Your Money Guide on the Side

Episod

• The 80% Problem: Why Wealthy People Don't Save for a Rainy Day 01.06.2026 30min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠tyler.gardner.com/book⁠⁠ and be eligible for all monthly incentives between now and December 1st! And as always, a MASSIVE thank you to this week's sponsors: ⁠Facet⁠: → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! LMNT⁠: → drinklmnt.com/tyler Become an INSIDER, just order the INSIDER Bundle–four boxes for the price of three, best value they offer–and get early access to limited time flavors and cool surprise gifts along the way. ⁠⁠Gelt⁠⁠: → ⁠⁠joingelt.com/tyler⁠ because Q2 is where strategic businesses (like mine!) make game-changing tax moves. If you're a business or a high-net worth individual, I'd encourage you to check this one out today. ⁠ Keeper: → keepersecurity.com/tyler for 60% off personal and family plans for our podcast listeners only! Use this link, so they know we sent you. And now, on to the show notes!! We’ve been taught that saving money is responsible: Save for a rainy day. Delay gratification. Spend less. Save more. But what if the way most people save is actually making them slightly poorer? In this episode, Tyler challenges one of personal finance’s most sacred ideas: that keeping large amounts of money sitting in savings is the safest thing you can do. Because safety and stagnation are not the same thing. In this episode, Tyler covers: Why inflation quietly destroys the value of traditional savings The hidden cost of opportunity cost — and what cash could have become if invested Why banks profit from your savings more than you do The problem with oversized emergency funds sitting idle Why fear — not math — drives many financial decisions Smarter alternatives for liquidity, from Treasury bills to Roth IRAs Why retirees often die with most of their wealth untouched The difference between saving as a tool vs. saving as an identity Tyler also makes a more personal argument: That many of us inherit financial beliefs built around scarcity, caution, and delayed gratification — even when we no longer need them. The core idea: Money is meant to support your life, not become the thing preventing you from living it. Invest broadly. Keep reasonable liquidity. Spend intentionally on the things that actually matter. And maybe, every once in a while… Eat the shrimp instead of the mashed potatoes. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
• The 5 Best (And Worst) Cars You Could Ever Buy (Financially Speaking, Of Course) 25.05.2026 39min

  Pre-order Tyler's book, Real Wealth, at ⁠tyler.gardner.com/book⁠ and be eligible for all monthly incentives between now and December 1st! And as always, a MASSIVE thank you to this week's sponsors: ⁠⁠Wispr Flow: → wisprflow.ai/tyler for one free month of Wispr Flow Pro free! (And to make your life immensely more efficient.) ⁠⁠Copilot Money⁠: → ⁠www.copilot.money/tyler⁠ — use code TYLER2 for two free months and find out why my entire finance-friend group chat uses Copilot Money daily. ⁠Bilt⁠: → joinbilt.com/tyler to see which credit card is right for you and to start getting rewarded for your biggest annual expense: your rent or mortgage!⁠ ⁠Fabric⁠: → ⁠meetfabric.com/tyler⁠ because if ANYONE depends on your income, getting term life needs to be moved to the top of your priority list today. And on to the show notes! The average American spends roughly $12,000 per year on their car. For many people, that’s more than they invest. In this episode, Tyler breaks down the real cost of car ownership — not just the sticker price, but the hidden financial drag of depreciation, financing, insurance, fuel, and maintenance. Because most people buy cars emotionally… and only look at the math afterward. In this episode, Tyler covers: Why the monthly payment is the least important number in a car purchase The true long-term cost of luxury cars, trucks, and financed EVs Why used Toyotas and Hondas dominate on total cost of ownership The financial trap of buying older German luxury cars out of warranty Why a financed Tesla can be far more expensive than people realize The surprising math behind the Toyota Prius and Corolla Why “boring” cars quietly create wealth over time The difference between a vehicle as a tool vs. a lifestyle purchase Tyler also explains why he believes people should stop optimizing every dollar purely for efficiency. Because personal finance isn’t about removing joy from your life. It’s about being intentional enough to know which things are genuinely worth spending on — and cutting ruthlessly everywhere else. The episode ends with Tyler revealing the one category where he knowingly ignores his own financial advice: A brand-new GMC Sierra Denali. Not because it’s the best financial decision. Because it’s the thing he genuinely loves. The core idea: Don’t spend blindly. But don’t optimize the humanity out of your life either. Know your “no’s.” Then spend unapologetically on your “yes.” If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
• How to Divorce-Proof Your Finances (Whether You're Married, Divorced, or Somewhere In Between) 18.05.2026 42min

