/status, while Amy has a Hilton Aspire and earns all the Hilton points/status.
Alternate cards: one person has a card open for some time, then closes/downgrades so your partner can open the same one and capitalize on bonuses. I know a lot of people that do this to earn Southwest Companion Pass with their partner constantly.

And once you find yourself with points spread across each person, we generally transfer the points between each other so we don't both need to keep an account in every program open. It's easy with Chase, Citi, Capital One, and most hotel programs, but Amex and most airline programs don't allow transferring between people. So remember that if you earn a big Welcome Bonus on an Amex card, you'll need to keep that card open (and keep paying the annual fee) if you want to keep your points active.

Or if you’re active duty military, annual fees for many credit cards are waived (and for your spouse). So you can get all those free night and travel credit perks with no fees (and you can do it twice with a Player 2.

😵 Preventing points from expiring

Credit card points typically don’t expire, but points in hotel/airline loyalty programs often do when there is no activity for an extended period of time.

The easiest way to have activity is to use an airline/hotel card that earns points in the program or to fly/stay. But if those aren't an option and you want to keep the card open, you can also try these:

Credit a rental car to the program
Donate points to charity
Buy a small number of points
Buy something through their shopping portal
Redeem points for a magazine subscription
Transfer points from a credit card to your airline/hotel account

Any of these activities should qualify as activity in your account and push out the expiration date for your points.

✖️ When/how to cancel a card (and not lose points)

If I'm no longer using a credit card I've signed up for, I have to decide whether I keep it. My rule of thumb is that if it has an annual fee, I only keep paying it if the benefits exceed the fee.

However, because canceling a card results in losing it on your credit report, which can hurt your score. So I prefer not to cancel a card when possible (especially if I've had it for a while). So if I'm not getting any value from a card, I try two things first before canceling:

Retention Offers

First, I'll call the issuer to tell them that the card’s benefits are no longer worth the fees. This usually prompts them to provide retention offers.

We tried this with Amy’s Platinum Card® card recently. We called and said, “Hey, the annual fees are high. We’re not getting as much value out of it.” That was true because I also have a platinum card. They offered that if she could spend around $3,000 in the next 90 days, she’d get a 30,000 bonus (which I value Amex points about 2 cents, so $600). It covers the fee, especially if you factor in all the different credits and perks that come with that card.

Downgrading

If the retention offers aren’t worth it, I’ll see if I can downgrade the card to a no-annual-fee option. Many cards have a downgrade path to no annual fee options. For example, the Chase Sapphire Preferred® or Chase Sapphire Reserve® cards can downgrade to the Chase Freedom Unlimited® cards. So you might be able to keep the card on your credit report without paying any annual fees. When I do this, I make a note to put at least one purchase a year on the card to keep it open.

However, if there's no good downgrade option or retention offer, I'll cancel the card, but make sure you don't lose points when you cancel.

Prevent losing points after canceling

When you have an airline or a hotel card, all the points you earn are linked to your hotel or airline loyalty account. So if you cancel a credit card, the points are safe, but you still need to have activity in the account to prevent them from expiring (see above).

But it's different with credit card points (e.g., Chase, Amex, etc.).

All these programs require you to have at least one card active in the program. So if all you have is a Chase Sapphire Reserve® card and you cancel it, you’ll lose those Chase Ultimate Rewards points.

But not all cards at the issuer are the same. While Chase Freedom® cards will keep your points balance alive, you'll need a Chase Sapphire Preferred® Card or Chase Sapphire Reserve® or Ink Business Preferred® Credit Card to be able to transfer your points to airline and hotel programs.

The same is true for Amex; only a handful are eligible for membership rewards. If you are going to cancel a card and you have points, you can make sure you transfer those points out to another airline or hotel partner before you cancel the card.

📊 The best ways to track points

If you have one or two cards (total), it’s pretty easy, but once you get into multiple accounts and factor in airline/hotel programs, not so much.

I’ve used a Google spreadsheet to track all my cards for years. I’ve even shared my template, but I will tell you it’s a completely manual process.

I kept it simple:

The rows for all the different card programs
The columns for different people in your household
For the point values, I defer to The Points Guy’s valuations
I use colors and notes to identify when things expire or need to act on them soon

Alternatively, you can use AwardWallet or The Point Guy app for a more automated process, but neither of them has complete coverage, so you'll still have to do some manual work. One day maybe I'll have to build a better solution.

💰 Make More Money With a Side Hustle

Tue, 27 Jun 2023 07:00:00 +0000

📈 Multiple income streams

First, let's ground the conversation on "What is a side hustle?"

Channeling my inner Nick Loper (🎧 Ep11), a side hustle is doing something else to make extra money outside your regular job. That could be delivering pizza with DoorDash, driving for Uber, or even starting your own side business.

Now you might think, "That sounds like a second job." While both serve the same purpose of putting more dollars in your pocket, a side hustle is more nuanced. I see two primary differences:

A side hustle has more autonomy. Whether it's a recurring gig, one-time thing, or business, you can opt in, whereas, with a second job, you typically commit to an employer's schedule and expectations.
A side hustle is more geared towards finding ways to replace your primary job's income in time-leveraged ways. That could be generating recurring revenue from online content or scaling a business.

Side hustles produce both active and passive income streams.

Let me take a moment to clarify passive income because I think it's often misused. Passive income is not free money; it is income that you generate based on investing your time (or capital) upfront.

If your current actions are generating income, that's active.
If previous actions are generating recurring income, that's passive.

Passive income is rarely immediate, so be cautious of anyone advertising its simplicity and ease.

But that's the ultimate goal, right? Getting paid more for your time already spent.

⚖️ Gigs vs. building a business

I spoke with Paula Pant (🎧 Ep13) about drilling deeper into the makeup of side hustles. She puts them in two subcategories: gigs and businesses.

Gigs

Gigs have become more prevalent, thanks to apps and Uber-like opportunities. It's easy to find jobs or tasks someone will pay you for (e.g., walking dogs, mowing lawns, or delivering food).

The problem is that the gigs have such a low barrier to entry, so you’re vulnerable to market changes, pricing, and availability. You can do them on short notice, but they aren’t scalable or sustainable long-term.

Building a Business

Building a business is a much more scalable option. But it also demands more than simply picking up a side gig.

Most people start solo in one of three primary avenues:

service-based business
physical product-based business
digital products-based, or around content creation

The service-based business is a popular route because it allows you to tap into your existing skills to offer freelancing, consulting, or coaching services. This approach requires minimal upfront capital, provides a faster entry into the market, and leverages your expertise. It's an excellent way to get started and gain valuable business experience.

To test out the consulting side hustle, I decided to set up a profile on Intro.co, a platform that makes it easy for people to book video calls with you. Since I'm eager to try it out (and get a few reviews), I had them set up a 25% off code (HACKS25) for the next 2 weeks.

So, if you want to have a call about your business, side hustle, credit card situation or really anything else, feel free to check it out and let me know what you think. And if you're interested in signing up yourself, you can become an expert too.

On the other hand, the physical product route offers a broader customer base and the potential for greater scalability. This path involves creating and selling physical goods, whether it's through platforms like Etsy or Amazon or even establishing your own direct-to-consumer product company. While it typically requires more upfront investment to create an initial inventory, it opens up opportunities for long-term growth and reaching a wider audience.

A third option worth considering is building a business around content creation and digital products. You can build a blog, podcast, YouTube channel, online course, or even offer productized services. These serve as valuable digital assets that can leverage your time.

With some success, you'll reach an inflection point where you must decide whether or not to scale operations (via hiring or outsourcing). But I’ll save the deeper dive into entrepreneurship for another time.

📏 How to measure opportunities

The purpose of measuring opportunities is to determine whether the side hustle is worth pursuing.

You can start with dollars per hour as a baseline metric. For example, you might come across an opportunity to mount TV stands for $100/hour. While this rate seems great (especially at a 40-hour week equivalent), measuring it this way can be misleading. The gig is limited to how many people need this service or if the appointments impede your day job.

Another way is to hone in on passive or semi-active activities. Visualize your annual income as a pie chart split between passive and active income. Then look for opportunities that are not time intensive instead of high dollar-per-hour amounts.

For instance, let's say you can digitize and organize a local business's files for $1 per file. Instead of manually completing the task, which might equate to an hourly rate of $15, you can invest some time upfront to create an automation process using AI or Zapier. Automating parts of the process can transform a low dollar-per-hour opportunity into a semi-active income stream.

🎯 Finding the right sight hustle

When it comes to gigs, there are thousands of opportunities.

A simple online search might uncover the following:

notary publics
online courses
print-on-demand
service marketplaces (Task Rabbit, Fiverr, Thumbtack, etc.)

Choosing the right side hustle comes down to you. So rather than telling you what to do, I’ll direct you to Nick’s article on 100+ ways to make $500+ in your free time from SideHustleNation, which should help jumpstart the process.

💡 Generating ideas and experiments

You will have some great ideas and some terrible ones for side hustles.

Jen Glantz’s (🎧 Ep61) approach is to monetize her curiosities and passions. She proposes you think about what you are doing on the weekend and build around it. If that isn't enough, talk with someone else to spark inspiration.

Nick Loper's approach is to find problems to solve. He uses a few tactics:

What sucks method - write down everything you do that annoys you, or someone complains about. If it sucks to you, then it sucks to someone else. It also means that if you solve the problem, someone else will find value in it.
Rip, pivot, and jam method - find an appealing business model in another industry, steal it, and pivot it to an entirely new niche. He saw an opportunity to build a virtual assistant review site modeled after a wine club review site that helped people rank wines to buy.
Sniper method - build a business as the go-to person for a super-specific need. Where a general handyperson may take a shotgun approach to home services, you can be the go-to person for flat-screen TV mounting.

I experimented with this podcast as a creative outlet. While I envisioned turning it into something bigger, it started as a podcast and newsletter I could use to share information on topics I care deeply about (how to optimize and upgrade your life while spending less and saving more). In the process, I built a side hustle (now full-time) while getting to ask some of the most amazing people how they do what they do.

While generating ideas is essential, it's more critical that you get started.

In full transparency, there will likely be failures along the way. Don't let it discourage you; operate with an experimental mindset. Being experimental makes dealing with the ups and downs easier and lets you see things opportunistically.

My conversation with Jen proves that your initial idea may not directly lead to success but can lead to many opportunities. She started her first blog in 2011 without any followers. It did not generate any income, but with iteration and consistency, she gained readers, leading to a book deal, freelance opportunities, and ultimately Bridesmaid for Hire.

👔 Talking to your employer

Side hustles can be a valuable source of additional income; however, it's crucial to consider the potential implications from the employers' perspective. In a recent conversation with Codie Sanchez (🎧 Ep119), she highlighted the importance of letting your boss know you have a side hustle.

She’s seen people get fired for not disclosing. While it may not be a requirement in your situation, she suggested you flip the perspective and think of yourself as the business owner.

Ask yourself, “What would you want your employee to do?”

Because in this case, you might see how an employee can be distracted and negatively impact your business. At the end of the day, if your job doesn’t allow it, then pick a different one that allows for entrepreneurial pursuits.

🔑 Consistency is key

It's essential to have consistency with whatever you are building, especially early on. Consider creating a side hustle with an audience attached, like a podcast or newsletter (😁). Even though it might be a little anxiety-ridden, having an audience gives you three benefits:

They will make you more accountable and likely to show up.
They are key to building time-leveraged assets since it takes the same time to produce a video, whether 100 or 10,000 people watch it.
They can follow you to new platforms and help you bootstrap endeavors or projects.

The best trick for building consistency is to set a quit date. Choose a date in the next 3-6 months (or, in my case, several episodes) when you will decide to continue or stop. But only consider assessing once that quit date happens, not before. Focus on executing and creating the habit. It will eliminate the doubts that can creep in daily.

💼 When to go full-time

It can be terrifying, and sorry, there is no one solution, but here are a few ways to look at it

What finally gave me the conviction to go full time on the podcast was realizing that if anyone asked me what to do in my own situation I would say you 100% have to try this full time. So I always suggest either 1) ask a trusted friend what you should do and/or 2) asking yourself what advice you'd give a friend if they were in the same situation.
Identify someone who has already made it in your industry, and ask about the day-to-day structure of their job. From there, you can determine if it matches your expectation or desire.
Let your past be your guide. If you have already successfully started a business or side hustle, you know what it takes to do it again.
Assess whether you can find a different job (if the current one does not work out) or return to the company where you previously worked.
It's also possible to decide not to go full-time, even if the numbers make sense. You may prefer to have a steady income as a backup.
You could also go just for it. I'm not saying you have to... but I'm just saying it could be magical 😜.

🤔 Simplify Decision Making with Razors

Wed, 31 May 2023 07:00:00 +0000

Today, let’s dive into the fascinating world of razors – the powerful mental tools to help make decisions in uncertain situations. I recently had the privilege of interviewing Sahil Bloom (🎧 Ep 116) for the second time.

In this post, I’ll highlight 10 mental razors you can use to make faster, better decisions with professional opportunities, personal growth, and how you spend your time. I’ll also highlight some of the benefits and limitations of each.

Sahil deserves much credit for his extensive writing on this topic, including developing some of the razors I’ll share today. Check out his newsletter: The Curiosity Chronicle, which shares two posts a week to build a high-performing, healthy, wealthy life.

🪒 What is a razor?

A razor is a guiding principle or rule of thumb that aids decision-making when faced with uncertainty. It draws its concept from shaving off unnecessary complexity, enabling us to cut through the noise and make clear choices.

Similar to how "life hacks" optimize our routines to overcome overwhelm and inefficiencies, razors simplify decision-making by providing a framework to navigate the complexity and streamline our thought process. They serve as mental tools to help us separate the signal from the noise, allowing for more efficient and effective decision-making.

😀 Occam’s Razor

The simplest explanation is often the best one

Occam’s Razor states that while the truth can occasionally be complex, there is no need to default to convoluted explanations when simpler alternatives exist.

Benefits:

Save time and energy: By embracing Occam’s Razor, you can efficiently identify the simplest explanation, saving precious time and conserving mental energy. Instead of getting caught up in many potential explanations, you can narrow your focus to the most straightforward and likely solution.
Avoid mistakes and false information: Occam’s Razor protects against being misled by false information. By prioritizing simplicity, you become less prone to errors and less likely to be swayed by misleading data. This razor also safeguards against latching onto unnecessary assumptions (conjunction fallacy).

Limitations:

Simplicity doesn’t always equate to accuracy: While Occam’s Razor favors simplicity, it is crucial to recognize that the simplest explanation is not always correct. More complex explanations can offer greater accuracy and provide a more comprehensive understanding of a situation.
Potential for limiting critical thinking: Over-reliance on Occam’s Razor can inadvertently hinder critical thinking and discourage asking difficult questions. Jumping to conclusions prematurely, based solely on the simplest explanation, may lead to overlooking more detailed explanations that could provide deeper insights.

By identifying the simplest explanation, you can save time, avoid mistakes fueled by false information, and evade unnecessary assumptions. However, it is essential to remember that simplicity does not always guarantee accuracy and to remain open to more complex explanations when warranted.

🤔 Hanlon’s Razor

Never attribute to malice that which can be adequately explained by stupidity

Hanlon’s Razor offers a powerful tool for understanding and resolving conflicts, particularly in the digital realm, where common misinterpretations occur.

Benefits:

Foster understanding and forgiveness: Hanlon’s Razor encourages us to adopt a more compassionate and forgiving mindset. Instead of immediately assuming malice, we consider the possibility that others may be acting out of incompetence or ignorance. This shift in perspective cultivates patience, understanding, and a greater willingness to let minor issues slide.
Conflict resolution: We can effectively defuse conflicts by applying Hanlon’s Razor. Rather than responding defensively or with hostility, we approach disagreements with a more empathetic and open mindset. Understanding that someone’s actions may stem from incompetence or ignorance enables us to seek peaceful resolutions and build harmonious relationships.

Limitations:

Potential for justifying improper behavior: Hanlon’s Razor should not be used to justify rude or inappropriate behavior directed towards us. While incompetence or ignorance may be valid explanations, it is crucial to establish healthy boundaries and address unacceptable conduct appropriately.
Avoidance of personal responsibility: It is essential to avoid using Hanlon’s Razor as an excuse to evade accountability for our actions. While incompetence or ignorance may contribute to mistakes, we must still acknowledge our role and strive for personal growth and improvement.

Hanlon’s Razor emerges as a valuable razor, preventing misattributing others’ behavior to internal motivations when external factors are at play. Applying Hanlon’s Razor empowers us to navigate interpersonal dynamics with greater empathy, fostering healthier relationships and personal growth.

😁 Optimist Razor

When choosing who to spend time with, prioritize spending it with optimists

The Optimist Razor recognizes the positive impact of the optimists mindset on outcomes. In a world where pessimists sound smart, the optimists seem to be the ones getting rich.

Benefits:

Enhanced well-being and positivity: Spending time with optimists naturally uplifts our spirits and instills a sense of well-being. Optimists radiate positive energy and tend to attract favorable outcomes. By aligning ourselves with their optimism, we increase the likelihood of positive experiences and a brighter future.
Success through persistence: The Optimist Razor aligns with the common trait of successful individuals—persistence (remember Burn the Boats?). By surrounding ourselves with optimists who inspire us, we reinforce our persistence and increase our chances of accomplishing our goals.

Ask yourself:

Who do you feel good when you’re around?
Who do I get energy from?
Who makes me happy and feel good to be around?

Limitations:

Acknowledge personal biases: While the Optimist Razor offers a valuable tool for self-improvement, it’s important to remain realistic and aware of our biases. Our inherent biases sometimes lead us to favor the most positive explanation for a situation, even when it may not be the most accurate. Strive for a balanced perspective.
Importance of addressing negativity: It’s essential not to dismiss or ignore negative aspects of life. Recognizing and addressing negativity enables us to take steps toward improvement and growth. Balancing optimism with a realistic assessment of challenges is crucial for holistic well-being.

Surrounding ourselves with optimists fosters a sense of well-being, fuels our persistence, and attracts favorable outcomes. Seek out those who radiate optimism and positivity, for they have the potential to catalyze personal growth and an enriched life experience.

👔 Look The Part Razor

With two options of seemingly equal merit, choose the one that doesn’t look the part

The Look The Part Razor suggests choosing the option that doesn’t conform to the expected appearance. By opting for the candidate or solution that “doesn’t look the part,” we acknowledge that individuals who have overcome significant obstacles to success often possess more valuable qualities than those who fit the mold perfectly. This razor is attributed to writer, analyst, and former options trader Nassim Nicholas Taleb.

Benefits:

Avoid being deceived by appearances: Embracing the “Look the Part” razor protects you from being fooled by surface-level judgments. Instead of relying on superficial appearances, you learn to recognize individuals who have worked hard to achieve their success, making them more likely to possess the qualities necessary for excellence.

Limitations:

Beware of self-deception: While appearances can be deceiving positively, they can also mislead in the opposite direction. We must recognize that our biases and preconceptions can influence our judgment. Blindly choosing someone solely based on appearances could lead to the wrong option.

You can make more informed choices by acknowledging the limitations of appearances and seeking out individuals who have overcome significant challenges. However, it is crucial to remain aware of the potential for self-deception and understand the context in which this principle may or may not apply. Adopting the “Look the Part” principle empowers you to navigate decisions more clearly and effectively.

💡 Crazy Idea Razor

If someone proposes a seemingly crazy idea and they’re both a domain expert and reasonable, you should take the idea seriously

The Crazy Idea Razor provides a framework for discerning valuable insights from seemingly outlandish ideas. Inspired by Paul Graham, co-founder of Y Combinator, this razor helps people lean into concepts with asymmetric upside potential.

Benefits:

Cutting through the noise: This razor acts as a filter, allowing you to separate the signal from the noise, especially if you attract many unconventional ideas.
Challenging biases: It encourages you to slow down and resist the common bias of dismissing crazy ideas outright. Doing so opens yourself up to remarkable possibilities that may initially seem incomprehensible.

Limitations:

Misjudging assumptions: Evaluating whether someone is a domain expert or a reasonable person can be subjective and prone to misjudgment. It’s crucial to exercise fair judgment without being too harsh or lenient.
Limited perspective: Relying solely on the expertise of others may restrict your ability to fully comprehend the idea’s potential impact, as you may lack the necessary frame of reference or knowledge.

By leveraging this razor, you can navigate the noise, challenge biases, and uncover extraordinary prospects. However, it’s important to exercise sound judgment and remain aware of the limitations, ensuring a balanced and informed approach to evaluating these ideas.

🥊 Man in the Arena Razor

When faced with two paths, choose the path that puts you in the arena—choose the path with real skin in the game.

The Man in the Arena Razor encourages us to choose the path that puts us in the arena – or has real skin in the game. It’s inspired by Theodore Roosevelt’s impactful speech on Citizenship in a Republic. It emphasizes the importance of being an active participant rather than a mere critic on the sidelines. While the arena may seem daunting, it’s where growth, understanding, and success await.

Benefits:

Cultivating understanding and forgiveness: By embracing the Man in the Arena Razor, we shift from judgmental attitudes toward others’ failures to a more empathetic and forgiving mindset. Recognizing that everyone faces challenges and risks in the arena, we develop a deeper understanding of their journey, fostering harmonious relationships.
Boosting courage and fostering success: Fear of failure often keeps us from taking risks and exploring new opportunities. Embracing the Man in the Arena Razor enables us to overcome this fear, empowering us to venture into uncharted territories. By embracing failure as part of the learning process, we unlock our potential for personal and professional growth, leading to greater success in life.
Resilience against negativity: Being in the arena, whether in online interactions or real-life situations, exposes us to criticism and negative feedback. The Man in the Arena Razor demands thick skin and resilience. Responding with empathy and understanding negativity can help diffuse tense situations and foster a healthier online environment.

Limitations:

Not all participants in the arena have good intentions: It is crucial to recognize that some individuals may be driven by self-interest and disregard the consequences of their actions. Discernment is necessary to differentiate between those genuinely striving for growth and those seeking personal gain at the expense of others.

How to take negative feedback?

The internet can be a mean place. The Man in the Arena can attract pretty negative feedback. Sahil suggests that you default to empathy as the healthiest and best way to combat negativity. He points to happiness because happy people don’t intentionally attack others. So, when someone attacks you, something is likely putting them in a tough spot. You can choose to engage; that’s up to you.

We cultivate understanding, courage, and resilience by actively engaging in the arena. Embracing and learning from failures paves the way for personal growth and success. Choose the arena, embrace the challenges, and let the journey toward growth and achievement begin.

📈 Uphill Decision Razor

When faced with two options, choose the one that’s more difficult in the short-term

The Uphill Decision Razor is a powerful tool guiding us to choose the option that presents greater difficulty in the short term. This principle recognizes that opting for the tougher path often leads to substantial rewards in the long run. Sahil references Naval, who emphasizes overcoming our instinctive aversion to discomfort.

Benefits:

Develop skills and knowledge: Opting for the more challenging option pushes us to stretch our abilities and expand our knowledge base.
Long-term success: Embracing short-term difficulties cultivates resilience and perseverance, ultimately positioning us for greater success in the long term.

Limitations:

Grind and frustration: Choosing the harder path can be mentally and emotionally taxing, especially when results aren’t immediately apparent.
Working hard vs. working smart: Blindly opting for the challenging option may hinder us from exploring smarter and more efficient approaches, potentially wasting valuable resources.
Beware of pride: Ego-driven decisions to prove ourselves by taking the difficult path can cloud judgment and impede progress.

The Uphill Decision Razor emphasizes the value of hard work and resilience. We pave the way for long-term success and personal growth by embracing short-term challenges. However, it’s important to strike a balance and remain open to alternative strategies when warranted.

🍀 Serendipity Razor

When choosing between two paths, choose the path with a larger serendipity surface area

The Serendipity Razor is a razor that proposes that you choose the path that has the greatest serendipity to increase your chances of valuable opportunities. It is based on the idea that the more people we meet, the more experiences we have, and the more we learn, the more likely we are to come across something that will help us achieve our goals.

Benefits:

Expanded network: By actively seeking encounters with diverse individuals, we broaden our network, opening doors to new collaborations, insights, and opportunities.
Fresh knowledge and ideas: Exposing ourselves to new experiences and ideas enrich our perspective, sparking creativity and enabling innovative thinking.

Limitations:

Time and effort: Pursuing serendipity can be time-consuming and effort-intensive. It requires dedication to engaging with new people, seeking novel experiences, and continuously learning.
Timing and focus: Serendipity is particularly impactful during the early stages of life and career, as we aim to expand our “luck surface area.” Once we identify the most promising areas, shifting our focus and delving deeper into specific opportunities is beneficial.

The Serendipity Razor is a valuable mental model that enhances our chances of success by intentionally positioning ourselves for fortuitous encounters. However, it’s important to recognize that it’s not a guarantee of success and requires dedicated effort and time to put into practice. We unlock new connections, knowledge, and pathways to achieving our goals by embracing serendipity.

🤝 Rooms Razor

If you have a choice between entering two rooms, choose the room where you are more likely to be the dumbest one in the room

The Rooms Razor urges us to seek out environments where we feel uncomfortable and potentially find ourselves as the ‘dumbest’ person in the room. Deliberately placing ourselves in such situations opens doors to remarkable growth and learning opportunities.

Benefits:

Active listening: Being surrounded by smart people encourages us to pause our own voices and genuinely listen, leading to valuable insights and new perspectives.
Expanded luck surface area: Placing ourselves in rooms where growth is most important expands our potential for serendipitous encounters and fortunate breakthroughs.

Limitations:

Imposter syndrome and discomfort: Overcoming imposter syndrome and embracing discomfort can be challenging, as it requires us to confront inadequacy and push beyond our comfort zones.
Initiating interactions: Approaching individuals randomly in social settings can be daunting, even for those who thrive on social interactions. However, developing a networking strategy can help alleviate initial unease.

How to navigate networking as the ‘dumbest’ person in the room?

Ask thought-provoking questions: Instead of generic inquiries, ask individuals, “What are you most excited about right now?” This question fosters personal connections and opens the door for deeper conversations beyond the typical surface level. But by becoming an interested individual, you help steer the conversation for everyone else.
Share personal interests: Discussing topics such as family or hobbies creates common ground and facilitates more engaging and meaningful interactions.
Steer conversations to add value: Identify areas where you possess unique knowledge or expertise and steer the conversation toward those subjects. Adding value to the discussion establishes yourself as an interested and valuable participant.

The Rooms Razor propels us towards growth and personal development by immersing us in uncomfortable environments. By embracing discomfort and seeking out rooms where we may be the least knowledgeable, we embark on a transformative journey of learning and expansion.

⏳ Time Billionaire Razor

When choosing between two paths, choose the path that places the highest appreciation on the value of your time

The Time Billionaire razor is a principle that emphasizes the importance of valuing and maximizing your time. It shifts the focus from monetary wealth to recognizing time as our most precious resource. Introduced by Graham Duncan, this concept highlights how individuals often fail to appreciate the value of their own time until it slips away.

As Sahil describes it, the essence of being a Time Billionaire lies in the awareness of the fleeting nature of time and finding fulfillment in the ordinary moments of daily life.

The American Time Use Survey provides a powerful visual representation of how people allocate their time throughout their lives. It serves as a reminder to consciously decide how we spend our time and with whom we choose to invest it. More importantly, it urges us to reflect on these findings and make deliberate choices that deviate from the patterns indicated by the data.

By embracing the Time Billionaire razor, we can gain a new perspective on the value of our time and proactively shape our lives to align with our priorities and aspirations.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Editor’s Note: Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

🤝 Mastering the Art of Negotiation

Fri, 12 May 2023 07:00:00 +0000

There is so much to cover in negotiation, but I want to focus on providing some tactics to help you become a better negotiator. In 2021, I interviewed Kwame Christian (🎧Ep 17) on mastering the art of negotiation. Among many accolades, Kwame is the founder and CEO of the American Negotiation Institute and host of the Negotiate Anything podcast. We uncovered common negotiation mistakes, identified better questions to ask, and broke down his compassionate curiosity framework to make negotiation simpler and more effective. You can use many of the lessons here for all the negotiations of daily life.

Today’s posts are the key lessons I learned from Kwame and other strategies and tactics from Chris Voss and Andy Rachleff.

Here’s what you can expect to take away from this newsletter:

Understanding the keys to better negotiating
How to use the compassionate curiosity framework
The importance of labeling and mirroring
How to prepare, even if you only have 3-minutes
The power of anchoring
When to walk away

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🗝 Key to Better Negotiations

Negotiation is an essential skill that can help you save money, increase earnings, and improve relationships. Many people struggle with it because the process is intimidating. The problem is they think about negotiation from the lens of what they need to say or how they say it. Instead, negotiation is more about listening and asking insightful questions.

You’ll get better results if you listen more and ask better questions.

🤔 Compassionate Curiosity

Negotiation is a logical game tied up by emotion. Even the most well-crafted arguments and statements won’t land if the person on the other side is in the wrong mental place to appreciate what you’re saying. It’s because you’ve done such a poor job of managing the emotional side of the conversation.

This is why Kwame created the Compassionate Curiosity framework, which can be used in highly emotional and challenging workplace and home conversations.

It’s a 3-step framework:

Acknowledge and validate emotions
Get curious with compassion
Joint problem-solving

You seek to hone in on emotion by asking open-ended questions, summarizing what’s being said, demonstrating understanding through empathy. Repeat steps 1 and 2 until emotionality reduces; only then can you transition into more substantive problem-solving conversations.

Here’s what this framework achieves:

Reduces that emotional distress at the beginning so that people can discuss at a higher level
Gathers more information in a compassionate tone so people don’t get afraid to share information
Creates an environment to work with the other side to figure out what works

This framework relies heavily on active listening, fully engaging with the other person’s perspective and emotions. It’s crucial because active listening builds trust and rapport.

🏷️ Labeling

Labeling is one tactic you can use in line with the Compassionate Curiosity framework. In his book, Never Split the Difference, Chris Voss talks about the power of labeling because it names the other person’s emotions to show that you understand and acknowledge their position.

Here’s how it works in practice:

Let someone talk in an emotional situation, rant, or aggressive discourse. When it’s your turn to speak, label.

Detect the other person’s emotional state
Summarize what they say and follow it with
- “It seems like…”
- “It sounds like…”
- “It looks like…”
Be quiet and let the other person talk

If your label is correct, they will agree and feel heard. If your label is wrong, they will correct you, and you lock in on the right emotion.

Here’s an example of negotiating a salary increase with your boss, but your boss is hesitant to give you the raise you’re asking for:

You: I’ve been consistently outpacing my quota and taking on additional responsibilities; I’d like to talk to you about a raise.
Your boss: I know you’ve done a great job, but I’m not sure now is right with our tight budget.
You: It seems like you’re concerned about the budget and whether we can afford to give me the raise I’m asking for. Is that right?

Labeling their concern about the budget shows that you understand their perspective and acknowledge their position.

Your boss: Yes, we are currently under some budget constraints.
You: I understand that budgets are tight right now, but I think my contributions to the company justify the raise I’m asking for. Can you help me understand what budgeting constraints you have and how we might be able to work around them?

By labeling your boss’s concern about the budget, you’ve diffused any potential conflict and shown that you are willing to work with them to find a mutually beneficial solution.

📣 Mirroring

Where labeling makes someone feel understood, mirroring encourages someone to keep talking so you can gather more information. It’s another technique that Voss recommends, and it is the process of mimicking body language, tone of voice, and word choice to demonstrate similarity and connection. When negotiating, Voss says you should only focus on mirroring words.

To use it effectively, repeat the last three words (or the most critical three) the person just said. By doing so, they will keep talking to maintain the connection with you.

Mirroring works so well because it taps into the human tendency to like and trust people who are similar to us. When we see someone who behaves similarly, we tend to feel more comfortable and open with them. This is known as the “liking” principle in psychology, which states that people prefer and be influenced by people they like.

Don’t just mimic everything; you want to mirror enough to show that you pay attention, but not too much that it comes across as insincere or manipulative.

Here’s an example of using mirroring to uncover more details about what your potential client is willing to spend before sharing the price:

Client: We have a limited budget and want to get the most out of it.
You: Limited budget?
Client: We don’t want to spend more than $10,000 and want to ensure we’re getting the best value.
You: Is getting the best value your top priority?
Client: Yes, we care about value more than anything, even more than the timing of completion.

In this example, you learned about the $10,000 and that the client cared more about getting value on price than the timing.

This technique can uncover critical information, keep the negotiation going, and give you more opportunities to reach a mutually beneficial agreement.

✍️ How to Prepare

Preparation is the most crucial step in the negotiation process. When stressed, your body produces cortisol, a stress hormone that makes it difficult to think clearly. You must be sharp in negotiations, and cortisol prevents this.

Try role-playing as a part of your preparation:

First, role-play as the person you’re going to talk to because you’ll start hearing yourself making arguments you never thought of before, which forces you to find validity and legitimacy in their statements.
Second, role-play with a partner, colleague, or friend pretending to be the other party, and focus on what you fear most in the conversation. Start by sharing exactly what you’re afraid of. Ask your partner to ramp up the level of emotion to an unrealistic level but within the boundaries of the conversation.

You’ll be beyond prepared whenever you have the actual negotiation.

If you want access to Kwame’s negotiation prep guide, you can find it here.

The 3-Minute Prep

Sometimes, you don’t have days to prepare. That’s okay; try this 3-minute process.

Ask yourself:

What do I want and why?
What do they want and why? (Use your best guess, verify during the conversation)
What are all of the open-ended questions that I could ask?

❓ Open-ended Questions

Knowledge is power and power in a negotiation is leverage. The most valuable information is only found within their mind. So no matter how many Google searches or AI-powered prompting you do, open-ended questions are a necessary tool.

Ask open-ended questions because it creates that narrative response and leads to more explanation.

In transactional negotiations (like trying to get a hotel upgrade or reduce the price of a car), Kwame’s favorite is “What flexibility do you have?” It’s open-ended; it contains the assumption that there is flexibility, and it’s non-threatening.

Another powerful open-ended question is one that doesn’t even end in a question mark, “Tell me more about this” or “Help me understand that.”

The goal is to get the other person to expand and share their thoughts with as many words as it takes to get there.

🙊 Talk Less

Kwame uses the 70/30 rule: Listen 70% of the time, talk 30%.

If you let people talk about things they enjoy, it creates dopamine in their system, and they’ll associate positive feelings with you. It builds more trust and becomes self-fulfilling because they feel better about themselves. They start to like you more during the process, become more vulnerable, and provide excess information.

⚓ Anchoring

Anchoring is a negotiation tactic involving setting a reference point by making the first offer (price, deadline, etc.). The first offer serves as the “anchor,” which the rest of the negotiation revolves around. It works well because people tend to rely on the first piece of information they receive when making decisions. You can shape the other person’s perception of what’s reasonable and increase your bargaining power.

Here’s how anchoring can impact our decision-making, even when the anchor has no real relevance to the situation at hand:

Dan Ariely is a behavioral economist who conducted a famous study on anchoring at MIT. In the study, he asked participants to write down the last two digits of their social security numbers and then asked them to bid on various items, such as wine and chocolate.

The participants with higher two-digit numbers ended up bidding significantly more for the items than those with lower two-digit numbers. This is because the higher numbers served as an anchor point for their bids, even though the numbers had nothing to do with the actual value of the items being auctioned.

In negotiation, anchoring has the same psychological impact. But making the first offer might not always be in your best interest. Here’s Kwame’s rule of thumb:

If you have as much or more information as the other side, you make the first offer.
If you have less information, you let the other person make the first offer and then counter because every offer has to be substantiated by information, and that’s how you learn.

How to defend against anchors?

Now that you know about the power of anchors, you will have to defend against them. Sometimes, people will throw out an anchor and try to read your body language and see how you’re responding to it. When the anchor is outside the range of possibility, you should clarify that it’s not in the range of possibility so the negotiation doesn’t continue to revolve around it.

Once the anchor is dismissed, Kwame suggests acting as if it was never even said because the more you talk about the anchor, the more legitimate it becomes and crystallizes in everyone’s mind.

That means that when you’re the one doing the anchoring, it’s best to find creative ways to anchor repeatedly so the other party will increasingly get comfortable with it the more you mention it.

If you aggressively receive an anchor, your reaction might be to attack the anchor. When you attack, the other person must defend it, forcing them to argue why that anchor is valuable and relevant.

This creates a psychological entrenchment scenario and makes the anchor even stronger. You want to shift the conversation away from the specifics of the anchor and instead try to figure out the rationale behind it.

🤝 Negotiating with Trust

One of the best lessons I’ve learned from legendary investor Andy Rachleff (🎧 Ep 19) wasn’t even on investing; it was negotiation. His usual tactic takes a different approach to anchoring. He prefers to give the other party your trust by telling them to “make me a fair offer, and I’ll take it.” Most people don’t want to be thought of as taking advantage of you, which means rarely will someone offer something unfair. If they make an unfair offer, you can always walk away, which is why he often describes this tactic as: “Put the gun in the other person’s hand. If they fire, you don’t work with them.”

I’ve used this tactic countless times, and it’s become my go-to for negotiatin. The only situation where it doesn’t work well is when you’re negotiating with someone with much less information about what might be fair. In that case, I usually share my information with them. For example, I’ve shared market compensation data with prospective employers and asked them to make an offer that’s fair to the market. I’ve also been on the other side of a hiring situation for some freelance work and given similar market comp data to someone and just asked them to let me know a fair rate for their work.

So far, I haven’t come across an unfair person, but I usually don’t like working with people that try to take advantage of others, so in a way, this tactic is also a great way to filter out people you might not want to work with in the first place.

🚶 Walk Away

Walking away is an art and a science.

When to Walk? It depends on how much you need the deal and how much time you have to close it because there’s an opportunity cost to continue. Kwame suggests having a defined stopping point to avoid wasting your time in a negotiation.

However, disclosing your stopping point can be risky because it can weaken your position. It is generally not recommended unless you have strong leverage or are confident that the other party will not take advantage of the information. If you are at a stalemate, disclosing your stopping point may encourage the other party to be more flexible in their offer.

Sometimes the worst outcome is a deal that should have never happened.

How to Walk? Don’t just throw your hands up and say, “I’m never coming back.”

Instead, try this (from Kwame):

“Based on the way the circumstances are right now, this isn’t a deal that could work for me/us…But if anything changes on your end [person’s name], let me/us know, and we would be more than happy to continue the conversation. And similarly, if anything changes on my/our end, we’ll do the same.”

You don’t want anyone feeling like a loser in a negotiation. You’ve given both yourself and the other side an out. If a party was bluffing, they could now use the excuse of more information to continue the conversation without losing dignity and respect. And if things legitimately changed, then the door is still open.

👪 Compassionate Curiosity & Family

Funny enough, a lot of what I shared above is also relevant at home. I have two young children…and my oldest daughter is at a point where the negotiations have started. For the parents reading this, I want to share an example where Kwame used compassionate curiosity with his son, who didn’t want to go to bed.

Kwame: It sounds like you don’t want to go to bed right now.
Kai: No, I don’t want to go to bed.
Kwame: Okay. That makes sense. Can you tell me a bit more about that?
Kai: I don’t want to go to bed right now. I want to stay up, and I want to cuddle with you and Mommy on the couch and watch TV until it gets later, until you all go to bed.
Kwame: So, it sounds like the reason you don’t want to go to bed is because you want to spend time with me and Mommy, is that right?
Kai: Yeah.
Kwame: That makes sense; we like spending time with you. So what is it about going to bed that’s important?
Kai: I have to go to bed, so I can get smart.
Kwame: Okay. What else is good about getting sleep?
Kai: Well, if I go to sleep, then I could grow up and be big and strong, like you.
Kwame: So, what do you think we should do right now?
Kai: I should probably go to sleep.
Kwame: Okay. Sounds good; I’ll see you later.

Using this framework helps Kai think for himself and develop his conclusions. As parents, your voice becomes the internal monologue for your children’s decisions, so instead of being the judgmental father, Kwame wanted to be compassionately curious.

Sometimes negotiations don’t go how you want them to, especially with your kids.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

0️⃣ Die With Zero: Net Fulfillment Over Net Worth

Fri, 05 May 2023 07:00:00 +0000

Advertiser Disclosure

Note: American Express is a ChrisHutchins.com advertiser

For decades, I tried to optimize and save money to build my net worth, believing it was the right way to achieve success. That was until I interviewed Bill Perkins (🎧 Ep 91) and read his fantastic book Die with Zero. Bill is a long-time hedge fund manager who challenged traditional financial advice by suggesting to maximize your net fulfillment instead of your net worth. After reading his book and talking with Bill, my view on money changed a lot.

Do I still think about net worth? Sure, but I’ve gone back multiple times to listen to the episode and review my book notes to remind myself to focus on the right things.

Today’s posts are the key lessons I learned from Bill:

What does ‘die with zero’ mean
Why the utility of money declines over time
Why time bucketing is more effective than bucket lists
Why you might consider banking memory dividends
Why health is a forcing function

Please share this post with a friend, colleague, or family member that would find this valuable.

📢 Join Our Membership

We’re building a community!

Think AARP for a younger demographic that loves deals, travel, and experiences.

Right now, I host a monthly members-only call and am about to invite all members to a private online community for discussions, questions and where you can connect with other members.

But a huge ambition of mine is to secure a set of incredible perks and deals for members. Think The Platinum Card® from American Express or Chase Sapphire Reserve® perks, but not tied to a credit card. While it’s still early, we’ve already set up two member-only deals:

50% off the CardPointers Pro membership, my favorite app for managing credit cards and shopping offers. (If you don’t want to join, that link will still get you 30% off)
50% off Trust & Will services, which we used ourselves to create and manage your estate plans and will

It’s a growing community with many ideas, including one member who wants to start a book club.

Join the other 146 members today:

Join Now

💰 Are you optimizing for money?

Here’s a test: Would you switch positions with Warren Buffet right now?

He’s 92, with billions of dollars.

Bill Perkins asked this same question to a bunch of 20-year-olds.

They all said no.

I bet you’d say no too.

Which means you’re optimizing for something other than money. Let’s dive a bit deeper into what you’re solving for.

😄 What does “Die With Zero” mean?

The Die With Zero philosophy emphasizes spending one's savings on enriching experiences to ultimately reach a balance of zero rather than working to build and die with wealth.

If you look at money as the means to enjoy life to the fullest, then the remaining balances in your account are wasted opportunities. It does not mean you should spend every paycheck immediately. It’s to be more thoughtful and forward-looking with your life planning and calming the fear that you’ll run out of money in retirement. It also doesn’t mean you shouldn’t leave money to your children or charity, it just suggested you might get more fulfillment making those gifts when you’re still alive and can see some of the impact.

As you read this, you may find yourself aligning more with net fulfillment over net worth (or maybe you already do). But it goes against the work culture in many countries. We have been conditioned to want more money, success, and status, making it easier to sacrifice for a higher-paying job.

Culture evolves slowly. And because it’s slow, it’s easy to backslide to autopilot mode of solving for net worth.

Net fulfillment demands a different approach to life. It requires you to:

Think deeply about what you want out of your life
Consider how your money and career decisions enable that life
Take risks and execute against the grain of culture and in line with the life you want to live

📉 Money has a declining utility

I don’t want to say money has less use to us as we age, but it does in many ways. When your physical and mental abilities decrease, your ability to enjoy specific experiences also decreases.

It means some of the experiences you were hoping to do when you are older won’t happen. The utility of money declines over time, whether for travel, leisure activities, or even life milestones.

Here’s what I learned from this:

Prioritize taking certain trips now over later. For example, if I had waited until I retired to see all of what Japan has to offer, I would not have nearly had the same experiences.
Do certain leisure activities now while I’m healthy. At some point, it will be the last time I ever snowboard. I hope not for a long time, but my body will eventually prevent me from enjoying it.
Celebrate significant milestones earlier than they occur. Bill celebrated his 50th birthday party when he was 45 because he knew he would get more out of it by doing it earlier.

Bill taught me to think about “what” experiences fit in my life and then determine “when” those experiences should happen.

🧠 Memory Dividends

You want to spend your wealth, health, and time to get the maximum fulfillment.

When you save money, that money is attached to some future experience.

And when you engage in that experience, it brings you joy. But you also get the joy when you recall that experience. That original experience is paying you memory dividends every time you relive it.

This is why you should consider experiences earlier because the experience plus the memory dividends add to the net fulfillment equation.

If you want proof of the power of memory dividends, rewatch your wedding video or the photo memory albums your iPhone or Facebook sends you. There is a sense of joy at the moment that you relive the experiences of the past and experience those memory dividends.

⌛ Time Bucketing

There are bucket lists, and then there are time buckets.

Bucket lists are the sum of experiences you want to do before you die
Time buckets are the windows for when you want those experiences in the future

Small but important difference.

Rather than just creating a list of things you want to do before you die, consider bucketing them on a timeline based on when they’re best suited to happen.

Here are a few examples:

Backpacking around the world and sleeping on people’s couches is probably better suited for your 20s when you have a lifestyle with lesser responsibilities.
Taking one trip to Las Vegas in your 30s instead of a few smaller trips to Atlantic City in your 20s might be the better choice since you’re more mature and can handle the ups and downs better.
Playing golf at Pebble Beach for a work retreat might be better in your 40s and 50s because you can afford the upgrades and go all out on the experience.

As you age, you may shift into a different bucket with experiences better suited for that season of life.

🗓️ Advanced Planning

I asked Bill, “How far in advance should you bucket your experiences?”

The answer depends on age and how far you can see into the future.

When you’re young, you can break your life down into smaller periods, like 5 years.
With age, your visibility into the future may become less clear, so you may need to increase the increments to 10 years or more.

My approach is in the middle because we have 2 kids under 3. I know how quickly they grow, so breaking it down into small periods might be over-planning. Right now, I’m thinking of my time buckets as follows:

Younger kids
Older kids
Kids out of the house

⌛➡ 💵 Converting Time To Money

If you are worried about money, experience what it’s like to make money without a job.

I mean, actually, go and do it.

I signed up as a Lyft driver a few years ago to see what happened.

I learned two valuable lessons:

It was rewarding to realize I could convert time to money at any moment
It put a threshold on what my time was worth

Bill took a different approach. He went panhandling. He earned the equivalent of $54,000 per year with the bare minimum effort.

The point for me was knowing there is a downside was freeing. Losing my job no longer meant $0. With little effort, I could convert my time to money. But I’ve burned the boats to go all-in on the podcast, so no more Lyft for me.

💵 ➡⌛ Swapping Money For Time

While I proved (to myself), it’s easy to convert time to money; sometimes my optimizer brain makes it hard to spend money to save time. But it is one of the best ways to make decisions aligned with net fulfillment.

The trick is to think about what you buy or do as units of time.

Condense each hour to some value so you can make the tradeoff decision:

Is eating this cookie worth 1 hour on the treadmill?
Is buying that pair of jeans worth 2 hours of work?

This applies to the more challenging questions too:

Does accepting a job with lower pay but a four-day workweek give you more fulfillment time than the one with a higher income and five days a week?

I have made strides in this area recently. I hired an incredible executive assistant from Oceans to help support me with the podcast and our family with all kinds of other tasks (travel, coordinating service providers, grocery orders, etc.). It has been a total game-changer. I’ll share more on this in a future newsletter, but so far, I couldn’t recommend Oceans more highly if you’re looking for any help in work or life.

💪 Health as a Forcing Function

Health plays a significant role in the timing. How your body and mind deteriorate as you age can affect your enjoyment of certain activities.

Being healthier and living longer is one of the best ways to extend net fulfillment.

Bill invests heavily in health (time, research, and money).

80% of your opportunity is in low-hanging fruit

Eating healthy and reducing processed foods and sugar
Exercise and maintaining a healthy weight
Don’t smoke

The other 20%…

It’s a topic for another day, but we briefly discussed the importance of diagnostics because early detection improves the chances of survival and outcomes for many fatal diseases.

Here are the 3 examples:

Inside Tracker. They give individuals an idea of their optimal ranges based on their genetics and inner age. They’ve been a sponsor of they’ve for a long time.
Grail test. This test can detect cancer early, allowing for prompt treatment before it progresses. Individuals at high risk, such as those with a family history of cancer, can benefit from these tests. I haven’t done this yet, but with a friend recently having a cancer scare, I just emailed my doctor to do it.
Full-body MRI. It can detect diseases and conditions before symptoms appear. Individuals with a family history of certain conditions may find this technology particularly useful. I did mine test with Prenuvo, and while they’re not a sponsor/partner, they said they’d offer you all $300 off with the code ALLTHEHACKS (though it might take a day or two to get loaded into their system) and I’ll also try to update this link to forward to the discount as well.

👋 How I’ve Implemented Net Fulfillment

Many of you know my financial path has been influenced by the FI/RE movement (Financial Independence Retire Early). My approach to money was save, save, save. And while I am grateful for the cushion it’s provided, I’ve been thinking about how greater my net fulfillment meter would be if I spent more on experiences in our 20s/30s.

The idea of net fulfillment impacted me so much that I included it in my Top Learning of 2022. In that post, I listed 3 important changes I wanted to make.

Here’s an update on that progress:

Life Change #1: Amy and I need to start thinking about the experiences we want in our 30s, considering that our kids will never be this young again and that these are the last few years of our 30s.

Update: This year, we’ve prioritized shorter local trips that will be much more enjoyable with kids, hoping to take one trip without the kids in 2023.

Life Change #2: I’m going to be more intentional about taking more photos and videos as we experience life so we can “harvest the dividends” of our memories in the future.

Update: We’ve tried hard to take a few family photos (nothing fancy, just using a tripod), and they’ve turned out great. We also started using iOS shared albums which have really unlocked the sharing of photos between Amy and me (which is an instant 2x to the memory dividends 😊)

Life Change #3: It's time for me to start making decisions in life that maximize my fulfillment. During our recent trip to Europe, we didn't make the best use of miles or find any hotel deals, but we still went because we wanted to have the experience at this point in our lives.