  Pre-order Tyler's book, Real Wealth, at tyler.gardner.com/book and be eligible for all monthly incentives between now and December 1st! And as always, a MASSIVE thank you to this week's sponsors: ⁠Gelt⁠: → ⁠joingelt.com/tyler because Q2 is where strategic businesses make game-changing tax moves. If you're a business or a high-net worth individual, you might want to check this one out today. Momentous⁠: → ⁠⁠livemomentous.com⁠ Use code Tyler for 35% for up to 35% off your first order! Facet⁠: → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! LMNT⁠: → drinklmnt.com/tyler⁠ Become an INSIDER by ordering the INSIDER Bundle–four boxes for the price of three, best value they offer–and get early access to limited time flavors like my new favorite, lemonade iced tea! And now, on to the show notes! Most people who get financially devastated by divorce didn’t lose because they were reckless. They lost because they weren’t prepared to operate independently when life changed unexpectedly. In this episode, Tyler breaks down the financial side of divorce — not just for people currently going through one, but for anyone building a life with another person. Because financial awareness inside a marriage is not distrust. It’s maturity. In this episode, Tyler covers: Why both partners should fully understand the household finances The importance of shared access to accounts, passwords, and financial documents Why every adult should have their own individual emergency account The financial reality of “winning” the house in a divorce What a QDRO is — and why misunderstanding it can cost tens of thousands Why beneficiary designations matter more than most wills How to build independent credit before you need it Why recently divorced people are especially vulnerable to bad financial advice The importance of a 6–12 month financial freeze before making major decisions Tyler also explains how some advisors specifically target recently divorced people — and how to tell the difference between real guidance and someone capitalizing on vulnerability. The core idea: Financial independence inside a relationship is not a backup plan. It’s part of being an adult. Because whether a marriage lasts five years or fifty, every person deserves the ability to confidently understand and manage their own financial life. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
• What I'd Do If $1,000,000 Landed in My Account Tomorrow: 3 Moves, 3 Mistakes, 3 Red Flags 11.05.2026 45min

  Pre-order Tyler's book, Real Wealth, at ⁠tyler.gardner.com/book⁠ and receive two chapters that didn't make the final cut in digital form in early June. And as always, a MASSIVE thank you to this week's sponsors: Keeper: → keepersecurity.com/tyler for 60% off personal and family plans for our podcast listeners only! Use this link, so they know we sent you. Anthropic⁠: → ⁠⁠claude.ai/tyler ⁠to find out why they continue to be my number one strategic thought partner. Thrive Market⁠: → ⁠⁠thrivemarket.com/tyler for⁠ $20 off your first three orders plus you’ll get a FREE $60 gift! Copilot Money⁠: → ⁠www.copilot.money/tyler — use code TYLER2 for two free months. And now on with the show notes! You wake up tomorrow morning and there’s $1 million sitting in your account. What’s the first thing you do? Most people think they know the answer. In reality, most people panic, freeze, or make expensive decisions out of emotion. In this episode, Tyler walks through exactly what he would do with a sudden lump sum of money — practically, immediately, and without turning it into a fantasy exercise. Because having money doesn’t automatically make people better with money. It just makes mistakes more expensive. In this episode, Tyler covers: Why the first move is protecting the cash, not investing it immediately The difference between parking money in a checking account vs. a money market fund Why paying off high-interest debt is often the best guaranteed return available The “bucket framework” for investing based on when you need the money, not your age Why low-cost index funds still beat most “sophisticated” strategies How investing in your primary residence can improve both lifestyle and tax efficiency Why most people confuse complexity with competence in investing The psychological traps that show up once you have money Tyler also explains why he wouldn’t immediately buy expensive depreciating assets — and why the goal is to get the principal working hard enough that the returns eventually pay for the lifestyle instead. The core idea: A million dollars isn’t the destination. It’s the infrastructure. The real question isn’t what you buy. It’s what kind of life the money gives you the freedom to build. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
• My Interview with Burton Malkiel (That You Will Never Hear) 04.05.2026 42min

  Pre-order Tyler's book, Real Wealth, at tyler.gardner.com/book And as always, a MASSIVE thank you to this week's sponsors: Fabric: → ⁠meetfabric.com/tyler⁠ because if you have dependents, and you don't have term life, getting term life insurance is the financial step you need to take right now. Gelt: ⁠→ ⁠joingelt.com/tyler because Q2 is where strategic businesses make game-changing tax moves LMNT: → ⁠drinklmnt.com/tyler⁠ Become an INSIDER, just order the INSIDER Bundle–four boxes for the price of three, best value they offer–and get early access to limited time flavors and cool surprise gifts along the way. Facet: → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! And see for yourself why I've partnered with Facet for almost TWO YEARS! And now on with the show notes! What if the most important investing conversation you’ve ever had… never got recorded? That’s what happened here. In this episode, Tyler reconstructs a lost interview with Burton Malkiel, author of A Random Walk Down Wall Street, and uses it to tell a bigger story — one about index investing, behavior, and why the simplest strategy is still the hardest to follow. Because this isn’t just about theory. It’s about what actually works in real life — and why people still struggle to stick with it. In this episode, Tyler walks through: The origin of index investing — and why Wall Street fought it for decades Why most active managers fail to beat the market after fees The role of academics like Markowitz, Fama, and Samuelson in shaping modern investing How fear and behavior — not knowledge — derail most investors Why trying to time the market (even when you’re right) can still cost you returns The risk of concentration in modern index funds — and why it’s not a new problem Malkiel’s core principle: you will never consistently outguess the market Tyler also shares one of the most important takeaways from the conversation: Even Burton Malkiel feels fear. He just doesn’t act on it. And that’s the difference. The core idea: Investing isn’t about being right. It’s about staying consistent when it’s hardest to do so. The episode closes with a broader reflection on retirement — not just how to invest, but how to live. Because according to Malkiel, the goal isn’t to stop working. It’s to stay engaged — with ideas, with learning, and with life itself. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
• The 0% Tax Bracket Most Retirees Walk Right Past 27.04.2026 41min

  As always, a MASSIVE thank you to this week's sponsors! LMNT⁠: → ⁠drinklmnt.com/tyler⁠ Become an INSIDER, just order the INSIDER Bundle–four boxes for the price of three, best value they offer–and get early access to limited time flavors and cool surprise gifts along the way. ⁠Bilt⁠: → ⁠joinbilt.com/tyler⁠ to get rewarded for your biggest annual expense! ⁠Copilot Money⁠: → ⁠try.copilot.money/tyler⁠ and use code TYLER2 for two free months. ⁠Gelt⁠: → ⁠joingelt.com/tyler and see if you can get your business tax planning to the next level in 2026 and beyond! And now, on with the show notes! Most retirement withdrawal conversations focus on one number: 4%? 5%? 6%? But that misses a much bigger variable: Taxes. In this episode, Tyler revisits his $2 million retirement portfolio framework and explains why the real issue isn’t just how much you withdraw — it’s how much you keep after taxes. Because two retirees can withdraw the exact same amount and end up with very different lifestyles depending on how their accounts are structured. In this episode, Tyler covers: Why after-tax returns matter more than headline portfolio returns The hidden cost of relying too heavily on traditional IRAs and 401(k)s How Roth conversions can reduce future tax pain Why taxable brokerage accounts are one of the most underrated retirement tools How the 0% capital gains bracket can legally lower taxes in retirement Why withdrawal order matters: taxable, pre-tax, and Roth accounts each play different roles How poor tax planning can quietly reduce spending power for decades Tyler also explains why the classic withdrawal-rate debate often misses the point entirely. A 6% withdrawal with poor tax planning may feel like 4.75%. A well-structured 6% withdrawal may feel like…6%. The core idea: The goal was never to withdraw less. The goal was always to keep more. This episode isn’t about tax gimmicks or loopholes. It’s about understanding the rules well enough to make smarter decisions with the money you’ve already built. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
• I Moved to Arizona for the Winter: The 5 Things Nobody Tells You About Snowbirding 20.04.2026 40min