Update: We hired an executive assistant to help with work/family projects, and we’ve been much pickier about travel. No more multi-layover trips like we did back in our 20s.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

🇮🇹 How to Travel to Italy Like a Pro

Fri, 28 Apr 2023 07:00:00 +0000

Today we’re talking about one of the counties at the top of my list to return to: Italy. Based on the number of emails I’ve received, Italy is also among the top of yours. I went with Amy back in college, but that was 20 years ago. To help think about a trip to Italy, I spoke with my good friend Leigh Rowan (🎧 Ep 107). Leigh runs a travel company, Savanti Travel, and has visited Italy 40+ times. Today’s newsletter will tell you where to go, what to do, and how to do it.

This is my second blog on traveling to a specific country. I received great feedback about the first one (Japan), so let me know what you find these types of posts valuable. And if you have been to Italy or planning a trip, please share your thoughts with me too!

🇮🇹 Italy: Overview

Everyone knows Italy is where one can enjoy great food, wine, and coffee, but more than that, it’s a country all about enjoying life. The Italian lifestyle is focused on the present moment. No hurrying. No rushing. No constant need to be busy. The people are out and about, strolling from cafe to cafe, being social, and enjoying Italy’s rich culture and beauty. It’s so ingrained in the lifestyle that this stroll (a traditional passeggiata) happens every evening.

“The thing that makes me feel most at home in Italy is that the Italians know how to live. They know how to live life, great food, wine, and coffee. But more than all of that, it's just this continual enjoyment of life.” -Leigh Rowan

🗺️ How to Approach Italy

Italy is the 5th most visited country in the world, with 60+ million visitors and 20 distinct regions to explore.

It can be overwhelming for first-time visitors with so much to see and do. Don’t worry about seeing everything in one go because there are more museums, churches, and sites to visit for a lifetime of trips to Italy. Consider your energy levels and aim for rest and relaxation activities.

Keep it simple (especially if it’s your first trip):

Start with Rome: Rome is known as the Eternal City because of its rich history and ancient monuments, like the Colosseum, the Roman Forum, and the Pantheon. These sites are some of Rome’s most popular tourist destinations and offer a glimpse into the city’s ancient past.
Visit Northern or Southern Italy: Northern Italy, including places like Venice, Milan, and the Italian Alps, is known for its stunning architecture, beautiful landscapes, and world-renowned art museums, such as the Uffizi Gallery in Florence. Southern Italy, including places like Naples, the Amalfi Coast, and Sicily, is known for its beautiful beaches, coastlines, architecture, and delicious food, particularly pizza and seafood dishes.

You might want to think about revolving your trip around one aspect of Italian life: food, art, history, or culture. Draw inspiration from travel shows, books, blogs, and social media to get ideas of what aspect you want to experience on your trip. Then focus on the places that best support that aspect. The next time around, select another.

🚗 Navigating Within Italy

Taking the train is often the most convenient and reliable way to travel from city to city. Train tickets can be purchased in advance; the cheapest rates are typically available between 30 and 60 days out.

Buses or private cars may be better for exploring the countryside. Renting a car can also be an option, but driving in Italy can be challenging because you’ll probably be going too slow, and the roadways are very small. The medieval streets were designed for cows and sheep, not humans or cars.

Flying within Italy is a manageable option for travel between cities, but it’s often a no-frills experience. Companies like Ryanair, EasyJet, and Vueling have many flights departing from major cities. While the option for business class may exist, it’s an economy seat with a blocked-off middle seat on many flights. I’ll make a note of one to avoid: ITA Airways. It’s the resurrection of a now-defunct airline notorious for its delays.

⌚ Best Time To Travel

There’s no wrong answer; it depends on what you want to discover.

Peak Season (June - August):

This is the busiest time to travel in Italy, with the largest crowds and the highest prices. The weather is generally warm and sunny, making it an excellent time for outdoor activities and beach trips.

Visit famous attractions like the Colosseum, the Vatican, and the Pantheon, but be prepared for crowds and long lines. You can also visit the Catacombs or the underground sites of Rome.
The Amalfi Coast is a popular summer beach destination. You can take a boat tour of the coast to see the scenery from the water or hike the famous Path of the Gods for panoramic views.
Many outdoor events and festivals occur during the summer in Italy.

Shoulder Season (April - May, September - October):

The shoulder seasons offer a good balance between good weather, fewer crowds, and lower prices. It’s a good time to explore Italy’s museums, galleries, and churches. April and May are particularly nice for outdoor activities and sightseeing.

Go hiking in the Italian Alps or the Dolomites
Visit Tuscany’s vineyards during the grape harvest season in September
Attend food and wine festivals such as the Fiera del Tartufo (Truffle Fair) in Alba

Off-Season (November - March):

This is the quietest time to travel in Italy, with the fewest crowds and the lowest prices. The weather can be cold and rainy, but winter sports are popular in the mountains. Many attractions, shops, and restaurants may have reduced hours or be closed during the off-season, so checking beforehand is essential.

Hit the slopes in the Italian Alps or the Dolomites for winter sports. Some popular spots are Cortina d'Ampezzo and Val Gardena.
Visit cities like Rome, Florence, and Venice without crowds.

Attend festivals such as Christmas in the Vatican and Carnevale.

🛵 Guides, Tours, & Meeting Locals

Booking a guide can be a great way to explore Italy, but you don’t have to. There are always free walking tours led by excited people ready to show off their town.

One exciting option is to take a sidecar tour of these different cities. You hop in a motorcycle sidecar while an experienced guide drives you around to explore the historical sites. While most options I saw are solo, there are options for group tours (each traveling in your own sidecar).

If you explore independently, use resources like Context Travel and Airbnb Experiences to see what’s offered in the area. If you Google activities, there are lots to see and do, so leveraging these resources to guide your options can prevent decision fatigue or the feeling of FOMO.

I always talk about the value of meeting locals everywhere I go. Life in Italy is very much about the present moment, but it doesn’t always feel that way in tourist places like the famous Piazza Navona. So if you want to experience locals, meet them where they live. In most of my experiences, locals are proud to show off their city, country, or neighborhood and are interested in where you come from and why you’re in Italy.

🍽️ Dining Expectations, Planning for Meals & Family Naps

Italians usually eat on a different schedule than North Americans:

Breakfast is light. It’s a coffee and a croissant or bread.
Lunch is a big affair. It can last as long as two or three hours.
Dinner takes place late. In the winter, don’t expect anything earlier than 7 pm; in the summer, an “early” dinner might be 8 or 9 pm.

To accommodate this schedule, it’s a cultural norm to take a break (and nap) from 12:30 until about 3:00. On Leigh’s family trips, they take a family nap to make sure they can make it to the late evening dinner schedules.

For restaurants on your must-visit list, it is essential to make reservations in advance. This is especially true for Pierluigi Restaurant (Rome) or Osteria Francescana (Modena). However, I wouldn’t try to plan out every meal to leave some spontaneity as well.

Websites like the Italian Michelin guide, Gambero Rosso, can help you discover great options. Whereas typical guides, blogs, and review sites will tap into the more popular places, some recommendations in Gambero Rosso offer richer and more meaningful experiences and affordable prices.

🇮🇹 Rome

The best way to experience Rome is by adding a mix of must-see tourist places and getting lost exploring places off the beaten track. There is a reason all roads lead to Rome.

🏃 Explore Rome Like the Tourist

The Coliseum, Pantheon, Trevi Fountain, and the Vatican are four of the most popular tourist destinations. Though they can be overcrowded, they are worth the visit, being maintained for over 2,000 years. It’s a good idea to pre-book some of these experiences and look for a unique one-off experience like the Breakfast at the Vatican. This experience allows you to visit the Sistine Chapel before it opens to the public and then enjoy breakfast at the Vatican cafeteria. If you want a more private experience, you can fully privatize your visit but be prepared to pay more.

🚶 Explore Rome Off The Beaten Track

Explore the little villages where Romans live. Have a meal in a piazza where you might be the only person who doesn’t speak fluent Italian. You’ll be welcomed in and eat an incredible meal while experiencing the sweetness of doing nothing that passes by in front of you.

🗺️ Northern Italy

Northern Italy is a region that boasts both natural beauty and a rich cultural heritage. From the enchanting city of Venice to the stunning Dolomite mountains, there is no shortage of places to visit and things to do in this part of Italy. Florence is an 80-minute train ride from Rome which displays a medieval village that is still alive and offers stunning sights, sounds, and food.

Venice attracts millions of tourists every year. Take advantage of St. Mark’s Square, the Grand Canal, and a famous gondola ride. However, the heart of the Veneto region lies not in Venice proper but in the surrounding area. Visit the rich farmlands, the Palladian villas, the stunning mountains, and the canal cities that make this area so rich.

But let’s also talk about other less favored places in the north.

One such destination is Umbria, known as the Green Heart of Italy.

With ancient villages dating back thousands of years, delicious food and wine, and fewer tourists than neighboring Tuscany, Umbria offers an authentic Italian experience that should be noticed.
The annual Corsa dei Ceri festival in Gubbio, where locals carry massive wooden slats with tall columns and saints on top through the medieval town, singing and playing music. It’s a party and a true celebration of Umbria’s history and culture.

Another destination is the town of Rapallo, close to the tourist location of Portofino.

You can use Rapollo as the place to stay, so you can visit popular sites without needing to stay there.
ParlaComeMangi highlights local cheese, salami, and prosciutto, which will be just as impressive (and much less expensive) as one in Portofino.

Northern Italy is a haven for foodies. While the Michelin guide or Gambero Rosso are great places to start, try looking for local places that are not necessarily starred but are still authentic and delicious. You could filter TripAdvisor reviews for the ones from Italian people to get a sense of what’s great or just be bold and ask locals for recommendations. Look for places that have been around for years and are still standing, as these are likely to serve great food that the locals love. Take advantage of the classic Italian coffee, and try the traditional biscuit in Rapallo, called Canepa, or the Espresso with cream from the famous Panella cafe in Rome.

🧭 Southern Italy

The warm and sunny climate makes it a popular destination for beach-goers and sun-seekers; however, the region is also home to numerous historic cities, each with unique culture, cuisine, and architecture. Popular destinations include Naples, Pompeii, and the Amalfi Coast, but here are some other places in the South to check out:

Sicily is the largest island in the Mediterranean Sea and offers a rich history, culture, art, and food.

Agrigento on the west side of Sicily boasts some of the best-preserved Greek temples in the world.
Palermo, located in the north of Sicily, is another must-see destination.
The Aeolian Islands, a chain of islands north of Sicily, offer beautiful beaches, mud baths, and incredible views of volcanoes.

Puglia is a rapidly growing tourist destination located on the heel of Italy.

It is known for its picturesque towns, olive groves, white sand beaches, and the famous ear-shaped pasta called Orecchiette.

It’s less expensive than other regions in Italy, such as Tuscany or Umbria, making it an affordable destination for travelers.

Ischia is a beautiful island across the Gulf of Naples from Capri.

The locals are friendly and proud to show visitors their island, and you can explore it with a rental car, Vespa, or a stylish little vehicle called an “ape.”
Ischia offers a glimpse into authentic Italian culture and is a more affordable alternative to Capri.

Ape

You can’t go wrong with Northern or Southern Italy unless you try to do too much. Instead, embrace and squeeze the most out of the few places you visit. Every town, big or small, has something they are known for. It’s about seeking it out.

✈️ Flights

Many US carriers, like Delta, United, or American, fly nonstop into Rome and Milan from their hubs (including an SFO flight starting next month). But there are other options to consider:

Emirates is the best option for getting to Milan from JFK (especially if you can use your points for business or first).
La Compagnie is an all-business-class airline that flies from Newark to Milan. While you can’t use points or miles, it’s usually much cheaper than other business-class options.
Air Canada also to Rome and Venice from Toronto and Montreal (Rome only).
Neos is Italy’s second-largest airline, with affordable flights to Milan from JFK.
North Atlantic Airways is another inexpensive option from JFK to Rome.

💳 Flights With Points and Miles

There are over a dozen airlines you could fly to Italy on using points, so with enough flexibility , you should be able to find a way to make it happen. The best way to increase your odds of finding availability would be to either book far in advance or book less than a month out. That said, I’ve booked plenty of trips with points 3-6 months out, so it’s not impossible.

When booking with points, it’s important to note that the way you search for flights can make a huge difference in the value you’re getting. For example, booking a one-way business class trip from SF to Rome on United’s website might get as low as 81,000 points, but that same flight could be booked for 63,000 points from Avianca’s mileage program, which is a transfer partner of many programs. So you might want to consider a few tools that make the process easier:

Seats.aero is a new award search tool, but it’s quickly becoming one of my favorites. While it only supports 9 airlines, it regularly runs searches for all the routes for the next year, which means that, unlike every other tool out there, it supports unique searches like showing all flights to Asia with business class availability from a specific airport for the next year. It’s free to see availability for the next 60-90 days, but the pro version is only $7.99/mo and gives you access to a full year of availability. While I haven’t managed to secure any discounts for you all yet, this is my referral link.
Point.me is another fantastic tool if you’re searching for specific dates. It searches 30+ loyalty and 100+ airline programs for award availability and then walks you through the exact steps to take to transfer the points and book flights. I got them to offer our readers their first month for $1 if you use this link, select the standard monthly plan and use the code HACKS on the final checkout page. And if all this searching is too much work they also have a consulting service, where they’ll do all the searching work for ~$200/person (but if they don’t find anything you want to book, you’re only on the hook for $25).
- Note: If you sign up for a free Bilt Rewards account, you can use their free flight search tool (which is powered by the point.me search engine) to find award availability on the 12 airlines that happen to be Bilt transfer partners (but the other 18+ loyalty programs on Point.me are excluded).
AwardLogic is a similar site to Point.me, and while they search a few less airlines/loyalty programs, their searches allow +/- 1day and results show up 10x faster than point.me. It’s also a little more expensive, but this link gets you a 3-day free trial.
SeatSpy is a great tool when you have a ton of flexibility. While you can only search for award availability on direct routes on 13 airlines, it shows results for the entire year at once. It also let’s you set up alerts for new availability. If you want to check it out with a 14-day free trail, you can click this link.

🏨 Hotels

Italy offers some of the world’s most iconic and unique hotels, like the family-run il San Pietro, which was built by hand into the side of a cliff overlooking Positano. Or the Hotel il Pellicano in Tuscany, which offers exceptional Michelin-starred food and an incredible experience. Or the Palazzo Manfredi, which offers one of a kind, unobstructed views of the Coliseum from its suites. These hotels are perfect for those seeking a once-in-a-lifetime experience and are ideal for bucket-list trips to Italy.

But there are always other options. For example, the most expensive hotel in Northern Italy outside of Venice is the Belmond on Portofino. But right around Portofino are places like Santa Margherita and Rapallo, which have 4- and 5-star hotels that are wonderful for a fraction of the price.

Chains like Hyatt, Marriott, and Hilton also have hotels throughout Italy and some of the best smaller luxury hotels are even part of Hyatt’s SLH program, offering outsized value for points. If you’re looking to book hotels with points, check out Awayz (below).

Reminder if you’re booking high-end hotels: we have a partnership that gives you free extra perks (e.g. upgrades, complimentary breakfast, resort credits) at hundreds of four-star and five-star hotels. You can learn more about that program here.

👍 Try Awayz

For years I’d been hoping someone would build an award search tool for Hotels, and they finally have. It’s called Awayz and it’s awesome. It makes it easy to find award availability and pricing (and even compare the cash price) at over 25,000 Hilton, Marriott, IHG, and Hyatt hotels. While you can do some searches for free, the premium version has many amazing features (like alerts, a calendar view, individual hotel search, and more). You can get a 1-day free trial of both premium plans here.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Editor’s Note: Special thanks to our partners: Point.me, InsideTracker and Awayz. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

🧠 Organize Your Digital Life by Building a Second Brain

Fri, 14 Apr 2023 07:00:00 +0000

We consume a vast amount of content that our brains struggle to keep up with. To make the most of valuable information, we need to organize it in a way that allows us to access it in the future. I spoke with Tiago Forte (🎧 Ep85) on this topic. He is the author of the fantastic book Building a Second Brain, a proven framework for managing, organizing, and retrieving relevant digital information. It aims to increase productivity, reduce overwhelm, and enhance creativity. I'll break down our conversation so you can incorporate the framework into your daily life. I'm amazed by how much simpler it has made work, and I'm confident that you'll feel more motivated and engaged too.

Here is what you can expect to take away from this post:

What is a Second Brain?
What does this journey look like?
How to set up your Second Brain?
How to choose what information is important?
How to CODE information for future use?
What apps and services do I use for my second brain?

🧠 What is Building a Second Brain?

Building a Second Brain (BASB) is a system developed by Tiago Forte to remember and organize all the good ideas, inspirations, and other things we learn.

It uses technology to remove the burden of remembering everything and offloading this information to a suite of applications to help us think clearer and better. It's about keeping things in one place and using them to make things happen.

🏗️ What is the ultimate goal of the BASB system?

The goal is to help you become more creative, regardless of your profession.

Creativity is the fuel for content creation. The term "content creation" is often misinterpreted to refer to full-time TikTokers, podcasters, and social media managers. Yet, content creation is part of many professionals' day-to-day jobs (e.g., delivering a sales pitch, creating a presentation, or writing a cold email.)

Creativity is often blocked by the unnecessary information stored in your brain, making it harder to produce such content.

Most people's minds have stuff they can offload.

That offloading leaves space in the first brain for creativity, intuition, relationships, and the ability to learn new things. It can also save you as the capacities of your first brain diminish, whether caused by kids, age, or in Tiago's case, a chronic illness.

When you optimize your Second Brain, you enable your first brain to follow curiosity and spontaneity.

3️⃣ The BASB experience is a 3-stage journey

Let’s walk through the journey of implementing a Second Brain at a high-level and the benefits at each stage.

First Stage: Tackle Information Overload

BASB is designed to tackle the problem of information overload first. With so much information coming at us from all directions - emails, calls, messages, social media, podcasts, articles - it's easy to feel overwhelmed and struggle to keep up. This can affect our attention, focus, and personal and professional lives.

So start with creating a habit of filtering out the noise, by selecting a place to store and organize the information you come across (i.e., notes app; as you’ll read later, success relies on a notes application). But it’s important focus on what matters when intaking information.
It can also help to develop a standardized process for capturing, marking, and prioritizing it for future use. You don’t want to store everything haphazardly; you want to build a structure to tap into it in the future easily.

Second Stage: Develop Mental Clarity and Bandwidth

Once you've tackled information overload, the second stage is to develop mental clarity and bandwidth. This means having the confidence to focus on the highest quality work that aligns with your personal and professional goals.

When you enter the second stage, you’ll find you use the notes app much more effectively. Instead of storing incoming content, you’ll use it to offload ideas, make connections, and prioritize your tasks. This will help you focus on your goals and projects and ensure you're making progress on what matters most.

Third Stage: Embed the System into Your Routine

The third and final stage is to embed the BASB system into your routine to become a cognitive exoskeleton. This will help you focus more on the work that matters most and define your life around it.

You’ll need to make it a practice by earmarking time daily to capture information, organize your notes, distill them, and revisit your ideas and tasks. Over time, the compounding benefits of this habit will make your Second Brain feel like second nature, allowing you to create rather than consume.

🧠 How to set up a Second Brain?

Think of it as an ecosystem of applications.

I wish I could say, "Here is a single app that does everything,” but unfortunately, that doesn't exist. Here is how you can build it:

Choose your notes system. At the center is your long-term repository of information, ideas, and data you have collected, organized, and synthesized for later use. Many note systems are available, so choosing one that works for you is essential. Some popular options include:
- Evernote - an all-purpose note-taking and task-management application
- Notion - an all-in-one workspace where you can think, write and plan
- Roam Research - a note-taking system designed to organize related thoughts
- Apple Notes - the notes app included free on Mac and iOS devices.

Choose your supporting applications. A series of applications help support your long-term repository, such as task managers, note transcription apps, cloud storage drives, databases, and workflow apps. Choosing apps that integrate well with your notes system and support your creative process is essential. Some popular options include:
- Readwise - saves highlights from ebooks and articles
- Todoist - a popular online to-do list and task manager
- Otter AI - an AI-powered note-taking app that generates a real-time transcription
- Dropbox - a cloud-based storage platform
- Airtable - a spreadsheet-database hybrid platform to connect data
- Zapier - a wor†kflow tool that automates actions and workflows

The ecosystem of applications will change.

If you want some inspiration, I’d suggest reviewing Tiago's curated list of established tools and recommended apps.

👨‍💻 My Second Brain “Stack”

Here are the specific apps I use to collect, store and process information:

Email: Superhuman saves me so much time on email that I couldn’t imagine every going back to regular Gmail.
Information: Notion has effectively become my second brain for everything from planning trips to running the podcast to managing family/home projects. Also, by connecting it to other apps (directly or with Zapier) it’s also become archive of most of the content I find on the web (e.g. articles, saved tweets).
Family Information: Trustworthy (← 20% off) is where we store all our family’s important information: Family IDs, insurance docs/cards, property records, tax returns, estate plan and a lot more.
Read Later: I’m currently using Readwise (← free month) and Matter to try and decide which is the best fit for me, but they’re both great options.
Notes: Apple Notes is where I store quick information before I’m ready to make the decision to store it in Notion for future use.
Recipes: Paprika is our go-to for saving recipes, meal planning and grocery shopping. There’s no free version, but some readers have suggested Crouton as a lower-cost alternative.
Credit Cards: Card Pointers (← 30% off) is where I manage all our credit cards and make sure I get the most value from all of them, by tracking all the credits they offer and auto-enrolling me in all the offers from issuers.
Data: I’ve long been loyal to Google Sheets, but I recently started using Airtable for a new project and I’ve been pretty blown away with what it can do. It’s definitely overkill for most things, but if you have a bigger project, check it out.
Files: I don’t have a perfect system here, but mostly use Dropbox for saving files, Google Drive for documents and iCloud for storing my Desktop, Documents and Downloads folders.

You may also enjoy checking out the post I wrote last year on My Top Apps/Products for a Productive and Optimized Life.

📂 What goes into your Second Brain?

It is important for your Second Brain only to contain information you have read, reviewed, and evaluated as valuable or actionable.

To best achieve this, use inboxes as the gatekeepers of your Second Brain.

The email inbox is the most common. Here's a 4-step process to filter inbound emails (and cut the reading of that email many times):

Does it contain a scheduled meeting or task? (If yes, send it to a calendar)
Does it have an unscheduled action? (If yes, send it to a task manager)
Is the information in the email necessary to store for later? (If yes, send to notes app)
Can I archive or delete it? (If yes, then do so)

The read-later app is another valuable inbox. Here's a 3-step process to filter articles and other content:

When you come across content, ask if it is interesting. (If yes, send to a read-later app)
Once it's read, is it worth saving? (if yes, distill the content into helpful information for future self and send it to your notes app)
Sometimes, it's no longer interesting (if this is the case, archive it from your app)

The quick-notes inbox is for jotting down half-baked thoughts (i.e., digital post-it notes). Write it down now, and go through the process of filtering later.

Does the note require a following meeting or task? (If yes, send it to a calendar)
Does the note require action? (If yes, send it to a task manager)
Does it require additional thoughts/notes to store later (If yes, write and send to the notes app)
Is this note still applicable and valuable? (If yes, then archive or delete)

Often times you’ll notice things you believe are important at the moment aren’t worthy of your time in the future.

🧑‍💻 CODE-ing information

The CODE framework is a proven model for organizing your creative output into four distinct steps:

Capture - write it down or document
Organize - add structure and prioritization.
Distill - boil it down, refine the takeaway, action steps, or punchline.
Express - put it back into the world through a creative medium.

Following these steps can streamline your creative process and increase your productivity.

Here's how to apply the CODE framework to your daily life:

Capture:

To capture information, you must set a higher standard for what enters your Second Brain. Instead of trying to capture everything, focus on ideas or concepts that will change your life in the future. This will help you solve the discoverability problem and make it easy to find and use the content you've read before. Use your capture system (i.e., notes) to write down or document valuable information.

It’s not about hoarding all pieces of information. As the expert on the system, Tiago shared just how much he captures:

I'll be reading a book and [I think to myself] is this a life-changing idea? Does this quote shatter my conceptions of how the world works? That is a high bar, but the great result of that is I'll read an entire book. I'll think the book is great (five stars on Amazon) and I'll have like five quotes…That's how it should be. The quotes are not everything that was even a little bit good in the book. The quotes are just like a bookmark. They're the digital equivalent of having a book on your shelf.

Organize:

Our minds are conditioned to organize through wide-ranging subjects (like a library does), but a more helpful structure is narrow and focused. Tiago believes "projects" are most relevant to how we work, so he developed the PARA organization to structure your Second Brain:

Projects: These are the 5-10 active workstreams linked to a goal with a deadline. Examples include product launches or planning an event.
Areas: These are the broader interests or activities which projects emerge from. Examples include health, travel, or finances.
Resources: This is everything else, a topic of ongoing interest but less critical than your projects and areas. Examples include coffee, marketing, productivity, and fashion.
Archive: This is a place for inactive anything from the previous three. Examples include dormant projects, areas, or resources that are no longer relevant.

To get started, archive everything you have in a folder (date today) and then identify your current projects.

Distill:

To make information easy to discover and understand for your future self, develop a structure allowing you to communicate and build on your past experiences and knowledge. This will help you avoid trying to decipher the value of old notes or articles. The information is boiled down to its key takeaway, action steps, or punchline.

Express:

The previous three steps aim to finish your work faster and with less effort. Use your creativity to put the distilled information back into the world. Express the information through a creative medium, such as writing, drawing, or presenting.

Applying the CODE framework to your Second Brain lets you manage, organize, and retrieve relevant digital information. Start implementing the framework today and watch how much easier it is to manage your work and personal life.

You can learn more about Building a Second Brain by checking out the book, the course, and Tiago's blog.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Editor’s Note: Special thanks to our partners: Trustworthy, Notion and CardPointers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

💰 Investing In Alternative Assets

Fri, 07 Apr 2023 07:00:00 +0000

I’ve always been fascinated by how wealthy people invest their money, and one common component of their portfolios is Alternative Assets, which I want to explore in today’s post. This interest was sparked after a conversation with Tad Fallows last year (🎧 Ep 87). Tad co-founded Long Angle, an online community for high-net-worth investors to discuss various topics, including asset allocation, taxes, philanthropy, insurance, raising kids, and more. I’ve been a member for the past year and have really enjoyed being a member.

Every year, Long Angle releases a benchmarking survey that uncovers the financial habits and attitudes of the wealthy. Among many interesting takeaways, there was one that drove me to write this newsletter.

The portfolio composition of Long Angle’s investors differs from that of the typical investor, with alternative assets and private company investments making up 24% of the portfolio.

So I wanted to dig into those and for the sake of the email, will be combining both into “Alternative Assets.” Also, this email is certainly not intended to be financial advice, and some examples shared may not be available or suitable for the average investor. Personally, I haven’t invested in the majority of them, but I still enjoy learning about all the different types of investments out there, so I hope you do as well.

And if your investable assets exceed $2.2 million (including illiquid investments, but excluding your primary residence), I encourage you to consider joining Long Angle (it’s free). I’ve learned so much from their community and try to contribute my thoughts as much as possible.

Apply to Join Long Angle

If you like this post, please consider sharing it with a friend, colleague, or family member that might learn from it. 🙏🏼 Thank you!

🔍 Exploring Alternative Assets

Alternative assets is a term that aims to capture investments that don’t fit into conventional stocks, bonds, and cash. You might often hear about cryptocurrency, private equity, hedge funds, collectibles, or commodities as common examples. Some people might classify real estate as an alternative asset (since it’s not a stock, bond, or cash), but since it’s so well-known, I’ll keep it out for this email.

The key considerations for alternative assets are that they often have fewer regulations, lower liquidity, and are harder to value. These are some tradeoffs investors take for the higher risk/reward that many alternative investments have.

I’ll group them into three categories:

Equity Alternative Assets
Commodity Alternative Assets
Other Alternative Assets

Note: The information below is not a comprehensive list of every alternative investment available. It’s designed to introduce you to some different assets you might not know.

Equity Alternative Assets

Equity alternative assets cover investment in private businesses. If you invest in most stocks, you’re investing in public equities that trade on a stock exchange, but the examples discussed here are not traded on public markets.

Angel investing provides capital to startups and entrepreneurs at the business’s earliest stages in exchange for equity. It’s a strategic bet on the idea, team, and potential impact. It’s even possible the business doesn’t have any customers or revenue. The purpose of the investment is to fund innovation and fuel growth. With angel investing, it’s often the investor's personal funds, whereas the options below are pooled funds.

Note: Despite working in venture capital, I’m still quite reluctant to angel investment because I’ve seen many companies fail (from people I’ve known to be extremely smart). It’s a challenging game where I think it’s best to go in expecting to lose everything.

Venture capital fund investing is similar to angel investing. The difference is that VC funds are pooled investments in various companies at multiple stages in their lifecycle. The funds access the capital to buy these companies from a network of high-net-worth investors or limited partners (LPs). Firms like Sequoia and Andreessen Horowitz are some of the biggest names. Investing in VC funds is technically less risky than angel investing because businesses are often at later stages with a more defined operating model and investments are spread out across many companies (however, it’s still risky in the grand scheme of investment options). Unfortunately, it’s very difficult for most individuals to get access to investing in the best VC funds.

Private equity is an investment of growth capital into a business to help them restructure to accelerate growth. Private equity firms typically invest some of their own money (from investors/LPs) and borrow the rest. Most of the time, the firm’s investment strategy is to sell the company at a higher price, but sometimes it’s to return the profits to investors. Like VC funds, it’s not easily accessible, requires a high minimum, and PE funds often have high fees.

Search funds are less well-known but have historically had some of the highest returns among all asset classes. It’s an investment vehicle where an entrepreneur receives financing and guidance from investors to search, acquire, and manage a private company. An example is an MBA graduate who spends a year or two looking for a small company to buy, seeking financial backing from investors to cover their expenses during that search window. Once a company is identified, the investors buy it from the founder and aim to improve the operations before selling it to another private equity firm.

The four examples above all take the lens of the initial asset purchase. But what if an investor wants to sell? Since these investments are illiquid, it’s not as easy as the public markets, but there is a market for secondaries. It refers to selling existing assets or securities that do not have day-to-day liquidity. An investor can sell their investment to another investor, likely for a discount on the asset’s market value.

Equity financing is a way to provide loans to individuals that want to tap into their valuable (but illiquid) assets, like private company stock. For example, an early employee at a growing private company may want to exercise their stock options. But exercising an option requires capital, sometimes a lot more than the employee has on hand. An investor can provide a loan to bridge the gap and receive a fraction of the options upside in exchange.

Category #2: Commodity Alternative Assets

Commodities are basic goods interchangeable between producers, such as gold, silver, wine, oil, or natural gas. As an asset class, they are highly speculative and especially sensitive to economic shifts.

Precious Metals is investing in metals typically to hedge against inflation or their demand for use in advanced electronics. This might be the most common or well-known form of alternative investments and are much more accessible than some of the options listed throughout. Investors can buy the physical state, future contracts, or mutual and exchange-traded funds.
Cryptocurrency is a digital currency and one of the most accessible alternative assets. While major tokens like Bitcoin and Ethereum are available on major exchanges like Coinbase, many smaller tokens are purchased with a digital wallet you manage/store yourself. Despite its accessibility, Crypto is much less regulated than stocks or bonds. The collapse of FTX, BlockFi, Celsius, and others should be a reminder of the risk that comes with these investments.

Fine Wine & Rare Whiskey is investing in the physical product or a pooled fund that holds an array of these goods. Investors can provide capital at the pre-production stage or years after it’s already been bottled. There are many factors to consider (scarcity, vintage, aging potential), but many investors just focus on strong business models and good operators.

Category #3: Other Alternative Assets

Other alternative assets serve as a catchall to the many highly unique investments. Here are a few interesting examples.

Private Credit means making direct loans to companies or real estate developers. Borrowers usually are too small to issue bonds, and are unable to access traditional bank loans for all of their financing needs. Private credit loans are often relatively short-term and carry interest rates in the mid-teens. Security can come in terms of real estate collateral, corporate guarantees, and personal guarantees from borrower executives.
Athlete revenue share: An individual could offer financial support to an amateur athlete in return for a stake in future earnings as a professional player. Since amateur contracts are much lower, investors could support a promising amateur and receive a percentage of the player’s professional future salary. However, the investor would lose their investment if the player never makes it professionally.
Trading Strategies aim to exploit pricing inefficiencies to generate profit without reliance on underlying market growth. These strategies can operate in any large liquid market, from forex and crypto to stock, bonds, and commodities futures. Trades are often very short-term, and can exploit historic patterns, mismatches between exchanges, or other strategies. Be aware that trading strategies are particularly risky from a fraud and leverage perspective, and identifying good partners is challenging.

Viatical Settlement: An individual can invest in someone else’s life insurance policy. They would assume the premium and receive the death benefit when they pass away.

Farmland falls under the real estate alternative umbrella. Since farmland is best designed for practical use, it’s typically rented to a farmer. It’s historically a lower-risk, lower-return alternative, and the yield can be more predictable. The edge cases where an investor might see more rapid appreciation in land value is when the land is situated near an expanding urban area.

Collectibles are assets like art, watches, or baseball cards. These assets do not generate a consistent cash flow and can be tough to value. While online marketplaces like eBay have made valuing some collectibles easier, many still have very niche markets that are very difficult to value.

☑️ Who Qualifies?

Eligibility depends on the asset class, but many require you to be an accredited investor or qualified purchaser.

An accredited investor is one whose financial sophistication warrants a reduced need for protection from unregistered securities. They must have earned at least $200k ($300k with a spouse) in the last two years, have a net worth exceeding $1M, or meet specific financial officer requirements.
A qualified purchaser is an accredited investor or a family business with an investment portfolio valued at $5 million or more.

🖥️ Online Platforms for Alternatives

Online investing platforms have made it much simpler to access alternative investments. You can invest without needing personal relationships or writing large checks since it’s digitally managed and funds are pooled. They also often have lower minimums, and some don’t require you to be accredited. There are a variety of options in many areas of alternative assets:

Some examples of online platforms include:

Masterworks provides clients access to blue-chip art and I’ve personally invested in 14 different pieces of art on the platform (which you can see here). They’re also a sponsor of show and have offered to give all subscribers priority access to skip their waitlist.

Long Angle has curated deal flow across all alternative asset classes. You must be a member to participate, but membership is free, and they’ve offered priority access to join for our subscribers.

Vinovest provides access to invest in wines from around the world.

Yieldstreet provides access to hedge funds and debt investments across various private market deals, including real estate, commercial, marine, legal, and art investments.

Fundrise provides access to real estate and venture capital.

WithVincent is a professionally-managed investment service that provides access to art, collectibles, crypto, private credit, real estate, and pre-IPO ventures.

Rally provides access to equity shares in collectibles.

Another way to source alternative pooled deals is by networking with people in the industry that are knowledgeable and experienced. There are also many ways to pool resources and reduce minimums amongst like-minded investors, like forming a special-purpose vehicle.

⚖️ How Much Should I Invest in Alternatives?

Most professionals recommend investing no more than 5%-10% of your portfolio in alternative assets, but it’s totally fine for you to have the answer be 0%.

While I haven’t explicitly said it yet, you have to weigh your risk, financial situation, and minimums required that come with these types of investments. Fortunately, I’ve also been able to ask this question to many financially-gifted minds on the podcast and aside from the conversation with Tad Fallows (🎧 Ep 87) that shaped a lot of this newsletter, here’s what they’ve shared.

Ben Carlson (🎧 Ep 42) suggests putting your financial house in order before anything else. That means doing all the boring stuff first, and then, only then, investing in alternative assets, maxing out 5%-10%, where it doesn’t get out of control.

Nick Maggiulli (🎧 Ep 59) focuses on cash flow-producing assets but believes there can be a place for investable assets in alternatives like crypto, art, and private companies. Keep it small.

Andy Rachleff (🎧 Ep 19) doesn’t believe in speculation. But he also knows that psychology prevents people from avoiding speculation altogether, so he suggests keeping it a tiny percentage of your portfolio if you choose to do so.
Joe Saul-Sehy (🎧 Ep 35) compares alternative investing to stock picking because, to succeed, you must do your research. When you’ve gathered enough information, you’ll reach an inflection point in the analysis that will prompt you to believe it.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

⛰️ Overcoming Fear, Processing Failure, and Why Having a Plan B Holds You Back

Fri, 24 Mar 2023 07:00:00 +0000

When I started the podcast two years ago, I had a dream that it would be my full-time job, but it wasn’t until recently that I committed to it. If you have an ambitious idea but are hesitant to commit, this post is for you. I recently interviewed Matt Higgins (🎧Ep 105) about his amazing book Burn The Boats, a framework to stop hedging and unlock your full potential. The conversation was so good that I knew I had to turn it into an actionable guide.

By the end of this post, you will have learned how to:

Uncover fear to build self-awareness
Unlock your motivations to discover your potential
Stress-test your ideas to avoid cognitive bias
Assess risk to solidify your plan A
Address failures to make sure you don’t quit

These frameworks will help you go all-in on your Plan A and finally burn the boats.

If you like this post, please consider sharing it with a friend, colleague, or family member that might learn from it. 🙏🏼 Thank you!

📢 Quick Announcement

I'm also excited to announce that during my recording with Matt, I was convinced to finally launch the our membership I’d been considering for a few months. I’ll share more at the end of this email, but I’m really looking forward to building it into a world-class program for all of you.

🚢 What does “burn the boats” mean?

Burning the boats originates from military strategy (and referenced in Sun Tzu’s The Art of War). The boat serves as a means of escape during battle. Therefore, burning the boats means cutting off the escape route, leaving only one path forward.

In modern times, this phrase refers to eliminating the obstacles that hold us back from starting something new or great. It’s a framework to ditch plan B and go all in on plan A.

For most people, the boats represent internal forces. To burn them, you must do the self-work.

The process of self-work is designed to reach deep, so this post will help make it easy for you to stay focused and clear.

Each section follows an order, beginning with the foundational questions. Some of you may have thought through certain questions, so you may start further down the framework.

To go even deeper, I recommend you check out Matt’s book, Burn the Boats.

◀️ Look Backward to Change Behavior

Uncover Fear and Build Self-Awareness

The first step towards unlocking your full potential is to look backward.

While self-awareness is a term used frequently, many resist the practice of reflection and assessment since it requires a level of vulnerability we are not used to. If you resist, start by thinking about the fear question:

“What am I afraid to [find out about myself]?”

We might fear truly understanding the deepest parts of ourselves for various reasons. Typically this resistance stems from fear of judgment from an authority figure, spouse, relatives, or friends or the stigma it creates. You weren’t born with this resistance; it develops from social and personal pressures.

Only once you understand the fear question and lean into the vulnerability can you ask:

“What’s holding me back?”

The purpose is to understand the obstacles and your relationships with them.

Are they physical or emotional?
Are they based on present or historical experiences?

Use Self-Awareness to Change Behavior

Once you’ve identified fears and isolated obstacles, you can change the behaviors preventing you from where you need to go. It’s easy to overlook the true nature of your behaviors in our day-to-day routines. This is why it’s important to observe and deconstruct our behaviors.

To do so, audit your thought patterns, motives, and behaviors by assessing the following:

“Why am I doing this?”
“Why am I acting like this?”
“Why did I do X?”

Your past behavior can only be resolved by looking at it with humility and facing it. If you do this, you’ll often realize you fooled yourself into believing these behaviors were helpful. Moreover, you have the mental strength to correct the behaviors.

Look Backward TL;DR

Tackle three obstacles to establishing self-awareness.

Determine fear —> “What am I afraid to [find out about myself]?”
Assess obstacles —> “What’s holding me back?”
Audit behaviors —> “Why am I doing this?”

▶️ Look Forward to Discover Motivations

Look at Who, Not What

The second step towards unlocking your full potential is to look forward.

Some people might find themselves here right at the beginning. They already know what’s holding them back but don’t know what to do with it. And it stems from asking the wrong question.

Don’t ask, “what do I want to do?” (e.g., be a lawyer, doctor, etc.), instead ask:

“Who do I want to be?”
“How do I want to spend my time?”
“What environment do I thrive in?”

Reframe the questions to focus on context, environment, and the cues that tell you more about yourself than what you want to do. This process is about helping you identify who you are as a person.

Don’t Accept Your Idea; Stress Test It

According to Matt (🎧Ep 105), most people fail at the idea stage because they do not ask themselves the right questions at the outset. Typically, when an idea surfaces, people are too quick to call it valuable and find a way to implement it. This puts you at risk.

Simply having an idea doesn’t make it a good idea. You must scrutinize it and focus on opportunity cost to determine if this idea will sustain you long-term.

When you develop an idea project yourself three years and ask yourself the following questions:

Is this idea big enough?
Is it interesting enough?
Is it valuable enough?

This exercise eliminates a cognitive bias we all suffer from when making decisions. We default to comparing our current situation vs. our idea because we are so desperately trying to escape our current situation.

Instead, we should assess that idea vs. our imagined situation three years from now. We can use it to determine whether we are “running to or away from something.” And you want to be running towards something.

The process of pressure testing our ideas aid in more sustainable decisions.

Look Forward TL;DR

Tackle two hurdles to identify motivations.

Determine who, not what → “Who do I want to be?”
Stress test ideas → “Is this idea big, interesting, and valuable enough to sustain me?

🅰️ Go All-in on Your Plan A

We’ve looked backward and forward and stress-tested our idea, so now we want to turn that idea into action.

What happens next is you get stuck.

Why? Risk and fear.

Getting unstuck and building a plan A requires synthesizing that risk and fear. Those who can fully commit have done the work at the forefront.

We will face external and internal doubts whenever we undertake a challenging endeavor that takes a long time. If you have gone through the synthesis process, you can draw on the memory and the clarity to overcome these doubts. If you haven’t done so, your doubts will prevent you from committing.

You can use this risk exercise to solidify your plan A:

What’s the worst possible thing (that could happen) if this does not work out?
What would I do if the worst thing happened (and how would I mitigate it)?
What’s the probability of the worst-case scenario materializing?
What would I be willing to endure for a Plan A workout?

You decide when it becomes a plan A.

🅱️ Plan B

When people think about Plan B, it’s in the context of “if Plan A doesn’t work out, what other options do I have?”

That’s a risk mitigation question.

But it should be clear by now that if you went through the Plan A risk exercise (above), you’ve already incorporated risk mitigation. That means Plan B is not about de-risking but achieving Plan A’s subordinate goals.

Wharton Business School found that mere consideration of a Plan B is enough to prevent you from achieving Plan A.

I’ll illustrate plan B using the same example from the podcast:

I want to be a musician.

Despite my father’s objections, I will do what I can to be a musician. I will work very hard to get into the band.

But if it doesn’t work out, I’ll work at Bob’s record store because I’m constantly browsing the aisles, and Bob thinks I’m smart.

Bob’s Record Store is the subordinate goal. Getting a job in music is very different from being a musician. Plan B is a way to relieve the pain and discomfort that comes with pursuing your true goal.

🤔 Having a Plan B vs. Knowing a Plan B Exists?

Some people are inherently thinking about all the possible scenarios and options to put themselves in the best position (…raises hand slowly 🙋‍♂️).

But there is a difference between knowing a plan B exists vs. planning for one.

Let’s look at some of the nuances with our musician friend again:

Pre-planning your escape route to Bob’s Record Store differs from knowing you could find a job somewhere “even if everything went wrong.”

The former is a plan B; the latter is not.

Suppose you have a conversation with a friend about wanting to be a musician. And during that conversation, they plant in your mind “even if everything went wrong,” you could work at Bob’s Record Store.

Just because you heard the concept of a plan B doesn’t make it a plan B. The key is in the sequencing. If you had gone to a friend before doing your risk synthesis exercise, then yes, you’ve likely opened yourself up to internalizing a plan B (and the doubt that comes with it).

But if you’ve gone through the framework and exercises, committed to your Plan A, then talked to a friend, it’s more likely their doubts will go in one ear and out the other.

You can’t have a plan B until you’ve established a plan A.

🤕 When Things Don’t Go Right…

Along the way, things will go wrong.

You wanted to be a musician.
You decided to go all in.
You do your first gig; no one shows up.

Processing failures are one of the main reasons Matt wrote Burn The Boats. His assessment of the most successful people shows that persistence is the most powerful predictor of success. As long as you keep going, you will succeed.

When things don’t go right, they expand their definition of success to accommodate setbacks. As a result, they redefine success differently. This is why processing failure correctly will help maintain persistence.

Here’s Matt’s framework addressing failures and missteps:

Accept that the goal is to continue (to survive)
Acknowledge the failure
Don’t let that failure penetrate your identity
Extract the value from that failure, iterate, and implement the change
Never look at that failure again

Think of it this way: when the musician fails to be the lead guitarist, they find a way to be in the band.

Plan A is not the delusional belief that you will get what you are entitled to; instead, it’s the utter commitment to the goal and decision frameworks you have installed. You should always course correct when necessary (with plan A in mind).

🥪 The Best Ideas are Gut Sandwiches

Many of you will find your Plan A to be emerging ideas. When you are at the forefront of innovation, it can be lonely. There is an inverse relationship between the potential upside of an opportunity and the amount of supporting data. And don’t expect your friends or family to be able to see it the way you do.

The lack of supporting data is an indicator to keep going.

Matt’s advice: opportunity arrives before the tipping point of evidence. So look for pragmatic optimists who can help you cradle and shepherd your idea without needing the data to prove it true. It’s important to trust your instincts and intuition.

With that in mind, I told you I committed to my Plan A this year with the podcast, so I have something new to unfold.

📒 Workbook Exercise

I got an amazing email from Ligaya at Malaya Publishing who specializes in turning content like these newsletters into short workbook activities for readers to apply the lessons to their own lives. I wanted to share the one she made for this post, so please check it out and let me know what you think.

Download Workbook

🙋 Join Our Membership

During my interview with Matt, I was convinced to burn my own boat by launching an exclusive membership before everything was finalized. While it’s still early, my vision is to create a valuable membership with perks/benefits that more than makeup for any membership fee. Think AARP for a younger demographic that loves deals, travel, and experiences.

That said, I don’t have any of that built yet, so here’s what I’m going to commit to offering those who sign up now:

Monthly members-only video calls
Ability to share ideas for upcoming interviews and podcasts
My eternal gratitude for your support of me and the show
All the future perks and benefits I'm working on 😊

So if you want to sign up and support me, you do that here:

Join Our Membership

That said, I know it can be annoying to feel pressured by so many creators to sign up for another membership, so please do not feel pressured to join. I truly hope I can deliver more value to you than it costs, but I never want anyone to feel pressured to join.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

🤑 Japan Flights/Hotels with Points

Fri, 17 Mar 2023 07:00:00 +0000

Advertiser Disclosure

In last week’s post I talked about How to Travel to Japan like a Pro and today, I wanted to share a bunch of tips about using your points and miles for flights and hotels for Japan. I’ll also add a few other ways to save on a trip, even if you’re not using points. Many of these tips should be useful for trips to other countries, so it should be good even if you’re not planning a Japan trip (though you probably should consider it). If you prefer to listen, check out (🎧Ep102) Traveling to Japan with Points & Miles.

Biz Class on my last flight home from Tokyo

🛫 Flight to Japan with Points:

Let’s first look at the best carriers for getting to Japan with points:

ANA

Flying with ANA through Virgin Atlantic is likely the best option if you can find the space. You can fly round trip from the west coast for

60,000 miles in coach
90,000 miles in business
110,000 miles in first class

Only round-trip bookings are available, but the taxes are reasonable, starting at ~$300. Here’s the process you can follow:

Search on Point.me or any site within Star Alliance to find availability.
Call Virgin Atlantic to book (or try to ask them to hold the spot).
Transfer points to Virgin Atlantic.

FYI - Virgin Atlantic has announced that they’re joining the Skyteam Alliance, so it’s unclear how long this will last after they officially join, because ANA is in Star Alliance.

ANA also offers direct booking and while it’s a bit more complicated, you’ll need fewer miles for a round-trip flight:

40,000 - 50,000 miles in economy
75,000 - 90,000 miles in business
150,000 miles in first class

Only round-trip bookings are available, and taxes start at ~$300. However, you can only transfer to ANA from Amex, which takes a few days. And calling an ANA agent to put it on hold is very rare. That means:

If you’re flexible on dates and have Amex points, you could transfer them, and if those flights disappear during the transfer, you can always keep looking.
If you’re set on specific dates and you only found one option, it could be risky.

Japan Airlines

Since JAL isn’t a transfer partner of any credit card programs, you must book through another airline (unless you have JAL miles). Here are some options:

Alaska Air

35,000 miles each way in coach
60,000 miles each way in business
70,000 - 80,000 each way in first class

Taxes can be as low as $100 round trip.

American Airlines

You can book JAL with American Airlines miles for about the same number of points and taxes as Alaska. If you don’t already have AA miles, they can be harder to come by than other airlines, because they aren't a transfer partner of any major program.

British Airways

You can transfer points from almost every credit card to BA Avios, but the taxes and fuel surcharges can be super high. So, make sure to factor that in.

Singapore Air

It is possible to fly from LAX to Tokyo on Singapore’s fifth freedom flight (where a carrier flies between two countries where it is not primarily based). You can book the flight directly with Singapore after transferring miles.

First-class tickets can be about 120,000 points, but the Singapore product is undoubtedly one of the best. Sometimes it’s easier to find availability last minute.

United Airlines

United has over a dozen flights to Japan, and it’s easiest to book those flights directly with United or with Air Canada. When lower-priced awards are available, you can book for as little as

35,000 miles each way in coach
75,000 miles each way in business

Almost every point program can transfer to Air Canada and/or United, and taxes can be as low as $50 round trip. You’ll need to search the calendar for availability (easiest on United’s site), but last-minute availability usually has a lot of great options.

Finally, if you have Capital One points, you might get a better deal on some of the United flights if you book through Avianca.