  As always, a MASSIVE thank you to this week's sponsors! Momentous: → ⁠livemomentous.com Use code Tyler for 35% off your first order! Thrive Market: → ⁠thrivemarket.com/tyler $20 off your first three orders plus you’ll get a FREE $60 gift! Facet: → ⁠facet.com/tyler for an exclusive $550 kickstart offer! Anthropic: → ⁠claude.ai/tyler if you're looking for the best business and thought partner I have EVER had. And on to the show notes! Most financial advice focuses on optimization. This episode is about something else entirely: alignment. In this more personal episode, Tyler shares five lessons from spending two months “snowbirding” in Sedona — and what the experience revealed about money, time, and the life we think we want. Because sometimes the biggest financial insights don’t come from spreadsheets. They come from living differently long enough to notice what actually matters. In this episode, Tyler reflects on: Why buying back time only works if you know what to do with it The idea of a “path dividend” — testing lifestyles before committing to them How lifestyle upgrades quickly become your new normal (and lose their impact) Why major life changes require understanding what you’re leaving, not just gaining The illusion that a new place will create a new version of you Along the way, Tyler connects everyday moments — cooking dinner, staying in Airbnbs, almost buying a house — to deeper financial decisions around spending, relocation, and retirement. The core idea: Wherever you go, there you are. Money can change your environment. It doesn’t automatically change you. This episode isn’t about maximizing efficiency. It’s about building a life that actually fits — before you build the plan to fund it. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
• 5 Hard Truths About Investing From 26 Years at Motley Fool | Chris Hill 13.04.2026 37min

  Pre-Order Tyler's First Book, Real Wealth, ⁠⁠here⁠⁠ & be immediately eligible for exclusive bonuses between now and December 1st! April Bonus: Free two-hour digital live event on Wednesday, May 6th from 7-9pm EDT, where Tyler will answer the most commonly asked questions and walk through what you can expect from the book! And as always, a MASSIVE thank you to this week's sponsors: LMNT just dropped a limited-time Pink Lemonade flavor — exclusively for LMNT INSIDERs, which means you need to order the INSIDER Bundle (four boxes for the price of three) to get it. If you like your electrolytes without the sugar and your hydration without the regret, this one's for you: → drinklmnt.com/tyler Fabric: ten minutes online, no health exam, no phone calls, a million dollars in coverage for less than a dollar a day — and if you're young and healthy, there's no better window to lock this in than right now. → meetfabric.com/tyler Copilot Money tracks your spending, net worth, investments, subscriptions, and savings goals in one place — and it's the only personal finance app to win an Apple Editor's Choice Award, with a 4.8-star rating from over 25,000 reviews. → try.copilot.money/tyler — use code TYLER2 for two free months. And on to the show notes! Most people think investing is about finding the next big thing. The reality is much less exciting — and far more effective. In this episode, Tyler sits down with Chris Hill, longtime host of Motley Fool Money, to talk about what actually drives long-term success in investing — and why so many people get distracted along the way. From launching a podcast during the 2008 financial crisis to interviewing some of the biggest names in business and finance, Chris shares lessons from decades inside one of the most influential investing platforms. In this conversation, Tyler and Chris discuss: How Motley Fool Money started during a crisis — and why simplicity won Why investors obsess over “hot stocks” and excitement (and why that hurts returns) The importance of time in the market — and not interrupting compounding Why the best companies are often the ones everyone already knows The balance between simple index investing vs. active stock picking Chris also reflects on what makes a great investor over time — and it’s not intelligence or access. It’s patience. Discipline. And the ability to ignore noise when it matters most. The core idea: Investing isn’t about being clever. It’s about staying consistent long enough for compounding to do its job. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
• The $172,000 Retirement Surprise (And Exactly How to Avoid It) 06.04.2026 46min

  Pre-Order Tyler's First Book, Real Wealth, ⁠here⁠ & be immediately eligible for exclusive bonuses between now and December 1st! April Bonus: Free two-hour digital live event on Wednesday, May 6th from 7-9pm EST, where Tyler will answer the most commonly asked questions and walk through what you can expect from the book! And as always, a MASSIVE thank you to this week's sponsors: Thrive Market: Get $20 off your first three orders plus a FREE $60 gift if you order at thrivemarket.com/tyler today. Facet: find out why I have been endorsing Facet for over 18 months now by checking out ⁠facet.com/tyler⁠. They are a one-stop shop for financial planning, investment management, tax strategy, and retirement planning. And best part: it's all for one flat annual membership fee. And on to the show notes! No one wants to think about long-term care. Which is exactly why most people don’t plan for it. In this episode, Tyler tackles one of the most uncomfortable — and most overlooked — parts of financial planning: what happens if you live long enough to need care. Because longevity is a gift. And financially, it’s also a risk. In this episode, Tyler covers: The reality that ~70% of people over 65 will need some form of long-term care What long-term care actually means (it’s not just nursing homes) The real costs — from home care to assisted living to memory care Why long-term care is separate from normal retirement planning The four ways to pay for it: self-insuring, Medicaid, traditional insurance, and hybrid policies Why Medicare doesn’t cover what most people think it does How to estimate your true long-term care exposure (and why it can reach seven figures) The biggest mistakes people make — including relying on kids or “figuring it out later” Tyler also lays out a clear, practical framework: Understand your numbers. Decide who pays. And make the decision before you need it. The core idea: A retirement plan isn’t complete until it answers one question — what happens if care is required? Because this isn’t just a financial decision. It’s a decision that affects your spouse, your kids, and how the last chapter of your life actually plays out. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
• Why I'm Taking Social Security at 62 (And Why the "Wait Until 70 Crowd" Might Want to Pay Attention) 30.03.2026 39min

  Pre-Order Tyler's First Book, Real Wealth, here & be immediately eligible for exclusive bonuses between now and December 1st! As always, a MASSIVE thank you to this week's sponsors: LMNT⁠: regardless of who much money you have, if you're not feeling your best physically and mentally, it means very little. That's why I drink ⁠LMNT⁠ daily (well, multiple times a day) to continue to be as productive as I can be after my workouts. Try ⁠drinklmnt.com/tyler⁠ today and let me know what your favorite flavor is! Copilot Money⁠: if you are looking for one of the most well-designed money apps out there, check out ⁠Copilot Money⁠ today. My friends and family continue to rave about it, and they now have all of their money needs in one place. Check out ⁠try.copilot.money/tyler ⁠today and use code TYLER2 for two free months, so you can see if it works for you! Anthropic⁠: I use Claude AI every single day as a thought partner and business strategist. To become more efficient and solve problems more quickly and effectively, check out ⁠claude.ai/tyler⁠ today. There is no single business move I have made in the past year that has been more worthwhile and productive. And on to the show notes! When should you take Social Security? It’s one of the most debated — and most personal — financial decisions you’ll ever make. In this episode, Tyler makes a serious, data-backed case for taking benefits at 62 — not as a blanket recommendation, but as a counterpoint to the conventional advice to always wait. Because this decision isn’t just math. It’s math layered on top of real life. In this episode, Tyler covers: The break-even math between taking benefits at 62, 67, and 70 Why waiting only “wins” if you live past your late 70s or early 80s The idea that a dollar at 62 isn’t equal to a dollar at 82 How the “go-go, slow-go, no-go” phases of retirement change how money is experienced The often-overlooked healthcare gap between 62 and 65 — and what it can cost How the earnings test reduces (but doesn’t eliminate) benefits if you keep working Why Social Security decisions should factor in your spouse’s survivor benefit Tyler also introduces a practical framework — six key questions — to help you make the decision based on your own life, not a generic rule: Health. Healthcare. Work status. Income needs. Spousal impact. And how you actually want to spend your time. The core idea: This isn’t about maximizing dollars. It’s about maximizing life. For some people, waiting is the right call. For others, taking it early — and using that money when it matters most — may be the better decision. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
• 5 AI Prompts That Will Change How You Manage Money (And 3 Things It Still Gets Dead Wrong) 23.03.2026 37min