Delta

While it’s very hard to come by a good deal flying Delta to Japan, it does happen from time to time, so it’s worth looking if none of the other options work for you. If you don’t have Delta miles or Amex points, you can search/book from FlyingBlue (Air France/KLM’s frequent flier program), which is a transfer partner for all card points.

ZipAir

This is actually a cash deal. ZipAir is a low-cost subsidiary of JAL with some fantastic fares and beautiful plane interiors. I’ve had a few listeners email me to say they had a good experience with the airline, but there are a few important caveats:

ZipAir only flies to Tokyo from San Jose, Los Angeles, and Honolulu in the US
The price of a round-trip ticket can be as low as $600 for coach or $2,000 for business, which is unmatched by any other carrier (especially the biz class price)
There are no changes/refunds, so you’ll lose your money if you can’t take the flight. So, if you’re booking on ZipAir, I would consider cancel for any reason (CFAR) travel insurance. (I’ve used Trawick International for this in the past)
The only thing included is your seat, so there are a handful of add-ons:
- $50-70 to check your bag (even for business class)
- $50 for carry-ons above the weight limit (they are strict about the limits)
- $11-12 per meal on-board (even water isn’t included)
DEAL: If you have an Amex, there’s currently a Zip Air offer for $150 off $750+

💳 Flight Options Based On Points

Since you can’t transfer to all airlines from all points programs, I thought I’d break down your best options by the type of points you have. Because booking ANA through Virgin is a top option and they’re a transfer partner from all programs, I won’t mention the details every time below, but they’d be my top option if there’s availability. Also, you can transfer to British Airways from every program except Citi and book on JAL or American, so I won’t include detail on that below either, but it’s on the list of options to check for all other programs (though given the fees, it’s probably at the end of the list).

Reminder that you can find my full list of airline transfer partners by credit card here.

Ultimate Rewards

After Virgin, I’d be looking to transfer to United or Air Canada and booking on United or ANA. Finally, I’d look into British Airways.

American Express Membership Rewards

If you’re ok with the ~2 day transfer time, I’d start by looking at transferring to ANA. If not, then I’d start with Virgin and then be trying Air Canada to book on ANA/United. If you’re flexible to fly out of LAX, I’d also look at transferring to Singapore.

Capital One Miles

With CapitalOne, I’d start with looking at ANA through Virgin, but then I’d try looking at transferring to Air Canada, Singapore, or British Airways (in that order).

Bilt Rewards

After Virgin, I’d try looking at transferring to American, United/Air Canada, or British Airways (in that order). Unfortunately, Bilt only has one card with no signup bonuses, so unless you already have Bilt Points, this probably won’t be an option for you.

Citi ThankYou Points

Virgin Atlantic is your best option, but I’d also check Singapore, Avianca (for booking ANA/United), or British Airways (in the order).

🏨 Hotels

Let’s cover the four major hotel programs you might want to use for a Japan trip.

Hyatt

Hyatt has 33 hotels in Japan. The rates range from 6,500 points/night for category 2 up to 35,000 points/night for category 8. Some highlights are:

Park Hyatt in Tokyo is famous from the movie Lost In Translation
Park Hyatt in Kyoto is where we stayed on our last trip, and it’s incredible
The Grand Hyatt and the Andaz in Tokyo
The Sowaka Hotel in Kyoto
There is a Park Hyatt and Kasara in Niseko

Hyatt is a transfer partner of Chase and Bilt.

Marriott

In Japan, Marriott has 85 hotels. Those range from 15,000 to 120,000 points a night. However, Marriott offers a fifth-night free program, so if you can do a 5-night stay, you can take 20% off.

While the only one of the 85 hotels I’ve stayed at was the St. Regis in Osaka, these stood out as some amazing high-end options:

The Prince Gallery in Tokyo
The Mitsui in Kyoto
Ritz Carlton in Tokyo, Kyoto, Okinawa, and Nikko
Courtyard at Tokyo Station

Hilton

In Japan, Hilton has 26 hotels. Hilton also offers the fifth night free, so you can save 20% if you stay 5 nights. Their hotels range in price from 25,000 to 95,000 points per night, with one exception: the Roku Kyoto, which looks incredible but is 110,000 points a night. However, you should know that when space isn’t available at these standard rates with points, Hilton sometimes shows insane points rates for those rooms (I’ve seen >1 million points/night).

I’ve stayed at the Hilton Tokyo twice, and it’s very solid. The hotel has a mini onsen (hot spring bath) by the gym, and the concierge is incredible. Some other great options include Conrad Tokyo, Conrad Osaka, and Odawara Resort.

IHG

In Japan, IHG has 45 hotels. A few options I liked were the Intercontinentals in Tokyo, Osaka, and Beepu (which is a hot springs resort).

Other Hotel Options

If you don’t have any hotel points, there are lots of local hotels and Ryokans to check out, or you can search Airbnb or stay at a hostel or capsule hotel. Overnight buses are also a budget-friendly travel method because you save money by not staying one night in a hotel.

A reminder for you with high-end hotels: we have a partnership that gives you the perks of four-star and five-star hotels with upgrades, complimentary breakfast, resort credits, early check-in, and late checkout. Email upgrade@chrishutchins.com if you are trying to book a high-end property. Yes, you get similar offerings if you book with some card company portals, like American Express Fine Hotels + Resorts, however…

We can do this with about 4,000 hotels, while most card programs only have access to a few hundred or maybe a thousand
We work with hotels directly, so you receive a reservation from the hotel, not the credit card company (and usually have higher upgrade priority)

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Editor’s Note: Today, I’m grateful for the support of our partners Point.me, Pacaso, BankBonus, and MileValue. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

🇯🇵 How to Travel to Japan Like a Pro (Even if it’s Your First Time)

Fri, 10 Mar 2023 08:00:00 +0000

I’m back to writing and today we’re talking about one of my favorite travel places: Japan. I’ve been there four times already, and I am eager for my fifth. And last month, I did a podcast episode with Brandon Presser (🎧Ep 101), who has been there over a dozen times, lived there twice, and written five guidebooks on Japan. Today’s newsletter will tell you where to go, what to do, and how to do it. We’re going to help you plan the best trip ever.

Share this post with your friends who love traveling so they can discover a fantastic Japanese experience. And if you have been to Japan, please share your thoughts with me too!

Look out for a bonus post in a few days where I’ll cover using your points for flights and hotels, as well as some ways to boost your points balances before planning your next trip.

🗾 Japan: Overview

Japan has a deeply modernized and evolved culture. It excels in transforming facets of other cultures into the best possible version with intentionality and care. For example, Japan has become an international leader in hospitality, cuisine, and leisure through the thoughtful integration of traditional and modern aspects.

The country has four major islands to explore:

Honshu is the main island, home to Tokyo and Kyoto.
Kyushu is in the south with active volcanoes and onsen culture (hot springs).
Shikoku is the quietest, with small villages and farming, where you can deeply immerse yourself in the culture.
Hokkaido is in the north and famous for skiing, but the wilderness and mountains are not to be overlooked.

“The more time you spend [in Japan], the more you realize you don’t know the destination that well. And every time I go back, there’s always a new thing to explore. There’s always a theme that needs unpacking. And it’s one of those places that’s, it’s not like in New York where you get to live there for ten years, and then you get to say you’re a New Yorker. The more time you spend, the more you’re like, wow, I’m not from here.” (Brandon Presser)

First time in Japan? Here’s a way to approach it:

Japan offers many options, so your first time might feel overwhelming. A simple framework for your trip is to think of it as a meal:

Appetizer: Soak in the vibe, and do some sampling while you get over the jet lag (Tokyo and Kyoto).
Main Course: Attend some must-see sights and experiences (Tokyo and Kyoto).
Dessert: Visit one of the other islands and treat yourself to an immersive experience (ryokan).

Language Barrier

In four trips, I’ve only picked up a dozen or so words/phrases, and I’ve never had a problem in Japan. Also, since my first trip in 2004, I’ve definitely noticed an improvement in the English spoken/written in Japan. Finally, while you might need to speak slower and point more often, there aren't any countries in the world that you can't visit if you don't speak the language, so I wouldn’t ever let language prevent you from traveling somewhere.

Photos From Past Japan Trips

⌚ Best Time To Travel

There's no wrong answer; it depends on what you want to discover.

In the Spring, you’ll experience sakura, the stunning cherry blossoms. While you will experience the crowds, the beauty is worth the hype. And you don’t need to be in Tokyo or Kyoto to see them.
In the Fall, you’ll experience koyo, the beautiful autumn colors. The red Japanese maples are just as magnificent as the cherry blossoms. Since the country is 70% covered in forests, it’s a sight to see into November.
In the Winter, you’ll experience perfect conditions for skiing in Hokkaido, wintry landscapes, and stunning sunsets. While the winter is colder, the crowds are fewer, and prices are lower.
In the Summer, you’ll experience matsuri, the festivals, and the country's liveliness. It’s a great opportunity to wander the city via walking or transit. While its vibrancy is in full effect, it can get hot and humid.

🏨 Hospitality Culture & Norms

Hospitality is centered around omotenashi, an elevated sense of service. There is an unspoken social contract unique to Japan that you are a “deferential” guest. In other words, the idea that “the customer is always right” doesn’t really exist like it does in the US, and you are expected to be as well-behaved and as friendly to hospitality staff as they are to you.

Also, punctuality is a core value in Japanese culture. Trains run on a perfect schedule. Brandon actually shared his experience of being on a late train, and he received an official notice from the rail operators to give his boss an excuse for being late. Also, in 2017 and 2018, rail operators issued nationally broadcasted apologies for trains that unintentionally left 20 seconds too early. The point is punctuality is important, so try not to be late for any of your reservations (restaurants, guides, trains, etc.).

Meeting locals in Japan is a bit harder than I’ve experienced in other countries. It's difficult to strike up a spontaneous conversation. However, I have found more success meeting locals through more structured ways, like attending a free walking tour.

Luxury Travel Planners, Guides & Hotel Concierges

There are many restaurants and experiences you can’t do without access to a connected local. It’s not as simple as booking online to eat at some Michelin-starred restaurants or attend certain cultural events. But don’t let that steer you away. If you can’t find a travel planner or guide, you can leverage high-end hotel concierge services for hard-to-book places. Book a few nights in a high-end hotel to take advantage of the concierge services and move to a more affordable place later. We had great success getting some tough reservations with the help of the Hilton Tokyo concierge.

It’s also important to note that many hotels offer a more comprehensive range of services and experiences than before the pandemic. They’ve invested in compelling food and beverage options and attracting locals to eat in their restaurants. Some even have secret personalized experiences with local artisans (Aman in Tokyo). For example, you could cut a kimono or yukata robe, hand etch chopsticks, or learn fan design.

Planning for Meals

Japan is a very populous country, so plan what you will eat and where you will stay ahead of time. The best tool for finding dining experiences is Tabelog. Just note that Japanese culture takes its food rating system very seriously. A great experience might be rated “3” because that qualifies as a great score.

Pro tip (ratings): The average for excellent is between 3-4 in Japan, so when you see a place with a really inflated score, it’s probably more frequented by foreigners than locals.

Dining Expectations, Etiquette Tips & Social Shopping

It is surprisingly cheap to eat in many places. For people who love to eat and try new food, it’s the perfect country for you. I will say “most” places are surprisingly cheap because Tokyo is notably home to 200+ Michelin-starred restaurants (the most of any city in the world).

If you want to optimize your daily food “allowance”, do two lunches. Do the first at 10:45 am, then another at 2:45 pm. You’ll get to try more places and, bonus, avoid some lines. But I will say this; you won’t be able to avoid lines forever. Waiting in line is just a part of the dining process, so it’s better to know this going into it.

If you eat with a larger group, expect to go in as pairs or trios. Many spaces are small, and dining is not always designed as a social experience. That said, there are less structured, informal venues perfect for socializing, like izakayas.

If you see a restaurant with multiple locations, don’t hesitate to try it (I’m talking of soba, gyoza, or ramen places, not McDonald’s). In America, having more than one location might be considered more corporate, but in Japan, having more than one location often means the food was good enough to expand. Since many restaurants are small, they might have added more locations just to serve more customers in different areas.

Note that Japan is a non-tipping culture and although your attempt might be well-intentioned, the act might be perceived as rude. So it’s best to get comfortable without leaving a tip.

Shopping in Japan (especially in Tokyo) is a social activity. Since people live in small spaces, it’s more accessible to hang out in public. Shopping can also be a super interesting experience for tourists. One reason is sizing. While I wear a L shirt in the US, I often found myself trying 2XL’s in Japan, and I never was able to find shoes or pants that fit.

Traveling With Kids

We’ve gone four times, but never with kids. We constantly walked around, tried new things, had cocktails, and ate four meals daily. Will we have another Japan trip like that with young kids? Probably not, but there are also family-friendly ways to experience the city, so I don’t want to discourage it. I’m excited to bring our girls to Japan to try new foods and enjoy many beautiful green spaces, open patios, and walking areas.

1️⃣ Tokyo

Tokyo is unlike any other city. It is enormous in every sense, yet more organized than any other city half its size. The best way to get around is by walking and public transit. Here are a few ways to get acquainted:

Explore Tokyo by Foot

Walk a triangle from Omotesando to Harajuku and then down to Shibuya. You can easily do this all on the same day and experience some great highlights of Tokyo.

In Omotesando, you’ll experience small boutique shops and luxury “rodeo drive” style shopping.
In Harajuku, you’ll experience a unique clash of styles (think hip-hop meets little bo-peep).
As you keep going, you’ll find the Meiji Shrine, which then turns into Shibuya Crossing, the busiest pedestrian crossing in the world.
Pro tip (from Amy): walk everywhere to burn enough calories for four meals daily.

Explore Tokyo by Train

Use the Yamanote Line. It’s a great option since the rail travels in a circle around the city. Also, if you try to take in the map of every single line, you’ll experience a sensory overload.
The Yamanote line is a perfect way to visualize Tokyo geographically because the city is structured like a clock:
- 1:00 - 2:00 are the older areas
- 3:00 is also a central hub of activity
- 6:00 - 9:00 are the newer neighborhoods (and Brandon’s favorites)
- 9:00 - 10:00 are the major stations
Pro tip: Use the Suica mobile wallet (instead of the physical card) and Google Maps to get around. Note that because there are two different subway companies in Tokyo the fastest route may require a transfer that makes it more expensive than another route.

Tokyo Restaurant & Drink Recommendations

Maisen is popular and famous for its tonkatsu (breaded pork cutlet).
Kagari Ramen offers chicken ramen you won’t find anywhere outside Japan.
Kikanbo is my favorite Japanese restaurant for spicy ramen.
Rokurinisha serves dipping-style ramen, which you should try at Tokyo Station.
Min Min possibly has the best gyoza in Japan, also at Tokyo Station.
Savoy Azabu Juban has the best pizza in the world (as a side note, you should try other types of food after your Japanese fix).
Tama blends Japanese and Taiwanese influences with parts of Okinawan culture.
Tatemichiya is a punk rock izakaya with such a fun vibe.
7-Eleven has some of the most amazing snacks. You might be surprised to hear this, but they have some of the most delicious pancakes in the world. Look for these and then heat them in the microwave and eat them there. Also, Brandon says the 7-Eleven egg salad sandwiches are so delicious that he can write poetry about them.
Deus ex Machina has outstanding coffee.
Bar Trench, Bar Tram, and Bar Benfiddich serve amazing cocktails (Japan takes cocktails to a whole new level).
Breakfast Club is a Japanese version of an American diner that combines breakfast with a bar-type atmosphere.
Bear Pond is a little hole in the wall that is massively popular for espresso (I’ve been told not to take photos).

The Best City View in Tokyo

Going to a high-end hotel is the best way to enjoy a city view in a relaxed atmosphere instead of in tourist-filled spots. The New Four Seasons at Otemachi has the best view of the Imperial Garden. Right behind it, you can see Mount Fuji on a very clear day (in the winter).

Tokyo Experiences Off The Beaten Track

If you want to do something different, you should explore some other Tokyo neighborhoods (Shimokitazawa, Kichijoji, Daikanyama, Nakameguro, and Jiyūgaoka), where you will find tiny traditional houses, tight spaces, boutique shops, and mom-and-pop shops.

Also, check out the immersive experiences from Team Labs – they’re filled with amazing immersive art with light, sounds, and textures. They are so incredible that we went to one and decided to do another one the next day.

2️⃣ Kyoto

Kyoto is the ancient capital with some of the oldest cultural relics, but it’s a place of learning at its core. It’s a college town with a thriving student culture worth visiting.

First time in Kyoto? Here are two simple things you should do:

Rent an electric bike. Since Kyoto is in the middle of the mountains, it is hilly, but there is less traffic, so things move slowly. Bicycle riders don’t need to worry about getting lost. You’ll be able to explore different neighborhoods and never be far from your hotel. Remember to ride on the left side of the road.

Wander. The back alleys in Kyoto are full of interesting things to discover. Some shops have been selling specific, handcrafted items for 300 or 400 years (like 11 types of scissors). You can still walk in and show interest in their work even if you don’t plan on buying anything. Be sure to thank them for their time and express interest in what they are doing because they take great pride in their work.

Pro tip: Any time you receive anything in Japan, hold it for a moment and accept it because it’s a sign of respect.

Restaurant & Drink Recommendations

Bar Rocking Chair will make you wonder if you should ever leave.
Yugen serves matcha, and it is one of the most beautiful shops I’ve been to.
Da Yuki specializes in Napoletana pizza with a chef trained in Italy who has brought everything back to master the art of pizza.
Ippodo Tea does tea tasting with a storied reputation in the country (think of wine-tasting for tea).
Monk is a restaurant that takes the sort of multi-course idea in Japanese cuisine and flips it to Italian style.
House of KI NO BI offers a fascinating gin-tasting experience utilizing local botanicals.
Yasai Hori is run and operated by the chef, only leaning into the local harvests of the area with simple ingredients that scream flavor.
The Bar at Park Hyatt Kyoto is excellent. It’s near Kiyomizu-Dera Temple. The hotel is extremely expensive, but Chase point transfer to Park Hyatt is probably one of the best deals in the world.

3️⃣ Other Destinations:

We stayed at Satoyama Jujo in Niigata, and while it’s not quite a Ryokan, Amy and I dream about going back all the time. It’s easily in our list of top 5 hotel experiences in the world. That’s not to say there aren’t 100 other similar hotels in Japan just as good, it’s just the only one we’ve experienced and would gladly go back. While the surrounding town is near a ski resort, we went in the off-season, and it was quiet and relaxing.

Kyushu is the motherland of onsen culture. Kyushu has two main onsen towns: Beppu and Yufuin. Whenever you see a photo of Beppu, it looks like steam is coming out of every vent in the town. It’s unique. And then there is Yufuin. It’s located in the mountains in a rural setting but is still a popular tourist destination. I’ve never been to Kyushu, but it’s top of my list because I love going to the Onsen (though make sure you read up on onsen etiquette and protocol, which involves washing your body before bathing fully naked).

Outside Hakone, there are some incredible places to stay, like Fuji Five Lakes, nestled right under the mountain in a natural and beautiful environment.

A UNESCO site, Nikko is an experience for the evening after all the crowds are gone. You can see the UNESCO sites, but Brandon recommends Lake Chuzenji as a breathtaking experience.

Kanazawa is an excellent alternative to Kyoto if you want to avoid crowds. It has one of the most beautiful gardens in Japan. The Japanese rank their gardens, and one of them is in Kanazawa.

Despite Osaka's reputation as a food city, the entire country is basically a food country. So you don't necessarily need to go there and go out of your way, but if you are there, the city is known for having fantastic okonomiyaki. We also had an amazing time at an amazing speakeasy-style bar called Bible Club.

💭 Final Thoughts

A trip to Japan is the perfect way to indulge in the joy of exploration and serendipity. That might be hard for people who want to tackle everything on the itinerary or have massive FOMO, but I promise you won’t regret just exploring.

I want to thank Brandon Presser again for this conversation and his depth of experience. Check out (🎧Ep 101) for more about Traveling to Japan. And please give him a follow on Instagram.

I also have a bonus blog post coming soon to help you maximize your Japan trip with points and miles. I’ll highlight the flights, hotels, and great deals on credit card sign-up bonuses, so you get the max out of your travel. If you can’t wait, you can listen to the episode on the topic here: Ep 102: Traveling to Japan with Points & Miles.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

🏡 Owning a Home: Build Wealth + Tactics to Save More

Fri, 27 Jan 2023 08:00:00 +0000

On average, Americans spend 25.8% of their earnings on housing costs, but there are plenty of creative ways to reduce that through house hacking. Now, don’t let that conjure up images of roommates or bunk beds, you don't necessarily have to sacrifice your lifestyle to make it work. In 2020, I discussed how to house hack like a pro with Andrew Kerr (🎧 Ep14), who hosts The House Hacking Podcast and last year I read Robert Leonard’s amazing book The Everything Guide to House Hacking. Between my personal experience and everything I learned from those two resources I hope this leaves you with a few ideas you can use to save money on your housing costs.

🏘️ What is house hacking?

It’s finding creative ways to reduce your housing costs. Think of it as a version of real estate investing but for the property you live in. It could be a great tool to get your foot in the door if you want to do broader real estate investing or even if you don’t ever want to be a real estate investor, you can use it to save money on housing.

🤔 A mental framework for house hacking

Andrew (🎧 Ep14) provided a simple way to think about the process. Here are the two fundamental questions to consider:

What’s the best type of house hack that fits my needs?
What’s the best type of tenant base that also fits the space, and what I like as well?

Let’s examine them more closely.

🏠 House hacking options

If you’re wondering, “What’s the best type of house hack for me?” here are six common types:

A small multi-family involves buying a house with 2-4 separate living areas (e.g., duplexes, triples, fourplexes). One space is yours, while tenants occupy the other spaces. A building with four or less units will usually qualify as a residence and not be treated like a commercial property.

A roommate rental involves renting out part of your living space to other tenants.

An income suite can maximize your home’s space and convert part of it into an income-producing area. You can turn an unfinished walkout basement into an income suite.

An accessory dwelling unit (ADU) is a separate structure on your property that can be rented as a secondary living space. The term is derived from the building code and is meant to be understood similarly to pool houses, garages, and guesthouses.

A work provided house hack is when you specifically choose a career path that includes housing, such as travel nursing.

Flipping a home is the process of buying, renovating, and reselling it. You can do a quick flip (under one year) or a slow flip, where you live there while renovating, which can be advantageous when it comes to reducing your capital gains tax on the appreciation… but more on taxes later.

🔍 A closer look at the ADUs

The multi-family market competes against a larger market of investors, so it might be hard to find a good deal. However, single-family homes with ADUs or income suites might be an even better option for house hackers.

Depending on where you live, building an ADU might be a much easier process than you think. In fact one of the co-founders of Airbnb just launched a company called Samara to make it even easier. You will probably still need permits to run electrical, plumbing, etc. but it can be an amazing option to start house hacking and earn some extra income. If we had room on our property for an ADU, we’d have already done it. They’re great because they’re so flexible:

The ADU can be rented while you live in the house
The house can be rented while you live in the ADU
The ADU can be rented while your children are young, then let them live in it when they are older

🏚️ Any property can be hacked

Here are three examples of house hacking:

Andrew’s multi-family (🎧 Ep14): He converted a corner store into three high-end apartments with an ADU. He and his wife lived in a two-bedroom, one-bathroom specialty-style home. Their property was fitted with high-end furnishing, 11-foot ceilings, and hardwood floors AND the rent from the other units covered the entire $20k/year in payments, plus gave them another $8-$10k in profit.

Brandon’s multi-family (🎧 Ep80): He has a multi-million dollar triplex on Maui with a pool that overlooks the ocean. He rents out the back unit to cover half of the mortgage and could easily rent out the other unit to cover the rest.

My income suite: I’ve had my own experience with house hacking (before realizing it was even a thing). We bought a three-bedroom San Francisco-style walk-up with a separate entrance on the ground floor. We didn’t need all three bedrooms at the time and I’m usually against getting a house bigger than is required, but we knew the income from renting would offset the additional cost and provide flexibility for future needed space. That was 7-8 years ago and it was amazing. We locked the door to the ground floor bedroom from the rest of the house and rented it to tenants that didn’t need a kitchen. Our rental income covered >50% of our entire mortgage payment and helped us meaningfully increase our savings rate.

🔽 Benefit: Reduced down payments

If you’re buying a 2-4 unit property for house hacking AND you plan to live in one of the units, then it should qualify as owner-occupied, which often comes with loan advantages like lower down payments or down payment assistance. Investment properties on the other hand often require at least 20% down.

In a future newsletter, I’ll talk more about loans and mortgages, but if you’re looking to hack your house, consider an FHA loan. It’s ideal for those who’ve never owned a home or haven’t had an FHA loan. There are restrictions based on your income level and where you live, along with a 3.5% down payment requirement.

💸 House hack while renting

You don’t even need to own a property to house hack. Although the options are a bit more limited, here’s some tips. Since the property is not yours, you should do two things. Check your lease to see if it allows you to sublease the space. Additionally, ensure the lease allows short-term rentals (as well as the area you live, some cities/counties don’t allow short-term rentals). You should also speak with your landlord and have a plan for managing the space. From the landlord’s perspective, “more people tend to mean more risk” (higher maintenance, more challenges), but if you work alongside them and ensure that the process is aligned with the lease and eases their concerns, it puts you in a better position. Here are some things you can do (and share with your landlord) to minimize risk:

Establish a screening procedure.
Obtain a security deposit or collect a few months of rent in advance.
Tell your landlord that you will be in charge of everything and remind them that more income for you increases their chances of getting paid each month.
If necessary, consider giving the landlord a portion of the sublease rent.

🛌 Tenants

If you’re wondering, “What’s the best type of tenant base that also fits the space and what I like as well?”, start by breaking them down into three timeframes:

Short-term tenants will stay less than 30 days
Mid-term tenants will stay for 30 days to 9 months
Long-term tenants will stay for at least 9 to 12 months

Like any business, focusing on a specific niche may help you save costs and get a premium price for your property. Apply that thinking to your tenant base.

When renting a short-term place (such as VRBO or Airbnb), tenants may be interested in something other than the home itself. They may not require a kitchen or laundry room, so having a microwave, mini fridge and coffee maker might be perfect. A minimal, streamlined operation, where the space is designed and intended for sleeping rather than living, might do the trick.

Mid-term tenants often want a furnished place, but only sometimes with all the bells and whistles. For up to 6 months, these spaces provide a more “home” feel than hotels. These spaces are ideal for corporate executives or traveling nurses who want to engage with a new city or community. The tenants may not require a full kitchen since they may eat in hospital cafeterias or out at local restaurants and cafes.

A long-term tenant will require more from your property, but keep in mind that if you’re in a city or near a college, your tenants may have access to food, laundry, or extra benefits that you won’t have to provide fully.

4️⃣ Building wealth with real estate

Since many house hacks involve owning the real estate, it’s important to remember there is more than one way to make money on a property:

Appreciation: The Case-Shiller index of real estate prices over the past 100 years shows that real estate prices have appreciated by 3% a year on average (despite dips, pullbacks, and recessions). While the stock market might have higher average returns, don’t forget that your real estate investment is likely leveraged because you didn’t put 100% down to purchase the home.

Cash flow: You could generate income on top of the monthly costs, like mortgage, maintenance, utilities, taxes and insurance.

Debt paydown: Even if your property doesn’t appreciate and you never turn a profit, your tenants might be helping you pay down your mortgage, leaving you with more equity in the home each month.

Tax advantages: There are so many real estate strategies available, but the best advice I can give is to find a CPA or tax advisor with whom you can talk so that you understand which ones are best for you. Here are some of the advantages Andrew Kerr (🎧 Ep14) and Brandon Turner (🎧 Ep80) mentioned:

If you itemize your deductions, you can deduct the mortgage interest on up to $750,000 of mortgage loans.
As a real estate/rental business, you can deduct your expenses from your rental income (including a prorated portion of expenses if you’re also living there).
You can depreciate the value of the buildings (not the land) to reduce your taxes, but remember that it will lower your cost basis, so you will have a larger tax liability down the road.
Capital gains up to $250k (or $500k if married) could be exempt if you lived in residence for two of the last five years.
By reinvesting your profits into other properties you can defer taxes indefinitely via the 1031 exchange.
If you rent out a property for 14 or less nights per year, the income is tax free thanks to the Augusta Rule.

💼 House hack like it’s a business

If you start to get serious about house hacking, you should really be treating it from the mindset of an investment property (even if legally it’s owner-occupied). That means you should understand the following:

Gross rents. Use tools like rentometer to determine how much your location could rent for.

Vacancy. Determine the general vacancy rate benchmark can be found online for your city, and match it to your situation. If a tenant moves out, the property will be vacant for at least a week, if not a month, for cleaning and marketing, so a vacancy plan is essential.

Maintenance. Account for minor repairs (e.g., window breaks) in your property. Common benchmarks are 5-10% of your gross rent.

Capital Expenditures. Account for the extensive repairs and replacements that will occur over time (e.g., roof). Plan to set aside money each year for the eventual need. For example, for a $20,000 roof replacement in 10 years, set aside $2,000 a year (and maybe adjust that amount each year for inflation).

Miscellaneous. Plan to pay or pass on the costs of running the property (e.g., utilities, lawn care, and snow removal).

Property management. Factor your time and level of expertise to manage tenants and the property. This is not required, but you could outsource the duties to a property manager that can cost ~8-10% of gross rents.

🧑‍🔧 Property managers

Whether you’re house hacking or running an investment property, let’s look at the responsibilities of a property manager because many amateur real estate investors don’t have one. They have three primary responsibilities:

Market and fill the property. Handle marketing, finding tenants, screening tenants (credit/background checks), pricing, and signing the lease.
Manage the property ongoing. Handles tenant requests and the coordination of services/contractors (e.g., plumbers and electricians). Their fee covers the cost of managing, but not the actual service costs, so you will still get those bills.
Manage the lease renewal and turnover. Handles the resigning process, lease updates, and verification process for renewals. And if there’s no renewal, they’ll handle move-out, cleaning, and start finding a new tenant.

If you’re new to real estate it might be helpful to manage your property for a year to better understand the process, but after that I’d encourage you to consider turning it over to an experienced property manager.

📃 Protect yourself though great leases

If you plan to house hack, you must have an outstanding lease. Having everything written down is extremely important in the worst-case scenario. Managing your life can be challenging, and adding tenants can make it harder. So use a standard lease document or let an attorney draft the lease to protect against headaches, stress, and financial losses.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Editor’s Note: Today, I’m grateful for the support of our partners Pacaso and MileValue. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

🎉 Top Learnings and Credit Cards of 2022

Thu, 29 Dec 2022 08:00:00 +0000

Advertiser Disclosure

Note: American Express is a ChrisHutchins.com advertiser

I have an incredibly packed post to share with you, so I’ll keep the intro short. I’m going to run through…

My 10 biggest takeaways from the past 94 episodes of the podcast (and what I will focus on in 2023 because of them)
My top 10 tips from 2022
My top credit cards from the past year (based on my spending data)

In each takeaway, I’ll highlight the episodes they’re from, so if you want to learn more, you can click through to read the show notes and/or listen to the full episode. While the takeaways aren’t ordered by priority, I did save my top two for last. And if you found any of this valuable, the most meaningful thing you can do for me is to share it with anyone else you think might enjoy it. Thanks so much and happy near year!

⌛ Productivity and Time Management

Takeaway #1: I have the time, but need to better prioritize and say no more often.

Laura Vanderkam (🎧 Ep7) was my first guest about time management and a story that really stuck out for me was when she demonstrated how a water-heater flood could magically make three to four hours appear in even the tightest of schedules. We all have time, 168 hours a week to be precise, so when I feel like I don’t have any, I try to realize I either overcommitted or didn’t prioritize well. I’ve begun to implement a Calendar Audit to be more diligent in how I spend my time.

Brandon Turner (🎧 Ep82) stressed the importance of setting boundaries. I've learned to say no to meetings and stop chasing things that are not at the top of the priority list. I now regularly propose Loom as an alternative to video calls, because it’s asynchronous and you speed up the video to 2x. An added benefit is that some people view it as too much work that they give up on trying to connect with you.

💲 Money

Takeaway #2: I can simplify my financial decisions with rules, and consolidate and automate my savings and retirement.

Ben Carlson (🎧 Ep42) and Andy Rachleff (🎧 Ep19) discussed the importance of simplifying finances, but it was Ramit Sethi's (🎧 Ep9) money rules that moved me to act. In his book, he shared his 10 Money Rules that help make his financial decisions easy. Amy and I started with one rule, "discuss any purchases over $200 with each other first”, but I hope we can put together a more comprehensive list in 2023.

Also, I opened a lot of bank and investment accounts while I was building consumer finance products. It is stressful to have my money spread across so many places, but fortunately, I have already moved my investments to Wealthfront (where I happily pay for a fee smaller than the taxes I save each year from automated tax loss harvesting). My goal right now is to consolidate accounts to:

1 checking (SVB, because our mortgage is there)
1 high-yield cash (Wealthfront for 3.8% APY ← $30 Free)
1 brokerage (Wealthfront for Tax-Loss Harvesting ← $5k Managed Free)
2 401(k)’s (Fidelity + Vanguard, where our employers picked)
2 Roth IRAs (Wealthfront because it coordinates with the brokerage)

Just seeing this list makes me smile because I’m so used to having a few dozen accounts with balances in them. Also, with fewer accounts, saving will be a lot easier. I’ll actually be using a product I built at Wealthfront called Autopilot, which lets you set an amount to always keep in your checking account and emergency fund, and it will automatically transfer any excess to your IRAs, 529 accounts, and taxable investment accounts.

🤝 Negotiation

Takeaway #3: I get better results when I ask better questions.

Kwame Christian (🎧 Ep17) runs the American Negotiation Institute and he showed me how his question-based framework can best prepare you for any negotiation. Think about the following:

What do you want and why?
What the other side wants and why?
What are all the open-ended questions you could ask in the conversation?

He also shared his Compassionate Curiosity framework. You begin by acknowledging and validating others' feelings, then by being curious and asking them questions with compassion, you can collaboratively solve your problems.

Finally, Andy Rachleff (🎧 Ep19) gave me an amazing negotiating tactic. He says to always “put the gun in the other person's hand. If they fire, don't work with them." Most people don't like to be thought of as taking advantage of others, which is why this works so well. Nevertheless, if the ask is well in excess of reasonable, you can just walk away.

😞 Regret

Takeaway #4: I should be more intentional about the things that are meaningful to me.

Regret was the subject of three incredible conversations.

First, Ben Nemtin (🎧 Ep36) talked about bucket lists. He had a whole journey that began after learning that more than 75% of people regret not living their lives on their terms.

Second, Dan Pink (🎧 Ep40) highlighted regret as the most instructive emotion we have and an essential part of our cognitive machinery. We discussed the four types of regret and how to deal with them.

Third, Jordan Grummet (🎧 Ep74) discussed living a more purposeful life. He spoke about how identity, purpose, and connections matter more than money.

What does that mean for me? In the same way that I want to be intentional with how I spend the hours of the day, I want to be intentional with the big things in life too, like the way our family spends time together, the trips we take, the friends we hang out with and more. So for starters, Amy and I plan to spend some time this week talking about what our lives in 2023 (and beyond) should look like.

💕 Relationships

Takeaway #5: I intend to strive harder to achieve an 80/80 marriage.

Nate and Kaley Klemp (🎧 Ep43) educated me on how marriage relationships have evolved. It started with the traditional 80/20 relationship, where one partner (usually the woman) does all the work in the relationship and for the family since the other serves as the breadwinner.

Many relationships today have now moved to 50/50, but the challenge is that many couples end up keeping a score of who's done what more. This competition can be exhausting.

After hundreds of interviews, Nate and Kaley have constructed the 80/80 relationship concept, in which both partners assume that they are doing their best and trying to pull more than half of the load.

I can say that our relationship has been much better as a result of it, even though it takes time and practice to get it to work. Check out our episode or their book on the topic to learn the tactics to make this work.

📣 Communication

Takeaway #6: I can engineer more charisma in my communication.

As Vanessa Van Edwards (🎧 Ep46) illustrated, charisma is a balance of warmth and competence. I try to employ this formula in all my work.

She shared a lot of helpful techniques for achieving the right balance between nonverbal communication, vocal cues, and verbal cues. For instance, I know that emojis and exclamations can make you feel warm, so I try to tone them down or balance them out when sharing data or charts to increase my “competence”.

✈️ Points & Miles

Takeaway #7: I don’t need to get the perfect deal when using points.

Tiffany Funk (🎧 Ep89) busted a bunch of myths about when to use your points. I've spent so much time optimizing for a dollar-per-point value that I'm doing myself harm. Though I know I'm very fortunate to have so many points, I’m also ashamed that I don't use my points enough. I often find myself paying cash for flights because the redemption value was as good as I’ve gotten before.

She also pointed out that contrary to the thought that international business-class flights are the most efficient use of points, in the past few years, domestic award redemptions have been excellent too.

It's time to burn down our points balance instead of just looking for the absolute best deals (though I'm sure I'll still look).

💻 Life Online

Takeaway #8: I need to start organizing my digital life better.

Tiago Forte (🎧 Ep85) inspired me to build a second brain and it’s already started changing the way I save and consume information. As an example, I'm now saving so much of the content I find online into a reader app called Matter, which saves me time in three ways.

I consume information in batches
I can listen to those long articles instead of reading them, thanks to Matter's text-to-speech option
It seems that half of the things I save seem to lose importance by the time I get back to them (so I save myself multiple 10-15 minute interruptions).

Next year, I want to focus on more intentionality and organization with my notes and tasks.

💯 Net Fulfillment

Takeaway #9: I need to focus more on net fulfillment than net worth.

The episode really rocked my world. In fact, Bill Perkins (🎧 Ep91) reframed my entire view of money by stating that we should actually start allocating our money so that, in the end, we will be at zero (or close to it).

I've been greatly influenced by FI/RE (Financial Independence Retire Early) for the past decade, and it has taught me to save and be frugal. I am grateful for all the savings, but wonder if we ended up saving too much instead of spending on things that were uniquely suited to our 20s/30s and would have had a huge impact on our fulfillment. You don't have to be reckless with your finances...just rethink the focus on growing net worth at all costs.

So what’s changing as a result of my conversation with Bill?

Amy and I need to start thinking about the experiences we want to have in our 30s, considering that our kids will never be this young again and that these are the last few years of our 30s.
I'm going to be more intentional about taking more photos and videos as we experience life so we can “harvest the dividends” of our memories in the future..
It's time for me to start making decisions in life that maximize my fulfillment. During our recent trip to Europe, we didn't make the best use of miles or find any hotel deals, but we still went because we wanted to have the experience at this point in our lives.

Multiple listeners and friends have told me this is the best podcast episode they’ve listened to all year (of all podcasts, not just ours), so if this takeaway is at all interesting, you should absolutely listen to the episode and check out the Die with Zero book. I’ve already re-listened twice and each time I find a new way it’s going to impact my life.

🙂 Happiness

Takeaway #10: I can capitalize on crystalized knowledge and happiness by going all-in on the podcast.

Arthur Brooks (🎧 Ep47) helped me redefine and find happiness and I’ve relistened to our conversation more than any other episode I’ve done (probably at least 4-5 times).

He says it’s important to remember that happiness is the combination of three macronutrients: enjoyment, satisfaction, and purpose. When you’re unhappy, you lack balance in one of these three, so you should start there to find happiness again.

In addition, we discussed how to make an impact on your happiness, and I learned a lot about fluid and crystallized intelligence curves.

Fluid intelligence is the capacity to learn, solve problems, and process new information
Crystallized intelligence is the stored, accumulation of knowledge over time

Fluid intelligence peaks in our 20's and 30's. Crystallized intelligence (wisdom) begins to form in our late 30’s and 40's. We must recognize that finding work that harnesses this crystallized intelligence will lead to our work happiness in the future.

While it may seem obvious to some, I was lucky that switching to podcast full-time seems to be mirroring my desire for leveraging crystallized knowledge, which makes me even more confident in the decision to leave my day-job.

Arthur also shared…

“If you want to be among the happiest people, they all do these things every day.

They practice their faith or life philosophy. You don't have to be religious, you just have something bigger than you that zooms you out on your own life. Life philosophy or faith or spiritual practice gives you that uniquely. So it's meditation or prayer or studying the Stoics, whatever it happens to be, you got to do your thing and you gotta do it seriously.

Second is family, the ties that bind and don't break. It's important that you do not choose them, but that you have them for your happiness. And God knows in many cases we wouldn't choose them.

The third is friendship. We have a major loneliness crisis in the United States. The average number of close friends that somebody 30 years old has been cut in half in the past 20 years. About half of people under 30 say that no one knows them well. It's horrible for every aspect of happiness. And part of the reason for that is that everybody knows how to make deal friends, but we know less and less about how to make real friends.

And the last is work. And work doesn't mean working hard all night long. It doesn't mean making tons of money. It doesn't mean having prestige. It means exactly two things: (1) earning your success, meaning your skills meet your passions, and (2) serving other people – the people who need you. If you earn your success and you're serving other people, I don't care if you're an electrician or a librarian or a podcast host or a Harvard professor, you will be happy from your work. And if you don't have those things, you won't be happy with your work.

Faith, family, friends, and work are the big four.”

The episode is chalked full of great advice and tactics to be happier in 2023, and I will definitely be putting a lot of it into action myself next year. If you want to join me, listen to the full episode or check out Arthur’s book on happiness.

🔟 Top 10 Tips from 2022

Book a hotel directly and email them to tell them you're excited to stay. I've heard from 100’s of listeners about using this trick to get upgrades, bottles of wine, free food, vouchers for drinks at the bar, free parking, and most ridiculously, pillows embroidered with your initials on them. Big thanks to Leigh Rowan (🎧 Ep1) and Julia Menez (🎧 Ep55) for sharing it.
Find free unclaimed money you're owed on your state's unclaimed money site. I think the biggest winner was a listener who found over $1,000, but I've had at least a dozen people find over $100 and even more that found $25-50. You can find your state’s site here.
Use Google Image Search to find vacation rentals for a lower price. For this trick, take the main photo from VRBO or Airbnb and put it in Google Image Search to find other sites that rent the same property for less. This also came from my first conversation with Leigh Rowan (🎧 Ep1) which is still the all-time most popular episode and worth a listen if you like travel tips.
Use Autoslash to save hundreds on rental cars. I interviewed Jonathan Weinberg (🎧 Ep66) for a Masterclass on all things rental cars. Before you book your next rental car or even if you already have your reservation made, check out the episode, or at a minimum check out Autoslash to save on your rental. Note: this may read like an ad, but it’s not, I just really like Autoslash.
Permit yourself to have 'it' in five minutes. Nir Eyal (🎧 Ep25) taught me how to be indistractible. My favorite lesson works wonders with the delicious things Amy loves to bake. When I feel a craving for something unhealthy, I just give myself permission to have it in five minutes. When the timer is up, I often have moved on to something else and have lost my craving (or at least eaten one or two fewer cookies than I wanted).
Tape your mouth shut at night for better breathing. I thought it was a little crazy, but thanks to Liz Moody (🎧 Ep52), I'm sold now. The team at Hostage Tape sent me their mouth tape earlier this year and I've been using it almost every night.
Take cold showers. Also from Liz Moody (🎧 Ep52) and I did it for 30 days straight after our conversation. When you start your day with a cold shower, everything else is manageable. I’m actually hoping to upgrade to a cold plunge this year, but until then it’s cold showers.
Never pay the first healthcare bill. I learned about the inaccuracies of medical bills and deceptive tactics of the healthcare industry from Marshall Allen (🎧 Ep34) and his amazing book. Armed with the knowledge, I pushed back and saved a ton when I fractured my foot and got shingles last year.
Build a memory palace to memorize anything. I spoke with, two-time world memory champion, Johannes Mallow (🎧 Ep30) about the tactics he uses to memorize everything from lists to names and numbers. In fact, I still remember the list we came up with in that episode over a year ago.
Get rid of dinner parties and host cocktail parties instead. They’re so much more efficient and when you don't need food, you can put a two-hour hard stop on the event. They also let you spend more time with more people and are just more fun in general. Thank you, Nick Gray (🎧 Ep68) and your awesome book. While my event in San Francisco probably bent the rules for an easy cocktail party, it was a blast and I look forward to doing more events and cocktail parties in 2023.

If you want more tips and tricks, go back and pick from any of almost 100 episodes of the podcast or go back and read any of my past newsletters.

💳 Top Credit Cards for 2022

My spending summary for non-business expenses was dominated by four cards.

The first is my American Express® Gold Card, because food was a big part of our spending the past year. And I was pretty efficient with this card, earning 98% of the points on that card this year in the 4x category as this card lets you earn 4x at restaurants worldwide, on up to $50,000 in purchases per calendar year.
The second is my Chase Sapphire Reserve®, which I used mostly for flights/hotels and dining when I forget my Amex Gold (or in the rare case Amex wasn’t). I was slightly less efficient with the CSR, earning only 92% of the points in the 3x bonus categories.
The third is Amy’s Prime Visa Card, which we use for Amazon and Amazon Fresh. I can tell you that the 5% back makes it worth it and because we only use it for Amazon we hit 100% of the spend getting 5% back. And while I don’t typically like cash back over points, I'll take 5% cashback when the alternative is only 2x points.
The fourth is my Capital One® Venture X Rewards Credit Card, which is my daily card for everything not earning a bonus above because it earns 2x points on everything. Also between the $300 annual travel credit and 10,000 point annual bonus, the $395 annual fee will pay for itself.

In terms of business expenses, I’ve put almost everything on my Ink Business Preferred® Credit Card for travel and the Capital One® Spark® Cash Plus (2x on everything if you have a Venture card).

If you're interested in any of those cards or any other cards, please sign up at chrishutchins.com/cards. I’d be super grateful because it will help support the show.

Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

✅ My 2022 Year End Checklist for Taxes, Money, Points and Miles

Thu, 29 Dec 2022 08:00:00 +0000

Advertiser Disclosure

Note: American Express is a ChrisHutchins.com advertiser

There are a few days left in 2022, so you still have time to do some year-end tax and financial planning. My approach is to avoid, minimize or postpone my taxes as much as possible while 100% following the rules of law. Given that, I’m hoping this newsletter is tactical, practical, and helpful.

While I love doing this kind of research, I am not a tax professional and I suggest partnering with a tax specialist/CPA., so you should discuss the content below. I use Gelt, a tax planning company that I was so impressed with after meeting the CEO, Tal Bender; I knew I had to invest a small amount in the company. Tal also helped me put together this email and offered to let any of our subscribers skip their waitlist when they schedule a call here.

I’ll also dive into everything you might want to consider before the end of the year when it comes to your miles and points. Finally, I hope you all have a wonderful holiday!

💰 Standard Deduction or Itemize

The IRS allows anyone to take an automatic standard deduction ($12,950 for a single filer and $25,900 if you’re a joint filer).

Alternatively, you can add up your qualified deductions to see if they exceed the standard deduction. Examples of qualified deductions include charitable contributions, state and local taxes (up to $10,000), mortgage interest (on the first $750k of mortgage if filing jointly), as well as some medical expenses, investment interest, gambling losses, and casualty losses.

For any year your itemized deductions exceed the standard deduction, you choose to use them instead, even if it means you switch back and forth each year. In fact, if every year it’s close, you may want to consider trying to consolidate deductions in one year by prepaying a mortgage payment or property tax bill and/or or moving up donations into the current year.

⏩ Accelerate or Defer Income

This may be harder for those that don’t own a business, but there are instances where you could push income into the next year. For example, a friend of mine recently lost their job. He will receive a severance package upon signing the final paperwork. His employer informed him that he had until the end of the year to sign, so he’s waiting to submit until the final week of December, so the first payment will be taxed in 2023.

✍️ Donate to a Charity

You can deduct any contributions you make to a non-profit, but you can also deduct clothes, electronics, or anything else you donate to places like Goodwill. For donated goods, you can get a tax donation of up to $5,000, but it comes with specific requirements. Make sure you complete a receipt and write down the amount you donated to have it on hand if you have questions.

It’s up to you to determine a valuation. You can use the Salvation Army or Goodwill valuation guides as a basis.

Donate Appreciated Assets

You can save even more when you donate appreciated assets instead of cash. Suppose you bought a stock for $100 years ago, and now it is worth $1,000 (nice! 👍). If you sold that sock, you’d owe long-term capital gains taxes on the $900 gain. In a state like California that could be as much as 33%, meaning you’d owe $300 in taxes.

Your $1,000 sale would net you $700. If you donate that $700, you get a deduction of $700. If, instead, you donate the appreciated asset (the $1,000 of stock), the charity receives $1,000 in value, and you get a $1,000 deduction. Just know the process can be a bit more complex than putting in on a credit card… unless you’re using a DAF.

Donor Advised Funds

A donor-advised fund (DAF) is a tax-advantaged account that lets you donate money, stocks, or crypto and qualify for the tax deduction in that year. Except you don't have to know exactly where you want to give the money right away. In fact, you can make your tax deductible contribution now and invest that money so it can grow tax free and let you have more impact in the future.

I manage my donor-advised fund with Daffy and you want to sign up, you can get $25 for free here. They are a partner of the podcast, but I was using their product long before we partnered and I’ll continue using them long after (which hopefully never happens, because I’m a big fan).

🧑‍🌾 Tax Loss Harvesting

The market hasn’t been great this year, but there are a lot of Tax Worth Knowing During a Recession. That link is to a guide that Gelt put together, but there are a few things worth sharing here.

Fortunately our tax code allows you to use capital losses to offset capital gains. And if you don’t have any capital gains, you can deduct up to $3,000 of losses each year against your income and carry forward the rest.

That means you might have an opportunity to “harvest” losses before the end of the year, but according to the wash-sale rule, in order to take a loss, you can’t repurchase the same security (or a “substantially identical” one) for 30 days. However, many ETFs and index funds have similar (but not “substantially identical”) pairings that are very highly correlated (e.g. VTI and SCHB), which would let you sell one for a loss and buy the other without the loss being disallowed by the wash-sale rule.

You can do this yourself, but you’ll want to be careful, because the wash-sale rule applies across all your accounts. Robo-advisors like Wealthfront (which I use) can automate this process, and for me have harvested over 10% of my portfolio’s value this year as losses, which I will use to offset gains inside and outside of the portfolio. I’m no longer at Wealthfront, but my investments are, and if you’d like $5,000 managed for free, you can use my link.

I also go more in-depth about this topic in the All About Investing Part 2 newsletter.

What about Crypto?

Crypto is not classified as a security, so the current wash-sale rule doesn’t apply. So if your crypto tokens are down, you can sell them to capture the loss and, if you want, repurchase them right away.

Unfortunately, if you’re like me and all your crypto is stuck on a platform like BlockFi or FTX, you can’t take the loss during bankruptcy proceedings, but if you’re confident you’ll never get anything back, you could look into taking an abandonment loss (but I’d definitely talk to an accountant first).

Also, speaking of BlockFi, many of you know they were a previous sponsor and I used their platform to store all my Crypto. Since they put a hold on customer withdrawals and filed for bankruptcy, they've left many people, myself included, with lots of their crypto tokens stuck on the platform. I'm angry about the way this was all handled and that they publicly communicated normal operations in the hours before pausing withdrawals. I still have all my crypto on the platform and hate the financial situation they've put me and many others in. I truly hope that they are able to find a way through the bankruptcy proceedings that results in everyone getting their crypto back.

📊 Investment Considerations

End of the year financial moves aren’t all about taxes. There might be a few other investment decisions to consider before the end of the year too.

Series I Savings Bonds

I-bonds are indexed to inflation and the rate locked in for six months. The current interest rate is 6.89% and it will reset in April 2023 based on the latest inflation data. Also, you can’t withdraw your money for at least a year and if you withdraw within 5 years, you’ll forego the last 3 months of interest. That said, even if in the worst case, the rate reset to 0% next year, you’d have earned an average return of 3.445% on the year, which isn’t bad for a downside.

You can invest up to $10,000 per person or entity. So you could put $10,000 in for your spouse, kids, or even your family trust. To invest you have to use the government’s Treasury Direct website, which despite looking like it was built in the 90s, does work.

Municipal Bonds

One thing I’m considering for next year is whether to add more California municipal bonds to my investment portfolio. Given rising bond rates and that muni bonds are triple tax-free from federal, state, and local income taxes, they’re now more attractive.

Exercise ISOs (Incentive Stock Options)

If you are holding unexercised ISOs, it might be possible to exercise some of them before year’s end without triggering any alternative minimum tax implications (you’ll still pay to exercise, but wouldn’t owe additional taxes). That said, I would absolutely recommend working with a tax professional to do this right.

Retirement Accounts

It’s probably too late to make any final contributions to your employer 401(k) for 2022, but you can still make contributions to IRAs and solo 401(k)s until you file your taxes next year. And if you’re not eligible to contribute directly to an IRA/Roth IRA, you could consider a backdoor Roth IRA (check out this FAQ if you’re interested). Finally, if 2022 is a low tax year, you could consider a Roth Conversion for your 401(k) or traditional IRA.

529s

If you want to save for your children’s college, you can contribute up to $16,000 per child annually in a 529 plan. Since it’s individual to individual, if a couple wanted to contribute to two kids, you could give $32,000 per person. You could also superfund five years of contributions at once. You may get a tax break for investing in some states, but you won’t at the Federal level (or in California). However, your money will grow tax-free without any penalty, as long as the funds are used for education.

I go more in-depth in the All About Investing Part 2 newsletter.

💊 Use up your FSA and max your HSA

If you don’t use your flexible spending account (FSA), you’ll lose it. Some employers allow you to rollover $570 to 2023, but typically you’ll just get a grace period to March.

Products and services like blood tests, genetic tests, new baby monitors, and thermometers are all eligible expenses. Or if you don’t need anything, you can contact a local shelter or charity, ask if there’s anything they need, and you can buy it for them.

While Health Savings Accounts (HSAs) don’t expire, they do have contribution limits each year. So if you haven’t maxed yours out ($3,650 for individuals or $7,300 for families), you have until the April tax-filing deadline to do so. While I don’t currently have an eligible healthcare plan, I love HSAs, because they’re triple-tax-advantaged. You put money in tax-free, the money grows tax-free, and you can take it out tax free.

I talk in-depth about FSA & HSAs in the Healthcare newsletter.

🏡 The Augusta Rule

If you’ve ever thought about renting your home on Airbnb while you’re traveling, you should know that it can be rented for up to 14 nights a year without needing to report the rental income. The name originated because it was a way to protect Augusta, GA, residents who rented out their homes for the Master’s golf tournament.

🌎 Grab Energy Efficiency or EV credits

Home enhancements to energy-efficiency windows, doors, insulation, roofs, heat pumps, water heaters, and furnaces qualify for up to $500 credit on your taxes or 30% solar credit. Also, if you purchase or acquire an electric vehicle (EV) assembled in the US before the end of the year, you could receive a credit of up to $7,500. I have a friend who just flew to Florida to buy an EV and take advantage of this before year-end.

💼 Optimize Business Taxes

It’s essential to think about tax optimizations if you run a business. I will highlight a few things that might be worth thinking about or discussing with your accountant.

Electing to be taxed as an S-Corp to reduce Social Security and Medicare taxes.
Taking a home office deduction to reduce some of your home expenses.
Deducting 100% of business-related meals from 2022
Hiring your children to work for your business, day-to-day, or as models for photos on your website/social media. With some income, your children would also be eligible for a Roth IRA, which could remarkably impact their financial future.
Accelerate depreciation in one year if you buy a vehicle with a Gross Vehicle Weight Rating over 6,000 pounds and use it for business.
If you are self-employed, you can access a lot of retirement optimizations, including the possibility of contributing more than you could as an employee.

💳 Review Expiring Points and Miles

I review all my accounts to see if they have expiring balances. If you have points related to a credit card, I wouldn’t worry because it usually just takes any activity within a year to keep points/miles from expiring.

While hotel points tend to expire more frequently than airline miles, it’s pretty easy to prevent that from happening. Many hotel programs allow free transfers between people that count as activity, so I just moved my Hilton points to my wife Amy’s account to keep them all from expiring.

Many airlines don’t have expiration dates, but for the airlines that do, you can do a few simple things:

Use their shopping portal to make a small purchase.
Buy a nominal amount of points.
Donate a nominal amount.
Redeem a few points for a donation to charity or a magazine subscription.

Any activity in your account should keep those balances active.

💍 Chasing Elite Status

If you’re chasing status (on an airline or hotel), you can always consider making a mileage or mattress run.

A mileage run is when you need an extra flight segment(s) before the end of the year to hit a certain status level. Even though I haven’t done this for a while, one year I remember flying to San Diego only to get right back on the same plane back to SFO because I was 800 miles short of getting that next tier of status.

For hotels, you could just book a cheap stay at any hotel in the program. You probably need to show up, but you don’t have to stay there the entire time (though if you do leave, I’d suggest ruffling up the sheets and putting up the do not disturb sign.

Also, if you have Delta or Marriott status, don’t forget to select your choice benefits before the end of the year.

🗓️ Use Your Annual and Monthly Credits

Many credit cards have different credits, some tied to the calendar year, some to the card member year (e.g. the 12 months following signup) and some monthly.

Calendar Year

The Platinum Card® from American Express, American Express® Gold Card, and Hilton Honors American Express Aspire Cards have airline credits. The card will reimburse you for non-ticket airline purchases, but you must select your airline first. (There are some great threads on FlyerTalk if you want to learn about creative ways to take advantage of these credits).
Citi Prestige® Card and the Bank of America® Premium Rewards® Card have annual travel credits that expire at the end of the year.
The Platinum Card® from American Express has a few other credits expiring at the end of December: the $200 prepaid hotel credit, a $200 Dell credit, and a $50 Saks 6-month credit.

Cardmember Year

Capital One® Venture X Rewards Credit Card and Chase Sapphire Reserve® have a $300 travel credit*. The Chase credit is straightforward to use - once it’s spent on travel, it automatically gets used. Capital One® Venture X Rewards Credit Card requires you to go into the portal and book something.
Chase Sapphire Preferred® Card: has a $50 hotel credit when you book on Chase Travel℠.
Hilton Honors American Express Aspire Card has a $250 resort credit at Hilton properties.

Monthly Credits

The Platinum Card® from American Express has a $15 monthly Uber credit ($35 in December) and a $20 monthly digital entertainment credit (for things like NYTimes).
American Express® Gold Card has two monthly $10 credits towards dining and Uber.

*Points are not earned until after the first $300 is spent annually on purchases in the travel category. The first $300 spent goes towards the $300 Annual Travel Credit.

🎁 2022 Holiday Gift Guide

Fri, 16 Dec 2022 08:00:00 +0000

As the holidays get closer, I thought I’d put together a list of my favorite products, gifts, past purchases and more. Hopefully some of them might make good ideas for gifts this holiday season. If you have any suggestions for things I should put on my list, please send them my way. Also, none of the products or services I included below have paid me to be included in the list, however some of them are sponsors of the podcast (probably because most of my sponsors were a result of me reaching out to them after loving their products). Additionally, some of the links are affiliate links that I’d earn a commission on, so if you don’t find a better price elsewhere, I’d obviously appreciate you clicking them :)

🏡 Home & Food

Breville Tea Maker: This has been in our kitchen for over a decade and gets used daily. If you brew loose leaf tea, it makes the process so easy, letting you dial in the temperature and brew time, and then automates the rest. And if you also brew coffee, it doubles as fantastic water kettle where you can set the exact temperature (though I imagine there’s a much cheaper kettle if you don’t want the tea making functionality).
Trade Coffee: Based on the smile that shows up on Amy’s face every time she opens up our Trade Coffee subscription, I feel confident saying that this would make an amazing gift for any coffee lover. Each delivery they’ll get a new curated bag of coffee beans from the top independent roasters around the country. Best of all you can get up to $50 off gifts here.
Coravin: There are plenty of nights when Amy or I (or both of us) want to have a glass of wine with dinner, but we don’t really want to finish a bottle. So we’d either skip the wine or end up drinking more than we wanted… but then we got a Coravin as a gift and it changed the way we drink wine. It’s a device with a small, hollow needle that pierces through the cork and let’s you pour out wine, replacing the space it took up with Argon gas, which keeps your wine fresh for a future day. If you really want to splurge, my dad got a Plum Wine Dispenser, which is like a supercharged Coravin machine, and it’s pretty amazing.
Toto Washlet: If you’ve ever been to Japan, you’ve probably been fortunate to enjoy a Japanese bidet toilet. If not, you get a heated seat, heated water bidet and more. And despite that some of those toilets cost thousands of dollars, you can actually just get the seat to attach to your current toilet for <$500. I love the C5 model, but we put the less expensive C2 in our powder room and it’s cheaper (especially if you have a Costco membership for the link I just shared).
Aesop: I feel ridiculous recommending a $40 soap, but I think we’ve gotten more compliments from house guests on the Aesop soap we have in our bathrooms than anything else in our house. Not to mention if you haven’t used your $50 The Platinum Card® from American Express for Saks, you can use that to make it free (that’s what I do – I could never actually pay $40 for soap).
Whiskey River Soap: They have a snarky candle for almost any situation you could imagine and have been one of my go-to gifts for friends/colleagues the past few years.
Paprika App: I’ve mentioned this app multiple times, because I think it’s the best way to organize recipes and family meal planning. However, it’s a bit pricy ($5 mobile / $30 desktop), so it could make a great gift. Not to mention you could curate all your favorite recipes and share the export so whoever you gift it to starts off with a whole list of amazing recipes loaded in.
Ooni Pizza Oven: We love making pizza at home and a few years ago we gave an Ooni Koda to a family member for Christmas and it was a big hit. Not to mention it gave us a great family activity for one night during the holidays.

🧑‍🔧 Tech, Gear & Clothes

Vuori: They make the most amazing performance apparel that’s ridiculously comfortable (seriously Amy and I are basically wearing it every single day). My favorite is the Sunday performance joggers, but you really can’t go wrong with anything they make and you can get 20% off your first order here.
Blunt Umbrella: We bought our yellow Blunt Classic Umbrella 6 years ago and it still works as well as it did when we got it. It’s also incredibly wind resistant. I haven’t tried their Travel Umbrella, but it looks like it’s going to rain this week in London and I’m wishing I had one with me.
USB Microphone: When I first bought a microphone for the podcast I ended up using it for all my remote work meetings too and got such good feedback on the audio quality (e.g., “wow, everything you say sounds so much better with that audio quality”) that some of my colleagues upgraded as well. A great starter mic is the ATR2100X, but if you want something even better, get the Shure MV7. And if you want an arm to mount it on your desk, I love the Røde PSA1.
M2 Macbook Air: It’s hard to think of a better purchase I’ve made in 2022 than upgrading my laptop to the new M2 Macbook Air. It’s so fast and having 14+ hours of battery life is absolutely incredible.
Uplift Desk: With so many of us working from home, it’s such a nice luxury to have a standing desk in my home office. They used to be so expensive, but Uplift has some reasonably priced option and they’re really well built. I know some companies will even reimburse you for home office equipment, so definitely worth an upgrade if you can get it free.
Goodr Sunglasses: These are my new favorite sunglasses. I got a pair from Wealthfront as company swag and they were so good that I’ve since bought a few more for me and Amy. They’re 100% polarized, lightweight, stylish, comfortable and only $25. My favorites are the OGs, but they have a few different styles and a seemingly unlimited selection of colors. You can get free shipping and a 30-day money back guarantee here.

🏃 Health & Fitness

Oura Ring: I know I’ve mentioned my Oura ring a lot, but it’s the one thing that I’m always wearing every day to track sleep, workouts, heart rate and HRV (the Gen3 also tracks blood oxygen levels). I’ve used up all my referrals, so if you know anyone who has one ask for their link to get $50 off.
Eight Sleep Pod Cover: Traveling just isn’t the same now that we’re spoiled by our Eight Sleep mattress cover at home. It not only tracks your sleep, but it also automatically heats and cools your mattress in line with your sleep cycles to increase deep sleep and improve your overall sleep quality. Get $200 off here (that’s my personal referral link, but I’m actively trying to get Eight Sleep to become a partner of the show).
Inside Tracker: I love getting more data on my health and I’ve been a fan of Inside Tracker since using earlier this year. After analyzing your blood, DNA, and fitness tracking data, they provide a personalized health analysis and action plan for the right exercise, nutrition, and supplementation for your body. You can also get 20% off here.
Why We Sleep: You could argue I should put this in the “Learning” category below, but since good sleep is so important to your health, I’m putting it here. If you want to check out my favorite book on sleep, look no further than this excellent read from Dr. Matthew Walker (who I’ve been trying to get to join me on the podcast since I started.
Peloton: Amy and I love our Peloton so much and I highly recommend it to anyone who wants to work out at home. Even if you’re not a cyclist (I’m certainly not), it’s a fantastic workout that’s even better if you have friends with a Peloton to compete with. Get $100 in free accessories with your purchase here.

👨‍👩‍👧‍👦 Family & Kids

Lovevery: We’ve had a subscription to Lovevery since our first daughter was born. Every few months they send award-winning, montessori-inspired toys to your home with a guide for exactly how to use them to help your child learn & grow. All their toys are designed by child development experts, well built and sustainably-made. Get $20 off your subscription here.
StoryWorth: If you’ve ever wanted to capture all the stories and memories from your loved ones, this is a great gift. Every week for a year, StoryWorth will email your loved one a single life-related question like: “What’s the bravest thing you've ever done?” or “What’s the farthest you’ve traveled?” Then they compile it all into a hard-cover book that you can pass down for generations to come. Get $10 off your first purchase here.
DeleteMe: It’s crazy how many sites are sharing your personal data (e.g. phone #, home address, relatives, email) and it’s a huge pain to get them to take it all down. DeleteMe does it for you, removing your info from hundreds of data broker sites. It might not be the most exciting gift, but I think it’s an amazing one for anyone who hasn’t done it. Get 20% off all DeleteMe plans here.
1Password: Until a few years ago my parents were using the same passwords for so many different websites, so I gifted them 1Password and helped them set it up. Since then I feel so much more confident about their cybersecurity practices.
Aura Photo Frame: Digital photo frames have been around for years, but I haven’t found one that works as seamlessly as Aura. It’s so easy for you and anyone else in the family to share pictures (or videos) with the frame you give someone. We got one as a gift last year and then gifted one to my Dad this year and it’s been a big hit.
Nugget: It’s part-furniture, part-toy, and all-around one of the best purchase we’ve made for our kids. We use it for story time, making a slide down the stairs, building forts and more. It looks like it might not arrive by the end of the year, but I’m still including it, because I’m sure it’d make a great gift for any kid.
Escape Rooms: Ok, I love escape rooms. Amy and I have probably done at least 50 together and try to do the best room we can find in every city we visit. So if you’re looking for a fun activity for the family or a good gift, I highly recommend an escape room. There isn’t a perfect place to find the best rooms in a city, but based on my knowledge of SF escape rooms, these rankings look pretty good.
Board Games: I love board games and think they make great gifts, so I thought I’d share some of my favorites that I think are worth checking out. I left off a few of the obvious ones (e.g. Catan, Carcassone), but if you have any other suggestions for me, please send them my way!
- Coup: This one is hard to explain but it’s the first game we pull out when friends are over. If you’ve ever played Werewolves or Mafia, you’ll definitely love it, but it does require a bit of bluffing. You can play with 2-6 people and each game is quick.
- Ticket to Ride: Maybe I should have excluded this because it’s so popular, but Amy and I love it so much, I thought I’d give it a mention. It’s a fun 2-5 player game that you can play as a family and unlike some other strategy games, it doesn’t take hours to play.
- Pandemic Legacy: Season 1: I hope it’s not too soon to play a pandemic-themed board game, because this one is so great. It’s a rare co-operative game that plays a bit like a choose-your-own-adventure book.
- Codenames: This one is great for groups and can be played pretty quickly. It’s also fun for team-building retreats.
- Jaipur & Splendor: This are two of our favorite 2-player games.
- Bohnanza: We end up playing this game a lot with family around the holidays, because you can have up to 7 players, you can play in under an hour and it’s not too difficult to learn the rules.
- 7 Wonders Duel: While we love 7 Wonders, we haven’t actually played this game. I’ve just heard so many good things about it, that I put it on Christmas list this year, so I figured it’d be worth sharing.
- Wingspan: I don’t have much interest in birdwatching, but during some quick research on the best board games I might not know about this one showed up on everyone’s list.

📖 Learning

If anyone in your family loves learning, you should obviously send them the podcast or newsletter :)
Masterclass: I could spend hours watching all the amazing classes they have and I’m confident a membership makes a good gift, because I gave one to my dad last year. There’s definitely something for everyone and you can get two memberships for the price of 1 here.
Die with Zero: This book (and my subsequent interview with author Bill Perkins) had such a big impact on the way I think about life and money, that it had to be on the list. Highly recommend!
2 Hour Cocktail Party: Not only could you use this book to host an amazing cocktail party this holiday season, but it’d make a fun gift for anyone.
Vagabonding: This book led Amy and I to travel around the world for 7 months, so it’s hard not to suggest it to anyone who likes to travel. It’s the book I’ve gifted others the most.
CozyMeal Cooking Class: We’ve booked pasta-making, donut-making and an iron chef challenge with CozyMeal and it’s never disappointed, so if you’re looking for a fun gift for someone that lives in one of the cities they operate in, I think it’d make a great a great gift.
Death & Co Cocktail Books: If you know someone who likes cocktails and books that look great on a coffee table, then any of the Death & Co. books would make a fantastic gift. My favorite is Cocktail Codex, which focuses on six “root cocktails” you can master that give you the knowledge you need to make so many more.

🛫 Travel

AirTags: I don’t have too many “travel gadgets” but now that we have kids and end up checking bags on every trip, I always make sure to keep an AirTag in every checked bag. I haven’t had to use them to locate a lost bag yet (and I hope I never have to), but it’s so comforting to be able to see that your bags made it on the plane or to your destination before they come off the carousel.
Stokke JetKids BedBox: This was an amazing gift to our daughter from my parents earlier this year and it’s been so awesome. It’s a suitcase with two amazing extra features for flying: 1) your kid can ride it, which lets us cruise through the airport and 2) it turns into an elevated platform that extends the chair to the seat in front, giving your kid their own first class experience. While over 50 airlines have approved it, United is the notable exception and says they don’t allow it on board (though I’ve heard it’s not always an enforced rule).
Babyzen Yoyo: We finally bought this stroller for the trip to Europe we’re on right now and it’s been awesome! It’s almost never on sale, but I bought it on this site for $50 off the price everywhere else online.
Away Luggage: Amy and I each have an Away Carry-On and it’s been a fantastic suitcase. It also happens to be Wirecutter’s top pick for a hard-sided carry-on. You can get $20 off your purchase here.
Dagne Dover Bags: I think Amy’s given Dagne Dover bags as a gift more than anything else. Her favorites are the Landon Carryall and the Dakota Backpack. Get $20 off your purchase here.
A Week on Necker Island: If you have 1.7 million points burning a hole in your pocket, Virgin just re-opened the ability to book a week on Richard Branson’s private island with points. I’m sure it’d be a fun adventure and this page has all the details, but realistically I’m not expecting any of you to actually do this (though if you do, please let me know how it goes).

💰 Saving Money When You Shop

Cash Back Portals: I always like to check CashBackMonitor to see the best way to earn cash back or points when shopping online, but more often than not I end up just using Rakuten, because it’s easier and you can earn American Express points. If you haven’t signed up for Rakuten, you can get $30 free after your first purchase here.
Promo Codes & Live Chat: I feel like it’s gotten so hard to find a working promo code to use online. RetailMeNot used to be my go to, but it seems like every time I try to find a working promo code it fails. The tactic that seems to work much more often is using the live chat on a site to ask for a discount, so give that a try!
Gift Cards: Most online retailers don’t qualify for bonus points on credit cards, so while I could always earn 2x points on the Capital One® Venture X Rewards Credit Card, I usually try to see if I can buy a gift card for the retailer somewhere I earn more points. My two go-to’s are buying them at the grocery store (for 4x points with the American Express® Gold Card) or on Amazon (for 5% back with the Amazon Prime Visa). Or you might get a better deal buying discounted gift cards from a site like CardCash.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Editor’s Note: Today, I’m grateful for the support of our partners Inside Tracker, Amazon, StoryWorth, Rakuten, Oura, MasterClass, DeleteMe, Goodr, Vuori, and Trade Coffee. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

🏝️ The Best Deals for Vacation Rentals and Homes.

Thu, 01 Dec 2022 08:00:00 +0000

I know many of you enjoy traveling (maybe even as much as I do), but sometimes, you want a place to stay that isn’t just a hotel. Finding the right option can take time because there are so many choices. A few weeks ago, I released a solo episode about vacation homes (🎧Ep86), and I was determined to make a practical guide so you can clearly understand your options and select the option the best one for you. I’ll break down all the options, from rentals and exchanges with little or no upfront costs to actual ownership options like fractions, destination clubs and timeshares.

Vacation rentals with "little/no upfront cost"

When you don’t have to pay any up-front costs, it’s all about the flexibility and simplicity of looking, choosing, and booking where you want to stay.

🏡 Home rentals

Home rentals are as it sounds. It's renting a property for a specified period (whether it is a house, villa, condo, or another unique-style property).

Pros
- Ideal for one-off trips.
- A wide range of options is available.
- The booking process is straightforward.

Cons
- Quality and prices may vary (including fees).
- You may find it challenging to regularly go back to the same place (since everyone else is competing with you).
- Certain cities/counties have restrictions on short-term rentals, which might severely limit the supply for that region.

Options
- Airbnb, VRBO, and several other sites offer the broadest properties based on location, size, type, and preference.
- AvantStay and Wander both provide properties with high-end design aesthetics and amenities. I have not used either service, but I am intrigued by them. Wander has 11 homes, most with fast wifi, EightSleep beds, a Peloton bike, a Tesla to drive, and multiple high-end workstations. (If you end up booking a place with Wander, email hello@wander.com and mention the podcast to get $250 off.)
- There are also options for the highest-end homes, villas, and resorts. HVN and Villas of Distinction have extensive collections of properties worldwide. (HVN is currently invite-only, but it looks like you can access with a AAA membership here)
- If you are looking to travel to a variety of places, there are also a lot of local sites and companies that have niche offers tailored to your needs.

How it works
- It is a one-time transaction (incl. fees) and you can sometimes get discounts if you stay longer.

Pro tips
- To get the lowest price, I suggest you save the image of the property you wish to rent, then do a reverse "Google image search" to find all sites that list the image. You can sort through the sites that offer the most affordable prices. For example, I found Merveil, which is a direct rental site for a few places I found in Paris on VRBO.
- You can always negotiate, especially if it’s last minute or your stay perfectly fits into an opening (e.g. they have 6 nights free and you’ll take all 6 vs. book 4). Just email and ask for an offer. I just did this for an upcoming trip and got 15% off both our bookings.

🏠↔️🏡 Home exchanges

Home exchanges differ from rentals because instead of spending money, you’re paying for your stay by letting someone else stay at your home. And some platforms have their own “currency” so you don’t need to stay in the home of the person staying in yours (or even exchange over the same dates). The variety and flexibility of exchange options are the true unlock to staying all over the world affordably and comfortably. And the personal experience can go beyond just access to someone’s home – sometimes you can use their transit passes, vehicles or they might even ask you to watch their pets.

Pros
- The cheapest way to stay in vacation homes around the world.
- When your home is empty, you can capture value and save money on future travel.

Cons
- Someone is staying in your house, room, and bed.
- May need an extra insurance policy to cover your belongings.

Options
- Some of the most popular exchange sites are Home Exchange (← my referral link), Love Home Swap and People Like Us. They all offer multiple types of stays (see below), including non-reciprocal (my favorite)
- If you already have a second home (including fractionals), there’s an exchange site exclusively focused on that called Third Home (← my referral link).
- Amy and I have spent countless nights staying with hosts on Couchsurfing, a platform for locals wishing to meet and host travelers for free. We hosted a bunch of people to build up a great profile with a ton of reviews and then spent >100 nights couchsurfing on our trip around the world. It was truly the best experience getting to meet so many locals everywhere we went. We aren’t doing it anymore now that we’re traveling with the whole family, but if we were in our 20s again we’d be doing it all the time.
- Finally, I recently joined My Place, which is like Airbnb, but you can only host or stay with friends and friends of friends. It’s like couchsurfing in that you don’t pay for the stay, but you can ask people to either cover basic costs (e.g. utilities) or pay for cleaning. However, since it’s not a rental service, they don't offer hosts any insurance policies like other sites might.

How it works
- Home exchanges come in a bunch of forms, but none of them have any nightly costs associated with them. However, some exchange sites have fees to support the service.
- Simultaneous means you stay at someone’s house while they stay at yours. If you've seen the movie, The Holiday, you'll know exactly what this is. I had always assumed this was the only option for a home exchange. And in my head this required a lot of things to align (including finding someone who had a home in a place you wanted to go and agree to swap it at the same time you were traveling, and they also wanted to go wherever you lived). But fortunately it’s not the only option.
- Non-simultaneous means that someone stays at your home while you are traveling, and then you can stay at their home at some future date. In essence, it's the same process as simultaneous, but the schedules don’t have to align.
- Non-reciprocal means you earn “currency” from an exchange site by having someone stay at your home, and you can then use that currency at another home in the program. This option is my favorite and most exchange sites now offer their own “currency” to make it possible.
- Hospitality exchange is when you stay with someone else (while they are there), and then they stay with you (while you are there). In this option you're not getting the house to yourself, but you are getting to spend time with a local. It’s similar to Couchsurfing.

Pet/House Sitting

Thanks to one of our followers, Becky, for sharing this option. She’s used it for 7 different trips (44 nights total) and has had a great experience. For a modest fee, assuming you get through an application you can become a vetted house sitter to stay in homes around the world and often watch their pets as well.

Pros
- Can stay free around the world
- Can stay during peak travel seasons when homeowners often take vacations.

Cons
- You often need to watch the owners’ pets (could be a plus for a lot of people).
- You have to apply and be selected by the platform
- It can be hard to get your first sit with no reviews (maybe you could get a friend to join the platform, pick you and leave a 5-star review)

Options
- The option Becky shared was Trusted Housesitters (← her referral link) and it’s $129/year (or 30% off with her link). She said that there are currently 5,500 sitting opportunities listed, with about 3,000 of those being in North America, 2,000 in Europe, and the rest all over the world.

How it works
- It’s pretty straightforward. After being approved for the platform, you can browse the sitting opportunities (which include photos of the homes) and apply for ones you’re interested in.

Vacation rentals with "upfront costs"

With this category, you might lose some flexibility, but you usually get some type of ownership and future upside. Some of these programs can save you a ton in the long run (especially if it's the right fit for what you're looking for), while others might be a bad investment. I’ve decided to give all the options below one of two labels: equity represents the options where you benefit from the appreciation of the property and non-equity describes options where you don’t own the property and don’t benefit from its appreciation.

➗ Fractional ownership (Equity)

Fractional ownership is a true deeded part-ownership in real estate.

Pros
- Taking out a mortgage is an option.
- A reliable schedule with a consistent place to go.
- Can often store your belongings.

Cons
- You will need to budget for annual dues to cover maintenance, property taxes, and utilities (roughly $5,000 to $25,000).
- You only have access to one place unless it has an exchange pool.

Options
- A do-it-yourself method in which you and a few family members or friends buy a home together and manage it together.
- In managed properties, a company handles the transaction, operates, and manages the property.
  - This is the option that we chose. We worked with a company called Pacaso, and because I liked their product so much, I later asked them to partner with the podcast. In their model Pacaso will buy a home, furnish it, put it into an LLC with eight member interests, and sell those to buyers. Since you hold equity in the home, you can get a loan from the purchase and benefit from any appreciation (Pacaso resales have sold in an average of 12 days with a 12% annualized gain). Then they manage all aspects of the property, including cleaning, paying utilities and property taxes, landscaping, maintenance, and repairs. They usually have a system for scheduling and try to keep everything equitable between owners. And more importantly, you could leave things in on-site storage.
  - Another option I found interesting was My 5 Homes. It’s more expensive, but you end up owning a fraction of 5 different properties instead of just one. To make that possible the company pairs you with 20 other families who all buy those five properties together.
- A private residence club is generally operated by a luxury hotel chain (such as the Four Seasons or Ritz Carlton) and offers amenities normally found in high-end hotels and resorts. Typically, you will also have access to partner resorts in the hospitality chain's portfolio. One example we looked at is The Orchard at Carneros which is related to Timber Resorts. While this is a real equity ownership, looking at historical real estate data, I didn’t see the property values appreciate much over the past few years.
  - One other perk is that you can usually rent out your stays through the resort management company if you won’t be using it. This lets you earn some extra money to offset any annual dues you pay for management or maintenance.
  - Also, while I mentioned you can usually swap your weeks with their partner resorts, friends who’ve tried this have told me the availability is extremely limited, and it fills quickly.

How it works
- The big advantage of fractional ownership is that you qualify for a mortgage as it is a real estate purchase. The level of investment varies according to the size and location of the property. The range of options is anywhere from $50,000 at the low end to >$1 million at the high end.

📊Vacation Investment Real Estate Fund (Equity)

A vacation investment real estate fund is similar to investing in a private real estate deal, but you can stay in the properties. A company creates an investment fund to acquire properties and allows its investors to use those properties at a rate proportional to their investment.

Pros
- You’re making an investment in a fund that expects to give a return to its investors.
- When properties in the funds aren’t in use, they rent them out to cover all the ongoing costs or list them on Third Home (so you can exchange your time for other properties outside theirs).
- You get access to 10-20 high-end properties around the world

Cons
- The upfront cost is high and because it’s a fund investment, you can't get a loan/mortgage like can with fractional ownership.
- One of the significant differences in the fund approach is liquidity. Due to the 10-year investment term, you are locked in for a fixed period. You can still benefit from the appreciation of the portfolio but cannot easily sell your “investment”.

Options
- Equity Residences was the one that caught my attention during my research. Getting involved costs $200,000 for one to three weeks of use and an annual fee of a few thousand dollars.

How it works
- Since this is an investment fund (and not a real estate purchase), you'll need cash to invest (sorry, no mortgage here).

🏠 Buying a second home (Equity)

You can’t be in two places at once, so unless you want to rent your second home out, I don’t think this option is the most financially optimal, so I won’t dive into it here.

🏝️ Destination Clubs (Non-equity)

Destination clubs offer members to pay a fee upfront to access a portfolio of residences (typically multi-bedroom, luxury homes with high-end concierge and hospitality services).

Pros
- Unique homes you won't find anywhere else, usually with space for a large family (or two)
- Many destination clubs offer concierge services with a turnkey nature.

Cons
- To get your value, you might need to be spending at least 4-8 weeks traveling a year and wanting to stay at very high-end properties.
- Limited (if any) financing options for programs with up-front costs (though some of these options have little or no up front fees).

Options
- Fees plus pay-as-you-go. The biggest example here is Inspirato, which starts at $600 a month, and then you pay as you go for properties (which aren’t cheap). They also offer the Inspirato Pass, which they describe as the "first luxury travel subscription" worldwide. For $2,500 a month, you can book any of their properties and depending on how big/nice it is, they lock” your pass for a fixed number of days (e.g. their best properties can lock up the pass for >200 nights. Then, once unlocked, you can book another place.
- Fee and dues only. There are a lot of options in this category, but one example is Exclusive Resorts. They charge $275,000 upfront and $36,000 a year in annual dues. It comes with 25 nights a year at their properties for the next 30 years.

How it works
- For destination clubs it varies between a low membership fee plus "pay as you use it" and a high membership fee with a limited number of uses. You can do more research using the Sherpa Report, which provides a comprehensive list of all destination clubs.
- Unfortunately, I don’t think we travel around the country/world enough (or need to stay at ridiculously nice properties) to get our value here.

⏱️🧳 Timeshares (Non-equity)

Timeshares are the most well-known of all these options (outside of home rentals). A timeshare is a right to use a property unit a set number of times each year or, in some cases, every week. Some variants include a vacation club, where you get a set number of points in a program each year.

Pros
- Lifetime use value (if you're willing to prepare well in advance and you want to come back for decades).
- Exchange opportunities around the world (especially in programs like Hilton’s Grand Vacation Club that lets you earn Hilton points each year). One listener named Joel emailed me that he’s been able to use the Hilton points from his timeshare to stay all over the world (e.g. South Africa, Hong Kong, Bali, Maldives), often at high-end Hilton properties like the Conrad or Waldorf.
Cons
- Poor resale values (my parents inherited one, and it wasn't easy to get rid of it. When they couldn't sell or give it away, they had to pay the timeshare companies a few thousand dollars to take it back).
- Many (but definitely not all) timeshare resort properties are a bit dated.

Options
- You could buy new ones. The sales pitches are excellent. They usually offer a gift certificate, spa treatment, or something else of value to attend a presentation. But the advice online is consistent: if you're interested in a timeshare, you should rent it from owners who aren't using it or buy one for resale at a reasonable price.
- You can use a site to rent from owners. They might make a profit, but if nothing else, they'll be able to cover their annual dues. Red Week, Tug2 and Koala are all rental sites.
- Buy resale. You'd be amazed how many people are trying to sell their timeshares on those sites for as low as $1. Some will even pay you to take over the timeshare by covering a year or two in maintenance fees. Another listener named Bill shared that he was able to pick up three weeks in Hawaii as a resale for ~$2k (including annual maintenance dues and exchange fees), which worked out to less than $100 a night!
  - Note: when you buy a resale, some of the benefits (e.g., extended advanced booking window) that were offered to original owners might not transfer to the new owner.

How it Works
- For a timeshare it is an upfront investment package plus annual maintenance fees. They can vary widely depending on location, but the US average is $21,455, plus $1,000+ in maintenance fees per year.
- For programs like Hilton’s Grand Vacation Club, you can effectively buy a Hilton Point annuity at a cost of $5-10 / point (e.g. $150k upfront might get you 1 million Hilton points each year). If this is interesting, you should check out this episode on the Geobreeze Travel podcast.

Additional Thoughts
- When it comes to sales pitches, be careful. If you’re confident you can walk away, I recommend checking them out and seeing how they work (and get a free dinner, spa treatment or whatever incentive they offer). But just know the deal sounds great, and they will put a lot of pressure on you to sign immediately.
- Despite having many exchange partners, they all tend to prioritize bookings to the properties' owners. It has been nearly impossible for my parents to book a property with the dates we want in the unit size we want if we don’t log into the website 13 months in advance at exactly 12:01 AM. However, I think if I dedicated more time to understanding the systems, this might be a different story.
- Before buying any timeshares, do a lot of research. Joining the user forums and Facebook groups or finding other owners can help you make sure you’re going to get the full value you want.
- It's best to try before you buy. If you're considering a timeshare, I recommend renting it first (or taking a subsidized trip that requires you to attend a timeshare pitch). Websites like Koala and Red Week make renting other people's timeshares so easy. You might realize that you could keep doing that every year and not need to buy one yourself

🏊 Non-home rental options (Non-equity)

I found two other interesting companies during this research that aren’t a perfect fit for this newsletter, but I thought were worth sharing.

Resort Pass lets you use all the amenities of a resort hotel (e.g. pool, cabanas, etc.) for a daily fee, without having to staying there.
Swimply is like Airbnb for pools. Their marketing targets people who want to host parties for their kids or events. Besides pools, tennis courts, home gyms, and backyards, they're planning on expanding into other areas.

😌 The feeling of validation

As I mentioned above, I purchased a fractional home through Pacaso, but I feared that I might end up second guessing the decision after doing all this. Thankfully, after 15 pages of research, I am now more confident in our decision to buy a Pacaso and excited for our next trip up there!

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Editor’s Note: Today, I’m grateful for the support of our partners Daffy, Vuori, DeleteMe, Inside Tracker and Pacaso. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

🏥 Beating Healthcare: Saving Money and Pushing Back

Fri, 18 Nov 2022 08:00:00 +0000

Today is one one of those newsletters you bookmark because I’m sure you want to reference it later. Take it from me… before 2021 I had an infrequent relationship with the healthcare system. Since then, I've experienced shingles, a broken foot, and we had our second child. That was enough to make me pay attention. For many of you, it's open enrollment season, so healthcare is top of mind. And a big thanks to Marshall Allen (🎧 Ep34) who wrote the book Never Pay the First Bill: and Other Ways to Fight the Health Care System and Win, which inspired this email and is an operating system to help you save money while getting better care.

Also, while I'd love to tell you which insurance plan to choose (trust me, I asked Marshall the same question), picking the right plan is too dependent on your circumstances (location, employer, health level, risk tolerance). Instead, this post will complement your insurance plan and also offer some thoughts on the tax-advantaged accounts your employer might offer.

💲 Tax-advantaged accounts

Two great ways to save on out-of-pocket expenses: Flexible Spending Accounts and Health Savings Accounts. Look into them if you haven't already since they both let you pay your out-of-pocket costs with pre-tax money.

Flexible Savings Accounts. These are employer sponsored-plans where you can designate a set amount of your pre-tax income into a separate account to pay for qualified medical expenses. It's like a dedicated checking account for medical expenses. Unfortunately, it's a "use it or lose it" type of account, so you forgo anything you don't spend that year. Typically, there is a 2 1/2 month grace period through next year. And some employer plans even allow for a carry forward of up to $610 (for 2023). Your employers may contribute as well, which could be a nice little bonus (and it is excluded from your gross income). For more details on contribution limits and rules, read this.

Health Savings Accounts. These work the same way as FSAs but have much more firepower. You can carry forward any unspent dollars forever. Since they are individual plans, HSAs are portable (i.e., you keep them when you leave your job). It’s like a dedicated 401(k) account for medical expenses. Contributions can earn interest or be invested with a tripled tax advantage:
- Contributions are 100% tax deductible.
- Gains on investments are not taxable.
- Withdrawals for qualified medical expenses are not taxable.

To contribute in a given year, the HSA must be paired with an HSA-eligible (high-deductible) health insurance plan. Please ensure your plan is eligible before trying to open or fund it. For more details on contribution limits and rules, read this.

💡 Ways to use your FSA/HSA

There are a few non-obvious ways we’ve used our FSA/HSA funds that I thought might be worth sharing:

Biomarker/Genetic Testing (like Insider Tracker, which is 20% off here)
Baby Monitors (our favorite is the Nanit)
Eye Surgery like Lasik (if it’s more than your total FSA budget, you can do it at the end of the year and ask if you can split the payments across years)

Also, while you can't typically pay for insurance premiums with an FSA or HSA, there are certain exceptions for HSAs (I don’t normally use the IRS publications for light reading, but I found the content on this topic clearer than others):

Long-term care insurance (subject to some limits).
Healthcare continuation coverage (such as coverage under COBRA).
Health care coverage while receiving unemployment compensation under federal or state law.
Medicare and other health care coverage if you were 65 or older.

Two last tips:

You can donate your FSA if you cannot use it. Don't let your FSA go to waste. Call a local shelter to see if they need any medical products and purchase them with your FSA money before it expires.

HSA reimbursements do not have a time limit. As I mentioned, HSAs can carry forward year after year so that you can withdraw your claims anytime. You can strategically let your investments compound and take withdrawals years later. For example, in 2022, you had $1,200 in out-of-pocket costs. You could choose to submit the reimbursement in 2022 or wait 10 years. At 8% per year, the $1,200 turns into $2,600. You can take the $1,200 reimbursement and still have $1,400 in the account tax-free. However, keep your receipts…. no receipt, no reimbursement.

💵 Always Push Back

If your employer plan offers such small copays, it may not feel worth fighting back on the bill's charges. But there is an argument to do so, even if it's tiny, because there is a misconception to think that your employer is paying for most of your healthcare. While much of our focus is on increasing wages, employers must consider whether they can afford the entire compensation pool. Wages are just one part: retirement, healthcare, and time off are others. If your employer is forced to pay higher medical bills, there is less in the budget for wage growth. Rising healthcare costs are eating into the compensation pool, so pushing back on those big bills may be a significant benefit.

Here are eight principles to complement your health insurance plan

💸 Saving before you get the bill

Principle #1: There are substantial price variations in all services. The same procedure five miles away could cost you $15,000 more. Doing some research can help you deal with these wild price variations. Most care is not an emergency, so you have time to research and find valuable options. Up until 2021, it took a lot of work to find cost data. In the US, A federal rule requires hospitals to provide clear, accessible online pricing information to patients (including cash prices, Medicare prices, and insurance-negotiated prices).

Since Marshall's research suggests care is virtually the same regardless of the price, finding the lowest price is in your best interest. Here are some ways to do so:

Visit the website of your local hospital.
Call the hospital or ambulatory surgical center (ask for the variations in pricing: cash, Medicare, and insurance negotiated).
Take advantage of startups that aggregate nationwide prices (Turquoise Health and Health Cost Labs).
Find out what non-local hospitals charge (Surgery Center of Oklahoma).

Principle #2: Everything is negotiable. Medical pricing is pretty opaque. If prices are negotiable across insurance companies, they are negotiable to you. I've witnessed bills decrease by $4,000 simply by refreshing the page. Knowing "the charges are not the charges, and the price is not the price" should give you the confidence to negotiate a better deal.

Principle #3: Stop assuming pricing makes sense. Don't expect a logical rationale for the high prices. In most cases, facilities and insurance companies are for-profit organizations, so their prices are not necessarily aligned with the patient.

🧾 Ensuring charges are accurate

Principle #4: Take an active role in reviewing your bills. According to Marshall's reports and interviews with experts (who review health bills regularly), most bills contain errors or overcharges. These errors compound, causing more medical debt (1 out of 3 Americans suffer from medical debt) and leading to debt collection (1 out of 5 Americans suffer from debt collection). To ensure that you are being charged the correct amount, follow these steps:

Request an itemized bill to see all of the individual charges.
Ensure the CPT (Current Procedural Terminology) code descriptions align with your services.

Don't let anything stay that shouldn't.

Principle #5: Ensure the bill is submitted to the insurance company and adjudicated properly before sending any money. The service provider may have sent you a bill before you submitted a claim. Instead of paying the bill, wait until you receive your insurance company's Explanation of Benefits (EOB), which explains how claims are processed. It includes:

Service description - the services you received.
Provider charges - the amount your provider bills for your services.
Allowed amount - the amount your provider will be paid.
Insurance processed or paid amount - the amount your health plan will pay the provider.
Owed amount - the amount you owe to the provider (after everything).

Before giving them anything, run them through Principles #4 and #5.

👊 Overpriced bills, erroneous charges and denials

Having to deal with any of these can be frustrating, annoying, and time-consuming. Unfortunately it’s a part of the process, but it is getting easier to navigate (with law changes and legal precedents that benefit the consumer). As I’ll mention in a bit, you can even go as far as taking them to small claims court, which exists to protect consumers from unfair transactions. Still it’s not perfect. In line with principle #6, here is an action plan to effectively push back to your insurance company or provider.

Principle #6: Argue with evidence, not emotion.

Step 1: Gather data to provide evidence-based data to support your claim
- If you suspect overpricing, find evidence of price and quality differences for the service or device.
- In the event of erroneous charges, please review your EOB, and the services received.
- In the case of insurance denial, review your insurance summary plan document (it outlines the contractual obligations between you and the insurance company).**

Step 2: Negotiate a better price on the bill (politely, yet authoritatively)
- Request a better price from the provider's billing department (they may ignore your request).
- Call the insurance company to complain about the discounts (they may say "the bill is the bill").

Step 3: Escalate the reduction (this is where most people don't want to do it)
- Demand a price reduction from the billing department (always ask for a supervisor as high as possible).
- Make a formal complaint.

Step 4: Issue a warning for small claims court
- Draft a letter for a 30-day warning (or take the sample letter in Marshall's book) to articulate that "If you don't correct this within 30 days, I am planning to sue you as is my right in my state for overbilling/price gouging." (There is a legal precedent as a consumer if they don't give you the price upfront, that it must be fair and set in good faith - open price term).
- Send the letter. The letter should demonstrate that you have tried everything possible to reduce it fairly.

Step 5: File a claim
- There is a good chance the 30-day letter will shake them enough to give them a chance, and if not, then file a claim with small claims (which will only take a few minutes and $30-$40).

You have now created a problem for the provider. They may have to hire an attorney, which could cost them more than your claim is worth. They now have the incentive to negotiate with you. If not, bring them to court (and use the evidence you collected along the way).

**In case of insurance denial: Check the contract for the clause indicating that your doctor's medical decision-making is respected. It means the insurance company isn't in charge of the decision. It may be possible to argue from your summary plan document that your doctor determined you needed this test. This is because it was medically necessary if your doctor ordered and recommended it. It will help strengthen your appeal if you combine it with studies showing the test/procedure you want to do is credible.

💊 Prescription deals & finding the best/right care

In many cases, generic medication has the same chemical composition as branded medication but is often far less expensive (but you should ask your pharmacist). Here are a few tips for saving money at the pharmacy.

Look up GoodRx. It's a coupon system that shows prices at different pharmacies and has been proven to offer some of the lowest prices. If you are getting multiple prescriptions from other areas, you must have at least one professional who knows everything you are taking.
Use membership plans. They are available through some providers (like GoodShepRx), where you can order a generic drug per month and deliver it to you.
Check the prices at different pharmacies. There can be price variation in your community, so call around.

Principle #7: Ignore the facility's credibility and look at the doctor's credibility. Since there was no publicly reliable data to benchmark credibility, Marshall and a team of investigative reporters took it upon themselves to conduct an analysis (ProPublica Surgeon Scorecard) to identify common complications from common elective operations. They published risk-adjusted complication rates for about 15,000 surgeons all over the country in a searchable format (the data is old, so please rely on it sparingly for current info). As a result of the study, they found to focus on the doctor. And more specifically, focus on a doctor's volume as the critical quality indicator. You should seek a doctor or clinician who has performed the same type of service many times before. It would help if you asked them these questions:

Have you performed this exact procedure before?
Did your patients suffer from infection, injuries, or bleeding afterward?

Ideally, you want to find answers that you feel comfortable with. However, many doctors cannot provide specific information about outcomes, so finding a doctor who tracks any outcome is a plus. Continue researching if you aren't getting the answers you seek.

🟢 The easiest thing you can do

Principle #8: Avoid care you don't need. Marshall points out that up to 25% of healthcare is not required (whether medicine, imaging, or procedures). Although every procedure has a low risk, it's still a risk. Pushing back is not all about confrontation - if you need more information, you should ask.

If we wait, what will happen?
Get a second opinion if it's invasive or expensive.

Open enrollment is an excellent time to fund FSAs and open HSAs, but healthcare preparation, proactiveness, and pushing back are worthwhile all year long. Simply taking the time to plan can save you thousands of dollars a year. Please bookmark or save this page because you'll likely reference it again later.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Editor’s Note: Today, I’m grateful for the support of our partners Goodr, Fabric, Masterworks, Inside Tracker, ButcherBox, DeleteMe, Pacaso and Rocket Money. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

🍸 Hosting Memorable Cocktail Parties

Mon, 03 Oct 2022 07:00:00 +0000

A few weeks ago I had an incredible conversation with Nick Gray (🎧 Ep68) on how to host a successful cocktail party. He literally wrote the book on building big relationships through small gatherings. I’m so used to hosting/attending dinner parties, but they’re so time-consuming, complicated, and stressful. I didn't realize cocktail parties are perfect for the life optimizer (80% of the benefits and 20% of the work). This blog post highlights the important aspects of Nick’s party operating system. Use them and you can organize and execute successful events.

After talking to Nick, I’m sold on how much a two-hour high-energy experience can help you live a richer life, so I’m going to try and adapt his plan to host an event in San Francisco for our listeners and readers (ie: you!). So if you’ll be in SF on 11/30, please RSVP here and I hope to see you there!