  As always, a MASSIVE thank you to this week's sponsors: Gelt: I will forever regret not prioritizing a tax strategist early in my solopreneur journey. Don't make the same mistake I did and leave money on the table. If you are a business owner or a high net worth individual, check out Gelt today at joingelt.com/tyler. Fabric: there is a reason that term life insurance is number 4 in my financial order of operations, before an Emergency Fund, and before funding the Roth IRA. If anyone else depends on your income, cross this off your list today in ten minutes at meetfabric.com/tyler. And on to the show notes! AI isn’t replacing financial advisors. But it is getting surprisingly good at doing one of the most valuable parts of the job: stopping you from making bad decisions. In this episode, Tyler breaks down how to actually use AI as a financial tool — not for stock picks or shortcuts, but for clarity, structure, and behavioral coaching. Because the biggest gap in investing isn’t information. It’s execution. In this episode, Tyler covers: Why most investors underperform the market — and how behavior drives that gap How to build a complete financial snapshot for better decision-making How to use AI to uncover your real risk tolerance (not the one you think you have) How to create a simple, diversified investment strategy using structured prompts Why asset location (where you hold investments) matters more than most people realize How to stress test your plan using worst-case scenarios and Monte Carlo thinking How to use AI as a behavioral guardrail during market volatility The real risks: privacy concerns, bad prompts, and AI hallucinations The core idea: AI is a tool, not a replacement for judgment. Used well, it can help you think more clearly, avoid emotional decisions, and build a plan you actually understand. Used poorly, it can give you confident-sounding answers to the wrong questions. If you take one thing from this episode, it’s this: Better inputs lead to better decisions. And if AI helps you slow down, ask better questions, and avoid one major mistake, it’s already paid for itself. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
• How to Make Your Child Absurdly Wealthy for Absurdly Little 16.03.2026 47min

  As always, a MASSIVE thank you to this week's sponsors: LMNT: regardless of who much money you have, if you're not feeling your best physically and mentally, it means very little. That's why I drink LMNT daily (well, multiple times a day) to continue to be as productive as I can be after my workouts. Try drinklmnt.com/tyler today and let me know what your favorite flavor is! Copilot Money: if you are looking for one of the most well-designed money apps out there, check out Copilot Money today. My friends and family continue to rave about it, and they now have all of their money needs in one place. Check out try.copilot.money/tyler today and use code TYLER2 for two free months, so you can see if it works for you! Facet: find out why I have been endorsing Facet for over 18 months now by checking out facet.com/tyler. They are a one-stop shop for financial planning, investment management, tax strategy, and retirement planning. And best part: it's all for one flat annual membership fee. Check out facet.com/tyler and see if they're the right fit for you! And on to the show notes! Many parents want to help their kids financially — but often focus on the wrong things. Saving for a wedding, helping with a down payment, or paying for grad school can help in the moment. But the biggest advantage you can give a child financially is time. In this episode, Tyler breaks down how investing small amounts early in a child’s life can turn into millions thanks to compound growth — and walks through the most practical ways parents can do it. In this episode, Tyler covers: How investing $3,000 per year for a decade could grow into millions over a lifetime The power of giving a child 20–30 extra years of compounding How UGMA/UTMA accounts work and their tax implications Why a custodial Roth IRA can create completely tax-free retirement wealth A lesser-known strategy: investing in your own brokerage account and passing assets down with a step-up in basis Why 529 plans are useful — but often overhyped and less flexible The key takeaway: when it comes to investing for your kids, starting early matters far more than the amount you invest. Even small, consistent contributions can grow into life-changing sums over decades. If this episode helped clarify your approach to investing for your family, consider leaving a quick review on Apple Podcasts or Spotify — it helps others find the show.
• How to Stop Buying a Life That Isn't Yours | Hanna Horvath, CFP® 09.03.2026 41min

  As always, a massive thanks to this week's sponsors: Anthropic: I use Claude AI every single day as a thought partner and business strategist. To become more efficient and solve problems more quickly and effectively, check out claude.ai/tyler today. Bilt: If you're not earning rewards from your biggest annual expense (rent and mortgage!), you might just be missing out. Learn more about their three new credit cards and how you can start earning rewards for your biggest expenses at joinbilt.com/tyler. Gelt: And I'll go to my grave with this one: the single biggest mistake I have made in business thus far is not prioritizing finding a tax strategist and partner before anything else. Go to joingelt.com/tyler to see if they can help your business find what it's been missing. And on to the show notes! Most financial advice assumes money decisions are rational. Spend less. Save more. Invest consistently. But in reality, our financial decisions are often driven by psychology, identity, and social pressure far more than spreadsheets. In this episode, Tyler sits down with Hannah Horvath, CFP and writer of Your Brain on Money, to explore why traditional financial advice misses the behavioral side of money — and why understanding your values matters just as much as understanding the math. In this conversation, Tyler and Hannah discuss: Why information alone rarely changes financial behavior How social comparison shapes spending and lifestyle choices Why defining “enough” is more psychological than financial How marketing profits from creating a sense of lack The hidden cost of hyper-convenience and digital isolation Why community and real-world connection matter more than we think The core idea: money is a tool, but if you don’t define what you actually value, it’s easy to spend your life chasing someone else’s version of success. If you’d like to explore more of Hannah’s work, you can find her newsletter Your Brain on Money, where she writes about the psychology and culture behind our financial decisions. And if the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
• The Only Investing Rule You Will Ever Need 02.03.2026 32min