🍸 Hosting Memorable Cocktail Parties

If the idea of hosting an event seems stressful, then the plan I learned from Nick Gray, that I’ll lay out below, should make things so much easier. Also, keep in mind this isn’t a dinner party that can require lots of cooking, last forever and have a lot of dishes to clean up. It’s a cocktail party that if done right, should be easy to plan/host. In fact, my favorite takeaway from Nick is that if you can get in the routine of hosting a cocktail party every few months, it can serve as the perfect way to reconnect with new people you meet. For example, instead of scheduling a follow up meeting/lunch with a new professional connection or play date with a family you meet at the park, you could just say “it was great meeting you, I’m hosting a cocktail party next month and would love to invite you to join.” So if that sounds good to you, or even if you just want tips for an event you’re already hosting, here’s everything you need to know:

The Pre-Party Stage

⌚ Scheduling

Choose a non-competitive time. The best nights are Monday, Tuesday, and Wednesday because they don’t compete with social schedules. Also consider a time that accommodates parents' needs. Make your party easy to say yes to by hosting it on a less-trafficked evening.
Give yourself a short lead time. Aim for a date that is 3-4 weeks away, so you’ll have enough time to prepare, without procrastinating. There is no perfect time, so don’t wait for it.
Set an end time. Communicate that the party has an end time, so guests will show up on time. Your party should last two hours, which means there will still be plenty of energy and conversation right up to the end. Having your party end on a high note will ingrain in the people's minds that they had a good time, and they will want to come back again.
Consider planning for childcare. If kids are invited, think about how you could make it as easy as possible for you and your guests. You could hire a babysitter and/or create a separate area for a “kids party.”

🧑‍🤝‍🧑 Start with your core group

It's crucial to get the first five commitments before you do any deep planning. Let your closest friends, neighbors, or colleagues that you will be hosting a cocktail party on (certain) date, and ask if they will join you. Using this method, you can test the date and time you selected to see if it’s viable. This approach saves you time preparing invitations (if the time ends up not working) and signals to the rest of the invitees that a party is happening. Here is what Nick suggested, “I am thinking of hosting a cocktail party on Tuesday 6:00pm-8:00pm. Would that work for you?” Simple, straightforward.

When the five commitments have been secured, create an online RSVP page and request those first few people RSVP online. This will help you get an accurate headcount. More importantly, it signals social proof that people are already attending, and entices others to come as well. RSVP pages are an effective way to create a social contract. After the five have RSVP’d “yes”, invite everyone else. Nick recommends Mixily and Partiful since they are both free, but Paperless Post has a bit more customization. See Nick’s platform suggestions here.

👭 15 to 20 attendees is ideal

As host, you don't actually want to play the role of “host” the whole time, so don’t have your event be too big. That can be exhausting, because you are always on and your goal should be to step back and serve as facilitator, since after all, cocktail parties are intended to bring people together. So it’s your job to bring them together.

But don’t go too small, having more than a few guests actually makes hosting easier (Nick mentioned Priya Parker's book The Art of Gathering). Conversations naturally split into two when you have more than 6-8 people. That's why Nick recommends 15-20 people. There are enough connections to be made with this many people, and the limit of two hours means your guests probably won't have a chance to talk to everyone. This will leave guests with a sense of curiosity about the next event.

😰 Take steps to reduce stress

Your goal to be should have an easy, simple, lightweight event that eliminates the stress associated with planning. So here are some tips:

No food. If you include food, serve simple snacks like chips/dip, pretzels and/or veggies. More food means more stress. This is not a dinner party!
Cocktails only (wine is OK, but no beer). Setting up a self-service bar would be ideal. Have a few different bottles of alcohol, mixers, and ice. Avoid serving beer, since everyone has different preferences. Nick’s hosted hundreds of parties without beer and said it always works (he also calls the extra bottles, cans, and space it takes up "party shrapnel”). Wine is fine, but stick to limited options. Two bottles of red, two of white, and maybe some rose, if it's summer.
Be sure to offer non-alcoholic options. Perhaps some juice, water, or seltzer.

🙋 Set clear expectations

The simple addition of structure and expectations can make your cocktail party so much better. Hands down, Nick says this is one of the primary indicators of hosting a successful event. Here is a simple way to articulate these expectations:

“Hey, I’m getting friends together for cocktails and icebreakers. Because I am terrible at remembering names, we’ll have name tags. You don’t have to bring anything, we’ll have mixers, drinks, alcohol and seltzer. Hopefully you’ll meet some new friends.”

More on the name tags and icebreakers below, but Nick includes some sample event pages and copy you can use on his website here, or in his book.

📣 Send a few reminders leading up to the party

One week before. This reminder is pretty standard. You want to send a brief note that highlights the date and time, but also points to upcoming details: “Hey everyone! We are looking forward to seeing you guys next Wednesday at 6 PM. More details to follow.”
Three days before. This reminder is unique. Again, repeat the date and time, but this time include some guest bios. It is a helpful way to ease anxiety for some guests and gives people an idea of who is attending and who they might want to meet. An example of a bio could be: “Nick Gray - recently moved to Austin, Texas. He lived in New York for 13 years. Ask him about green tea.” This process should not take you longer than an hour.
The morning of the party. One last message! You can use the same email that you sent three days before just to give a last reminder. You’ll send all of these messages to keep your party top of mind and ensure a great attendance.

The Party Starts

📛 Use name tags

It’s an easy way to make an introduction and an easier way to remember someone's name. It’s a simple but effective strategy. Nick says this is a hill that he will die on and even for a casual social gathering of friends and neighbors, name tags are a must.

🧊 Use icebreakers

I can see a few of you rolling your eyes, but hear me out. Icebreakers, when done right, let people share a bit of their personality and help spark new conversations. You could introduce them saying “I do icebreakers, so we can all meet somebody new. I hope you'll say hello to a few new faces.”

Set the rules for sharing. Before each icebreaker, tell guests how to include their names, their work (or something they're excited about), and the answer to the icebreaker question. Repeat this format each time you do an icebreaker.
Provide clear instructions. Instructions reduce surprises. The host should lead first, then ask permission for the person on their right or left to proceed next, and then indicate the direction the group should go.
It should take five minutes to complete. The trick is to have everyone standing. Sitting down leads to follow-up questions.
Lead yourself. There is nothing more frustrating than someone taking forever with an introduction, so go first and set a good example yourself. Also, don’t be afraid to stop people that are talking too long (or even have your spouse or close friend go second and intentionally take a long time so you can politely follow up with a reminder to be quick).
Do three rounds throughout the party. Icebreakers serve as natural conversation starters and endings. The first icebreaker should be done in the first 10-20 minutes of the party, before everyone has arrived. It is an awkward time, when energy levels aren't high, but an early icebreaker will help release that energy. Then you can do it again 20 minutes later when everyone is present and another 30 minutes later.
Get started with something simple. Make sure your icebreaker is easy to answer, will move quickly, and the answers won’t elicit judgment from others. Ask questions like “what’s one of your favorite things to eat for breakfast?” because breakfast is light, human, and taps into your personality. Stay away from “what’s your favorite book ever?” Books are subjective, definitive, and can elicit judgment from others. The icebreakers can get deeper as the party progresses, but ease your way into that (e.g., “what is one of your favorite purchases that made you life better the past year?” or “what is one of your favorite pieces of media that you have consumed over the last couple of months?”)
As the host, be quiet. As soon as everyone has had a turn, the host shouldn’t say anything. Let the natural awkwardness turn into liveliness. Turn up the music volume again and continue.

🎵 Put on background music

Don’t stress about a playlist, just use a curated playlist that someone else curated. The music should be upbeat, positive, easy/happy, and not too loud. (Or you can use Nick's playlist)

👋 When it’s over, kick people out (respectively, of course)

Time flies when you are having fun, but stick to the end time. The proper way to handle this is to communicate it during the party. Make a last call announcement 15 minutes before the party ends.

“Thank you all for coming! You all made it very special. It's 7:45. I said the party would last until 8:00. Since this is a school night, I want to make sure everyone gets home early. Grab a last drink, say hi to somebody you haven't met yet, and we will wrap it up in about 15 minutes.” (then turn the music back on)

After 15 minutes, turn the lights up and the music down. Thank everyone again for coming and take a group selfie (it'll be helpful, trust me). The goal with this is to clearly demonstrate the party's finality.

Post-Party

✉️ Send a thank you note with the group selfie

In the morning, send a short message thanking everyone for attending. Include the group photo (as more social proof) and ask them if they'd like to be invited again. It's an easy "yes" and is a way to start your guest list for your next cocktail party.

It may be obvious, but as the host, you want it to feel like an awesome and easy experience. If you felt more energized than you were before the party, it’s an indicator that you are doing something right. I am sure if you followed all of these tips, you gave people the structure and opportunity to feel comfortable and meet many other people.

🤔 Now what?

If you loved this and want more, I know you will enjoy my conversations with Nick: Check out the full episode on cocktail parties and museum tricks (🎧 Ep68) and our follow up on maximizing points, travel destinations and jet lag (🎧 Ep69).

And definitely check out Nick’s awesome book (The 2-Hour Cocktail Party: How to Build Big Relationships with Small Gatherings) and the website to share so much more content on party planning.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Editor’s Note: Today, I’m grateful for the support of our partners ButcherBox, Masterworks, InsideTracker, Trade Coffee, MasterClass, Vuori, Daffy, Fabric, and Linkedin. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

🔒 Protecting Yourself from Scammers, Phishers, and Identity Thieves

Thu, 22 Sep 2022 07:00:00 +0000

Advertiser Disclosure

The combo of increasingly sophisticated scammers and so much of our personal data living online is a scary and frustrating thing to think about. I’d been curious about the topic of cybersecurity and identity since someone tricked Chase into ordering a Macbook Pro with my Ultimate Rewards points, but I finally got connected with an expert in the space, Adam Levin, and learned so much from our conversation (🎧 Ep77).

After talking to Adam I went really deep on the topic myself and wanted to share all the ways you can protect yourself and your family. I’ll try to cover it all here, but for more detail, I also recorded an action list episode of everything you can do (🎧 Ep78). While I know this whole process can be stressful, I can’t tell you how much better I feel having gotten through it.

🔒 Cybersecurity

Let's start with easy ways to protect the devices you use most to minimize your risk of exposure.

Computer: Ensure your encryption is turned on on your computer or laptop. If you have a Mac, you can use FileVault. And for PCs, you can enable it in the device encryption settings.
Phone: Set up a PIN and passphrase that will automatically erase after multiple failed attempts. When your phone is locked, prevent notifications that may contain private information from showing up while the phone is locked and disable automatically connecting to new USB devices.
Internet: I don’t trust internet service providers (ISPs) to not sell my data, so I always recommend changing DNS from using the one provided by your ISP. But on top of being more secure, using another DNS like Cloudflare 1.1.1.1 is much faster.
VPN: Since most traffic is now happening over HTTPS, you probably don’t need to worry about someone stealing your credentials or reading your emails, when you’re using public wifi. However, the owner of the WiFi and their ISP will see the domains of the sites you’re visiting, so if you want a bit more privacy, you should use a VPN like NordVPN (← big discount here). This is especially important when traveling internationally, where many countries have much less restrictive data privacy laws.
Ad Blocker: There are a lot of ad blocker chrome extensions (like uBlock Origin) that will prevent ads from seeing info about you. For iOS users, if you pay for iCloud+; you can use Private Relay to add additional privacy in Safari and the Mail app.
Email: Set up dedicated emails for social media and financial institutions that you don't give out to anyone.

Also, if you ever receive a link to login to a site you have an account at, please be very careful and look at the entire URL (there are so many tricky ways to make it look authentic, like opening a new window for mail.google.com.[something else].com that’s so small you only see the mail.google.com). Or better yet, instead of clicking any of the links to site logins, just go to the site yourself. Most organizations with any credibility and authority (IRS, police departments) will not be sending you emails as the first line of communication. But in the few instances where it appears to be official, call the agency to confirm.

🔑 Login Credentials

A lot of people have terrible password practices. First, they pick easy-to-decipher passwords because that's what they can most remember. Second, they use the same password for everything. For hackers, it's low-hanging fruit. However, even the strongest, most sophisticated password can be useless if it’s exposed in a security breach (check Have I been Pwned? to check if you’ve been exposed and set up free monitoring alerts). And if you use the same password for multiple logins, a single breach can cause you a massive headache. This is why password managers are becoming a standard practice. They will help create a unique hard-to-decipher password for every site/login and you only have to remember one master password.

My favorite is 1Password, but they have moved to be a fully cloud-hosted platform, which means your credentials are encrypted and stored on their servers (though they don’t even have access to your data). Alternatively, you could self-host your passwords on your devices, but despite that might be more secure, the convenience of cloud-hosting, to me, is worth it.

Here is how you can add even more strength to your login credentials:

Email: Use the "+" feature on Gmail. If your email address is: johndoe@gmail.com, you can use johndoe+twitter@gmail.com, and it will create a unique user ID but still route all emails back to your primary address. So now you have a central email, but the login is now different for each site.
Security Questions: Make up new (and fake) answers to all of your security questions. It doesn't matter if it is true; what matters is that it's hard to decipher. You can store these new answers in your password manager.
2FA: Set up two-factor authentication for all your logins, and where possible avoid the use of SMS (it’s just too common for someone to hijack your phone number and get your 2FA codes). You can use Google Authenticator or Authy or even store them in 1Password (while this might negate the TWO factor part, I still think it’s better than SMS, and you can use true two-factor authentication to get into 1Password). However, If SMS is required (looking at you banks), set up a second phone number (e.g. Google Voice) that you haven’t shared anywhere. You can take it one step further and use a physical security key. I use a YubiKey 5C NFC and as a bonus, you are now eligible for Google Advanced Protection which adds an extra layer of security to your account.
Authorized Permissions: Audit all the apps you’ve given permissions to your accounts (e.g., Google, Facebook, Twitter) and delete the ones you no longer need. You may also want to delete and refresh the ones you want to keep, because many services have improved the permissions for what is shared.

💳 Credit & Financial

Your money and credit are major targets for hackers and scammers and you should probably assume your SSN and personal info is online. Here are some precautions you can take to protect yourself:

Credit Reports: Review your credit reports, which you can get free each year at AnnualCreditReport.com (though because of the pandemic, you can get them free each week right now). When reviewing, keep an eye out for any accounts you don’t recognize. If you find something wrong, contact the credit reporting agency. You can also set up free credit monitoring alerts with Credit Karma and Experian. If you have been part of a security breach, you might also be eligible for a premium credit monitoring service from the company that leaked your data.
Credit Scores: Monitor your credit scores for any big changes that you can't explain, which may suggest you need to investigate further. You can get your score free from Credit Karma and many credit card companies also give you access to your free score (e.g., Chase’s Credit Journey).
Transaction Alerts: Sign up for transaction monitoring alerts through your financial institutions and credit card companies. It's free and notifies you anytime there's any activity in your account over the dollar amount you select.
Credit Freezes: Freeze your credit through Experian, Equifax, and Transunion, which prevents anyone from opening accounts with your name. You can unfreeze or temporarily lift the freeze when you want to open a new card or take out a loan. There are also two new credit bureaus that I recommend you freeze your credit at as well: Chex Systems and Innovis. You can also sign up for fraud alerts with the credit bureaus, which require additional verification to open any accounts, but it’s likely unnecessary if you’re already going to keep your credit frozen.
Banking Permissions: Like Google and Facebook, many financial institutions now support authenticating apps to your financial accounts, so review these regularly as well.
Virtual Credit Card Numbers: Some credit cards now offer the ability to generate a unique card number for every merchant you shop at, minimizing the risk that anyone will ever get your primary card number. I mostly use my Capital One® Venture X Rewards Credit Card for online purchases (since it earns 2x points on everything) and the CapitalOne Eno browser extension lets you generate free virtual card numbers that still earn points. Alternatively Privacy.com has a similar service to generate virtual card numbers for free, but you have to connect them to you bank account and won’t earn any points.
Credit Card Offers: You can opt-out of all the credit card offers you receive in the mail.

🆔 Identity Theft

Millions of people have become victims of identity theft and in many instances, it’s through no fault of their own. While identity theft is a broad term, there are multiple variations to be aware of:

Account Takeover: your cards or credentials are stolen.
New Accounts: someone opens loans or accounts in your name.
Medical: someone pretends to be you and has medical services billed to you or your healthy insurance provider.
Child-related: someone steals/uses your children’s information.
Criminal: when your identity is falsely used and involved in a crime.

Some of these are harder to mitigate than others, but here some things you can do to protect yourself:

Security Requests: Call your financial institutions and cell phone providers to ask for an increased level of security.
Identity Monitoring: Monitor your identity with services like Lifelock or Aura. I’m not sure it’s worth it, but I know that both companies are reputable services.
Insurance Policies: Check if your home/renters insurance policies (homeowners/renters) have identity protection added to the policy. If not, you could add it.
Resources for Victims: If you’ve been a victim of identity theft and don’t have a paid service to help out, you should check out the Identity Theft Resource Center.

🙋 Personal Data

There are hundreds of data brokers that collect your information. If you Google your name and city or your phone number (in quotes like “212-123-4567”), you’ll likely find many websites with your data. I know I did and it wasn’t very comforting.

I wanted to figure out how to tackle it myself (more on this mistake later), so I found a great list of all the data brokers on GitHub and started manually removing my data from each site. For some of them it's straightforward, others not so much. While the process is tedious, some states are adopting privacy data acts that benefit you and require data brokers to comply with your request.

With so many sites to remove my data from, I ended up spending 10+ hours on what seemed like a never-ending journey. While I (kinda) appreciated the learning experience, I ultimately found DeleteMe, a service that will take care of removing all your personal data from the web. Sure enough, despite my best efforts, they found a handful of sites I had missed that still had my personal data. So if you want to save yourself the time/hassle, I reached out to their CEO to get you 20% off DeleteMe. I also had him join me for a short interview in my protecting yourself action list episode (🎧 Ep78) to explain where all this data comes from and why it’s so hard to remove.

Note: If your data is gone from the source, but still showing up in search results, you can use these tools to remove outdated content from search results: Google and Bing.

There are also a few other ways you might want to manage your footprint online:

Home: Contact real estate sites (e.g. RedFin and Zillow) to remove any photos, floorplans or virtual tours of your home. You may also want to contact the real estate agent who sold you the home and request they remove all the photos from the MLS. Finally, for the ultimate level of privacy, you can reach out to Google, Bing, or Apple to blur your property from their maps.
Location Services: Remove the geotags from public photos you have posted online.
Marketing Data: Request your data be removed from marketing sites like Axiom and LexisNexis.
Trusts/LLCs: If you want to privately buy/hold property or assets, your best bet is to do it through an LLC (likely two-tiered in many states). However, if that’s too much work and you’d rather just use a revocable trust, consider giving it a name that’s less identifiable than “LASTNAME Family Trust.”
Mailboxes: If you want to limit giving out your address online, you can sign up for a mailbox with a service like iPostal1 or Earth Class Mail for as little as $10/mo and use that address when you don’t expect to receive anything important from the site asking for your address. Alternatively you could get a local mailbox or PO Box at the Post Office or UPS store for as little as $20/month.
Unsolicited Mail: You can use DMAchoice to prevent unsolicited mail. And if you get catalogs, you can call the company and ask to be removed.

After reading this email, I wouldn't blame you for wanting to turn off all of your technology and never leave your home. The truth is, your information is already out there, so what you can do is stay vigilant and continue to monitor things. There is a lot of valuable information here. For more, check out the two episodes I did on the topic (🎧 Ep77 and Ep78). It's only time before you become a target, so why not make yourself a harder target?

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Editor’s Note: Today, I’m grateful for the support of our partners NordVPN, MileValue, DeleteMe, Daffy, Goodr, InsideTracker, 1Password, ButcherBox, MasterClass and Vuori. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

🚀 My Top Apps/Products for a Productive and Optimized Life

Thu, 08 Sep 2022 07:00:00 +0000

Last week I wrote about productivity, including strategies and tactics to combat procrastination, fight distractions, and engage in deep work. If you missed it, you can read it here. This week I wanted to follow that up by sharing all my favorite apps, tools and products for staying productive and optimized.

👍 Favorite apps and services for an optimized life

I covered a lot of this in my bonus podcast episode (🎧 Ep73) but here are my favorites apps, products and services for a productive and optimized life:

Email: I've been a long-time Gmail user. If you are too, you've got to turn on your keyboard shortcuts because email is 10x faster when you master them. Now, I've switched to using Superhuman, which lets me quickly see all the emails from a single person among my alias accounts. It also has email shortcuts, undo send, delays send, and instantly send functions. It will pull up social profiles for recipients and senders (especially for someone you don't know). I pay monthly to use this product, and I love it. You get one month free at chrishutchins.com/superhuman.
Calendar: I've used Calendly for years. Nick Gray (🎧 Ep. 68), whom I had on to talk about cocktail parties, has a post on his site that went into all the details of how to use it to be a bit more friendly.
Storage: I use Dropbox, Google Drive, and iCloud. Dropbox is the primary storage for work and my personal files. Google Drive is for backing things up (and it's replaced Microsoft Office), and iCloud is for all my photos and videos.
Everything: Notion has become my second brain. There's an entire notion board for our family, where Amy and I do everything from planning upcoming trips, organizing information, kids' activities, doctor visits, and meal planning. I also use it for the podcast for absolutely everything.
Finding Stuff: I love Alfred. If you're a Mac user, you probably know that you can hit the command + space bar to pull up a search for a file or go to a website. Alfred is the supercharged version of this. I have an emoji library. I use it as a calculator and to find files. The best part is that it will store my entire clipboard history, whether it's images or text. So sometimes, I want to grab a few lines from one email and move it to another; I can copy each one individually and store it in the history for later use. I use Alfred at least 100 times a day.
Multiple Screens: Another app I use is Rectangle. It moves stuff around the desktop. I often have two windows, so I can change them dynamically to fit my needs. I find that if you pause and drag your mouse or trackpad around, it just distracts me. So if I could just get it out of the way quickly.
Chrome extensions:
- Library Extension when searching for a book on Amazon to tell me if there's a book available for free at your public library.
- Eno from Capital One lets you create free virtual cards for any retailer. I love that this can generate unique card numbers you can turn off after making a purchase.
- Lusha will auto-pull emails when you are looking at someone's LinkedIn profile.
- don't f*** with paste let’s you paste into fields when sites don't allow it (especially important because I'm much more likely to mess things up if I manually type in, say, an account number).
- Card Pointers extension to manage my credit cards and makes it easy to find the right card to maximize category bonuses and offers on everyday purchases. They also have an amazing app (especially the upcoming iOS 16 version I’ve been testing. If you want to try Card Pointers Pro, you can get a free trial and 20% off here.
- Keepa shows you a chart tracking all the Amazon price history of any item you’re looking at
- OneTab will consolidate and save multiple tabs, so later, I can bring them back.
Mobile Apps on Desktop: Before I found out you can install and run most iOS apps on a Mac (as long as it has an M1/M2 processor), I used Bluestacks to run Android mobile apps on my laptop. My primary use case was watching our daughters Nanit cams, but I’ve since found so many more.
Food & Groceries: I love the app Paprika. Every time I want to clip a recipe, it does so quickly and easily. My wife and I use the app to organize what we cook. And then you can take everything and throw it into a grocery list. It auto sorts it, and lets us check things off while shopping.
Password Manager: I use 1Password. I use it to store and ensure all my passwords are strong. I also use it instead of Google authenticator.

I also want to share some of the hardware I use for the podcast and daily life:

Microphone: I recommend that almost anyone recording audio get the Audio-Technica ATR2100X. It's a USB and XLR microphone, but the quality is so good. When I first used it for remote meetings, everyone said, "Your audio sounds so good…I just want to hear you say something."
Headphones: I think the Apple AirPods might be one of the best products of the last decade. I use them for everything except when I record the podcast or when I’m on a long flight (Instead, I use Audio-Technica M50X over-ear headphones).
Camera and Lights: A good camera and lights significantly boost the video quality. I use Logitech C920 and C930 with an Elgato ring light; I had a Lume Cube before that, which I still use when traveling.
Teleprompter: I use the ILOKNZI. If you're giving many presentations, it could be worth it. And there's this great app, DuetDisplay, that can turn your iPad into a second screen. So I use the iPad with a teleprompter to take notes and see their faces while I'm looking at the camera.
Wifi: I think a critical thing for anyone online is wifi reliability. I upgraded to a Unifi system. I don't think I've had to reboot a router in the last 18 months. All the ports route to a dream machine pro device. We also bought Unifi cameras because it's all locally stored, so I'm not using my bandwidth to upload feeds.
Locks: I love August locks. I haven’t carried a key to our house in years.
Security: We added a Ring security system, which is a great system.
Sound: We have Sonos around the house. No surprise to anyone here.
Health: I wear my Oura ring every day. It tracks my sleep, workouts, heart rate variability, and blood oxygen levels. I think it's such a good product.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Editor’s Note: Today, I’m grateful for the support of our partners Dry Farm Wines, Vuori, Pacaso, Amazon, Oura, 1Password, CardPointers and Superhuman. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

🚀 Productivity Tactics to Optimize Work and Life

Thu, 01 Sep 2022 07:00:00 +0000

Hi all, Chris here! I love finding ways to become more productive. There is so much to cover on the topic, but today I want to focus on providing you the strategies and tactics to combat procrastination, fight distractions, and engage in deep work.

⏲️ Procrastination is a problem with starting work

If you haven't watched Tim Urban's Ted Talk on procrastination, you're missing out. It does a great job of highlighting the chaos inside your brain insightfully and hilariously. Procrastination is not a problem with doing the work; it's a problem starting the work. I spoke with Ali Abdaal (🎧 Ep72) about how he combats productivity (as an entrepreneur, writer, YouTuber, podcaster, and former doctor). He sees it as a three-stage challenge:

🌫️ Fog of Obscurity. Procrastination begins at the intersection of two emotions: the thrill of starting something new and the overwhelm of not knowing what to do first. It's the crucial mental barrier that you need to overcome. Ali says the solution is to (1) separate the doing from the planning and (2) schedule time on the calendar to do it. Put the steps on paper, sort it out, and develop a path. The process will provide clarity and enable you to figure out the one action you can take right now that will guarantee you'll actually do this thing. That one action can be as simple as writing the caption for the video you want to post or drafting the email if it's finding a guest for a podcast. Do that now.

🌉 Bridge of Anxiety. Once things become clearer, you are likely to run into a rush of anxiety. Ali says the solution is asking yourself targeted questions to understand the emotion better. He proposes using the RAIN method (from meditation practice). Recognize that a feeling of anxiety is getting in the way. Allow it to happen and acknowledge that it's okay because you are human. Investigate and explore why this emotion may exist. Nurture the mind and let it know that just because you feel anxiety does not need to hold you back from starting. Embrace the idea that just because you feel anxious does not mean you can't still act (just act while having the anxiety).

🐪 Hump of Inertia. Finally, with your emotions understood, it’s time for an initial energy boost to get some momentum. Ali's way of doing this is to make a pact with himself to try the first step in the plan for two minutes. And after two minutes, you can stop doing it and try again later. He finds that most of the time he builds the motivation and confidence to keep going. Two minutes, that's it.

You can find more of Ali's lessons on productivity in his Ultimate Guide to Productivity.

⌛ Distraction is a problem with continuing work

Where procrastination is a lack of clarity to start, distraction is the desire to escape discomfort in the moment. While it's logical to believe that it's the desire to seek pleasure (think dopamine spike of checking Instagram), we rarely realize discomfort is the driving factor. I spoke with Nir Eyal (🎧 Ep25) about becoming Indistractible. Nir says to look ahead, schedule your time, and then do what you plan to do in the allotted time. Time management is pain management.

The concept is more formally known as timeboxing. It is a technique of assigning a fixed period to a task, scheduling it in a calendar, and sticking to it. In a study of 100 productivity tricks, timeboxing is the most effective. This means you should ditch your checklist for a calendar. It's not that checklists are bad; it's that they are never-ending. The feeling of checking off one task may be a short-term win; but tomorrow's checklist seems to always have just as many things on it, if not more. And that can leave you defeated. With a calendar, you are constrained by a limited supply.

Some people take timeboxing to the extreme, scheduling everything literally. I suggest starting with your working hours and then building up if you feel the need. Use a planner. And don't forget to schedule your "thinking time" and "free time." While timeboxing is designed to keep you productive, you still need time to be creative and spontaneous (just schedule it in).

👀 Watch out for false productivity

Conventional wisdom suggests that the opposite of distraction is focus. Nir’s research indicates that the opposite is action, precisely an action that moves you closer to your goals or values. A distraction, by definition, is an action or nonaction that pulls you farther away. Technology and social media are the distractions that quickly come to mind, but less obvious ones can all trick you into thinking you're being productive.

Take reading a productivity newsletter (😁) or re-organizing your inbox folders. Both activities are beneficial, but if they infringe on the critical action you planned to work on now, then they are a distraction. Schedule time later to do them.

🤺 Your nemesis is context-shifting

Your best results will come from focus without distraction (deep work). Multitasking has historically been a badge of honor, but you can't actually be productive by shifting back and forth. People highly underestimate this cost of “context-shifting.” Cal Newport (🎧 Ep63) is the author of Deep Work and many books on productivity. Every time you switch your focus, it negatively impacts your brain. Even a quick email check or notification ping will put you at a disadvantage (especially knowledge workers). Context shifts worsen your output, extend the time to complete, and tire your brain more easily, which means it will likely fall for even the most minor distractions. Cal also strongly advises timeboxing and training your brain as productivity techniques.

Try interval brain training. If you haven't run in years, don't expect to run 15 miles in one day. The same is true for your brain. If you need to focus intently but routinely leave notifications on, don’t expect to stay focused for 90 minutes. Set up a time to train. Use a timer and try not to break concentration. Keep doing it and gradually extend the time. After a few months, you can routinely get 90 minutes to 120 minutes (which in Cal's research puts you in the top 25th percentile of all people).
Practice boredom therapy. Give yourself intentional doses of boredom. When we constantly check our phones during downtime, our brain creates a pavlovian response to boredom. So, when we experience boredom, it triggers us to pick up our phones. Why does this matter? Deep work can feel boring to our brains since it's a single task for an extended time. And without training, you will prevent yourself from doing the work. Try this next time you stand in line.
Be productive in smaller periods. Pull apart the work you are mixing together. When working on one thing, work on only that one thing. It may mean that you have small chunks of time on your calendar, but you can calm the hyperactive mind from having to switch.

📩 Email can really do cognitive damage

Let me be clear, email is an essential tool and required for almost any job, but it's also one of the biggest hijackers of our productivity. It's not replying; it's checking and rechecking. It can take 15 minutes to refocus on your essential task. When you get a notification or just go for a quick inbox check, your attention immediately diverges from your work. 80% of the time, the email can wait. 60 minutes of productivity is gone with just 4 non-essential emails.

Here are ways that you can make email more productive:

Set up a time for email. Schedule a block of time in your day that is dedicated to email only. Remove notifications and don't check your inbox throughout the day. Communicate to your closest colleagues that you have these rules in place. You can even include an away message that informs the sender not to expect an immediate reply.
Use the two-touch rule. Interact with emails twice. The first is to label it, and the second is to respond. To do this, use time-based labels instead of categories (e.g., respond today and respond this week). If it doesn't fit either label, archive or delete it. Then use your email time block (mentioned above) to reply to emails labeled respond today, then to the rest. It’s likely that many emails that once needed a response don’t need your attention because the sender did the work or the email is no longer a priority. I use this method with Superhuman. It helps me achieve inbox zero without spending countless hours.

🕓 Implement office hours to help optimize back-and-forth conversations.

Collaboration has evolved to require this persistent unstructured, back-and-forth messaging. At first, it was email, but now we have instant messaging tools like Slack and Microsoft Teams. These asynchronous conversations demand a lot of attention. Since it has become the common form of communication, decisions can stall if there is too much time between messages. Even setting up a meeting could take 3-4 messages.

According to Cal, these asynchronous conversations are the biggest enemy of your deep work. To fix this, you really need to pull your work apart. Separate the communication from the focused work. Implement office hours on your calendar to open all your communication channels dedicated to conversations requiring more than one message. Make the office hours public to let everyone know that this is the dedicated time for these types of conversations. You will protect your attention.

🪝 Create an end-of-the-day routine with an unusual hook.

"Schedule shutdown complete" is the phrase that Cal routinely uses to signal to his brain that work is done for the day. It closes open loops and distinguishes between work and non-work times. Too often, your work mind tries to creep in during the wrong times. The rumination prevents attention recovery, reduces sleep quality, and can impact family or hobby time. He proposes you develop a unique phrase and routine to complete the day. Over time, your brain will adapt to the process, and you can combat that rumination more effectively.

You can use this routine even if you have to work later in the evening ("second shift"). Cal proposes to still end your daily routine (with the unusual hook) but specifically plan the task for your second shift. It will tell your brain that you are done with your typical work day, and the only thing scheduled for later is one specific task. Consider ending your first shift earlier if you consistently do a second shift.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Editor’s Note: Today, I’m grateful for the support of our partners Amazon, Trustworthy, Inside Tracker, Wren, Daffy, Trade Coffee, Wren, LinkedIn, MileValue, UpgradedPoints, Vuori, BlockFi, Oura, 1Password, CardPointers and Superhuman. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

📣 Pitching & Effective Communication

Thu, 18 Aug 2022 07:00:00 +0000

Today we’re talking about a few aspects of effective communication. I’ve been fortunate to host some of the world’s best communicators on the podcast and have had my fair share of experience as a former founder and venture capitalist. It's not just the words, but the energy, preparation, and presence to build the rapport to sell yourself and ideas.

🤐 Overpitching is cringy, so say less

You know that feeling when someone is overselling or wraps up a long monologue with a clever closing line. Your politeness keeps you there, but inside you want to run. Overpitching, oversharing, or giving too much information… just doesn't work. People are repelled by the things that chase them. When you say less, you display more confidence and conviction and invite people to ask for more.

I spoke with award-winning Hollywood producer Brant Pinvidic (#67) about his "3-minute rule" to say less and get more. He believes every business, product, or service should be conveyed clearly, concisely, and accurately in 3-minutes or less. Don’t give all the details upfront; instead, give the other person a clear understanding that makes them curious and encourages them to lean into the conversation. The pitch is simply the door that leads to the discussion; it's the engagement that invites your audience to foster your idea.

✉️ Invite ownership to your idea

It's natural to treat your audience as buyers, especially when the conversation intends to persuade them (e.g., buy your product, invest in your idea). But that way of thinking is not optimal. Viewing your audience as builders who can grow your idea is much more effective. When you do this, you create a sense of ownership. People place a higher value on the things they put their effort into (IKEA effect) or already own (endowment effect).

Also, most decisions today are made by committee. You share what you heard with your boss or share an idea with a friend, and you do so in the way you heard it and felt it. That means the people who didn't hear the idea directly can influence the outcome. So you want your audience to feel a sense of ownership and value, so they can become a megaphone for your ideas. Inviting them in is only half of the equation because they also need to share your idea in the way you want them to. So don’t just give numbers, features, and perspective… you must tell a story. That's how they will remember.

🏰 Storytelling is not “once upon a time”

Storytelling has been a buzzword for a while, but it still has this reputation as 'once upon a time' (clearly, someone a long time ago marketed that well). Storytelling provides a natural flow of communication to lead the listener to a conclusion in an engaging and clear progression.

In my conversation with Suneel Gupta (#37), he discusses the importance of marrying a story with substance. We naturally desire to persuade with substance (think numbers, content, etc.). While the substance may keep up there, it’s the story that brings us in. One way to do this is to focus on a central character. Develop the story around that character to first build that level of understanding. Then, once you have done that, use the understanding and story of the character to zoom out and apply to the larger audience.

For example, when I was running my last company, which offered online financial planning, I always told a story of a couple that were friends of mine. They had recently gotten married and were struggling to figure out if they were on track for the financial goals they were planning together (house, kids, etc.). I shared what it was like for them to meet with an in-person financial advisor who asked them to print out bank statements and bring them to a sterile office. I used their journey to paint a picture of the problems we wanted to solve and it worked so well. Unfortunately, the company didn’t work nearly as well as the pitch, but that’s a story for another newsletter…

🪜 Structuring your message

There is an improvisational, off-the-cuff style that every communicator aims to master. It comes from two things:

A lot of practice (I'll get to this next)
Structuring and setting yourself up for the conversation

Planned conversations typically require sending materials in advance, which means the content for in-writing and in-person are going to take different forms. If you want the audience to read the slide, then put the words on there that you want them to read. If you are speaking out loud and want them to listen to you, don't put the words on the screen that will reshift their attention. Use images or bullets that will enhance whatever you are saying. Your slides should support you, not do the work for you.

When I build presentations, I try to put almost nothing on my slides – usually just an image or 1-3 words. I also want to know the content so well that I can move through the conversation more seamlessly. It allows me to drive home the point I want to make, but in a way that might evolve after reading the room. If there are words on the slides, I have locked myself into how I deliver the message.

Finally, I can't talk about structure without mentioning Brant's WHAC method. It's a simple organizational formula for giving a great pitch.

W - What is it? Inform your audience of what you are offering.
H - How does it work? Explain simply and clearly how your idea works.
A - Are you sure? Give them validation for your claims.
C - Can you do it? Prove that you can put this into action.

🎯 Putting in the practice

My biggest piece of advice for when you are presenting, pitching, or selling is to avoid reading your notes. It gets awkward, and if your audience is too consumed with that feeling, they don't listen to your content.

Practice enough that you don't need to speak with notes.
Get comfortable knowing that you will forget things, and that it’s ok. If it’s important enough, it will resurface later.

Suneel’s research found that the best communicators, on average, practice 21 times before delivering the real deal. And we aren't talking about the 'director's commentary' either. You must go through the presentation as close to the natural environment. Use the words and slides you plan to use. Pitch your spouse, kids, friends or colleagues. You can even go as far as practicing at the same time of day that you are planning to give the presentation. It's about building the right muscle memory.

😵 Steer into the objection and own the negative

I love calling out objections upfront. I used to say, "Look, I don't have XYZ information yet; if that means you aren't even interested to hear me talk, we can end this meeting early and save you time." Not only does it add credibility, but it also doesn't become a distraction in your audience's mind during the entire pitch. You've owned it. Also, by having an objection, you invite the audience to share their solutions to the problems or ideas, giving them ownership. Everyone likes to be a hero to a problem. Let them be.

There are still some objections that you can’t overcome. If you provided the information clearly enough for them to understand it, but they still aren't engaging, move on. It takes so much effort to turn a 'no' into a 'yes.' Other people are interested and believe in it, so don't waste your time trying to change a ‘no.’

To make this easy, I like to give people a simple out. When I was raising money, I always followed up with:

“Really enjoyed our conversation! Things are moving along, so just wanted to see if there’s anything else you need from me to help with your internal discussions. If not interested, just let me know..”

I wanted to make it easy for someone to say 'no,' so we get to the answer faster and reduce the anxiety of not knowing what they will say. If they don't see the value, let it go and find someone else.

📣 Getting Feedback

I can't stress hard enough how valuable feedback really is, and there are three great ways to gather it:

The first is to build a circle of people around you that will offer you the feedback that will elevate your idea. In Suneel’s book Backable, he describes the four types of people you could include:

The collaborator is the person that helps you build on your idea with an eye on market fit and demand.
The cheerleader is the person that gives you the energy to propel you forward.
The coach is the person that tests your idea to make sure it fits you as a person.
The critic is the person that pokes holes in your idea.

While a single person can be more than one, what's most important is that you set expectations as to which type you need in a particular moment.

The second is reading between the lines. Pay attention to the questions people are asking you to get accurate answers. For example, if the people are asking questions that you're eventually getting to, it might indicate that your presentation is out of order. If the questions were trying to comprehend what you just said, it means you probably weren’t clear enough. The questions people ask you are indicators of how well things are going.

The third is direct feedback. It's taking critique, owning it, and applying it. I used to write down every question an investor asked in a pitch meeting. I would make a single slide of just that addressed the question for the next pitch and drop it in the appendix. So I had this short, sweet deck with dozens of appendix slides in case someone asked a question I had heard before. It had an added benefit instilling more confidence than if I had just said it on the fly. On the off chance you don’t get questions, you can always try asking:

What part of all that stood out the most?
How would you describe this idea to someone else?
What could I have done to make this a 9 or 10?

And then use the info you collect to improve for next time.

💯 Stand out by doing the things others don't

My final piece of advice is do the things that people typically won't do. Find the unique insight that doesn’t show up in Google or demonstrate a level of effort above the norm. Even if what you share doesn’t end up being valuable, the effort you demonstrate is often worth it. When I was hiring, it’s remarkable how most candidates all do the same thing, but the ones that don’t always stand out.

I once reached out to a company I wanted to work at and told them that I made a presentation about their industry that I wanted to share with them. Looking back, the presentation was terrible, it had no unique insight and probably added no value to the company. But the fact that I made the presentation showed them that I did care. Standing out made all the difference and I was working there a few months later.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Editor’s Note: Today, I’m grateful for the support of our partners Vuori, Dry Farm Wines, Athletic Greens, TrueBill, Inside Tracker, Wren and Daffy. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

🚗 Saving Money on Rental Cars

Fri, 05 Aug 2022 07:00:00 +0000

Advertiser Disclosure

Note: American Express is a ChrisHutchins.com advertiser

Last month I had a great conversation for the podcast with Jonathan Weinberg (🎧 Ep66) where we talked about all the deals, tricks and tips for rental cars. So with Labor Day travel coming up, I wanted to share takeaways to help you all save money. Even if you’re not traveling for Labor Day, everything below should help you save real $$ on your next rental.

🤔 It's time to rethink how you plan your trips

It’s pretty normal to wait to think about booking your rental car until you’ve booked your flights and hotels, but that’s no longer always true. I've recently heard stories of people canceling trips and rearranging flights simply because there were no rental cars available. My conversation with Jonathan Weinberg (Ep 67) was packed with tricks, and money-saving lessons for rental cars and I’m excited to share them with you to help you save $$ on your next trip. After all, he has helped save renters over $100M since starting his company Autoslash 12 years ago.

🤪 The rental car market has been crazy

Before the pandemic I remember renting a car in LA for as low as $10/day, but now current market rates are more like $80 - $200/day. During the peak craziness, some people even rented U-Hauls for $250/day, because it was the cheapest (or only) option available.

Why? Well the extremely low demand during the pandemic basically imploded the rental car market. Companies sold many of their cars to right-size their inventory with the plan to repurchase new ones when the demand came back. Except when they started buying, they couldn't, because there was a computer chip shortage (cars need 1,000-2,000 computer chips to operate). So it’s a whole new world for rental cars.

And while rates and availability have gotten a little better, there are still entire states and countries with extreme inventory shortages.

🥅 Casting a wider net in your search process

The rental car companies are in constant price competition. They are undercutting prices against each as often as by the hour to steer business their way. All of this means an opportunity for the savvy renter. You just need to cast a wider net for your search. I live in the Bay area with three airports. If I were flying here for vacation and wanted a car, I would figure out the rates for each airport and add them to costs for flights to those airports and compare the total prices for each to find the best deal.

Look at off-airport. Off-airport rentals can be cheaper, but you have to factor in the time and cost to get you there (Uber or Lyft). Also, off-airport rental car agencies are typically open 8AM - 5PM, so a late arriving flight (whether booked that way or delayed) can make it a challenge. However, you can pick-up and drop-off from separate locations, and while one-way rentals across long distances (pickup in SF, drop off in LA) can be expensive, they’re often the same price if the two locations are in the same city. Unfortunately switching between on-airport and off-airport locations usually require two different searches. Two examples for using this to your advantage:
- If renting a car off-airport saves you a lot, you might still be able to drop it off at the airport at the same rate, so you’d only have to figure out getting between the airport and rental car location once.
- If you’re to drive around to explore an area, but don’t need the car for your whole trip, you could pick up at the airport and drop off downtown. Our au pair recently did this and picked up her car at LAS airport for a trip to the Grand Canyon and dropped her car off at a hotel on the Strip before spending a few days in Vegas.

Weekly vs. daily rates (and late returns). Different rental periods can often offer significant price differences. For example, the weekly rate (≥5 days) can often be a better deal, so it might be cheaper to rent for 5 days, even if you only need 4. And fun tip: if you return the car a day early, you might get that weekly rate prorated, because you only used 4/5 days. Also keep in mind that a rental car “day” is a 24-hour period and the timer starts when you pick up the car, so if you pick up early, you’ll have an earlier drop off time before additional charges kick in. Here’s how a few of the major brands charge for late returns:
- Grace Period: 59min (Enterprise), 29min (Avis/Hertz)
- Additional Day Charge: Late by 2.5hrs (Enterprise), 1.5hrs (Hertz/Avis)
Change pickup times (day, afternoon, evening, within the hour). This one frustrates me, but for some reason, your pickup time can actually change the rate you pay. Sometimes even just booking on the half-hour instead of the hour can change things too. However, the major companies usually let you pick up anytime on your reservation day (after all flights land early and get delayed), so you could book at the lowest price and just come when you arrive. That said, discount brands might not be as flexible, so it may be worth calling and asking.

Prepaid rates. I try to avoid prepaying for rentals. Not just because plans can change but because with pay at the counter rates, you can easily cancel and rebook if the rates come down. However, most prepaid rentals don’t require you to forfeit the entire rental cost, there’s usually a fee to cancel depending how far in advance you do it. However, sometimes the cancellation fee is so low (e.g. $25) that prepaid might be worth the savings. However, just keep in mind that prepaying the rate doesn’t give you any more priority for guaranteeing a car for you… you’ll have the same priority as someone who chose to pay at the counter, which is usually just “first come, first serve.”

Prepaid fuel. Don't pay for prepaid fuel. It may seem like a better deal because it has much lower cost per gallon than what you pay if you don’t bring the car back full. However, you are likely wasting money, because you have to buy the entire tank and it’s very difficult to manage your fuel levels so you bring the car back exactly empty. The most cost-effective option is to just fill up the tank in the 10 miles before drop off.

🚘 The rental car process

There are many things to consider when renting a car, so let’s briefly discuss the process and highlight some of the important considerations.

Searching for your rental. The search process is fairly intensive because variability in options is tremendous (pickup times, types of cars, and from hundreds of locations within a particular area). I used to assume that the company with the cheapest compact rate would have the cheapest full-size or SUV rate too, so I would try to simplify my results by searching for one type of car and then picking the car I wanted from that company. Well that assumption was totally wrong, so definitely make sure to search for all the types of vehicles you’d be ok renting.

Booking your rental. The site you book your rental on matters because different sites offer better discounts, pay-later flexibility, and provider reservation tracking functions to keep looking for a better prices. However, all those rentals are ultimately booked with the same rental car companies, so I would book wherever you find the best price (unlike my recommendations to book hotels/flights directly with the airlines).

Tracking your reservation. This part of the process is often overlooked, but because most rental car reservations have no fee to cancel, you can take advantage of any drops in price. You can do this manually by rerunning your search every so often, or use a site like Autoslash, which will just track your reservation daily and send you an email if rates drop and they find you a better price. The best part is that you don't need to book the original reservation with them, you can upload your reservation, and they’ll still track it for a better deal.

Picking up the car. Without joining a loyalty program, you usually need to go to the counter to confirm your reservation before going to the lot to pick up your vehicle). I’ve seen lines with dozens of people in them, which is why I think the best loyalty program benefit is the ability to skip the line and go straight to the lot to get your car. These programs are free to sign up for, so there is no reason not to. Here are some tips for selecting your car:
- Check the mileage. It's an indicator of the car's condition
- Look at the tread on the tires. And think about the weather forecast
- Open the door and check the amenities that fit your preferences (e.g. bluetooth, usb chargers, etc)
- Take a picture or video of the car before driving it off the lot (for your damage protection)

Dropping off the car. The drop off process is mainly about protecting yourself. The most important thing is to get a receipt (whether physical or digital) before you leave. Also, take pictures or a video of the vehicle to document the condition you left it in. Any damage under a quarter size shouldn't be a concern (at least in the US), but it's safer to document. The last thing you should do is take a picture of the gas receipt, fuel level and the cars mileage in case you ever need the proof down the road. This sounds like a hassle and 99% of the time is totally unnecessary, but I promise you’ll be glad you did if you’re ever in the 1% of the times it matters.

🏆 How do the brands stack up?

There are three major brands (Hertz, Enterprise, and Avis) that own a ton of the rental car market.

Hertz owns Dollar & Thrifty.
Enterprise owns Alamo & National.
Avis owns Budget & Payless.

How do they stack up? (according to Jonathan and his team):

National sets the standard for the best overall experience. You can choose your own car, they have better model cars, excellent service and have the best loyalty program for earning free rentals. I was really surprised to learn this and am excited to rent from National in the future and how Jonathan’s take holds up.
Hertz follows closely, offering their “Ultimate Choice” program that let’s you choose your own vehicle at most airports and get on your way quickly.
Avis is next, still solidly in the top tier of rental car companies.
The next tier is Enterprise, Alamo and Budget. Enterprise has great customer service, Alamo lets you choose your car, and Budget provides a fast check-in service. But none of the three are as seamless as the higher tiered brands.
Dollar, Thrifty and Payless are deep discount brands. The cares are still solid, but you’ll often get the service/experience that’s expected from a discount brand.

💰 You need to be using discounts

Memberships (AAA, Costco, AARP), credit cards and many employers offer valuable discounts that are essential to use for savings on rental cars. But these are not the only ones, you can also find them directly from rental car companies, local or national organizations, college alumni associations, for military personnel and for senior citizens. When I was at Google, their discount with Hertz was so good that I could almost never beat it, but sorting through all the others can be a lot of work. Especially when the discounts from programs like AAA or Costco can be so big it would more than justify getting a membership just to save on one reservation. That’s why I love that Autoslash will compare discount codes from all programs across the board, even before you’re signed up for them. The process takes a few minutes, so you don't have to run multiple searches or maintain a spreadsheet of all the discount codes.

It’s also tricky because different membership programs offer discounts with different brands (AAA works with Dollar, Thrifty, Hertz; Costco works with Alamo, Avis, Enterprise, and Budget). And not only will the discount codes save you money on booking, but they also save you on extra fees:

AAA will save you on fees for under-25 renters at Hertz
AAA rates include a free car seat and provide road-side assistance
AAA and Costco rates offer a free extra driver
Most major rental car companies will let spouses drive for a fee (note: that if the lines are long and the loyalty program let’s you skip the line, you can usually add an extra driver at the check out window)

🛑 Use caution with employer discounts

Using a discount code from a previous employer or even a company you’ve never worked at may be tempting, but I'd be careful. Many rental car companies are cracking down because the company rates are so much cheaper. Some people have even been put on a 'do not rent list' for fraudulent use. And you can put yourself in a deeper hole if you get in an accident, because many times the employer has contractually agreed to cover the cost of repairs, but likely won’t cover them if they determine that the renter isn’t actually an employee. So if you’re using a corporate discount code you’re not eligible, always make sure to decline the insurance.

🤬You show up, and there is no car available for you

This happened a lot in the early wake of the pandemic, but it’s probably not something you should be too worried about. However, it’s important to know that rental car companies don't actually hold a car that matches your reservation (see video below). Because most reservations are not prepaid, many people cancel at the last minute or just don’t show up, so companies usually oversell their inventory by up to 30% to ensure they’re maximizing utilization.

However, your rental contract is binding, so if you show up and they have no cars, the company should do everything in their power to get you one. Don't accept “there is nothing I can do” because you should not pay for the inconvenience. It's an opportunity to ask for:

Free transportation to pick up a car at another location
Request they bring you a car from another location
Rental from a competitor (where they cover any difference in price)
Free points, upgrades or add-ons for the hassle

So should you book a backup reservation? Doing this will just compound the problem and impact someone else waiting for their reservation, so I’d suggest only using a backup reservation for when you absolutely need a vehicle. You can also call ahead to the company to get a sense of the inventory, especially if you're renting off-airport because they have smaller fleets.

Also, sometimes companies will also use “cheap upgrades” to mask the fact that they don't actually have the car you booked. It may look good, but challenge them before you take it, because if they don’t have a car in the class you booked, you could be in a position to get that upgrade for free. And if that forced upgrades means less fuel efficiency, I’d definitely ask for free fuel or some other discount.

❌ In most cases, it's safe to decline the insurance

The best way to avoid the rental car company's pricey insurance is to use a credit card with primary coverage combined with your personal car insurance policy (assuming it extends coverage to rental cars, which it usually does). The credit card will cover damage to the rental car, but it will not cover liability (damage to other vehicles and injuries to others), so make sure you have enough coverage and liability with your personal car insurance policy before driving off the lot. If you don't have your own car insurance policy, you should probably pay for liability coverage, but you can decline the collision coverage if you have it through a credit card. There are also frequent renters' policies for those without a personal car insurance policy.

One gray area is the relationship between credit card insurance coverage and paying with credit card points. While it’s not always explicitly defined, as long as you put some part of the transaction on a card (deposit, taxes, fees), the insurance will most likely kick in. If you booked with points and you get in an accident or want to be 100% sure the insurance will kick in, you could also intentionally extend the rental or return the car late so you’re forced to make a rental payment on your card.

💳 What are the best credit cards for rental cars?

My best cards for rental cars are the ones that offer primary coverage, which include:

The Platinum Card® from American Express doesn’t offer primary rental car coverage without paying extra for their Premium Car Rental Protection (which costs money). However their Hertz discount code offers:

Complimentary one-class upgrade (when available).
Four-hour grace period on returns in the U.S.
10% bonus points with every rental.
Special cardholder rates at select locations.

Reminder: If you’re interested in signing up for any of these cards (or really any other cards) you can support me and the show by signing up at chrishutchins.com/cards 🙏🙏🙏

👑 Free Rental Car Status

Many credit cards offer free elite status with rental car programs, so if you’re eligible you should definitely take advantage:

The Platinum Card® from American Express: Avis Preferred Plus and National Emerald Club Executive®
Visa Infinite Cards (e.g. Chase Sapphire Reserve®): Avis Preferred Plus, National Emerald Club Executive®
Capital One® Venture X Rewards Credit Card: Hertz President's Circle (their top tier)
Delta: Hertz Five Star for Gold and President's Circle for Diamond/Platinum
United: Avid Preferred Club for Silver/Gold and President's Club for Platinum and higher

🌎 International rentals

International policies are quite different. Make sure you check the contract, quoted rate, and add ons before you leave the desk. Also do a through look over the car for any existing damage/scratches, as even the smallest nicks can come with charges abroad. And get a receipt when you drop off the car and document the condition you returned the car in.

This is all because local companies often subcontract from the major brands (like a franchise), but they can set their own policies and terms. For example, when I was in Cabo last year the rental rates looked abnormally low, but liability insurance is mandatory, so they were all going to add on and required daily fee for that policy that would drive up the rates significantly.

🏎️ Using non-traditional rental car services

Outside of the major rental brands, there are a few alternative companies worth checking out. For example, Turo provides an AirBnb style rental option, where you are renting from owners (hosts) instead of rental car companies. Kyte aims for convenience and will drop off, pick up, and fill the tanks for you. Silvercar rents only Audi’s and comes at a premium, but usually less than a luxury car from a traditional company (and Visa Infinite cardholders save up to 30% here). The one place I consistently use Silvercar is when I need to rent an AWD/4WD car, because it’s usually cheaper than an SUV and all Silvercars are AWD. Unlike the major agencies, these companies aren’t in every city, but they’re worth comparing to traditional options if they’re in the city you’re going to.

🚗🏨 Autoslash & Hotelslash

I have mentioned Autoslash several times in this newsletter. It's not because I was asked to or paid to, but because I think it’s the best option to save you money (unless you have a better corporate rate). In fact, even using all the discounts I have for a 7-day rental in Maui this October Autoslash beat the next best rate by ~$200. I guess I should believe their claim that they save 30% on an initial booking and another 20% during the tracking process – and the service is completely free.

They’re also developing a similar site for hotels (Hotelslash) and Jonathan set up the code “allthehacks” for you all to get free lifetime access. Note that you won’t be able to enter your hotel loyalty #s and you’re not likely going to get any free upgrades, but if you can save a ton on the booking, it might be worth using the site.

📈 All About Investing Part 2

Thu, 21 Jul 2022 07:00:00 +0000

It’s hard to beat the market, especially if you aren’t doing it full-time. Good investing should be boring. However, there are techniques, tips, and tools that professionals use in order to improve their odds of success. Let’s go through some of them.

In this post, we’ll dive into more advanced investing topics like taxes, inflation, debt, and strategies for becoming a successful investor. If you haven't already read All About Investing Part 1, I recommend you do so because it covers some of the fundamental considerations that will add value to the conversation.

🏆 Make sure you compete against the market

When we talk about investment return, you have to look at the performance of your investments relative to the overall market. And take it from me; it's a bit of a mental playground. It's entirely possible to have your portfolio go up 36% in one year, and you feel amazing, only to realize that the entire market went up by 52%... and your portfolio actually underperformed. A common benchmark that people use is the S&P 500, but if you have a globally diverse portfolio of stocks, it might make more sense to use something like VT (Vanguard’s Total World Stock ETF) or if your portfolio has a mix of stocks and bonds, one of Vanguard’s Target Date Funds with a similar stock/bond ratio might make more sense.

💸 Minimize taxes with tax-advantaged accounts

There is more to be gained by saving on taxes than almost anything else. However, just remember that for many tax benefits, there will be a tradeoff with liquidity – meaning that while you may save on taxes, you may not have easy access to the funds.

The most common tax-advantaged accounts are Individual Retirement Accounts (IRAs), 401(k) plans, and 529 college savings plans. They all offer advantages of deferring tax (paying tax later) or growing tax-free (paying tax now, no tax later). The tax advantages will help accelerate growth, but for IRAs and 401(k)’s, you don't have access to these funds until 59 ½ years old without penalty. And for 529 plans, you can maintain tax advantages only if the funds are used on allowable education expenses.

IRAs

IRAs include two different types. The first is a Roth IRA, where you can invest after-tax money and never pay tax on the growth or withdrawals in the future. The second is a traditional IRA, where you can invest pre-tax money and skip paying taxes on gains until you make future withdrawals. Both IRAs allow you to contribute $6,000 per year (or $7,000 if you are 50 or older), but if your income is high enough or you’re eligible for a retirement plan at work, you may not be eligible for either unless you take advantage through the backdoor Roth IRA process (below).

If you are eligible for both, it's up to you to choose which one is better for you. Here’s how I would think about it: my wife and I are in our peak earning years and we live in a state with some of the highest income taxes in the country. While I don’t know what the future holds, I think it’s more likely we’ll have lower tax rates in retirement, so I would opt for the traditional path if I were eligible.

The backdoor Roth IRA process is tricky (so I suggest talking to your CPA), but it’s also one of my favorite tricks and I’ve been using it for most of the past decade. In general, this is how it works. First, you make non-deductible contributions to a traditional IRA (after-tax money). Then, you roll the funds over to a Roth IRA (and don't pay taxes since you already used the after-tax one in the first step). Then you can invest in whatever your account allows and the account will grow tax-free into the future. The most important consideration is if you already have funds in a traditional IRA, you’ll need to do pro-rated rollovers, which will likely incur taxes, so if that’s your circumstance, I would strongly encourage talking to an accountant.

I personally hold my Roth IRAs at Wealthfront, but I was originally hesitant to put my IRAs there, because you don’t get the amazing value of tax-loss harvesting in a tax-advantaged account. However, I love my passive investments to be hands off and I’m happy to pay for convenience and automation… but even more importantly, Wealthfront will coordinate trades between all your accounts (including IRAs) to avoid triggering any wash-sale rules (see below), which could result in an extra tax bill.

401(k)s

A 401(k) is similar to an IRA but is tied to your employer. The default option is a pre-tax / traditional contribution, but many plans offer a Roth 401(k) option for after-tax contributions that functions similarly to a Roth IRA. For both, you can elect to contribute a portion of your paycheck directly into the plan, up to $20,500 per year. And in some cases, employers even match a portion of your contribution amount, which acts as free contributions.

While that number is the employee tax-advantaged limit, you can actually contribute up to $61,000, and if your employer allows it (sadly it’s not that common), there is a process called the mega-backdoor Roth 401(k) that can be used with 401(k) plans and would allow you to make significant Roth contributions each year. I talk about the backdoor and mega backdoor Roth IRAs in episode 65, so you should go check it out.

529s

A 529 plan is not a retirement account but has similar tax advantages. It's designed to help pay for education costs. Like a Roth IRA, you make after-tax contributions but grow the account tax-free and make tax-free withdrawals so long as you use them on qualifying educational-related expenses for you or your kids. There is an exception for scholarships, so if your child receives one, you can withdraw that amount penalty free. However, if you end up with more money than need for educational expenses, you’ll have to pay a penalty to withdraw it or it can be retitled in anyone else’s name, so it could be given to a grandchild or other family member. Contribution limits match the IRS gifting limit of $16,000/year (in 2022), but you can actually superfund your 529 with up to 5 years of contributions at once.

I personally hold my 529 plans at Wealthfront, and while I was originally hesitant to pay the fee for the same reason I was about my Roth IRAs (see above), I couldn’t find another 529 plan that offered as globally diverse a set of ETFs and I think the value of that diversification is greater than the 0.25% fee. On top of that, I love the automation of everything and having all my investments in one place.

Wealthfront

If you’re interested in any Wealthfront accounts, I’d appreciate you using my referral link, which will get us both $5k managed for free.

Note for anyone self-employed: I didn’t cover SEP IRAs or Solo 401(k)s above, but I’m hoping to include them more in a future newsletter (and by then I will have set my own up, so I’ll have some firsthand experience to share).

🧑‍🌾 Capture losses with tax loss harvesting

In any year, the IRS will let you deduct capital losses from your income (up to $3,000 per year) or against any other capital gains you have. If you have more losses than you can use, you can even carry them over to future years. It's a huge tax advantage to pay attention to. But there is an important rule to consider. It’s called the wash sale rule. The IRS will not allow you to take a loss if you buy back the same investment (or a substantially identical one) within 30 days before or after the sale.

For example, let’s say you had originally bought $10,000 of VTI (Vanguard’s Total Stock Market ETF) and it's now down 25%. If you sold it, you’d have a $2,500 loss that you can use to reduce your taxes this year. Now ideally, you’d want to buy back the $7,500 of VTI so you’re not out of the market when it (likely) recovers. However, the wash sale would prohibit you from realizing that loss if you rebought VTI.

But the trick is that you can buy a similar investment that’s very correlated to your original investment. So, for the example above, you could buy SCHB (Schwab’s US Broad Market ETF), which is so correlated to VTI that you can barely see that there’s two lines in this chart comparing their performance over the last 5 years:

So how much does this matter? Well, Derek Horstmeyer reported in the Wall Street Journal that tax loss harvesting can, on average, boost an equity portfolio’s annual return by 1.10% - 1.42% percentage points, meaning if you had an expected return of 5%, tax loss harvesting could increase it to 6.1 to 6.42%. However, you should be careful because there are many ways that wash sale mistakes could revert the benefits, so you need to make sure that you know what you are doing. Software handles this much better than most humans, so I urge you to automate this process.

🤔 Think twice about funding retirement accounts

The above conversation may lead you to believe it's a no-brainer to take every tax advantage, but maybe you shouldn't.

Yes, you invest right from your paycheck, making it easy and pain-free.
Yes, you can grow the money without paying taxes each year

However, many of my past guests agree that it may not be the best thing to do, because you are locking up your money for a long time and you may not know when you’ll need that money. In episode 19, Andy Rachleff points out that using every retirement contribution opportunity to minimize taxes might lock up all your money when you might need it most, like for a down payment, advanced degree or other emergency. To use the funds for any of those, you’d likely be penalized for early withdrawal and lose the advantage of accelerated compounding growth.

However, there’s one thing everyone I know will agree on: if your employer matches any portion of your retirement contributions, invest as much as you need to get that free money, because there aren’t many places in life that you get free money like that.

🔥 Inflation is hard to beat short-term

Inflation is front and center today, and we are all feeling its impact. And for anyone under 40, we have never experienced this type of environment before. So, what can we do about it? One option is to invest in I-Bonds with current rates at 9.6% (listen to episode 64 or read this past newsletter for a full rundown on them). Another option you might consider is trying to hedge against inflation, but in episode 42, Ben Carlson said putting on a short-term hedge can be tempting, but also is really hard to do successfully. Gold is a perfect example. Historically, gold is said to be the best hedge against inflation and the past few years provided a great opportunity for gold to explode. But spoiler alert: that didn't happen. So I say ignore trying to solve for the short-term and focus on the long-term, where I think the stock market is your best inflation hedge.

🏦 Debt will magnify gains and losses

If you need money, but want to avoid selling and realizing gains, you can always just borrow against your portfolio, but things can also go very badly. In theory, when expected returns are greater than the interest rates, it's a good bet, but it's a very risky proposition. When thinking about it, I am often challenged by the question, 'Why is it okay to take on debt in my house but not in my portfolio?' I actually had a great conversation with Joe Saul-Sehy in episode 35 about this exact topic.

There are two specific risks when using debt in your portfolio: margin calls and variable rates. If you take out a loan on your house and the value goes down, the bank does not come knocking to take your house (as long as you keep paying your mortgage). But if the value goes too low in your portfolio, the brokerage firm will request you to add more funds to the portfolio to meet the debt requirements (margin call) or even sell your positions if the balance gets too low or you don’t make your deposit in time. The second risk catches more people off guard. If you locked in a fixed rate mortgage, your rates (and payments) don’t rise when interest rates rise. But your portfolio loan usually has a variable rate, and in today's environment, the federal reserve is keen on raising those rates. So please consider those risks before borrowing.

My two rules of thumb when borrowing against your portfolio are 1) borrow a small enough amount that if we experience a major market crash, you likely won’t get a margin call (for me that means borrowing <30% of the value of the account) and 2) make sure you have a plan to pay back the loan. And for those of you thinking about home equity lines of credit (HELOC), many are subject to the same variable risk as a portfolio loan. So you need to pay close attention, or you could be paying way more interest on your debt than you expected.

🎰 Get comfortable making many bets

I talk a lot about passive investing because it makes up the vast majority of portfolio. But the numbers don't lie; there is a rise in active investing. And the truth is, whether you are a passive or active investor, you will be wrong a lot. In episode 6 with Morgan Housel, we talk about how normal it is that the majority of your gains will come from a small number of investments. You don't need to be right always; you just need to be right sometimes. Good investing is about putting the odds of success in your favor. And this is staying in the game and making many bets.

📄 Summary

Let's take stock of some actions from the newsletter and podcasts. And for those who skipped to the end, think of this as your TL;DR.

Be a boring investor.
Determine what risk you are willing to endure.
Balance tax advantages with liquidity.
Think long-term.
Consider a dollar cost averaging strategy.
Build an investor policy statement to guide your decision-making (see episode 48 with Brian Feroldi).
Create an investment checklist and filter with your criteria.
Hire a financial advisor, if needed.
Keep an investment journal to track your decision process.
Automate the investing process with tools and software.
Compare your returns against the market.
Leverage tax advantages accounts and tax-loss harvesting.
Fight inflation with long-term investing (or I-Bonds).
Be careful with debt.
Stay in the game and make enough bets over time.
Read and listen to intelligent people (so go back and listen to all the money and investing episodes of the podcast 😃)

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

📈 All About Investing Part 1

Thu, 07 Jul 2022 07:00:00 +0000

The markets are down, inflation is up, and the thought of a recession is looming. It's heavy stuff. And it puts strain on our emotions and brokerage accounts. It takes some mental fortitude even to consider long-term investing in tough times, but historically, they present long-term investors with the opportunity to build substantial wealth. That’s why I want to spend the next two newsletters talking about investing. In this email I’ll share the fundamental considerations you need to build a foundational investment mind and then in my next newsletter, I’ll get a bit more advanced and technical.

😫 Investing can be hard

I'm not going to sugar-coat it. Investing can be hard. Amidst too much information, differing opinions, and endless tools to choose from, the process can feel overwhelming. So, over the next two newsletters, I’ll share my thoughts and pull wisdom from some of the smartest investing minds I know to give you what you need to know to invest for the long-term.

While one thing is sure - there is no perfect formula for investing success. It largely depends on your circumstances, personality, and timeline. The good news is that there are specific things to know and do to increase the likelihood of success. And while none of this should be misconstrued as personalized financial advice, I hope it will help you make decisions and actions that propel you to become a successful investor.

I'd love to hear how you think about investing, so please reach out and share your ideas, thoughts, and tips that have helped you along the way.

🥱 Good investing should be boring

While growing your wealth through investing is exciting, I have learned that nothing about good investing should feel exciting. In Episode 19, Andy Rachleff explains that investing should be boring, and that you should put your money in long-term index funds and let it go. Why? Well, because it's hard to pick stocks and even harder to pick long-term winners that beat the market. Only ⅓ of professionals outperform the market in a given year. And when you extend the timeframe to 10 years, the number of professionals consistently beating the market is shockingly tiny. This means it makes it even harder for an individual who doesn't spend all their time picking stocks to be successful long term.

Investing is like a diet. It should be boring. And what's more boring than index funds? Low cost. Diversified. Passive. But it’s the favorite strategy among professionals.

🤑 Scratching the itch

Boring sounds logical, but some of us need that bit of excitement. It's hard to overlook the stories of people making quick wealth through angel investments or early crypto bets (though might be worth checking back in with those folks now). While these are engaging and fun, those investments are often much more speculating than investing.

One approach to making these types of bets comes from Ben Carlson in Episode 42. He suggests you only consider alternative investments after you have done everything to get your financial house in order. Protect your downside first. And while boring index funds are the preferred strategy, if taking 5%-10% of our portfolio to scratch our investment itch with investment ideas that excite us, it may simply be the cost to keep the rest of our portfolio on track.

And when I say alternative investments, I mean real estate, commodities (e.g. gold/silver), cryptocurrency, NFTs, art, private companies, wine, and even royalties.

📝 Important investment considerations

The term asset allocation gets thrown around a lot. And while asset allocation is how you shape your portfolio among different asset classes, the trick is to think about asset allocation as it relates to your world, not others.

At its core, asset allocation is the answer to a simple question, "what should I invest in?" And while we've talked about index funds already, the answer really depends mainly on your risk appetite, liquidity needs, volatility tolerance, and time horizon. Let's talk about what those are and why they are essential.

Risk. It is the level of downside exposure you are willing to endure for the potential return you are expecting to receive. While no investment is purely risk-free (even cash is exposed to inflation risk), lower-risk investments will carry lower returns while high-risk investments come with higher-upside (in theory, of course).
Liquidity. It is the ability to access money quickly and easily. Cash sitting in a savings account is liquid, while an investment in a private company probably is not. While you can think of liquidity as short-term needs, you can also think of it as a planning mechanism for future needs. For example, if you know that you need money to use for a downpayment on a home in 3 years, then you may need to plan your asset allocation around future liquidity needs, not just emergencies. Re-listen to Episode 19 to hear Andy Rachleff highlight the importance of liquidity and why it might be undervalued.
Volatility. It is the speed at which prices or the value of investments can go up and down. While volatility is not a cost per se, it is an emotional fee. Nick Maggulli explains in Episode 59 of the podcast that it's an admission fee to investing, except it’s not paid with your dollars, it's paid with your emotions. And volatility is embedded in the fabric of the markets.
Time horizon. It is the time between buying and using the money for non-investment purposes. With a short time horizon, you might be better off not trying to squeeze that extra yield so you’re sure you have the money you need. However, with a long- term horizon, you might be willing to accept more drops along the way, because you don’t need the money for a while.

📉 I'm ready to buy low and 📈 sell high

While asset allocation is what to invest in, you must also consider when. I'll save you the trouble of guessing. You probably won't be able to time the market, so don't try. I know from experience. Trying to hold cash to wait for the perfect entry exposes the risk of losing a lot of upside. Many are worried about investing during 'all-time highs' but that phrase is doing a disservice to investors, because the market should always be at all-time highs because on average the market is always going up. So yes, in theory, the market should always be up and to the right.

So when is the right time to buy? Well according to this Vanguard study it’s as soon as possible. Mathematically, if the market goes up in the long term, then the average daily return is positive, and therefore you should invest all your money right away to not miss out on those returns. And any mathematical argument against that would have to assume you can time the market, which I'm going to assume you can't do.

However, you really need to factor in emotions, because spreading an investment out over time (Dollar Cost Averaging) has psychological advantages you can't ignore. For example, if investing everything all at once and seeing it all drop 5-10% over the following wee week (which has already happened a few times in 2022) would make you miserable and worried, then it might be worth investing that money over time, even if it has the possibility of smaller returns.

However, I would strongly encourage you to make a plan and commit to it, because too often I hear people say things like "now that the market it going up, I'll just wait for it to go down a little more before investing" and I've seen people wait for years and miss out. In the past I've typically done my dollar cost averaging over a shorter period of time like 3-6 months. But given that I should have some extra cash to invest later this year, I might as well share exactly what I plan to do.

First, I'm going to set aside all the money I'll need for taxes and put it in my Wealthfront Cash Account (currently paying 1.4%). For the rest I’ll probably invest it all over a 3 month period, split 1/3 each month into my Wealthfront Investment Account (get $5k managed free at Wealthfront here). However, knowing myself, if the market is down after the first investment, I'll likely start to accelerate the rest...

While I don't think you can time a dip, I'm not afraid to buy it if I find myself in the middle of it.

💰 When do you sell?

All too often, I hear about panic selling when the market declines. Those instances are when emotions get the best of us. It runs counterintuitive to investing, but it's a common theme among many. We’ve talked a lot about buying, so let's discuss the logical instances for selling your investments.

You need to rebalance your portfolio. You may need to trim some positions because a single investment now dominates your portfolio. Or a losing position may amplify your risk and you need to cut it. Or if your time horizon or lifestyle evolves, you might need to shift to a safer asset allocation. It's less about selling entirely and more about repositioning your portfolio to suit your needs.
Your original investment thesis turned out to be wrong. When you bought it, there was some method to your madness. But as time passed, it didn't go up as much as you expected. When you compare your initial thesis to the current situation, it might not make sense to keep going.
There is a better use for the funds. Sometimes a better option comes along. Maybe it's for tax advantage purposes, a lower-cost option, or an investment that meets all of your criteria. When there is a better option, don't feel pressured to stay just because you’ve already made the investment.
When you wouldn’t make the investment today. One of my favorite thought exercises for investors struggling to decide if they should sell, is to pretend they accidentally sold the position (and temporarily ignore any tax consequences) and then ask if they’d use their cash to make the investment again. Often times (especially when the investor is an employee at Google or Facebook with 95% of their net worth tied up in their companies stock) the answer is no, in which case I think you should definitely think about selling.
You’re using the money to spend on your lifestyle. I don't mean buying a fancy car or something out of your means, but instead spending it reasonably on the things that fit your lifestyle. Isn't this the reason we invest in the first place?

Selling is a different mindset, an entirely new set of decision parameters. The problem is that we often can't remember why we bought it in the first place (other than hoping to make more money). In Episode 48 of the podcast, Brian Feroldi says to use an investment journal during the buying process to help during the selling process. Include three items: the type of investment, the price, and why you buy it. So when it comes time to consider selling your assets, you can recall why you invested in the first place and match your current decision process with the previous one.

A final reminder... every sale of an investment that’s gone up triggers a taxable event (if it's not in a retirement account). So don’t forget to set aside money to pay the IRS at the end of the year. I’ll never forget hearing about a colleagues friend who sold an early crypto investment in 2017 and netted over $1 million, only to lose it all on a risky investment in 2018. Unfortunately, when it came time to file and pay his 2017 taxes, he didn’t have the money and ended up having to file for bankruptcy. Whenever you have gains, always set aside money for taxes.

🧑🏻‍💼 Hiring a financial advisor

Should you hire a financial advisor? While an index fund strategy does not require a financial advisor, that doesn’t mean they should be ruled out forever. In Episode 42, Ben Carlson discusses options for when a financial advisor might make sense.

When you're just not that interested in investments
When you don't have the time to invest at all
When you experience a life event and don't want to mess it up
When your life gets complex enough that it prevents you from taking action

Suppose investment overwhelm prevents you from investing, and a financial advisor enables you to act rather than do nothing. In that case, I'd say it's a better option than doing nothing at all. However, financial advisors are not the only options to help you with your investments. Finding a great tax advisor can get you a lot of the way there at a fraction of the cost.

🔍 Focus on the things that you can control

To wrap up this post, I want to revisit Andy channeling his inner Burt Malkiel in Episode 19. You cannot outperform the market, so you shouldn't try. Instead, it would be best to focus on the things you can control: diversification, minimizing fees, and minimizing taxes. And what most people don't realize is that there are far more advantages to minimizing taxes.

I look forward to sharing the next investment newsletter, where I’ll dive deeper into investing topics like tax strategies, inflation, debt, and more. Stay tuned!

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

😃 Finding Real Happiness and Leveraging Kindness

Fri, 03 Jun 2022 07:00:00 +0000

Is seeking happiness a worthwhile goal? Is it something we can actually achieve? Or just an elusive pot of gold at the end of a rainbow? Perhaps it’s more of a journey with no final destination. While we all may have different takes on the ways in which happiness pays us a visit and how long it stays, we know it’s something we all want. Below are some creative ways you can spread it to your own world and those around you!

😃 What is Happiness?

It’s not all just feelings and emotions – there’s actually a science to happiness. I really dug into the topic after coming across the work of Arthur Brooks, who teaches on the topic at Harvard and recently published the #1 NYTimes Bestseller “From Strength to Strength: Finding Success, Happiness, and Deep Purpose in the Second Half of Life.” He defines happiness as “a balance and abundance of enjoyment, satisfaction, and purpose” and if there’s a deficit in any or all of these areas, your happiness levels will go down.

When Arthur joined me on Episode 47 we discussed how doing the wrong type of work for your stage of life can be a big reason our happiness declines over time. He points out that it’s because our “fluid intelligence” (e.g. analytic speed and problem-solving ability) follows a curve that increases through our 30s and then starts to decline, which often leaves people doing similar work in their late 30s, 40s and 50s feeling like they’re burning out.

Source: From Strength to Strength

However, Arthur explained that there’s a second curve based on our “crystallized intelligence” (e.g. accumulated knowledge or wisdom) that we can find much more happiness on. The challenge is that it often means moving from the analyst/innovator to the manager/teacher, which can often mean changing jobs and is quite stressful.

He shared how Charles Darwin, who came up with his theory of natural selection at age 27, continued to try and innovate for decades, but couldn’t keep up with younger scientists, never transitioned to his 2nd curve, and died frustrated at 73. He juxtaposed that with Johann Sebastian Bach, considered by many to be the greatest composer of all time. Instead of getting stuck when he couldn’t keep up with the new styles of music coming out, he switched from writing original music to teaching what he knew so well. Moving from innovator to instructor left him very happy in old age.

While I’m not sure if I’m ready to jump curves yet, I was interested to know if there were any other habits I could adopt to maximize happiness. Arthur shared four things (the “Good 4”) we can invest in that pay dividends towards happiness: Faith, Family, Friends and Work. He also shared the “Bad 4”: Money, Power, Pleasure, Fame. So try tweaking your routine to spending a bit more time in the former and less on the latter.

And if you’re not comfortable with organized religion, Arthur shared two alternatives for practicing faith: secular meditation and reading about big ideas like The Brothers Karamazov, Man's Search for Meaning or the Meditations of Marcus Aurelius.

Listen to my full interview with Arthur to learn more about happiness.

😞 Using Regrets to Your Advantage

Regrets… we’ve all got them! They’re part of the human condition. In Episode 40, bestselling author Dan Pink and I discussed “The Power of Regret” and he reminded us that while regret is an emotion that can make us feel bad, it can also be one of our most instructive, clarifying and informative emotions.

In his research, he gathered over 17,000 regrets from 105 countries and grouped them into four categories he calls the “Four Core Regrets.” While the nuance of all our regrets may seem very different, the main ones typically fall into these four areas:

Foundation - “If only I’d done the work” (e.g. didn’t pursue education, health or financial well-being)
Boldness - “If only I’d taken the chance” (e.g. didn’t ask someone out or start that business)
Moral - “If only I’d done the right thing” (e.g. infidelity, theft, betrayal, bullying)
Connection - “If only I’d reached out” (e.g. family/friend we neglected or drifted away from)

The big takeaway was that instead of letting your regrets keep you sad or bummed out, let them inform you on how to take future action. By reflecting on our regrets we can actually learn what we value the most and use that information to make better decisions and create deeper meaning. There’s a lot more to unpack in the book, but he left me with a few suggestions for everyone to try to avoid some regret down the road:

Always make the call - If you have an inkling to call someone to reconnect, take it.
Always go to funerals - No explanation needed.
Ask yourself what would you tell your best friend to do - sometimes it’s easier to make a decision when we pretend we’re not part of the outcome.
Convert your regrets from thoughts to words. Disclosure research is powerful. Instead of holding the heavy emotion inside all alone, convert it to language or even share them with others.

Listen to my full interview with Dan to learn more about the Power of Regret.

🤔 Is More Better?

In advance of baby #2, we went through our closets (and a few other rooms) to apply the “if I haven’t used this in the last few years, it goes” strategy. Three overflowing trash bags and a trip to Goodwill later, we felt lighter, clearer, and dare I say happier!?

As Denzel said, “You’ll never see a U-haul behind a hearse.” Acquiring stuff is surely not the key to happiness. Yet so often we buy things we don’t need, to impress people we don’t even like. In 2014, the LA Times shared that the average American home has 300,000 items inside of it! 🤯 Want to get started on the path of minimizing your possessions but need some motivation?

In Episode 54, Joshua Becker (award-winning author and founder Becoming Minimalist) did a deep dive on how minimalism can be a key to unlocking greater meaning. Yes, getting rid of some of our stuff is one piece of the puzzle, but he also suggested people unpack their why. There’s an emotional piece there too. He suggests everyone fill in the blank:

I desire to own less so that I can ____________

Digging into your why is a great exercise that makes it much easier to start the actual purging. And when you do get started, he suggests working through your home room by room, easiest to hardest, starting with the most lived in areas first.

Not only will you feel better about the lightening of your load, it’s an added bonus knowing that a lot of the stuff you aren’t using anymore can find a home with someone who needs it. A win-win!

A great truth is that our outer world reflects our inner. Creating a calm, peaceful, clear external and internal world is well worth the effort.

Listen to my full interview with Joshua to learn more about Minimalism and The Things That Matter.

📆 Schedule Some Kindness

While we all want happiness in our own lives, I’m sure we’d also benefit from everyone around us being happier too. One way to make that happen is to practice a bit more kindness, which can actually have a profound impact in our lives. Why? Well after getting introduced to Emmy award winning journalist Adrienne Bankert, I read her book “Your Hidden Superpower: The Kindness That Makes You Unbeatable at Work and Connects You with Anyone” and was fascinated.

She points out that kindness isn’t merely about getting along with people and being nice – it’s a game changer in business, the door-opener to opportunity, and the key to authenticity and confidence. We had a fantastic conversation in Episode 58 where she proposed that instead of having kindness be an afterthought or something that might make it into your day if there’s any leftover space, put it on your calendar like you would anything else on your calendar.

Whether you decide to make time for it once a week over your morning coffee or every afternoon, the idea is to build that muscle so that kindness becomes part of our natural DNA and is always top of mind. Some of her ideas for practicing kindness are:

Friendship Gratitude - reach out once a week or month to remind friends or colleagues that you appreciate their mark on your life (even if time has passed and you don’t see them regularly)
Past-Present-Future: cycle through those time periods to find people you can uplift with kindness. So if you’re a coach, you could send a positive text to a former player about the impact he/she had on your program, then let a current player choose their favorite drill to finish practice with and finally send a hand-written letter to a future recruit and let them know why they’d be a great addition to your team down the road.
Don’t ask, just do - If you ask the question, “what can I do to help you?” likely the person will give the obligatory “nothing”. Instead, try learning someone’s coffee order and bringing it for them one day. Or offer to mow the neighbor’s yard while you’re out doing yours. Or buy lunch for the person in line behind you. The list is endless, but the idea is to be on the lookout for ways to be kind to others.

Listen to my full interview with Adrienne to learn more making Kindness a superpower.

🌅 Start Your Day Right

It’s been said that the first 8 minutes in the morning sets the tone for your day. Consider taking inventory next week on what your morning habits include (you may have some you didn’t know existed). Do you jump straight on social media? Flip on the news? Start looking at your calendar for the day? Wolf down a quick breakfast? What kind of intentional routine do you have?

While a newborn is going to make changing my routine tricky the short term, I’m fascinated by Tony Robbins’ morning “priming” ritual. It’s only 10 minutes and encompasses breath work, gratitude, blessings, goal setting and celebration. Short and sweet, but powerful. Tony says it primes him for success in the day ahead and “if you don’t have 10 minutes for yourself, you don’t have a life.”

Another interesting routine comes from author Hal Elrod. He sets his tone for the day with “The Miracle Morning”, which is a daily personal development ritual he incorporated into his life that includes six of the most timeless personal growth practices (Silence, Affirmations, Visualization, Exercise, Reading, and Scribing). His results were monumental and he ended up creating a massive community out of this philosophy, and helping millions change the direction of their lives through morning habits.

Borrow some of these ideas or create your own. The important thing is being intentional with how you start your day, and ultimately, putting more emphasis on happiness!

⭕️ Your Circle

Lastly, and perhaps one of the most important indicators of our overall happiness, is the quality of our relationships. Do you have that inner circle of people that you can count on and live your life alongside? Or do you have a best friend at work?

National Geographic writer, Dan Buettner, has done a ton of research on places in the world where people live the longest and are the happiest and he found that one of the biggest predictors of whether you’ll be happy on a day to day basis is how many hours of face to face time you get with people you like. The happiest people are getting in 7 hours! And unfortunately for everyone working from home, he doesn’t think video calls have the same effect.

In his book “The Blue Zones of Happiness” Dan highlights a few places around the world where people are the happiest, but if you don’t have time for a book right now, I’d recommend his interview on The Marie Forleo’s Podcast.

So in an effort to make wherever you live a little happier, I’ll challenge you all to commit to a few more in-person connections with others on the regular. And if you want to take it further, try to strike up more conversations at the different places you spend your time each day, like the office, gym or park.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

💳 Hidden Credit Card Benefits

Thu, 19 May 2022 07:00:00 +0000

Advertiser Disclosure

Note: American Express is a ChrisHutchins.com advertiser

For the post, I want to dig into all the credit card benefits I think so many of us (myself included) forget we have (or didn’t even know about in the first place). I’ve know I’ve saved at least $1,000 in the past few years using many of these (and probably a whole lot more). So hopefully this helps you save some some $$$ too.

💳 Credit Card Purchase Benefits

Almost every credit card out there has a guide to benefits that will explain all the benefits of a particular card. You can usually search online to find it, but here is an example of one for the Chase Sapphire Reserve®. For many of these benefits the only requirement is that you put the cost of your purchase on your card and you can usually file a claim easily online. I know I’ve filed at least 4-5 claims over the years and have been reimbursed well over $1,000, so it’s definitely worth reading through the list so you’re ready to get back some free money next time you have the opportunity.

🧾 Purchase Protection

This is one of my favorites, because you can get reimbursed to replace/repair items purchased with your card that are stolen or damaged within 90-120 days of purchase. This is a common benefit offered on many cards, but usually requires the entire purchase to be on the card and is often limited to $10k/item and $50k/year. While there are lots of exclusions (e.g., animals, software, perishables and vehicles), many common purchases like electronics or home goods are covered.

I’ve used purchase protection to replace an SD card I ran through the washing machine and to cover the cost to repair at least 3 cracked iPhone screens. Note: normally the screen needs to have been cracked within 3-4 months of the original purchase. However, one time I cracked my phone screen 9 months after buying the phone (so it wasn’t covered), but then managed to drop the phone again and crack the screen a second time a few weeks later. I was able to get the second repair covered by pointing out that the screen that cracked was not the original phone purchase (outside of the 90-120 window), but was replacement screen I “purchased” a few weeks earlier (I promise I don’t break my screen as much as paragraph makes it seem). Also, see Cell Phone Coverage below for more details on getting phones repaired cheaply.

🧑‍🔧 Extended Warranty

Extended warranty coverage is another common benefit that increases the original manufacturer’s warranty of an item by an additional year (or two with some Citi cards). Similar to purchase protection, it’s usually limited to $10k/item and $50k/year. This came in handy for me when I needed to get a Macbook Pro repaired in the second year (since I don’t usually buy AppleCare).

🙅 Return Protection

This commonly offered benefit will extend the return window of an item or creates a return policy where one didn’t exist (either because a retailer doesn’t accept returns or an item was “final sale”). I haven’t used this benefit yet, but I’ve been hesitant to purchase a few things that were final sale in the past and now I don’t think I’ll be worried about it in the future. However, know that return protection has much lower limits than other benefits, usually up to $250-$300/item and capping out at $1,000/year.

📉 Price Protection

Price protection is a less common benefit that reimburses you the difference when the price of something you purchased drops within a few months. This used to be a common benefit, but now is limited to a much smaller list of cards, so it’s unlikely you have it. Fortunately, I’ve had a lot of luck chatting, emailing or calling a retailer to ask them to refund the difference when a price drops within the return window.

🛫 Credit Card Travel Benefits

Similar to purchase protection, most cards (especially travel/rewards cards) have a lot of different types of coverages while you’re traveling. Fortunately I haven’t needed to test most of these (except the discounts), but I’ve certainly heard enough success stories that I wouldn’t hesitate filing a claim if it meant I could get some money back.

🚗 Rental Car Coverage

If you already have personal auto insurance, your coverage will likely carry over to a rental car (though if you’re renting a more expensive car than you drive, you might not want to supplement). That said, my understanding is that filing a claim for your rental car to your auto insurance carrier might result in your rates going up, so I don’t like to rely on this option. Also, when renting overseas, your US insurance might not cover you at all. Now, in many other countries, liability coverage is included in your rental, but damage to the vehicle is usually not covered.

Given all this, I always pay for rental cars with a credit card that offers primary rental car insurance. This is a common feature of most travel cards (e.g. Chase Sapphire Reserve® or Chase Sapphire Preferred® Card, Capital One® VentureOne® Rewards Credit Card or Capital One® Venture X Rewards Credit Card, Bilt Rewards), but notably not included with most common American Express cards. Instead, to get primary coverage you need to pay for their Premium Rental Car Protection. While this is probably a better deal than paying the rental car company for coverage, it does cost $12.25-$24.95 pre rental, so I use one of my other cards.

All you need to do to use your credit card rental car coverage is decline the collision damage waiver (CDW) from the rental car company and put the whole rental on your card. However, if you happen to not own a car and thus don’t have car insurance, you’ll want to check if your rental includes liability coverage (required in some states, but often at very low limits), and make sure to add that, since your credit card won’t cover any damage to other vehicles or injuries to other drivers.

⏱ Delayed Luggage

While I’ve only seen this on Chase cards, it covers the cost of things you might need when your bag is delayed (e.g. change of clothes, toiletries etc.). It usually requires your bag to be delayed at least 6 hours, and covers up to $100/day.

🧳 Lost/Damaged Baggage

Common on Chase and American Express cards, this is backup/secondary coverage to whatever the airline provides if your bag is lost, damaged or stolen. It usually covers the cost of the contents and either replacing or repairing the lost/damaged baggage. Most policies have a maximum coverage of anywhere from $500-$3,000 per person, as long as the flight was booked on the card.

💺 Trip Delay

This is another common coverage on most travel/rewards cards and will reimburse you for any additional reasonable expenses that occur as a result of a trip delay (e.g. delayed or cancelled and rebooked flight). Most cards require a delay of at least 6-12 hours and coverage is usually capped at $500/person.

❌ Trip Cancellation/Interruption

Trip cancellation and interruption insurance provides reimbursement for nonrefundable or prepaid trip expenses when you have to cancel or change your trip due to a covered situation. That typically includes major medical situations/injuries, sever weather/named storms, jury duty that can’t be postponed, death/hospitalization of travelers (or sometimes family members). This coverage is common on many travel/rewards cards, and usually covers anywhere from $3,000 - $10,000 per person. Note: while CapitalOne offers this insurance, their covered situation list is much smaller and is primarily for major medical situations/injuries to a traveler.

🛩 Emergency Evacuation

If you were in need if serious medical attention, this benefit would cover the cost of transportation to the nearest medical facility capable of proper care. While probably not necessary on a trip to Paris or Tokyo, it could be really valuable if you were on safari in Africa or on a remote island in the Maldives. The Platinum Card® from American Express is the most generous card for this benefit, having no cap on the cost and not even requiring you to have used the card to pay for your trip. Other cards (e.g. Chase Sapphire Preferred® Card) have a cap on the cost and require you to have paid for part of your trip with the card. Also, while many of these benefits can be claimed after the fact, this is one where you need to coordinate with the card benefits team.

🤕 Travel Accidents

While I don’t know of anyone who’s used this coverage, it would pay out in the case of death, losing eyesight or losing a limb(s) while on travel booked with your card (excluding cars/taxis). Coverage varies widely by card with some cards (American Express) not offering it at all and some (Chase) offering up to $1,000,000 in coverage.

🥂 Lounge Access

Most travel cards with an annual fee over $300 include a PriorityPass membership you can sign up for on the card benefits page. While there isn’t much benefit to having multiple PriorityPass memberships, it’s worth noting that memberships through American Express don’t offer credits at PriorityPass restaurants, but most others will.

🤑 Travel Discounts

Aside from all the insurance benefits, many cards offer travel discounts worth checking out. For example, Visa Infinite cards like the Chase Sapphire Reserve® offer discounts up to 30% on Avis, Hertz, National and Silvercar. Also, World Elite Mastercards like the Citi Premier® Card offer status/discounts with Hertz, Sixt and Avis . And finally, The Platinum Card® from American Express offer status/discounts with Avis, Hertz and National.

Also, this week Bilt Rewards members announced you can get 15% off Hyatt stays booked before 8/15/22 using the “Special Offer Code” BILT4YOU. Though Hyatt members already get a discount off the public rates, so this likely won’t be worth the full 15%. While you don’t need the Bilt Mastercard® to sign up for Bilt Rewards, it’s the only card that pays points on rent (and also 3x dining/2x travel if you use the card 5 times each statement period to earn points), so if you’re a renter you might want to consider signing up (using my referral link of course 😉). More on rewards & benefits here.

🎉 Other Credit Card Benefits

With thousands of different credit cards offering dozens of benefits each, this section could be infinitely long. So instead of outlining all card benefits, I’m going to focus on that I find most valuable/interesting that are offered by multiple cards.

🍷 Free Sonoma Wine Tastings

Now here’s a fun one I’ve used a lot. If you have a Visa Signature Card (e.g. Chase Sapphire Preferred® Card, Capital One VentureOne Rewards Credit Card, United Explorer℠ Card) or Visa Infinite Card (e.g. Chase Sapphire Reserve®, Capital One® Venture X Rewards Credit Card) you get 2 for 1 tastings and $1 ground shipping at 50+ wineries in Sonoma County. Here’s a map of participating wineries and more details on the program.

📱 Cell Phone Coverage

This benefit will reimburse you for a stolen or damaged cell phone. It usually requires a $25-$100 deductible and covers up to $800-1000 in damages/repairs twice a year for any phone on your plan, as long as you pay for the plans monthly bill with your card. This is a great option for any damage that happens outside your free Purchase Protection window. Cards that offer this benefit include the Capital One Venture X Rewards Credit Card, Bilt Rewards, The Platinum Card® from American Express, Chase Freedom Flex® and Ink Business Preferred® Credit Card.

🛍 Shopping Discounts

Every card issuer now seems to have some collection of merchant offers on their site and they can be more valuable than you might think. For example, I just looked at my American Express offers and across my 3 cards I’ve earned $973.95 through American Express offers on purchases from retailers like Home Depot, Best Buy, Delta and Marriott. Offers vary by card, so if you have multiple cards it’s worth checking each one. If you’re new to these offers ThePointsGuy has a writeup for Chase, American Express and Citi. They didn’t do a writeup on CapitalOne offers, but I uploaded a screenshot of all the offers I see here.

Also if you haven’t checked out the CardPointers app, it does a fantastic job of organizing/tracking all these offers and all the other perks/benefits you get with your cards. I’m a huge fan of the app and managed to convince Emmanuel (the founder) to offer the biggest discount he’s ever offered on CardPointers Pro to our subscribers, so you can check that out here.

📞 Concierges

Most travel rewards cards offer a complimentary 24/7 concierge service that you can use for things like: restaurant reservations, vacation requests, personal shopping, or event tickets. While I probably don’t use them as much as I could, I have two types of requests that I often use the American Express or Chase concierge for: 1) making reservations in a foreign country where they’re likely to have someone who speaks the local language and 2) researching places that sell specific things (e.g. I need to find a store that’s open on Sunday in San Francisco that sells a #1 balloon). Here are a few articles that might help with some inspiration for how you could be taking advantage of this free service.

📊 Free Credit Score

While sites like Credit Karma offer free credit scores, they almost never showing you your FICO score, and instead usually show the VantageScore (you can read about the differences here). While the scores are usually similar, many lenders still use your FICO score for lending decisions, so I like checking that score as well. Thankfully, many card issuers, including Amex, Bank of America and Discover give you free access to your FICO score. This page has a full list of who offers free FICO scores.

👮 Free Global Entry and/or TSA Pre

If you’re travel, are eligible for Global Entry/TSA Pre and haven’t enrolled, you really should consider it. And according to the TSA website there are 37 different cards that offer a credit to cover the cost, so it’s reasonably likely you have a card that would fully cover the cost. Or since many people have multiple cards that cover the cost, it might not be too hard to find someone that could get it free for you. One important thing to know, if you sign up for Global Entry, you get TSA Pre included, so I’d recommend doing that instead of just signing up for TSA Pre.

📦 ShopRunner

World Elite Mastercards and many American Express cards get you a free ShopRunner membership, which offers free two-day shipping (and return shipping) at over a hundred online retailers, including Saks, Allbirds, Under Armour and CB2. Sign up here: American Express and MasterCard.

🙏 Card Signup Links

If you’re signing up for any cards mentioned here (or really any cards at all) and you also want to support me and the show, I’d really appreciate you using this link:

🍎 Optimizing Your Health

Thu, 21 Apr 2022 07:00:00 +0000

With the world opening up and summer on the horizon, I wanted to go back through all the health tips I've learned since working on this show and put them in one place.

However, just because there’s so much here absolutely does not mean you have to do it all. Health and wellness looks different for EVERYBODY, so just pick a few to try and see what sticks for you. Also, I’m sure you know this, but I’m definitely not a doctor, so keep that in mind :)

Finally, I’d love to hear how your experience with these went, so please reach out and share! I’ve already heard about the joys of cold showers from a few of you 🥶.

🍜 All Things Food

It’s no secret that food is by far the most difficult and stressful aspect of healthy living. From failed diets, to shelling out for expensive health foods, to feeling out of control around our favorite ‘unhealthy’ meals, we have a lot of emotions attached to eating. And even the mood you’re in when you think about and eat food has a huge impact on your health.

For me, I think it’s so important to eat foods that make YOU happy! So whatever you do, just know that it should be highly tailored to your needs and your routines. Start with a strong foundation and build up. Being food-healthy is a relationship you can continually build and strengthen with yourself, so take a few of these ideas and run with them!

🥕 Buying organic and in-season

Eating only organic foods isn’t necessary, but there are some foods that really are safer to eat organic. Spinach, for example, has more pesticide residue by weight than any other form of produce—so eating organic spinach instead can have huge benefits.