  As always, a MASSIVE thank you to this week's partners: Fabric: if anybody relies on your income, you need to consider term life insurance asap. Check out meetfabric.com/tyler to find out the right coverage for you and your loved ones. Facet: and even though I WANT to offer you all direct advice, I can't, as I don't know you. But Facet can, and they continue to practice exactly what I preach. Check out joinfacet.com/tyler today. And on to the show notes! “How should a 60-year-old invest?” It sounds like a reasonable question. It’s also the wrong one. In this episode, Tyler dismantles the idea that your age should determine your portfolio — and replaces it with a framework that actually works: invest based on when you need the money, not how many birthdays you’ve had. Because two people the same age can — and often should — invest completely differently. Instead of age-based formulas like “110 minus your age,” Tyler introduces a simpler system: The Three Bucket Framework Bucket 1 (0–2 years): Cash, money markets, short-term treasuries. Zero stock exposure. Bucket 2 (2–10 years): A glide path. Years until goal = % in stocks. Bucket 3 (10+ years): 100% stocks in low-cost index funds. That’s it. This episode walks through real examples — retirees, early retirees, 30-year-olds saving for houses, 70-year-olds investing for grandkids — to show why timeline beats age every time. Tyler also explains: Why sequence-of-returns risk matters more than age How to structure withdrawals using the bucket system Why most “conservative by default” advice is lazy The 10 investing terms you actually need to understand How to match allocation to goals without overcomplicating it The core idea is simple: Your timeline is your allocation. Stop asking how a 60-year-old should invest. Start asking when the money will be spent. If this framework changes how you think about your portfolio, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
• The $2 Million Plan No Advisor Wants You to See - The Details 23.02.2026 27min

  A special thanks to this week's sponsors: Bilt: if you are looking to level up your rewards game, time to check out how to get something back for your biggest annual expense: your rent or mortgage. Check out joinbilt.com/tyler today. Copilot Money: it's rare that I recommend apps to my friends, but when I do, it's because they're actually useful and dialed on what we need in finance. Check out try.copilot.money/tyler to see if Copilot Money is right for you. Gelt: I've said it before, and I'll say it always: if you haven't prioritized finding the right tax partner as a high net worth individual or business owner, you're prioritizing the wrong things. Check out joingelt.com/tyler today. A simple retirement plan is easy to explain. Living with it is harder. In this episode, Tyler revisits his 90% stocks / 10% money market retirement strategy — not to defend it, but to answer the practical questions that matter: When do you cut spending? When do you increase it? How do you rebalance without overreacting? And how do you rebuild cash after a downturn without missing the recovery? This is the execution episode. In this conversation, Tyler covers: How to use guardrails to adjust spending automatically When to reduce withdrawals — and when to raise them How often to rebalance (once a year is plenty) Why you only replenish cash after markets recover How automation keeps emotions out of the process The strategy remains intentionally simple: spend from cash during downturns, rebalance annually, and let math — not headlines — drive decisions. This episode isn’t about market timing. It’s about having rules in place so you don’t panic when volatility shows up. If the original 90/10 allocation made sense to you, this episode shows you how to actually stick with it. And if the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
• How to Invest $5 Million (The Only 4 Portfolios You’ll Ever Need) 16.02.2026 33min