The Environmental Working Group (EWG) releases two lists every year called the Dirty Dozen and the Clean Fifteen. They highlight the most and least pesticide-laden produce on the shelves, and it changes every year.

My general general rule of thumb is to try and shop organic when you’re eating the skin of your produce… that said it’s always better to be eating more fresh vegetables (and fruits), no matter where they come from.

💊 Vitamins and supplements

While a perfectly well-balanced diet is certainly the best way to ensure you’re getting the vitamins and minerals you need, I think it’s impractical (and sometimes not fun) to do that every day. So I’ve been taking Athletic Greens every day as my all-in-one insurance for nutrition, gut health and immunity.

Note: Athletic Greens is a sponsor of the show, but I do genuinely love their product and the link above will get you a free 1 year supply of immune-supporting Vitamin D and 5 free travel packs.

🍎 Diets: Why they fail and things to try

My past guest and foodist Darya Rose Ph.D. shared that 95% of diets fail in the long term (longer than 3 years). In fact, dieting was more often a better to gain weight than to lose weight.

She explains that diets fail because they rely on willpower and restriction for achieving health goals, and ignore the reasons these tactics always backfire. Most people aren’t willing to change their entire lives to accommodate their diets. Instead, focusing more on consistent healthy habits like adding more vegetables or moving more are more effective.

She also suggests trying to adopt a habit of mindful eating, which research shows will help you eat less, eat slower and improve digestion. As a side benefit you usually end up enjoying your food more.

🍵 Intermittent fasting

Intermittent fasting can offer a variety of health benefits and many studies show it can have powerful effects on your body and brain and may even help you live longer. If you’re interested in trying it out, I highly recommend checking out Zero, an app that helps you to optimize your health and metabolic wellness.

If you do decide to fast (and depending for how long), it’s important to focus on taking in enough protein at meals and incorporating strength training to prevent too much loss of muscle mass.

🍽 Eating out tips

Eating out can be tricky. There are so many options and a lot of them just aren’t good for us. So to start, make sure you always order as many vegetables as you can. I think it’s better to spend a little extra on an appetizer with veggies than skip out on them in the meal. Also, keep an eye on the language on the menu, things like ‘glazed’ or ‘crispy’ are good signs that a dish probably isn’t very healthy.

My favorite eating out tip is to check the menu before I get to the restaurant and decide what I want to eat in advance. It has two benefits for me: 1) I make healthier decisions in advance and 2) I’m usually making those decisions when I’m much less hunger, instead of a few minutes before a meal.

Finally, don’t forget that eating is also about pleasure and social bonding, not just being healthy. So if you can use the 80/20 rule and try to make healthier choices for breakfast, lunch and weekday dinners, then it’s probably ok to have a suboptimal weekend dinner out.

🍦 Dessert trick

Liz Moody was curious about exactly what made dessert so ‘bad’ for you, and it really boils down to the spike in your blood sugar after having sugary foods. So she suggests incorporating more food groups like fat, fiber and protein into your sweet treats. So consider including greek yogurt, almond butter or almond flour to make your dessert a more stable blood sugar experience.

My favorite dessert trick came from Nir Eyal’s episode, where he suggested that if you really want something unhealthy, don’t tell yourself no. Instead, give yourself permission to have it, but only after waiting 5 minutes. It’s much easier psychologically and almost every time I get to 5 minutes I’ve moved on to something else and lost the urge.

😋 Make food more delicious

A lot of us remember not liking vegetables as a kid, and as great as your parents might be, their cooking might be the reason why. Adults often think they don’t like vegetables, when in reality they just haven’t prepared them correctly. Experiment with different fresh, in-season vegetables by cooking them in new ways, adding new spices, and always remembering the salt. When in doubt, a little oil and salt can drastically improve the flavor of most foods.

Liz Moody believes that people way under season/spice their foods, and that just doubling the spices called for can really improve the flavor. I usually double up the garlic and ginger in recipes, but I’m going to start doubling the spices from the spice rack and see how it goes.

Finally, while spices don’t go bad, per se, most dried seasonings, herbs and spices lose a lot of their flavor after a year or two of oxygen exposure. I’m personally struggling to replace all my spices, but this Bon Appétit article says I should probably throw everything out.

🍚 Cauliflower rice

While it’s definitely not a perfect replacement for Rice, Liz Moody suggested using it half and half with other ingredients to get a lot of the benefit. When using it in place of half the ground beef in a Bolognese, she says “you hardly notice it’s there, but you just immediately added a significant dose of veggies in your favorite sauces”.

If a recipe calls for white rice, she’ll only replace half of the rice, leaving something much closer to rice a dish with some subtle nutty notes. Or, she sometimes blends it up and uses it to thicken soups.

🥦 Frozen veggies

This surprised me: most frozen vegetables actually have more beneficial nutrients than their fresh counterparts. Liz shared that most of the time, vegetables are flash-frozen at their peak freshness, which means when they are cooked and eaten, you’re enjoying the veggie at its healthiest!

In contrast, fresh vegetables are harvested, processed, transported dozens to thousands of miles to your supermarket, and then displayed in the produce section for days until you buy it and bring it home. Then, it waits for a few days in your fridge until it’s ready to be cooked.

This is great news for busy people! Store frozen veggies for as long as you’d like, roast them on a pan (with no oil or seasoning!) until all the water has evaporated, then oil and season them to your heart’s content and bake them at the end. This will keep them crisp and delicious, instead of soggy.

🌮 My Favorite Healthy-ish Recipes

Now that we’ve talked about a ton of food-related tips, I wanted to share some of my and Amy’s favorite healthy-ish recipes. We’ve cooked each at least a dozen times the past year and at least one of them makes a weekly appearance on the dinner table.

If you have any top recipes, please send them my way. I’d love to add them to our rotation and share out top listener recipes in the newsletter.

🏃 Body Health Tips

When I say “body health tips”, I am referring to anything health-related that matters to our physical bodies and movement. In other words, cold therapy, sauna therapy, regular exercise, meditation, and more. Here are a few of the coolest things I’ve learned from my podcast guests in the past year.

🚶‍♂️Circadian Walks

Walking is incredible for your health and Low-Intensity Steady State training (LISS) is actually a great way to burn calories from fat without burning calories from muscle. But choosing the right time for a walk can make a world of difference. Walking with the rising sun (before 10 o’clock in the morning) or winding down on a walk with the setting sun can help your body to reset and follow a healthy daily pattern. Better sleep means better health, and circadian walks, even if they only last ten minutes, can be a huge help.

🏋️‍♂️ Workout Motivation

For most of us, working out is a pain in the ass, but my favorite trick to make it happen is only committing for five minutes. I tell myself that if after five minutes I want to quit, I can, and even though I know I won’t give up, it still makes it easy for me to get started.

In Episode 52, Liz Moody swore by a reward method, in which you save something you really love for your exercise. For her that’s saving her favorite podcasts for the gym so she can make the gym feel like a reward.

🧘 Meditation

Meditation is a perfect example of how sometimes, a tiny dose of a healthy habit can be much better than too much at once or none at all. The key here is to set the bar really low. That way, you’re more easily achieving small goals, giving you more and more reasons to celebrate yourself and your newfound healthy habits. Only 5 minutes of meditation can be enough to gain the benefits of meditation without forcing yourself to carve out an unrealistic chunk of time every day to practice.

Meditation has been shown to dramatically reduce stress, but also improve emotional well-being, such as increasing self-awareness, focusing on the present, reducing negative emotions, and more.

One way to incorporate meditation into your daily life seamlessly is to practice brief moments of mindfulness. My favorite way to meditate is to tap into my senses while I’m walking. I feel the way the ground feels on my feet, the sun and breeze on my face, and the way the air feels entering my lungs. I don’t have to sit in a pretzel every day, but I do walk every day. That way, I can instantly meditate whenever I get a moment.

One listener, Zach, had trouble making meditation stick until he came up with his own trick of doing it during his regular trips to the bathroom. Sounds crazy, but he’s been successfully meditating with these “bowel movement mindful minutes” for the past 6 months.

🧖‍♂️ Sauna Therapy

Many people think of the sauna as little more than a luxury, but it can come with quite a few health benefits too. In fact, research shows that spending regular time in the sauna can actually lower your risk of death by heart disease. Rhonda Patrick has a great page on her FoundMyFitness site all about the benefits of Sauna, which includes one study that found people who regularly use saunas are 22% less likely to die from a sudden cardiac event. It's also quite relaxing and feels great to sweat out all those toxins built up in your body. In fact, I’m constantly looking at Saunas on Amazon like this or this, but don’t know where I’d put one.

🚿 Cold Plunge and Cold Showers

Cold water might not sound like the most pleasant experience, but it comes with countless health benefits. Whether you buy The Cold Plunge, build a DIY version or just take a cold shower, cold water can not only help us to build resiliency by showing us that we can adapt to hard things, but also can support our immune system and give a huge mood boost. It can also improve memory, decrease tension and fatigue, and make your immune system significantly stronger.

In Episode 38, 3-time gold medalist Kerri Walsh Jennings absolutely swore by the cold plunge. She’s been committed to it for a few years now, and she says that nothing compares to the mental strength or the immune benefits of cold plunging. Her time-honored routine four days out of the week is to sit in the hot sauna for 45 minutes to sweat out any toxins and then plunge for 4 minutes a time.

If you’re looking for a DIY cold plunge, a listener named Justin sent in details on how he made his DIY cold plunge using a chest freezer he purchased on Craigslist for only $180. It’s lasted him five years so far:

You can find his recommended resources here:

In Episode 52, Liz Moody shared that she just spends the last 60 seconds of every shower moving the water to as cold as it gets. Though the water hitting your face can come as quite a shock, this can have some great benefits ranging from balancing brain chemicals to giving your body the reminder that you can endure discomfort! In fact, studies show that cold showers can give your immune system an upgrade and help you to bounce back from being sick more effectively.

In that same episode I committed to doing cold showers for the month of April and actually really enjoyed it and will probably keep it up this month. Though in full transparency I didn’t do it the 100% of the time I promised, because my daughter was in the shower with me a few times and I didn’t think the benefits would outweigh the reaction of an ice cold two year old.

😶 Taping Your Mouth

Studies show that breathing through the nose is actually healthier than breathing through your mouth, and some of us need a little extra help to do that. In Episode 52, Liz Moody shared that she tapes her mouth shut most nights to make sure she’s breathing through her nose—and it can do a lot for mental clarity and comfort by supporting your immune system and increasing oxygen intake!

😴 Sleep Tips

Sleep influences how alert we are, how we battle certain diseases, and how we feel on a daily basis. Knowing how to improve your sleep can be a valuable tool that will help you to live a better life. Matt Walker, sleep scientist, author of Why We Sleep and host of the podcast, Sleep Diplomat, is full of tools to sleep better and get the quality sleep that you need. Personally, my top two sleep tips are 1) charging my phone overnight in the bathroom and 2) tracking my sleep with an Oura ring (I don’t think I’ve slept without it for the past year).

💉 GLP-1’s for Weight Loss

In Episode 32, Kevin Rose talked about Ozempic (semaglutide), a type of GLP-1 medication originally used to help manage blood sugar levels in people with diabetes. And while Ozempic lowers blood sugar, it turns out it can also help the body lose weight. In fact a recent NEJM study found patients without diabetes achieved 14.9% weight loss after only 68 weeks on the drug. Last year, the FDA approved a different semaglutide for weight loss. Kevin mentioned that Ozempic can cost ~$1,000/mo, but a few startups like Alfie and Calibrate have launched to help navigate the insurance process and bring the cost of the drugs down to ~$25/mo.

While I don’t have any business relationship with Alfie, they did respond to my email and offered me a discount to share with you. If you use SPRING2022, you’ll get an additional 33% off their current discounted price for your first month.

🩸 Check Your Biomarkers

Blood testing is an amazing way to see what’s going on inside your body and an important way to keep track of your overall physical well-being. You can see if something is wrong, or you can see if something is right. And getting tested at routine intervals can allow you to see the way your body changes over time and empower you to make informed decisions about your health.

But getting the results is just half of the story, knowing what to do with those results is what I was really interested in and unfortunately my primary care doctor seemed to only have generic advice. So far the best platform I’ve found is InsideTracker and you can upload your own results or they can order the lab work to be done nearby (I’d tried WellnessFx in the past, but I found their recommendations to be lacking). What’s even better is that I’ve gotten InsideTracker to offer readers a limited time 20% discount on everything on their site.

Full disclosure: After seeing the product, I reached out to InsideTracker and they are now a sponsor of the show.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

🏝 Optimizing a Babymoon with Miles & Points

Thu, 24 Mar 2022 07:00:00 +0000

Advertiser Disclosure

Note: I also recorded a full podcast episode on this entire topic that you can listen to here or if you want to see me share share my screen as I do some searching/booking, you can watch the video version below:

🌎 Where do we Go?

If you didn’t already know my wife and I are expecting our second child in June and for the past month we’d been talking about whether it’d be possible to take some type of vacation before it was too late to travel. Thanks to my parents volunteering to watch our daughter last week, we had a week we could go somewhere, but weren’t sure where to go.

Since we only had a week and Amy was just entering her 3rd trimester, we were looking for a place that wasn’t too far away and that we could spend a lot of time relaxing. I like to start searches for a destination off with Google Flights, because I can search for non-stop flights for a one-week trip in the next month from SFO/OAK/SJC that are less than 10hrs and get a map of all the destinations and prices:

Google Flights “Where to?” Search

Those criteria really narrowed it down, but when we saw flights to Tahiti for < $600, we thought whether it’d be possible to try and recreate the magical trip we took to Bora Bora back in 2018. French Polynesia had always seemed so far away in our minds but when direct flights from SFO-PPT were announced back in 2017 we realized it was actually only an 8 hour flight and it seemed so much more feasible.

View from the St Regis Bora Bora

For anyone not familiar, Bora Bora is one of the most beautiful places in the world and with a handful of incredible resorts with rooms that sit right on top of the water. It’s also home to some of the most expensive hotels in the world, but fortunately a few of the hotels on the island can be booked with points, so let’s walk through how we made it all happen.

🛫 Getting There

Once I’ve picked a place, I have a bit of a process for how to get there and some tools I use to make it easier to plan, so I thought I’d just walk through that process:

Find the Direct Flights. Before looking for fares, I like to get a sense of all the non-stop flights that fly to my destinations, so I can better search for specific flights/airlines. I like doing this search at flightconnections.com. And I do that because they show you all the routes that you can get to a certain airport from. For this trip, that showed me that unless I want to change planes in Hawaii, the main flight would be from SFO or LAX.
Check Fares on Google Flights. After I know where I’m coming from, I like to use Google flights to get a sense of the fares. While I’d ultimately need to fly from SFO (or OAK/SJC), I know that some airlines don’t always have partners that fly domestically, so you might miss out on their flights if you search from another city. So for this trip, I just searched for non-stop flights from SFO or LAX to PPT and then when you click the dates, you can choose to see prices for 7-day trips. As you’ll see below, it makes it really easy to understand what days are cheapest to fly on. I also like to check Business Class too, because sometimes (though rarely) it’s only a little more expensive. In the case of Bora Bora it was about $4,800 (or 8x the cost of economy).
Do Points Even Make Sense? Now that I know the $ cost of the trip, I ask myself whether it makes sense to use points. In general, booking most international award tickets in economy will cost at least 50,000 (miles that would be worth ~$600-$1,000), so when I saw these tickets for ~$600, I knew it wouldn’t make sense to use points unless I could fly business class. Also, when you buy your tickets you earn miles from the purchase and the flight, so that makes it a little more attractive too. However, international award tickets in business usually only cost ~2x the number of miles as economy, so when the fares are 9x, there can be a good opportunity if there’s availability.
Check Award Availability. So if I’m looking for award availability, there are a few different options:
- Search the airline websites. In a situation like this, where there are only a few routes on a few airlines, a good option is to just use the airline websites to search for availability. On many airline sites, when you search for miles, you can see a week or month at a time, making it much easier to find days with cheap flights. For example, United shows a month at a time and made it easy to see that most Sunday flights were only 72k miles one-way in business class.
- Use an award search tool. Point.me (first month for $1 with code HACKS) is a good entry level tool that can search a lot of airlines and help you figure out how to transfer your points from different programs like Amex or Chase to make it happen. However, if you want to go further down the rabbit hole you can check out ExpertFlyer, AwardNexus or KVS Tool.
- Use an Award Booking Service. You can also just pay for a professional to use all the tools above to find the best options for you. While I’ve had a good experience with FlightFox in the past, they seem to be more focused on business travel now, so I’d recommend trying the point.me concierge or BookYourAward.com, both of which don’t charge their full fee unless they’re able to find you something.
Book it the Best Way. The reason I love points programs like Chase, American Express, Citi or CapitalOne are that you can can transfer your points to so many different airlines, with each one requiring a different # of miles for a specific route. So when an airline has their lower priced award tickets available, like United did above, that doesn’t mean you need to book the flight with United miles. In fact, I ended up booking that same United flight that would have cost ~72k United miles for only 55k Air Canada Aeroplan miles. Now I didn’t have Aeroplan miles, but they’re a transfer partner of Chase, CapitalOne and American Express, so it was easy to move the miles over and book it a few minutes later. This is actually where the Point.me search comes in handy because it shows you the best way to book a flight:

I know that was a lot, but let’s recap what happened. I ended up booking $4,783 round-trip business class flights to French Polynesia for 110,000 Air Canada miles each (+$37 in taxes), which I got by transferring 220,000 Chase points. That’s a value of 4.3¢ per point, which makes earning 3x points on my Chase Sapphire Reserve® card effectively getting 12.9% cash back, which is awesome. It also means we were both flying to Bora Bora in Business for 220,000 points + $148 in taxes.

🏨 Where to Stay

Now that we can get to our destination, let's talk where to stay. Here’s the process I follow for hotels:

Look at Prices First. I often use Google Hotels, but I’m less particular on the tool here, and more that it has the right filters you need. Depending on your trip it might be filtering by star-rating, hotel chain or having specific amenities like a spa or pool. But I like to make sure I know what the $ cost is before I think about points. For a big trip, it’s also worth checking out some travel packages. For Bora Bora, half the people we met at the St. Regis said they got an incredible deal from Costco Travel, so definitely search around to see if there are any special deals or vacation packages.
Find the Award Hotels. There are two options here, depending on where you have your hotel points. If they’re all in one program, then you can just look on the hotel chain’s website (e.g. this Hyatt map of all their hotels). Or if you have points in multiple programs, I like to use awardmapper.com which has aggregated all the different hotels across all the major chains. Now hotel award costs are constantly changing, so I don’t rely on it for that, but it does a good job of helping find all the hotels in a city (though their data in Bora Bora is actually out of date).
Check Award Availability. Once I have a hotel in mind, I go to the chain’s website and search for availability with points (there’s no award tools like points.me for hotels yet). Hilton and Marriott have a flexible search that shows you the full month and points required, so I like to do a flexible search for 1 night, so I can see all the availability at once. Both chains also offer 5th night free, so you can maximize your points with 5 night stays.
Are Points Worth It? Other than Hyatt, unless you already have points with a hotel chain, it’s often not worth transferring points from Chase/American Express to a hotel chain because you get a similar transfer rate as airlines but hotel points are worth ~1/3 as much. However, if you do have points from staying at hotels or a hotel credit card, then sometimes it’s a great deal. My general rule of thumb on whether it’s worth it depends on the hotel chain, so I usually reference ThePointsGuy valuations and see if I’m getting a deal. So in the case of Marriott, their value is ~0.8¢/point right now, so if I’m going to spend 85k/night, it should be saving me at least $680. However if you book 5 nights, you save 20%, so you could argue it’s a good deal if it even saves you $544. In the case of Bora Bora, the rooms were over $2k/night, so it was no question. It was an incredible deal.
If You’re Paying Cash. When you’re not using points, there are hundreds of sites you can book on, but as I’ve mentioned before, I like to book directly with the hotel, so I can send them a follow-up email to introduce myself and increase my chances at an upgrade. However, many high-end/luxury properties actually offer amazing benefits to guests who book through certain travel agencies. Those perks can include free breakfast, upgrades, late checkout, and resort credits, and sometimes can be very meaningful (e.g., breakfast for 2 at many resorts can be >$100/day). If you have a Platinum Card you can get some of these perks if you book at one of the ~1,100 properties in their Fine Hotels & Resorts collection, but I’m working on getting our newsletter readers free access to these benefits at ~4,000 properties around the world (see more below).

So to recap the savings for our trip, we booked 5 nights at the St Regis Bora Bora for 340,000 Marriott points + $20 in taxes/fees. That same room was going for $2,783, which means we got a value of ~4¢/pt, which is ridiculous for a Marriott point. In fact, it’s so good that despite my advice above about not transferring points to hotel chains other than Hyatt, I would consider it if you can get value like this (or honestly anything >2¢/pt would be worth it).

🏝 Total Bora Bora Trip Costs

So here’s the damage for our trip:

Round Trip (SFO-PPT) in Business: 220,000 points + $148 (vs. $9,566)
Round Trip (PPT-BOB) on Air Tahiti: $884 (no deal here)
5 Nights at St Regis Bora Bora: 340,000 points + $20 (vs. $13,915)

Total: $1,052 + 560,000 points vs. $24,365

Editor’s Note: We also spent $1,315 on hotel food/activities, but there wasn’t really a way to avoid it.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

🏡 When Renting is Smarter Than Buying

Thu, 10 Mar 2022 08:00:00 +0000

Earlier this week I had a conversation with someone who was sick of “throwing away money on rent” and felt like it was time to buy a home. It’s a common invisible script that you need to own a home – after all, isn’t it the American dream? Well I don’t think it has to be… and there are actually some great reasons that renting can be a better option. However, instead of writing this from scratch, I thought I’d share a post I wrote on the topic for the Wealthfront Blog (which has so much good content from my colleagues, including three great guides on Financial Health, Home Planning and Equity & IPOs).

🏡 Why Renting Is Sometimes Smarter Than Buying

This post originally appeared on the Wealthfront Blog (here)

Home-buying has made a lot of headlines lately. Many people are buying earlier than anticipated, in part because mortgage interest rates are relatively low and because a year of remote work has made it tempting to get a little more space. Maybe you even know a few people who have taken the plunge and bought a home recently.

There’s no denying that owning a home can be pretty great. You get to lock in your cost of living (which serves as protection against potential rent increases), you can personalize your space any way you’d like, you get significant tax benefits, and you can enjoy the psychological benefits that come with knowing your home is yours. As a result, many people look forward to buying a home and consider it a major life milestone.

If you’re still renting and are experiencing some FOMO, we’re here to help you think things through before you jump on the buying bandwagon. Renting can be a good choice too. It might seem like “throwing money away” in the sense that you aren’t getting equity in a home, but buying also forces you to “throw money away” on costs like property taxes, mortgage interest, HOA fees, and maintenance. Here are four advantages to renting you might not have considered:

1. Renting gives you more flexibility

Renting comes with a lot more flexibility than buying does. If you need more space, you can rent something bigger. If you want to downsize, you can rent something smaller. You can move to take a new job and you can switch school districts. It’s much easier to move when you rent. Ending (or even breaking!) a lease is much simpler than selling a home and buying a new one.

2. Renting means fewer responsibilities

Renting comes with fewer responsibilities than owning. If you’re renting an apartment and your washing machine breaks, your landlord should coordinate and pay for the repairs. But if you own your home and your washing machine breaks, it’s your problem. In some places (like San Francisco), homeowners are even responsible for repairs to the sidewalk in front of their home. These responsibilities can end up costing you a lot of time and money. If you rent, upkeep is generally the responsibility of your landlord.

3. Renting comes with smaller transaction costs

When you rent an apartment, you’ll sometimes have to pay an application fee or, in some cities, a one-time broker fee. These costs don’t usually add up to much in the grand scheme of things.

When you buy a house, the transaction costs are bigger. In addition to your down payment, you’ll also need to pay fees known as closing costs, which generally add up to 2-5% of your home’s purchase price. These costs could include fees for an appraisal of the home, attorney fees, title search fees, transfer taxes, and any other fees your lender charges.

When you’re ready to sell your home, there’s another set of costs. It’s usually the seller’s responsibility to cover the commissions of both the buyer’s and seller’s real estate agents, which costs around 6% of the sale price on average. You often pay taxes and fees on the sale, too, which can total 2-4% of the sale price, which brings the total closing costs for sellers to 8-10%.

Between buying and selling, you could be paying as much as 15% of the value of the home in transaction costs and fees (although that percentage is likely to be lower in areas with higher home prices). If you’re going to stay in your home for a long time, this isn’t a huge deal. A good rule of thumb is that you need at least five years for your house to have the chance to appreciate enough to make up for the money you’ll spend on transaction costs.

4. Renting leaves you with more cash to invest

Large purchases like buying a home come with large opportunity costs. When you rent, you can invest the money you otherwise would have spent on a down payment and transaction costs.

For example, let’s say you’re able to save $150,000 this year by renting a home instead of making a down payment on the purchase of one. We’ll imagine you invest that $150,000 in a Wealthfront Investment Account with a risk score of 8, which has had an average annual pre-tax return of 8.9% since late 2011 (net of our annual 0.25% advisory fee). If you waited five years to buy a home and didn’t touch your $150,000 investment until then, it would grow to $229,736.85 based on that rate of return. That said, if you invest money you’ll need for a down payment – particularly over the short term – you should be prepared for the possibility that it could decrease in value. Markets behave unpredictably in the short term, which is why we recommend investing for the long term.

The takeaway

Many people look forward to buying a home, but you don’t need to rush into it just because it seems like everyone else is doing it. Buying a home is a big decision, and it’s important to think through the details and feel confident before you do it. In the meantime, don’t feel bad about renting – it has plenty of advantages.

When you’re ready to buy, Wealthfront has your back. Check out our home planning guide for everything you need to know about purchasing a home.

📺 Video: Rent vs. Buy

While we’re on the topic, I thought I’d also share a video I made in 2019 on the topic of renting vs. buying when I was running my last startup Grove. I made a few different points here, like how buying a home often forces you to pre-buy space that you wouldn’t have needed to rent yet (since you’re planning for a longer time in the home).

💰 Deducting Mortgage Interest on $1m+ Homes

The IRS allows you deduct home mortgage interest on the first $750,000 of a mortgage ($375,000 if not married, filing jointly)1 which is an amazing benefit for homeowners. However in places like San Francisco or New York, it’s almost impossible to find a home where your mortgage isn’t going to exceed that limit, so you’re not able to deduct all the mortgage interest you pay. Well if you fall into that scenario, there’s a tax tip that when executed correctly, will greatly increase the amount of interest you can deduct (note: this is NOT tax advice). Also, I know this won’t be relevant for everyone, but it’s such a great tip for some of you that I wanted to share.

So how it works is that the interest on any money you borrow and then use to invest can be categorized as investment interest expense and deducted from investment gains (e.g., interest, dividends, cap gains) and thus reducing the taxes you’d owe. Two practical ways this could work:

If you already have a mortgage over $750,000, you would use your cash to pay that mortgage down to $750,000 and then later do a cash-out refinance to bring the balance of the mortgage back up to however much you want. Then use all the money you cash out to invest.
You want to buy a home and can pay for it in cash. Then within 90 days you do a Cash Recoup Mortgage and use all but $750,000 of the cash you get back from the mortgage to invest.

I don’t expect most people to have this much cash just sitting around, but if you recently had a windfall that you’re planning to invest, this could make sense before you make the investment. Or the tax savings could be enough for it to make sense to sell your investments to execute this strategy and then reinvest the money after.

If any of this is interesting, I’d recommend reading this great blog post from SVB and ABSOLUTELY talking to an accountant beforehand. Also, part of the complexity here is around a concept called “interest tracing” which requires you trace the funds to show that they were used for the correct purpose. If you’re interested in learning more about it, Deloitte has a great Interest Tracing Guide.

Today, I’m grateful for the support of our affiliate partner: MileValue.

Wondering why you received this? It’s probably because we know each other or you signed up for emails from me or one of my previous companies (LaidOffCamp & Grove). Hopefully you’ll enjoy the content, but if not, you can easily unsubscribe at the bottom of this email.

https://www.irs.gov/publications/p936

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

🛫 Travel, Points and Miles in 2022

Thu, 24 Feb 2022 08:00:00 +0000

Advertiser Disclosure

Note: American Express is a ChrisHutchins.com advertiser

In a few short weeks, winter will officially be over and if you’re like me, you’re looking forward to the hope of things getting closer to normal again and travel to get back to normal. Conferences and festivals are already being announced left and right and after last years booming holiday season, those credit card reward points you racked up might be burning a hole in your pocket. So, it seems fitting to take a moment to look at some of the changes happening in the travel, points and miles world recently.

💳 Card & Loyalty Program Changes

Covid has caused a massive disruption in travel over the last three years. That disruption has a cost and airlines, hotels, travel companies, and everyone in between are all too eager to make back. That means some big offers to entice travelers for some programs and a devaluation of points for others, so I wanted to share some of what’s happened lately.

The Good

Free Southwest Companion Pass is one of the best travel tips there is, giving you the ability to name a person to fly free with any ticket you purchase, even if you bought it with points. All you pay is the taxes. You usually have to earn 125,000 points in a year but right now, through any of their consumer cards, you can get Companion Pass free through Feb 2023 by opening a new card and spending $5,000 within the first three months. You can support me and the show by checking this offer out here.
American AAdvantage totally revamped the requirements to earn elite status, switching to a focus on earning “Loyalty Points” instead of flying a certain number of miles. Why is this good news? Because you can earn loyalty points from spending on an AA credit card or using their shopping portals. That means you could actually earn status on American (even their highest tier) without ever stepping on a plane. Now if you’re not flying, then status doesn’t do much for you, but in a post-pandemic world with much less regular travel, I’m excited to see more ways to earn status without flying so often.
Richard Kerr touched on offer stacking in this week's podcast episode and it’s one of the easiest ways to get the most out of your rewards points (and becoming more common in recent years). The idea is that in addition to loading American Express or Chase offers to your card, you can use shopping portals (I find the best deals at CashBackMonitor) and other coupons/deals too. FrequentMiler has a detailed post about taking this to the extreme if you want to explore further.

The Bad

Hyatt Award Chart Changes - While Hyatt still boasts one of the best hotel rewards programs, a recent change to their award chart update is a little disappointing for those of us who like booking at their high-end properties. As of March 2022, 70 of Hyatt’s hotels are moving to a higher award category. This means you need to use more points per night. That said, even with this changes, I think redemptions at places like Park Hyatt Kyoto or Ventana Big Sur are worth the extra points.
Marriott switches to dynamic pricing - The reason I love the points game is that the number of points or miles you need for some of the most expensive flights/hotels is usually fixed, so you can get incredible deals at the higher end of travel. That was especially true with Marriott Bonvoy, but they recently announced they’re switching to a model where the points required for booking will be based on market rates of their rooms. While they haven’t shared all the final details, this is about the worst news you could get and likely means I won’t be trying to accrue Bonvoy points going forward. Despite the Hyatt changes above, I’m all-in on Hyatt Rewards for 2022 hotels.
Chase Sapphire Reserve® and The Platinum Card® from American Express might be losing their luster - I recommend you check out this weeks podcast (specifically at 27:30), where Richard Kerr and I discuss whether these cards are holding up to the test of time. Their annual fees have gone up to $550 and $695 and it’s started to feel like you need to use their coupon book of benefits to recoup that value. And that’s all while other Chase and American Express cards are increasing their value proposition with a much lower fee (e.g. Chase Sapphire Preferred® Card is now 3x dining and 2x travel for $95/year). With so many cards offering lounge access through priority pass, I’m starting to wonder how many of these top tier cards I need to keep holding.

🌎 Where can you go?

Despite that many countries were on track to open up last year, the Omicron variant put a hold on the reopening plans for many countries. Given how often these things change, I wanted to share a few resources I have bookmarked to be able to reference before planning a trip. This NYTimes article is my go-to for country-by-country guidance on travel restrictions, but I also enjoyed ThePointsGuy’s post on the same topic, which is organized by region (much more helpful for trip planning).

However, in the last few months, many of those plans to open have either happened already or been announced, so I wanted to highlight a few of the recent changes I’m most excited about:

Australia is now open to international visitors. My trip here deserves a longer story some day, but it was the highlight of my 2015. In fact, I remember asking almost every person I met “Why doesn’t everyone live here?” I highly recommend a trip and if you’re up for an adventure, hire a guide and go rock climbing in the Blue Mountains. Specifically climb the Sweet Dreams route, which is one of the easiest and most beautiful climbs I’ve ever done.
Thailand reopened its doors to vaccinated international travelers without needing to quarantine, thought their “Test & Go” program still has a few rules to follow. Amy and I loved our time in Thailand and look forward to going back one day. I highly recommend all the street food you can handle and a few days at the Railei Beach Club.
While Japan’s limited reopening is only for students and business travelers, it’s the first step towards a broader reopening for tourism. There is no country I’m more excited to re-visit than Japan. Despite having been to Japan four times already (certainly the most of any international destination outside of Mexico), I’m ready to go back to eat all the ramen, relax in the most amazing hotels (Satoyamo Jujo and Park Hyatt Kyoto being two of my favorites) and spend time with some of the nicest people in the world.

Finally, if you’re planning on traveling internationally during the pandemic have questions about travel insurance, check out my post from two weeks ago.

💸 Optimizing Insurance Part 2 (Life, Disability and Travel)

Thu, 10 Feb 2022 08:00:00 +0000

Advertiser Disclosure

In Optimizing nsurance Part 1 I wrote about a few main types of insurance: homeowners/renters, auto, liability/umbrella and pet. While those made up most of the policies I had since going to college, there are a few other types of insurance I’ve had to learn about since then that I want to talk about: life and disability. I also want to briefly talk about travel insurance since I’ve gotten a few questions on that as well.

🩺 Life Insurance

Life insurance is one of those important things that can have a huge impact in your loved ones' lives should anything happen to you. It will primarily replace the loss of your future income for those you’re leaving behind, but can also help cover funeral expenses or pay off debt. It’s highly advised for those with young kids or those who have people that depend on you and your income to survive.

What kind should you get? This is where life insurance gets very confusing, so I’ll keep this short and sweet. You should get term life. It’s a policy that has a term limit for which the policy is active. 10, 20, or 30 years for example. If you pass away within that term, your beneficiaries get the face value of the policy, also called a Death Benefit. If you pass after the term expires or age out of the term without renewing it, they get nothing.

So why go with term life insurance if it expires? Because it’s a better deal. Other permanent (aka whole/universal) policies market themselves as offering you a benefit that lasts your whole life, which is easy to do when they have much higher premiums, complex rules and high fees. You’re almost always better off taking what you save with the lower premiums of a term life policy and investing the difference in low-fee index funds yourself.

So why is it so hard to find that advice? It’s crazy how common the advice to get Term Life is amongst those “in the know”, yet when searching online it’s almost impossible to find an article that agrees. Why? Because the commissions are so high for permanent life insurance that companies can spend fortunes on marketing, affiliate fees and sponsorships to nearly every site on the internet (except this one… I’ll never take money from someone selling permanent life insurance). That said if you search hard enough for the right content you’ll find articles from The White Coat Investor and NerdWallet that speak the truth. You can also find countless posts on Bogleheads or r/PersonalFinance that offer the same advice.

Also, one great strategy for Term Life is laddering (or layering) your policies. That means having multiple policies that expire at different times. This lets you lock in your policies when you’re younger/healthier, but have the payout decrease over time as your family's needs decrease (e.g. kids get older, mortgage is paid off). This PolicyGenius article explains the tactic in more detail.

Finally, I’d be remiss if I didn’t mention that I’m not a life insurance professional, so please do your own home work or talk to a certified professional if you want more info (just not a permanent/whole/universal life sales person please).

🧑‍🦽 Disability Insurance

Anyone, at any age, can become disabled and unable to work, whether it be from illness or injury. In fact, 1 in 4 of today’s 20 year-olds will become disabled before reaching age 67¹. So how do you make sure you’re financially covered should you have an accident or sudden illness that prevents you from working? By having some type of disability insurance in place (especially if your income supports more than just you).

There are two main types of disability insurance:

Short Term Disability, which usually only covers you up to six months
Long Term Disability, which can cover you for a few years or until you retire, but usually has a waiting period of 3-12 months before kicking in

Many of us might be offered or given short-term and long-term coverage through our employers or have access to short-term disability through a state fund like we have in CA. While those policies might “replace” 60-80% of your income, they often have weekly/monthly caps that might result in them replacing a much smaller %. If those policies aren’t enough or if you don’t have coverage from work, you can also buy full or supplemental policies on your own.

If you have enough of an emergency fund to cover living without your full income for 3-6 months, you might find it easier to self-insure your short term disability needs (or at least self-insure the difference between the coverage you have and your full income).

However, unless you’re financially independent, you probably won’t be able to self-insure against the chance you become disabled for the long term. So if you don’t have a policy through work I definitely recommend looking into one. Or if you don’t have enough coverage from your employer to live on comfortably until retirement, I’d recommend looking into a supplemental policy. From my research, two of the top providers are Guardian and MassMutual, but I don’t have experience with either.

It’s also worth pointing out that there is Social Security Disability Insurance and Supplemental Security Insurance. Those FICA taxes you see deducted from your paycheck are what fund these programs. Because of this, you need to have paid into these services for a certain amount of time to be able to use them. Luckily, most of us have hit the threshold of 40 work credits or about 10 years of employment. If you’re unsure how many credits you have, you can check through the Social Security Administration website.

While so much of the insurance content online is from providers, I did like this NerdWallet article for a more detailed overview of short and long term disability.

🛫 Travel Insurance

In the past few years airlines have been pushing travel insurance so hard that I’ve gotten more questions than ever about travel insurance, so I wanted to share how I think about things. The short answer is that most top credit cards offer most of the travel protections you need without buying any supplemental policies, as long as you book the trip with that card. That means, they’ll cover things like:

Delayed, lost or damaged bags
Trip delays, cancellations or interruptions
Medical evacuation and emergency medical treatment
Rental car collision damage

This coverage varies widely, so I definitely recommend finding your “Guide to Benefits” online and confirming (here’s an example for the Chase Sapphire Reserve®). With this coverage in place, I’d feel good traveling without other insurance except for a few circumstances:

If your health insurance doesn’t cover you while traveling abroad, I’d consider a travel insurance policy that covers non-emergency medical treatment
If you’re concerned with getting stuck abroad after a positive covid test, I’d get a policy like the Safe Travels Voyager from Trawick that specifically covers flight changes and lodging costs after a positive covid test (we did this on our trip to Mexico and it was only $343 for 8 travelers. Or if you want to be sure you can still travel back home, you can get a Covac Global policy for ~$600/person that will charter you a private flight if you test positive abroad.
If you plan to do adventurous activities like Scuba Diving or Rock Climbing that might not be covered under your existing insurances, I’d suggest a travel insurance like WorldNomads that will cover these activities.
If you’re booking a very expensive tour/vacation like this Galapagos Cruise, I would double check your credit card policies and specifically your limits to make sure you’d be fully covered in the case that you test positive for covid in advance or your flight is canceled/delayed and you miss the cruise departure.

1) https://www.ssa.gov/news/press/factsheets/basicfact-alt.pdf

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💸 Optimizing Insurance Part 1 (Home/Auto/Liability/Pet)

Thu, 27 Jan 2022 08:00:00 +0000

Last year, weather-related disasters cost the US $145 billion dollars¹ and in 2020 the total cost of motor-vehicle deaths, injuries, and property damage in the US was $474 billion². Now despite that insurance companies are still making lots of money while Americans overspend on just auto insurance by nearly $21 billion per year³. So, why does all this matter? Because getting the right policies in place at the best price can protect you and your family without overpaying insurance companies. In fact, 76% of consumers who have shopped around say they’ve saved money by doing so⁴.

So, what kinds of insurance am I talking about? In this issue, I’ll focus on home, auto, liability and pet insurance, and in the next issue I’ll focus on life, disability and travel insurance.

🏡 Homeowners and Renters Insurance

Any homeowner will tell you that things can and will always be breaking. Water heaters burn out and roofs always seem to find the most inconvenient time to need replacing. Then, there’s the scarier stuff. Things like what the residents in Colorado are dealing with after a wildfire burned through two towns or the massive flooding residents in Washington are still cleaning up.

Enter, homeowners and renters insurance.

Generally, homeowners insurance will cover destruction and damage to your home, the loss or theft of possessions, and personal liability for harm to others. I don’t think there’s really a question of whether you should have homeowners insurance (you should) since most mortgage lenders require it. Also, depending on where you live, natural disasters like floods, hurricanes and earthquakes are often excluded and require separate riders or policies.

Renters insurance works similar to homeowners insurance in that it’s there to protect your personal property and offer liability coverage, but damage to the building is the responsibility of the landlord and covered by their homeowners insurance.

Homeowners/Renters Insurance Tips

Document Everything - As Joe Saul-Sehy said in Episode 35, this can be as easy as making your own MTV Cribs video, going room to room to capture everything you own. For expensive electronics (TVs, computers, etc.) it’s worth writing down the model/serial numbers somewhere in case you need them.
Compare Prices - Every year I comparison shop from multiple providers. While I wish there was a perfect comparison site, I often have to go straight to the companies’ websites. My favorite trick here is that the quizzes about your home size, roof material, etc. are often just to help you figure out how much coverage you need, so once you know that number you can put whatever you want to get to the end where you can just dial up the numbers to exactly what you want. Also, you don’t need to wait until the end of your policy to make a change. If you switch in the middle, you’ll just get a check for the difference.
Get Your Discounts - Alarms (especially if they report to local police/fire), fire sprinklers and security cameras can reduce your premiums by as much as 15-20%. You may also get a discount for an organization you belonged to (I think I once got one for my college fraternity) or if you’re eligible for military-related insurers you can check them out (my fathers’ past military service makes me eligible for USAA – though they weren't the cheapest).
Bundle with Auto - This may help you save money, but don’t assume it’s always the best. For us, it ended up being less expensive to get our homeowners policy from Lemonade than buying policies together from any one carrier.
Raise Your Deductible - Statistically, the cheapest insurance should be self-insurance, because insurance companies make profits. However, very few of us have enough in our emergency fund to rebuild our home nor we want to take that risk. That said, if you have enough emergency savings to cover a higher deductible, it can be a great way to lower your premiums.
Have Enough Coverage - We were fortunate that our first condo in SF appreciated quite a bit and while a lot of that was the value of the land, the cost to rebuild had gone up a lot too, but our policy wasn’t close to having enough coverage. So, keep an eye on the value of your home and rebuilding costs so you can adjust your policies as needed. Similarly, when we upgraded from IKEA furniture and started to acquire more things, we increase our coverage as well.
Dial Back Coverage You Don’t Need - This varies by policy, but a specific example is around “Loss of Use”, which covers putting you up in a nice hotel or similar rental home if you can’t use your home. If you have a second home or family you could easily stay with, you might not need as much coverage here.
High Value Items Aren’t Covered - It’s important to note that if you have fancy jewelry, art, bikes, cameras or other high-value items, you’ll probably need an additional insurance rider for those items. It varies by policy, but a common threshold is ~$1,000. Also, these policies aren’t that expensive, often costing ~1% per year.
Premium Insurers - If you have a really expensive home(s) and need coverage beyond what the traditional insurers cover, there are two high end insurance companies that I’ve heard great things about: Pure and Chubb.

🚗 Auto insurance

According to the Association for Safe International Road Travel, about 4.4 million Americans are involved in a traffic accident that requires medical attention. That doesn’t even touch on the cost of time off work, vehicle damages, rental cars, or possible litigation costs. So, car insurance is a must-have.

But before we talk about ways to save, I’ll do a brief run through what type of damage each of the common components of auto insurance covers:

Collision - Accident regardless of who’s at fault.
Property damage - Property if you were at fault.
Uninsured motorist - Accident with someone who doesn’t have insurance / is underinsured.
Comprehensive - When you’re not driving (tree falls on your car or you get keyed).
Personal injury - You and any passengers in the car at the time of the accident.

Car Insurance Tips

Compare Prices - The same advice for homeowners above applies to auto insurance, but it might be even more important. While I saw 10-20% variability in pricing for our homeowners policy, the quotes I got for covering our Model 3 were about 2x higher at State Farm and USAA than we pay with Geico.
Raise Your Deductible - Same as for homeowners.
Low Mileage Savings - If you don’t drive much there are a lot of companies that offer “pay-as-you-go” insurance that often involves adding a device to track your driving. If you’re driving less than 10,000mi/year this could make sense, but even if you don’t find good pay-as-you-go rates, you can select a lower number of miles/year with any policy and often get a lower rate. I know we saw the rate drop when we picked 5,000mi/year with our Geico policy.
Pay in Full - Many insurance companies charge a fee to pay your bill monthly, so you can save by paying in full every six months.
Increase Your Credit Score - In some states (though not CA), insurance companies charge less if you have good credit, so if you
Anti-Theft Devices - I’ve heard of big savings for adding anti-theft devices, so you may want to see if you can get a discount worth paying the cost, but I’ve never seen this promise come true.
Good Grades - Students can get discounts for having good grades.

☂️ Liability/Umbrella Coverage

While home and auto policies can cover your personal liability for accidents in your car or home, their coverages may not be enough. For example, your auto policy might offer $250,000 of liability coverage, but that doesn’t mean you couldn’t be sued for $1 million for an accident involving a serious injury or death. In fact, in some states, you can be sued for future earnings, so if you have a higher net worth or are a high earner, your home/auto policies might not offer enough liability coverage.

That’s where umbrella or personal liability insurance comes in. It sits on top of your home and auto policies and covers your liability for as much as you want to pay for. Umbrella policies aren’t too expensive, usually costing $150 to $350 per year for the first $1 million of coverage and about $100 for every $1 million in coverage after that. This piece from NerdWallet has a bit more detail on umbrella insurance coverage.

🐕 Pet Insurance

Pets are a walking example of Murphy’s Law. Whatever can go wrong, will go wrong. While pet insurance can be a good option for any pet owner, it might be more interesting those with exotics like birds and reptiles that require specialty care as well as those with breeds prone to health issues (e.g., flat-faced dogs and cats with breathing issues, working dogs with a predisposition to hip dysplasia).

Premiums are usually $15-100/mo, but vary widely depending on age, breed or species, and previous health history. The older the pet, the higher the rate. In the past I’ve taken the path of self-insurance, but after spending almost $1,000 this year to try to diagnose an issue with our dog Finn (which resulted in finding nothing and him just getting better), I thought about reconsidering. Then in my research for this newsletter I saw a lot of positive feedback for Lemonade’s pet insurance. I priced it out and I’m reconsidering even more (though have not pulled the trigger yet).

Ultimately, I think pet insurance is a really personal decision that comes down to how much you’d be willing to spend on medical treatment for your pet. If that number is more than $10k, then pet insurance might make a lot more sense. Also, it’s important to note that pet insurance is typically reimbursement style, so you’ll pay for services upfront and then submit your claims to be paid back.

📋 Final Insurance Tips

I’ll probably repeat this section in two weeks when I tackle Life, Disability and Travel insurance, but wanted to share this time as well. Here are some final tips that apply to all insurance:

Shop around! I’ve said this multiple times, but prices vary widely between companies offering the same coverage.
Thoroughly read policy terms. There are too many terms to list, but some common examples are waiting periods for the policy to fully kick in or exclusions for certain things.
Avoid Insurance Myths. Some of what you assume about insurance may be incorrect, like credit not affecting rates for certain insurance, suicide voiding a life insurance policy or what beneficiaries may have to pay in taxes upon receipt of benefits
Up your deductibles. Stacking Benjamins creator, Joe Saul-Sehy shared a great tip in Episode 35 of the podcast. If your emergency fund or other savings are solid, you may not need to worry about securing lower deductibles. By upping your deductible, you can save money on your premiums, which puts more money in your pocket and ups your cash flow.
There’s insurance for everything. There’s special insurance for boats and other recreational vehicles, rental car coverage, additional coverage for certain illnesses like cancer, wedding insurance and even bed bug insurance.
Some insurance is a waste. Not all insurance options are worth it. A disease-specific insurance policy probably isn’t needed if you already have good medical coverage. Rental car insurance is probably already covered in your own auto policy or credit card. While having all this additional coverage may sound important, chances are it’s not necessary or covered in a policy you already have.

While we all hope to never have a car accident or flooded basement, realistically, these things happen to lots of us, so hopefully these tips will help you save money getting the insurance you need to protect yourself.

1) https://www.cnbc.com/2022/01/11/weather-disasters-cost-145-billion-last-year-in-the-us-says-noaa.html

2) https://www.nsc.org/newsroom/motor-vehicle-deaths-2020-estimated-to-be-highest

3) https://www.marketwatch.com/story/this-is-the-ridiculous-amount-youre-overpaying-for-car-insurance-2018-10-03

4) https://www.valuepenguin.com/consumers-shopped-around-insurance-saved-money

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

📝 Bucket Lists and Living a Life Without Regret

Thu, 13 Jan 2022 08:00:00 +0000

Coming into a new year has always had the feeling of starting fresh. The calendar year starts over and we all have a proverbial blank slate to work with. Some of you may be working on new resolutions and others might still be figuring them out.

What do you want to achieve this year? What do you want to leave behind? Add on the massive reality slap brought about by the pandemic and we’re all forced to consider, what the hell do we want to be spending our time on?

It’s timely that last week’s podcast with Ben Nemtin happened to touch on bucket lists and how we can achieve our goals even when life is trying its damndest to get in the way. So I thought it would be a great topic to tackle in this newsletter.

📝 Creating a Bucket List

If you’re not familiar with a Bucket List, it’s a list of things you want to accomplish before you die. Or as Ben said, “it’s a list of all the things that are going to bring you joy and happiness in your life.” If you’ve never had the opportunity to dream big, figuring out what might bring you joy can be hard. Almost like having to re-learn what you like all over again.

For me, it involved talking to a few good friends, daydreaming a bit, and lots of google searches. I now have over 100 things on my list, but here are a few highlights that are done (✅) and still outstanding (☐) :

✅ Come within 100ft of a predator
✅ Shake hands with the President of the United States
✅ Star in a movie, even a short one
✅ Travel around the world
✅ Marry my true love
☐ Do stand up in front of a live audience
☐ Learn to do a standing backflip
☐ Run with the bulls in Pamplona
☐ Set (or break) a Guinness World Record
☐ Go on a police ride-along

And while I was pretty happy with my bucket list, after getting a copy of Ben’s book The Bucket List Journal, I realized I had way over-indexed on experiences. So if you’re looking for some help building out a broader list, I definitely recommend his breakdown of categories:

Travel and Adventure - Cage diving with a great white shark!
Physical goals - Being able to do a handstand. It’s harder than it looks!
Material goals - Getting that beautiful Le Creuset cookware set.
Creative goals - Starting a podcast.
Professional - Becoming a partner at your law firm.
Financial - Saving $1 million.
Intellectual - Learning a new language.
Mental Health - Seeking out therapy.
Relationships - Checking in with friends more often.
Giving - Becoming a Big Brother or Big Sister.

And if you’re looking for inspiration, you can certainly find plenty of websites on the topic, but I’d also recommend checking out the epic bucket list Ben created a TV show about and/or one of these books:

While creating your bucket list is a great first step towards living a life of more joy and happiness, it’s certainly not enough. I asked Ben about his inspiration for so much of his work and he shared some really sad and eye-opening research about what people regret at the end of their lives.

😔 Top Regrets of the Dying

During my conversation with Ben, he referenced a study by Cornell professors Thomas Gilovich and Victoria Medvec, which found that 76% of people had one glaring similarity at the end of their lives:

They regretted living life according to other people and their expectations.

There have been numerous studies and memoirs that reflect the same sentiment. For example, best-selling author Bronnie Ware explored this topic in her book, The Top Five Regrets of the Dying, based on her work as a palliative caregiver. Her list starts with a very similar regret: “I wish I’d had the courage to live a life true to myself, not the life others expected of me” and continues with:

I wish I hadn’t worked so hard.
I wish I’d had the courage to express my feelings.
I wish I had stayed in touch with my friends.
I wish I had let myself be happier.

If these regrets are so common that they appear in multiple studies, interviews, and memoirs, why do so many people still reach the end of their lives with them?

❓ Why Don’t We Live Life on Our Own Terms?

Gilovich and Medvec found three distinct reasons why people had this particular regret:

1. We tend not to set deadlines on personal goals.

It’s easy enough to say, “I want to save money.” Truthfully, it’s a great goal. Most everyone could do with better saving habits. But just saying you want to save money doesn’t really help you save money. It’s too open. You’re not bound to any sort of plan to make it happen. Because of this, it’s easy to have a want or desire but never work towards attaining it.

Elon Musk explained this well, saying “if you give yourself 30 days to clean your home, it will take you 30 days. But if you give yourself 3 hours, it will take 3 hours. The same applies to your goals, ambitions, and potential."

We set deadlines for so many professional goals, but hardly ever for our personal goals. So if you want to save $10,000 to buy a really nice road bike, you don’t wait to be handed $10,000, do you? If you did, you might be waiting a long time. Instead, try making your goal “save $10,000 for a new bike by June 1st.”

If you want to put the odds of hitting those deadlines in your favor, here’s a shocking stat for you. People who have accountability partners tend to increase their chances of success by 95%1!

An accountability partner is someone that can check-in and ask about your progress or talk you through any hang-ups. They might be a professional in the area you’re working on or a friend that has a similar goal. This article from Clever Girl Finance makes a great argument for why we should have accountability partners to help us accomplish our goals.

Finally, some goals might not need deadlines. Maybe it’s a habit you want to incorporate more. If you intend to communicate with friends more often make sure you set calendar reminders for their birthdays or for times to check-in. If learning a handstand is a goal, set aside half an hour at same time every day and practice.

2. We wait to feel inspired before starting to pursue them.

I think this is one we’re all guilty of. Especially at the start of a new year. We have the drive and motivation to start fresh, eat right, go to the gym, quit smoking, etc. Then, we settle back into our post-holiday routines of work, school, and various responsibilities, and suddenly that energy is shifted towards other things. After all, most people start giving up resolutions by the third week of January and nearly 80% of people have fully given up resolutions by February.

You can’t just sit around waiting for inspiration, you have to create that inspiration by taking action. That doesn’t mean you need to know the full path to achieving that goal, it just means you need to take step one. Also, taking time to celebrate or reward yourself for accomplishing those steps along way can help rewire your brain to be motivated to reach the next milestone.

You should also focus on goals that truly excite you. If you hate traveling, airplanes, heights, and bugs, would you feel inspired to work towards traveling to Costa Rica to go zip lining? No, you’d look at it more like a chore than something exciting. Your goals and bucket list should reflect the things that bring you joy as you’ll actually want to keep working at them. Fun fact, for the longest time, I thought “spend a night in prison” would be an amazing thing to cross off my bucket list. Somewhere between getting older and having a child, I realized this would definitely not bring me joy and took it off.

3. Fear of failure and fear of others' perceptions.

In the blog post that was the basis for her book, Bronnie Ware writes, “Many did not realize until the end that happiness is a choice. They had stayed stuck in old patterns and habits. The so-called ‘comfort’ of familiarity overflowed into their emotions, as well as their physical lives. Fear of change had them pretending to others, and to their selves, that they were content. When deep within, they longed to laugh properly and have silliness in their life again.”

While I’m not sure I realized it at the moment, fear is the primary reason it took me so long to start the podcast. Many of my closest friends have heard me describe wanting to do something like this for almost a decade, but not thinking anyone would listen or read held me back for so long. It wasn’t until a good friend forced me to overcome my fears by announcing that I was launching a podcast during a conversation we had on his show. I didn’t love it at the time but am now incredibly grateful for the push.

While hard, it’s important not to be afraid to fail or find that achieving your goal didn’t feel as you thought it would. And as the saying goes, “If you aren’t failing, you aren’t trying.” After all, we’d all be living in the dark if Edison hadn’t overcome 1,000+ unsuccessful attempts at the light bulb. Even when others think your goal is too weird or crazy, never forget that they aren’t the ones who have to live with the regret of not at least trying.

If you find out after achieving a goal that it wasn’t really what you wanted, think about how much you learned through the process! Sometimes those learnings can show you other things that might interest and energize you more.

Finally, if you’re worried about what others might think of you, the truth is that people are probably thinking about you a lot less than you think they are (and probably because they’re too worried about what others are thinking of them).

🎯 The Takeaway

If you want to set yourself up for success in achieving your bucket list or any other big life goals, make sure to do these three things to overcome the top three reasons people end up living life according to others and their expectations.

Set deadlines for your goals and share them with others to create accountability
Create inspiration through action by taking even a small step towards your goal
Overcome fear by understanding it and embracing learning through failure

🤔 What’s on your list?

Hopefully you feel inspired to make (or update) your bucket list and start living life with far fewer regrets. As I mentioned earlier, I really love adding to my own bucket list and collecting amazing experiences, so if there’s anything on your list you think I should consider adding to mine, please reply to this email and share it!

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

👨‍👩‍👧‍👦 Protecting Your Family with Estate Planning

Thu, 30 Dec 2021 08:00:00 +0000

We’re coming to the end of the holiday season. With 2022 just around the corner, many of us may be reflecting on the time we just spent with family and friends and ways to do right by them. It’s been a wild few years and we’ve all seen how quickly a sudden emergency can force us to course-correct. One of the best things we can do to help our families weather these emergencies is having our affairs in order.

If you’re not sure what estate planning is, think of it like risk management. It’s a way to protect and guide your loved ones should you die or become incapacitated. During these times, giving clear instructions on how to handle your affairs, assets like bank accounts and real estate, or even your pet bird Princess Sophie, is the easiest way you can remove frustration and doubt during a stressful situation.

The most common estate planning document you hear about is a will, yet less than half of adults in the US have one. However estate planning can be much more than that and we can actually plan for anything that would require our loved ones to step in and handle our day-to-day affairs.

Now, we all have different plans and wishes for how we want our affairs handled. But estate planning can be so time-consuming and confusing! So, let’s break this down…

🧑‍🏫 Basic Planning

Organize your account logins and passwords. If you’re subscribed to this newsletter, I’m going to assume you already have all of your passwords setup in a password manager like 1Password (my fav). If not, you should. Even the New York Times thinks Everybody Needs a Password Manager. I also migrated all my two-factor codes from apps like Google Authenticator to 1Password to make it easier to share secure logins (and has eliminated most of the “can you send me the code you just got” texts with my wife).
Organize important documents. This should include things like your insurance docs, medical records, a list of financial accounts and any important contacts. If you’re not sure where to start, EverPlans has this list or two inexpensive books that provide guides are: Sorry for Your Loss - It’s Me and Get it Together. My easy/free system is organizing everything in a Google Doc that links to various files in Dropbox or Google Drive (that I assume anyone needing to read the doc will at that point have access to). That said, I’m really interested in an online platform that would make this much more organized. My top pick would be Trustworthy, followed by EverPlans, but they’re just expensive enough that I haven’t pulled the trigger yet (though I could see that changing soon). You could also check out Cake, which is less expensive, but I haven’t spent much time with it.
Decide who gets access to your docs. This doesn’t have to be the same person you want to handle things like your finances or health care decisions. Google has Inactive Account Manager which is like a kill-switch for your accounts and makes it easy to grant access to your account if you’re inactive for a period of time. For everything else I rely on 1Password’s family access and emergency kit. I’d also suggest checking out this Wirecutter article about getting your digital accounts ready in case of death.
Create a Last Will and Testament. Consider this your final wishes for your possessions, dependents, and arrangements. While I put most estate planning docs in the next section, this one is especially important if you have any valuable assets (money, real estate, etc.) and want to specify where they go. It’s also important if you have children or pets, so you can designate who you would want to look after them. It also can include how you want your assets divided, who gets what portion of your assets, special wishes, or other designations (like charitable donations). If you take my advice below to set up a full estate plan, then this will be part of that. If you’d rather not, or you know you’ll put off that project for long enough that you should at least set up a quick will sooner, my pick would be Trust & Will (who I used for my full estate plan), but you could also check out Willing or LegalZoom.
Designate your beneficiaries. While you can specify what happens to your financial assets in a will, one major exception is that in most cases if you’ve specified a beneficiary on a specific account (most common with retirement accounts and insurance policies), that designation will take precedence over your will. In many cases we set these up when we first opened the account, often before we met our spouses, had kids or even got divorced, so make sure to double check that you have the right beneficiaries specified.

📝 Full Estate Plan

When it comes to the next level, I’d definitely recommend a full estate plan, because it helps cover other circumstances than just your passing. You also need to consider any event that would leave you unable to make your own decisions. Who do you want to handle your affairs if you’re unconscious in the hospital? How do you make sure your medical or financial wishes are executed? How can you help your loved ones avoid the hassle of probate court?

When I first set up our estate plan 10 years ago, I enrolled in Google’s legal benefits during open enrollment and used an in-network attorney to do a comprehensive estate plan for (almost) free. However, since then some great online/DIY options have entered the market. So when we updated our estate plan after our first child, I decided to do everything with Trust & Will (← 15% off for our readers). It was a great experience and I plan to continue using them as things change in our lives. However, if you have a large estate, complicated wishes, lots of possessions, or a “blended family” (kids from multiple marriages, second spouses, etc.), I’d recommend working with an estate planning attorney. Here’s what a full estate plan commonly includes (and when/why it’s important).

Revocable Living Trust. This will be the hub of your estate plan and specifies the management, control, and distribution of your assets during life and after death. A trust offers more control than a will, especially when it comes to how and when your assets will be distributed. Another benefit of a trust is that it will help prevent your loved ones from lengthy and costly proceedings in probate court (see this article on How a Simple Estate Plan Pays for Itself). For example, in California, estates valued over $166,250 have to go through probate when the assets aren’t held in a trust.. While some trusts can be quite complicated (have you watched Succession?), a basic revocable living trust is easy to set up, doesn’t change your tax situation and is easy to revoke (hence the name).
Pour Over Will. You’ll want your trust to be your primary tool for distributing your assets after you die, but you might not end up having all your assets titled in your trust – maybe because you forgot or maybe because some online financial institutions don’t even support trust accounts. So think of a pour over will as a kind of “safety net” that takes any property you didn’t put in your trust while you were alive and transfers it into the trust.
Advance Healthcare Directives, Living Wills, and Medical Powers of Attorney. These detail how you want your medical care approached if you can’t make those decisions yourself. What kind of medicines and treatments will you allow or not allow? Who is allowed to make these decisions for you? When do you want to cease life support should you get to that point?
Financial Power of Attorney. Much like a medical POA, a financial POA designates how you want your money handled while you’re incapacitated and who can handle that for you. Remember, bills don’t stop in the event of an emergency. Having a financial POA in place means less worrying about if your bills are getting paid on time and more time focused on healing.

Finally, you may also want to consider writing a Letter of Intent. It is an informal document that will give your loved ones important information that isn’t covered in your estate plan. Letters of intent aren’t legally binding but can be a nice complement to those documents. For example, even if your trust dictates that your children wouldn’t receive any inheritance until they turn 30, it likely also states that the trustee in charge of the money has the authority to make distributions for “health, education, maintenance, and support.” In this circumstance a Letter of Intent could give them important guidance like wanting to support private education or providing them with funds for their first downpayment.

🧐 Advanced Tactics

When most people think of estate planning and trusts, it’s often about tax avoidance. However, in 2022 the estate and gift tax limitation will be $12.06 million per person, meaning a married couple could transfer up to $24.12 million in their lifetime before being subject to high estate tax rates. So realistically, unless you think your assets will approach this level, you likely won’t need any advanced estate planning tactics to avoid estate or gift taxes. That said, I think it’s fun to read about some of the ways you might legally avoid taxes should you be fortunate enough to cross those limits (or if the limits actually drop back down like they’re supposed to in 2026). I’m not a lawyer, so this is obviously not legal advice and I might have gotten some nuances wrong in the summaries below, but here are some of the most common tactics:

Grantor Retained Annuity Trust (GRAT): An irrevocable trust you would establish to minimize estate tax on highly appreciating assets (investments or businesses). It allows you to transfer assets into the trust and then receive annual payments of a fixed amount of principal and interest for a prescribed number of years. Any appreciation that stays in trust can be passed to your spouse or children and avoids estate tax.
Charitable Remainder Trust (CRT): You typically transfer appreciated assets into a CRT and retain a stream of income from the trust, but unlike a GRAT, the beneficiaries at the end of the trust term are not family; they are charities. However, even though the charitable gift is not made for years, you get the charitable income tax deduction when you first transfer the assets into the trust.
Family Limited Partnership/Limited Liability Company (FLP or FLLC): When I first heard about this tactic it was described as letting you stuff a big peg through a small hole. It works by transferring assets into a corporate entity and making your heirs limited partners (or non-managing members of the LLC), and because they don’t have any management control or ability to demand distributions, the value of their ownership of the business is only a fraction of the value of the assets owned. Therefore you can transfer the interests to your children at a discounted value and minimize estate taxes. Also, because you’re a managing member, you still maintain control of the assets and can receive distributions throughout your life.
Irrevocable Life Insurance Trust (ILIT): This tactic allows you to avoid estate tax on life insurance proceeds by setting up a trust to purchase life insurance on your life (or you can transfer an existing policy). You also need to gift the trust the cash necessary to pay premiums on the policy. Then, upon your death, the payout is paid to the trust and not subject to estate tax. The ILIT states where the proceeds end up, frequently in trusts for your spouse or children.

☑ Things to Keep in Mind

As with anything, there are certain things that are helpful to be aware of as you start getting your information together.

Estate laws vary by state. Whatever documents you have drawn up need to meet state requirements or else the document(s) can be voided. That means if you move to a new state you may need to update your documents.
Parents, start having conversations with people you would like to become guardians for your kids should you pass away while they’re still minors. It’s a big responsibility, and those people need to be aware of and agree to your wishes well ahead of time.
Check your employer benefits for low-cost, discounted, or free legal services. This can cover things beyond just estate planning too.
Remember to include important contacts like your boss or HR rep, financial advisors, landlord or tenants, etc.
Don’t forget pet care in your directives. Who gets Buddy if you pass away? Who is designated to take care of Felix if you end up hospitalized?
You should probably do a quick review of everything every year. Hey, the start of a new year is a perfect time huh? Some things to keep in mind: reviewing beneficiaries on new accounts, updating addresses/contacts, adding any new assets you’ve acquired.
Make sure you follow through with notarizing and filing paperwork. The last thing anyone wants to deal with is finding out a will isn’t enforceable because someone didn’t get it notarized. While some states allow online notaries, many don’t, but it’s really easy to get a mobile notary to come to your home (and surprisingly not much more expensive). However, before you pay for a notary, check out this list of places where you might get your docs notarized for free.

👵👴 Estate planning isn’t just for yourself

Many of us are getting to that point in life where our parents and grandparents are noticeably aging. We need to start thinking and having conversations about their wishes and how best to support them. If your parents didn’t have the chance to establish an estate plan or some sort of central information hub, I highly suggest having the conversation with them. Yes, it’s uncomfortable and can bring up so many emotions. However, if anything happens, you need to know the same things for them as your family would need to know for you. In this week's podcast, Joe Saul-Sehy recommended this book: Mom and Dad, We Need to Talk: How to Have Essential Conversations with Your Parents About Their Finances. It’s also beneficial to share this with siblings so everyone is on the same page as far as who is responsible for what and the overall wishes of parents and grandparents.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

🎁 A Season of Giving & Year End Financial/Tax Checklist

Thu, 16 Dec 2021 08:00:00 +0000

We are in the thick of the holiday season. Not only are we in the spendiest time of the year, but also the most charitable. Charities see a huge boost in donations from November to December. In fact, the busiest days for charities tend to be Giving Tuesday (the Tuesday after Black Friday) and the last three days of the year. We all know that giving can help others in need, but most people don’t realize that it can benefit us as well.

One of my favorite books, Happy Money: The Science of Happier Spending, the authors showcase five principles of spending that can drive happiness. One of those principles is “Invest in Others” and I wanted to share a few of my favorite learnings from the chapter that highlights the impact giving to others can have on ourselves.

A study of over 200,000 people around the world found that in 120 of 136 countries, people who donated to charity in the past month reported greater satisfaction with life. This relationship emerged in poor and rich countries alike, and held up even after controlling for individuals’ income. In fact, donating to charity had a similar relationship to happiness as doubling household income.
This study showed that people who report donating money to charity feel wealthier than those who do not, even controlling for how much they make.
Finally, in a study of more than six hundred Americans, the more they invested in others, the happier they were. This relationship between prosocial spending and happiness held up even after taking into account individuals’ income.

💸 Tax Benefits

Another great incentive to give is the tax benefit the IRS offers for donating to charities. Charitable donations can be listed as a deduction on your taxes. Yes really! This means your taxable income is lower and therefore, a lower tax bill. How wonderful is that? Not only are you helping an organization continue life-changing work, but you also get the benefit of paying less taxes for doing so. However, there are certain rules and limitations to this.

The charity has to be listed as tax-exempt by the IRS. An easy way to recognize if a charity is tax-exempt is if they label themselves as a 501(c)(3). The IRS has a tool to check their status here.
To get the full tax benefit of your donations, you’ll need to itemize your tax return, otherwise you can only claim up to $300 (single) or $600 (joint). Check out this article from TurboTax to learn more about when it might be better to itemize.
Not all donations are deductible. Check out this article from TurboTax or this article from H&R Block that detail more about what is and isn’t tax deductible. Also, make sure to keep all your receipts in case you need to prove the donation down the road.
There are limits on how much you can contribute based on your income, but most people won’t come close to hitting them. If you want to read more on these limitations, may I suggest this super thrilling read from the IRS website. Normally the cap is 60% of your adjusted gross income, but the IRS announced it’ll be 100% for 2021.

🎗 Charitable Donation Strategies

With the internet, it’s never been easier to make charitable donations, so I’m not going to show you how, but I have found a few donation strategies that are worth sharing:

Amazon Smile - I can’t believe I didn’t know about this sooner. With Amazon Smile, you can shop exactly like you normally would, except that Amazon will donate 0.5% of your purchases to a charity you pick. All you have to do is use the Amazon Smile shopping link and you’re all set.

Donor-Advised Funds - They allow you to contribute cash, stocks, or crypto and take an immediate tax deduction this year. However, instead of needing to make all your donations this year, you can invest your contributions and donate the funds in future years to any charity you want. It’s great if you’re going to be in a high tax bracket this year and you want to front-load your donations for future years. If you’re interested, I’d recommend checking out Daffy.org where I moved my DAF to this year.
Donate Miles - Donating points and miles can be a great way to give back without shelling out any cash, and it’s also an easy way to extend your points balance if it’s about to expire. ThePointsGuy has a great post about how you can do this.
Buy a Zoo or Museum Membership - Most of your local Zoos and Museums are registered nonprofits and membership fees are tax deductible. Even better, many are members of the ASTC or AZA and memberships include free or discounted admission at Zoos and Museums across the country.
Watch out for scams - Before you hit that Send Money button on Paypal, make sure your information and money is going to a legitimate source. Check this article from AARP that details red flags to watch for as well as sites to check the validity of a charity.

☑️ Year-End Financial/Tax Checklist

December is the perfect time to check in on your finances and make any last minute money moves before the end of the tax year. Not only will you save time and money but your accountant will be so grateful and a happy accountant makes for even happier tax returns. Here’s a few things you might not have considered in 2021:

Make a charitable contribution: I already covered this extensively above, but certainly didn’t want to leave it off the list.
Contribute to a Backdoor Roth IRA. A Roth IRA is a great way to invest after-tax money for retirement – it grows tax-free and all future withdrawals are tax free. However, if you’re not eligible to contribute to a Roth IRA (income limits are $140k for single and $208k for joint filers) there’s an easy workaround (that proposed legislation might change in 2022). You just need to make after-tax (nondeductible) contributions to a traditional IRA, which virtually everyone can do, and then immediately convert the funds to a Roth IRA. If you already have funds in a traditional IRA it might not make sense, but this Schwab article explains the process in more detail.
Harvest your losses to save on taxes. If any of your investments are down, you can sell them and use the losses to offset gains or your income (up to $3k) and lower your tax bill. If your investing app doesn’t do this automatically (Wealthfront does it for me) you’ll have to do it manually. And if you still want exposure to the investment you sold, you’ll need to buy something similar, but not exactly the same to avoid the “wash sale rule”. This NerdWallet article explains a lot more about how it works. There’s a tax loophole for Crypto, because it’s not subject to the wash sale rule, so you could sell your bitcoin, capture the loss, and buy it back right away.
Spend down your FSA. Normally these are “use it or lose it” funds, and come January 1st, any money left over goes POOF. However, those rules might be more lenient this year, but only if your employer opted in. If not, you’ll want to stock up on any medical items you might need. The FSA Store is a treasure trove and you can get 2% cash back through Rakuten. If you still have funds left over these two articles from Wirecutter and CNBC have some good inspiration. Or since we’re in the spirit of giving, consider buying items to donate to local shelters or charities.
Open or fund a 529: If you have kids or you’re planning to get another degree, a 529 college savings account can be a great way to save. You can invest your contributions and withdraw them tax-free to pay for college or private school. In most states, the contribution deadline is December 31 although in a few states the deadline is in April. You can even consider superfunding a 529, which lets you fund up to five years’ worth of contributions at once.
Exercise stock to stay under AMT. If you work at a company that grants you incentive stock options (ISOs), exercising them can trigger the Alternative Minimum Tax, but for many people it’s possible to exercise just up to the AMT crossover point and avoid owing any taxes. This article has a good overview, but I’d recommend discussing this with an accountant as well.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

💵 Cash: How Much To Keep + Where To Put It

Thu, 02 Dec 2021 08:00:00 +0000

I try to invest as much of my money as I can in the market because I’m a huge fan of compound interest and am focused on building my wealth. Personally, I keep my long-term investments at Wealthfront, where the 5-year return for a 9.0 risk score portfolio has been 11.94%¹. However, the market can be volatile… that same portfolio would have been down by over 30% in just a few months in 2008 and 2020, but since those lows, it would have recovered and been up by ~400% and ~180% respectively. The key to benefiting from those recoveries was not having sold when you’re down and since I never know when the market might be down, I keep some money in cash for three reasons (I’ll talk about how much I keep in each later):

Regular expenses like mortgage, groceries and credit card bills
Emergency funds in case something large and unexpected comes up
Savings for big expenses in the next 3-5 years like a downpayment

While I keep cash for regular expenses in my checking account where I don’t earn much interest, I want to keep #2 and #3 somewhere I can earn the most I can. Until the beginning of 2020 there were so many high yield savings accounts paying >2% interest. That was possible because the effective fed funds rate (EFFR), which is the average rate banks lend and borrow funds to each other, was above 2% for all of 2019.

Last 3 Years Fed Funds Rate (source)

That all changed in 2020 when the EFFR dropped to 0.05% (and hasn’t risen above 0.10% since), which meant that top online banks had to drop their rates and are now only paying 0.10-0.50% APY in their “high yield” savings accounts. That’s not just a problem because we all want to be earning more, it’s a problem because inflation (the increase in prices) is on the rise, hitting 6.2% in October (the highest level since 1990).

🏦 Where to Put Cash

So where do you put cash? I don’t want any restrictions on the account I use to pay bills each month, so I’m ok living with a low or no interest checking account. But where does the rest of the cash go? Here’s where I put my cash, along with one new option I’m considering:

Crypto Interest Accounts: Many crypto products have popped up here in the past few years, but the BlockFi Interest Account has now become the primary place I store cash. My deposits are automatically converted to USDC stablecoin and earn 9% APY accrued daily and compounded monthly. If you’re like me, you might wonder how this is possible. They generate interest by lending out your deposits to borrowers and because most large financial institutions aren’t tied into this ecosystem to lend money (similar to the cannabis industry) the rates are much higher. While most loans are overcollateralized, these accounts are not FDIC insured, so I would consider it higher risk than a traditional bank. However, despite multiple big crashes in the crypto markets, my account hasn’t been impacted once so it remains my primary place for cash. In fact, I’ve been such a fan of BlockFi for the last year that I reached out to them to see if they’d be interested in sponsoring the podcast. They said yes, so if you sign up with this link you can get up to $250 free. Also, I recorded an episode with the CEO of BlockFi to talk about how these accounts work, so if you want to learn more, you can listen here.
AA Miles Savings Account: Bask Bank offers an FDIC-insured savings account, but instead of paying $ interest, they pay American Airlines miles at a rate of 1 mile per dollar per year. With AA miles valued at 1.4¢ that’s an effective APY of 1.4%, but here’s the kicker: for tax purposes, Bask only values AA miles at 0.42¢, so if you assume a 35% marginal tax rate you could argue that the effective APY is 1.93% because you’re paying less taxes. I like having some miles with every airline and AA isn’t a transfer partner of any major credit card program, so I always keep some money at Bask to help boost my AA balance. However, keep in mind that if you don’t already have some AA miles you’ll probably need to keep at least $10,000 in this account to earn enough miles in one year for the cheapest award flights (e.g. one-way domestic).
Investing and not holding cash: This is a controversial one, so hear me out. Almost all of my long term investments are at Wealthfront, where I can take a PLOC loan against my portfolio for 2.4%. I also hold a few stocks at Interactive Brokers who offers the same option at 1.07%. Now, borrowing against your portfolio has a few major risks to call out: 1) your interest rate isn’t fixed and might go up at any time and 2) if the value of your investments falls significantly, you may receive a margin call and have to repay some of the loan to meet your equity requirements. However, if the amount you need to borrow is a small fraction of your portfolio, it’s much less likely that this will happen (example below). So, for short term needs during a low interest rate environment, where you have enough in your investment account that you’d need to borrow a small percentage of your portfolio, this might be a viable alternative to cash. For me, it’s replaced holding a large emergency fund in cash.
- Example: If you had $100,000 in a Wealthfront portfolio and borrowed $25,000, you wouldn’t need to make a repayment unless your portfolio dropped ~60% to $40,000, which I don’t think has ever happened in my lifetime for a globally diverse passive index fund portfolio.
High Yield Savings: Yes, they might not pay enough interest to beat inflation this year, but they’re FDIC insured and the safest place to put cash. I only keep a small amount in a few of these accounts to ensure the account isn’t closed, in hopes that interest rates rise again soon. The bank with the best rate changes almost daily and most comparison sites prioritize whoever pays them the most. I think the best place to find the banks with the highest rates is Doctor of Credit. Two important things to keep in mind: 1) an extra 0.1% on $10,000 is only $10/year, so depending on your balance it might be better to focus on whatever bank is most convenient or offers the features you need (e.g. Wealthfront makes it fast to transfer to my investment account and Ally makes wire transfers easy) and 2) you don’t earn interest while your money is in transit, so chasing the best rate might actually hurt you (explained in more detail here).
LifeGoal ETFs: I’ve always struggled with giving friends a recommendation for an easy place to save for goals like a downpayment that keeps up with inflation but isn’t as risky as putting it all in the stock market. I recently came across LifeGoal Investments and am intrigued by their model. They offer a handful of ETFs, each designed specifically for goals like a child, downpayment or vacation. But most interestingly, a big part of the stock allocation in each fund is invested in companies they found to be correlated with that specific goal. For example, the largest holdings in the home downpayment ETF are Lowe’s, Home Depot and Zillow, which they hope will all be correlated with home prices and thus help your portfolio grow more if housing prices rise. They’re not a sponsor and I haven’t done enough research to endorse them, but it’s something I was excited to check out.

📊 How Much Cash To Hold

Using the three reasons I mentioned at the beginning of this email, here’s how much cash I hold for each:

Regular expenses: I typically only keep ~2x my average monthly spending in cash, however, my spending has been fluctuating quite a bit recently with a big family holiday trip and furnishing our home, so I’m now keeping a larger buffer (~4-5x monthly spending) of cash in my checking account. In a few months I hope to get back to ~2x and invest the extra cash.
Emergency funds: I like to make sure I have easy access to 6x my average monthly spending without selling my investments. However, as I mentioned earlier, I’m comfortable relying on a portfolio loan for emergencies, so I’m not currently holding any cash for this purpose.
Short Term Goals: This amount is entirely dependent on the major expenses you have planned in the next 3-5 years. For me that includes a downpayment for a new car next year, the au pair agency fee we’ll owe in January and some planned expenses for the show. I keep ~90% of this money at BlockFi and 10% at Bask Bank.

I hope all this was helpful, but I’ll be doing a Q&A episode on money, savings and investing soon, so please send any follow-up questions (or really any questions) my way by just replying to this email.

1) https://www.wealthfront.com/historical-performance

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

🛍 Saving on Holiday Shopping (+ Advice from Listeners)

Thu, 18 Nov 2021 08:00:00 +0000

Advertiser Disclosure

As we get closer to Black Friday, some of you may be finalizing your holiday gifting plans or looking for ways to minimize the spending we’ll be doing through the end of the year.

I have some tricks for navigating the holiday shopping season that will keep you from having to reenact the plot from Jingle All the Way. If you were born after this movie came out, please keep it to yourself, I’m already feeling old enough this year.

💻 Online Shopping

Cyber Monday is 11 days away and is when retailers drop all kinds of deals that can only be found online. Using Cyber Monday to your advantage is a huge strategy to save on money and rack up some cash back.

Sign up for a retailers’ newsletter for exclusive drops or coupons. Many do a “Deal a Day” throughout the shopping season and send item-specific or one-day-only coupons.
Save time by reading roundups of the best deals. A quick search of “best cyber monday tv deals” will land you on pages like this and this. I love to let sites like these do the research, so I don’t have to spend time looking at every retailer’s site. Note: this also works for Black Friday deals.
Triple stack your savings with cash-back, coupons, and credit card deals.
1. Companies like Rakuten and TopCashback offer free cash-back on many large retailers. Cash Back Monitor can also help you figure out which company offers the most cash back for any retailer.
2. On top of these cash-back deals, browser extensions like Honey will make it easy to find promo codes before you check out.
3. Finally, most credit cards offer store-specific cash-back deals too, so make sure to search their apps before shopping (I just looked through Amex’s list and found that I could get a free $25 on a purchase from Lovevery that I was already going to make (if you have a kid under 4, you should check out their play kits).
Best of all, you can stack all of these and get a discount, cash-back from a cash-back site AND cash-back from your credit card.
Online shopping helps you stick to your list. We all know venturing into Target or Costco can be dangerous. Online shopping means you physically can’t wander through a store and buy things you really don’t need.

🛒 In-Person Shopping

Let me start by saying, you are a brave soul. That said, going into a store can have great advantages.

Retailers offer In-Store Only promotions throughout the holiday season that can be better than their online offers. You can usually find the local in-store flyers on the retailer websites to find these deals. Also, some cash-back apps like Rakuten have in-store cashback offers when you use a linked credit card. Finally, don’t forget some stores offer free gift wrapping!
In-person shopping can also eliminate shipping costs and issues. While I appreciate free returns, I’d much rather pick right the first time, which is why I appreciate being able to try out products in person before buying them. Also, while large retailers can waive shipping fees, it usually takes hitting a certain dollar amount in your cart to reach it. Is spending another $25 worth getting free shipping that costs $7?
It’s easier to support small businesses in person. Your money has a much bigger impact when you shop with local merchants. Not only can you avoid those shipping costs mentioned above, but that money spent goes directly back to your community in much more impactful ways. This article from Time Magazine dives deeper into the benefits of shopping local.

🛍 Shopping Strategies

I know that shopping for gifts, or shopping in general, isn’t fun for some people. Don’t worry! I have ways to make it less torturous.

Protect your information when shopping online. Extensions like Privacy allow you to create “virtual” credit cards so retailers never see your actual card information. You can also turn them off or set spending limits at any time. Whenever I’m shopping on a site I don’t trust, I use a Privacy card.
Do some research before committing to big-ticket purchases. A site like WireCutter is perfect because they have all the lists, all the reviews and will even let you know when something goes on sale.
Always ask about return policies and keep receipts. Some retailers put more strict return policies in place over the holidays. And if you don't like keeping track of receipts, my friend Allison suggests taking a picture of every receipt so you can always look up the purchase date, return policy and even use the photo to make returns where the receipt is necessary
Don’t be afraid to ask for a discount. I’ve done this over Live Chat on some retailers’ sites and been pleasantly surprised to get coupons. If you’re in person you might also get a deal if notice things like damaged packaging, seam rips, or want to purchase a floor model.
Look for price-matching. BestBuy, Walmart, and Target all have great price-matching policies. Compare online prices and competitor prices to get the best deal.
There is nothing wrong with second-hand gifts! Not only does it save money, but it can be easier to find specific or out of circulation items. Places like Facebook Marketplace, Mercari, and eBay are ripe with deals for everything from clothes to electronics to beauty products.

💳 Holiday Credit Card Strategies

There are so many advantages to putting these credit cards to work this season. We already know about things like cash-back and redeeming those travel points, but there are so many cool perks you might not be thinking about.

Purchase protection - This is a big one! What if you shatter the screen of the brand new iPhone you just bought? By using a credit card with purchase protection (which is most of them), you can get refunded if purchases get lost, stolen or damaged. This article from Value Penguin had a fantastic breakdown of plans by credit card issuer. I’ve personally used this multiple times for broken iPhone screens, SD cards that went through the wash and more.
Travel insurance - Traveling is a high-stakes game lately. Luckily, purchasing trips through your credit card means you have access to some great travel insurance. Check out this piece from The Points Guy that covers credit card travel insurance.
Return and Extended Warranty Coverage - Some cards (like the Chase Sapphire Reserve®), will step in when a store won’t accept a return. You can also skip the extended warranty add-on because many cards will extend the manufacturer's warranty by an extra year. Definitely check your terms though as it varies between cards and certain items are not covered.
Exclusive Offers - If you want to give an experience instead, some cards have entertainment perks like early ticket releases, exclusive Invite Only events, and tickets to everything from fine dining to theater shows. For example, Marriott has a bunch of Super Bowl LVI packages on their Moments website.

🎉 Fun Gift Ideas

I don’t usually like to spend money on random silly gifts, but I’ve come across two this season that I didn’t hesitate to pull out my card for.

For the friend, sibling or in-law you love to drive a little crazy, here’s a perfect holiday card for them! Once you open it, the music won’t stop until the battery dies :)

Or if you just want to put a smile on someone’s face, Whiskey River Soap has a snarky candle for almost any situation. My most recent gift really summed up how I feel about so many of the events on my calendar over the years.

📬 Top Listener Tips

I’m so thankful to the amazing readers and listeners who shared their favorite tips and tricks with me, so I thought I’d highlight some favorites. Please keep them coming!

If you get deep in the points game, tracking your cards, minimum spend requirements and perks can be a lot of work. Al Chen emailed me to share a complete system he designed to remind him when he needs to hit signup bonuses, when certain credits are expiring, perks that need to be used, etc. He published his full template online with detailed instructions for anyone else to copy it for themselves.
After hearing me say that it’s hard to use up the entire balance of a gift card, JB emailed to share that you can add any amount (down to the cent) from an Amex/Visa gift card to your personal gift card balance on Amazon. I’ll never leave a balance on a gift card again!
John wrote in to share one of his favorite sites for deals: DealNews. His strategy for the site is signing up as a member (free) and adding alerts on all the brands or products you buy. He uses it to save $$ on the everyday purchases he makes each month, like Tide Pods and Kleenex. (John clarified that he’s not affiliated with the site, he just loves it).
A listener and famed New Yorker Cartoonist Jason Chatfield wrote in to share an amazing workout tip. He loves coffee but was never making it to the gym. He decided to throw out his coffee maker, which forced him to get out of the house each morning. He picked a coffee shop near his gym and because he already got over the hurdle of leaving the house, he’s now regularly going to the gym before getting his coffee. I love it! He’s written about this strategy and many more on his blog.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

⏱ It's About Time...

Thu, 04 Nov 2021 07:00:00 +0000

We can sometimes forget that time is a currency on its own. You can always make more money, but unfortunately you don’t get that option with time. Once it’s gone, it’s gone for good.

We can, however, find ways to minimize the time spent on those annoying or painfully mundane things which then allows us more time for things like dinner out with loved ones, rest during busy weeks, or simple moments of doing nothing on a Saturday afternoon guilt-free.

What does buying back your time look like?

Buying back your time can happen in a variety of ways.

Using Amazon Fresh or Thrive Market for grocery shopping or using a meal prep/delivery service to deliver fresh meals (here’s the ad I put on Craigslist to find a chef to deliver meals twice a week)
Hiring a cleaning or landscaping service to come to your house on a regular cadence.
Finding an au pair or nanny instead of using a daycare. This not only can save on travel time, but the savings are significant with an au pair.
Hiring a virtual assistant for your business so you can have more downtime.
Paying for a Point.me (first month for $1 with code HACKS) subscription for easier travel planning with your credit card points and airline miles.

There are services, apps, and freelancers for just about everything you can think of. Every one of those things has the ability to free up your time so you can start scheduling regular date nights with your spouse again (especially for you parents) or be able to put an extra four or five hours a week into that SQL bootcamp you signed up for.

More importantly, what does it cost?

Price is not indicative of value because value looks different for everyone. When it comes to the cost of buying back your time, it’s really a question of what is this convenience worth to you?

There are plenty of ways to buy back your time that actually don’t cost anything. It can be about finding ways to be more efficient with your time. As Laura Vanderkam states, “Being mindful allows you to seize the time that is there. And if we think about how we’d like to spend our time we vastly increase the chances that we use it for things that are meaningful for us.” This could look like:

Teaching children how to make their own snacks or do their own laundry so parents don’t have to stop one task to complete another. Laura Vanderkam details more of these in Episode 7.
If you work from home, doing chores like laundry during the week so you don’t have to stay home and do it over the weekend.
Limiting time on social media or on your phone in general. Patrick McGinnis spoke directly about this and gives tips on how to avoid time wasted on your phone.
Learn how to become indistractable so you use your time efficiently in the first place. Nir Eyal shared his four steps to becoming indistractable in Episode 25.

Other things, like hiring a virtual assistant, have a significant cost. However, if hiring that VA means your workday is cut from 12 hours to 8 or even less, would gaining those hours back be worth the cost of their services? That trade-off between what you spend and what you gain is something only you can weigh and answer.

There’s no right or wrong way to save time. We all live very different lives and how each of us maximizes the hours in our days should look different. As long as whatever you’re doing works for you and gives you the desired results, I’d say it’s a successful strategy.

Do you have tips and tricks to buy back your time? I’d love to hear about them! Respond to this email with your favorite time-saving strategies and we’ll feature some in upcoming newsletters.

Need help finding ways to save time or steps to find out what you actually want to spend your time on? Check out these previous podcast episodes.

The Four Research-Backed Steps to Be Indistractable with Nir Eyal
The Science of Behavior Change with Kristen Berman
FOMO, FOBO and How To Make Great Decisions with Patrick McGinnis
Managing Your Time To Get More Done with Laura Vanderkam

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

$2,000 Discount on a Peloton

Thu, 21 Dec 2017 08:00:00 +0000

Living in San Francisco, it’s hard not to find yourself in a regular discussion about the latest startups or living a healthy lifestyle. So when a Peloton launched a in-home cycling experience similar to SoulCycle, it seemed to come up in quite a few conversations. Then I saw it show up on HuffPo as the top 2017 holiday gift.

Now, I don’t even own a bicycle, but since starting Grove, I’ve found myself with less and less time to get to the gym. So when a few friends mentioned how much they loved their Peloton, it piqued my interest. Between its beautiful design, my wife’s love of spin classes and the prospect of more frequent exercise, I immediately decided I wanted to one…

Then I saw how much it cost:

There MUST be another way

If you know me, you know that at that price, a Peloton was off the table. But I’d convinced myself that I needed it, so it was time to optimize. After learning that Peloton had an app with access to all their live and on-demand content, I quickly found a group of 1,000+ people on Facebook doing what I wanted to do. It was time to build a DIY Peloton.

The plan was to find a belt driven (much quieter) indoor bike that I could pair with a bluetooth cadence sensor (an important metric used in all thePeloton classes). For streaming classes, I was going to put an iPad mount on the bike, but since the Peloton app supports AirPlay, I decided I would just stream classes from my iPhone to the Apple TV in our living room.

What it Cost

Just a few hours later, I was checking out with everything I needed on Amazon. Here’s what I ended up buying and how much it cost:

Sunny B1509 Belt Drive Bike ($351.14) - currently unavailable, so I’d recommend the B1002 and a new set of pedals with clips
Peloton app + subscription ($12.99/mo)
Wahoo Cadence Sensor ($39.99)
Sbode iPhone Mount ($11.99)
Old iPhone ($0, already owned) - to show cadence from the Wahoo sensor
Apple TV ($0, already owned) - to AirPlay classes from the app to my TV

Total Cost: $403.12 = $2,011.46 saved = 83% discount

Not only did I ended up saving >$2,000 on the bike, but since Peloton’s monthly subscription is $26/month more when you have their bike, I’ll end up saving an additional $312/year.

My Sunny B1509

Do I wish I had the real thing?

The DIY experience isn’t perfect and certainly has its shortcomings (see below). That said, I don’t think any of what I’m missing is worth the extra $2k + $26/mo. Here’s where the DIY approach falls short:

Setup for each class: Before every class I need to open the Wahoo fitness app on my old iPhone (which needs to be charged), then open the Peloton app on my current iPhone and stream it to my AppleTV.
Ride tracking/sharing: A Peloton bike tracks all your ride metrics and allows you to see how you’ve improved over time and compete with other friends on the platform. Since the Peloton app doesn’t have any integration with my bike or cadence sensor, the only metrics I track are from logging the workout on my Apple Watch.
Precise resistance: In Peloton classes, the instructors tell you what cadence and resistance to ride at. The Peloton bike displays your real-time resistance level, so it’s easy to set to the precise level, but since there isn’t a 3rd-party resistance sensor, my DIY setup means you have to get a feel for the right level. After my first 2–3 rides, I found this super easy to do.
Motivation/leaderboard: For classes on the Peloton bike, you can compete in real-time with everyone who has taken the ride and in live classes, the instructors often give shoutouts to riders at home. No workaround here, but not a big deal to me.

The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Life Lessons From Granddad

Mon, 14 Apr 2014 07:00:00 +0000

John Leslie Sayre (March 28 1924 - April 11 2014)

In The Sun Also Rises, Hemingway writes:

Don’t you ever get the feeling that all your life is going by and you’re not taking advantage of it? Do you realize you’ve lived nearly half the time you have to live already?

If you posed that question to my granddad, he’d tell you he never once got that feeling. He lived his life to the fullest, taking every opportunity to explore new places, meet new friends or have an interesting conversation. A man so full of goodness, kindness, and love, he remains a lasting example to all the lives he touched long after their last encounter. Here are just a few of the things my grandfather taught me that have already shaped my life and will continue to guide me for many years to come.

Love

I’ve never seen two people more in love than John and Herwanna Sayre. From an early age, I always knew I wanted to find a relationship like theirs. They had so much in common and enjoyed all of life’s experiences together. Whether it was playing bridge, cooking, traveling or singing in the choir, it was incredibly easy to see that they were best friends. Even this year, 66 years after they were first married, they were still in as much love as I’d ever witnessed.

No love is all fun and games… I’m sure disagreement took place behind closed doors, but the only arguments I ever saw them have were about things, mostly jewelry, that Herwanna wanted to buy (or already did). Granddad always said her name was so fitting: “Her wanna this, her wanna that”). And every time she heard him say it, she would laugh, partially because she knew it was true and partially because she knew he was the ultimate saver. Which is why a few years ago, when my grandpa dropped some serious cash to buy his wife a forever ring as his grand gesture that their love was endless and would last forever, the entire family was floored and in awe.

Granddad, you’ve inspired all of us to be the best husband or wife possible, and to work hard to share all the experiences we can with the ones we love. I can’t wait to show the world that, after 66 years of marriage to my incredible wife Amy, you’re not the only couple that can be as happily married as you two were.

Family

My grandfather’s love didn’t just stop at Herwanna. He loved the rest of his family just as much and made sure that love was instilled in every generation to come. During my time with him a few weeks ago, one of his neighbors casually mentioned that she had a great family… Granddad didn’t hesitate for a moment before belting out “Well I have an amazing family too, and I love them very much.” He was so proud of every one of us, never pushed to be something we weren’t, loved us unconditionally (even when we all went through that phase of life we’re not proud of), and did whatever it took to encourage the whole family to get together as often as we could.

This love of family started as early as my mother can remember. Their family of six ate every meal together, traveled together on every vacation, and even after the kids left for college, everyone reunited at my grandparents house for the holidays. Every Christmas they’d pack the family up and traveled to both of their grandparents’ homes (my great grandparents) and spent time with the whole extended family.

While my own family may not have eaten every meal together or taken every trip together when I was a child, we all still recognized and understood the importance of family, thanks to Granddad. It’s unrealistic to expect my future family to do absolutely everything together, with the added chaos that life brings us each year, but you can bet that I will do everything I can to make them see and understand just how much I love them and care for each and every one of them.

Travel

It was in the late 1950s, while living in Stillwater, Oklahoma that my grandpa began to travel with his family. Each year they drove to a different part of the country, to visit national parks, world’s fairs and even to Canada when they were ambitious enough. It wasn’t until 1975 that my grandparents crossed the Atlantic on their first overseas trip. What would follow for the next 33 years was a world of adventures to dozens of countries across almost every continent.

Some of my earliest memories of my grandparents were of stories they told about the places they’d been and the people they’d met around the world. For them, traveling was never about checking countries off their list, it was about immersing themselves in new cultures and experiencing the people, the local music, the traditional foods and all the other unique things each country had to offer.

I don’t remember when I got my own travel itch but it came early and it’s been a core part of who I am ever since. There was something about hearing those stories, learning about those cultures and seeing the thousands of pictures from each of their experiences that made me want to get out and see the world, too. I feel lucky to have found a wife who shares this passion with me, and who wakes up every day and dreams of the next adventure we’ll take together. I haven’t yet had the chance to see as much of the world as my granddad has, but I’m catching up, and will continue to explore until there’s nothing left to see.

Saving

Anyone that knew my grandfather knew that he was far from a big spender. My mother tells me stories about growing up in a house filled with extra paper towels, aluminum foil and every other household supply you could imagine, all bought on sale, because Granddad never wanted to risk having to buy something at full price. This tendency didn’t stop at home. Anyone who traveled with him saw his suitcases filled with cans and boxes of food, because Granddad didn’t want to spend money going out for dinner every night.

You might be reading this wondering how two people could travel so much when one of them is has a near-allergic reaction to spending money, and the answer to that is that Granddad simply knew how to be frugal. In their early days, family trips were all by car and the family camped everywhere they visited. When my mother or her brothers and sisters were hungry, Granddad pulled to the side of the road and took out the Coleman grill to cook a meal instead of stopping at a restaurant.

But once Grandma and Granddad started exploring the world, they couldn’t bring their car and camping gear, so Granddad needed a new solution. He started Sayre Tours and organized group trips at home and abroad, where he and my grandmother would lead their friends and others around the world. As the tour guides, they always traveled free, stayed free, ate free, and, well, you get the point.

It’s easy to see that I’ve adopted Granddad’s same behavior. I, too, am a travel agent, and I use those credentials to get discounted travel all the time. The only difference is that my secret weapon has been mastering the game of credit card points and frequent flier miles. They’ve allowed my wife Amy and me to travel all over the world, just like my grandparents did, on the cheap. So thank you Granddad, without your inspiration, I’m not sure I would have been able to see things I’ve seen, meet the people I’ve met, or learn the things I’ve learned so far in life.

As I write this, I can’t help but think of hundreds of other things my granddad taught me. He was kind and passionate, adventurous and thoughtful, and always wanted the best for everyone. He will be a hard act to follow, but has served as a role model and an inspiration to everyone he met. I’ll never forget the person I’ve become thanks to his guidance and wisdom.

I love you Granddad.