  A massive "thanks," as always, to this weeks's sponsors: Anthropic: I use Claude every hour of every day to optimize my life. If you haven't explored what Claude can do for you and your business, it's time. Check out Claude today at claude.ai/tyler LMNT: I drink LMNT before and after each workout, and I have never felt better. Mango Chili and Watermelon Salt are my go-tos, and take advantage of the sampler pack, so you can find yours today. Check out LMNT before your next workout at drinklmnt.com/tyler Facet: I continue to partner with Facet in 2026 because I have yet to find a financial planning resource more fitting and cost effective for my audience. Check them out today to see where you've been leaving money on the table. Go to facet.com/tyler to learn more. And now on to the show notes! At some point, the financial industry starts telling you that once you cross a certain number — $5 million, $10 million — you need something more sophisticated. In this episode, Tyler explains why that’s mostly nonsense. After his “How to Invest $2 Million” episode, the big follow-up question was whether wealth changes the strategy. The answer: it doesn’t. The fundamentals stay the same — time horizon, asset allocation, tax efficiency, fees, and real diversification. In this episode, Tyler breaks down five portfolio options: One fund (VTI or VOO) for maximum simplicity Two funds (stocks + bonds) for risk control Target date funds for true autopilot investing The three-fund portfolio for global diversification The five-fund “2.0” version for small allocations to real estate, gold, or crypto None require hedge funds. None require private equity. None require paying 1% for unnecessary complexity. Tyler also explains why “accredited investor” status often just means you’re being sold something expensive — and why many ultra-wealthy investors still stick with index funds. This episode isn’t about leveling up your portfolio. It’s about keeping it simple — no matter how much money you have. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
• The 3 Retirement Numbers You Actually Need 09.02.2026 35min

  If you're interested in learning more about this week's partners: Copilot Money: I rarely recommend financial apps to my friends, but after suggesting that a few of my friends (all of whom work in finance) check out Copilot Money, not only did they all sign up, but they all think it's the best money app they've seen to date. So if you want to get your financial life in order, check out Copilot Money today at try.copilot.money/tyler. Gelt: My biggest business mistake to date? Waiting too long to establish a relationship with a reliable and proactive tax strategist. I left tens of thousands on the table. If your business is consistently netting over $200k, and you're lost as to next steps, you need to check out Gelt today at joingelt.com/tyler. And on to the show notes! Most retirement advice sounds confident and means almost nothing. “Save a million.”“Ten times your salary.”“Seventy percent of your income." None of that tells you what you actually need. In this episode, Tyler walks through how to calculate your real retirement number — one based on your spending, your timeline, and the kind of life you actually want. The goal isn’t motivation. It’s clarity. Instead of vague targets, Tyler breaks retirement planning into three practical numbers: Traditional FIRE — the “never work again” number, and why it’s too extreme for most people Coast FIRE — the Goldilocks option that lets you save hard early and ease off later The bare minimum — a realistic bridge for people closer to retirement who need options, not perfection Along the way, he explains why investing matters more than saving alone, why time beats contribution size, and why conservative assumptions create flexibility instead of fear. This episode isn’t about chasing a magic number. It’s about knowing what you’re building toward — so you can stop guessing and start making decisions with confidence. If you’ve ever wondered whether you’re on track, this episode gives you a framework you can actually use. And if the show’s been helpful, leaving a quick review on Apple Podcasts or Spotify genuinely helps. Hope this gives you something to think about this week.
• 5 Ways to Invest (And Spend) $2 Million 02.02.2026 38min

  A massive thank you to those who make this show possible! Facet: Every January we obsess over physical health. But what about your financial health? If you're ready to actually get a plan instead of just hoping for the best, Facet pairs you with CFP® professionals who build personalized strategies for a flat fee. Head to facet.com/tyler to get $250 into your brokerage account when you invest $5,000 in your first 90 days, plus waived enrollment fees for new annual members. Fabric: If anyone relies on your paycheck, term life insurance isn't optional—it's the safety net that catches them if you're not there. Fabric by Gerber Life lets you apply online in ten minutes with no health exam, and a million dollars in coverage often costs less than a dollar a day. Head to meetfabric.com/tyler to get covered before you finish your coffee—policies issued by Western-Southern Life Assurance Company, not available in certain states, prices subject to underwriting. And now on to the show notes! Saving money for retirement gets all the attention. Spending that money intelligently is the hard part. In this episode, Tyler tackles the part of retirement no one really teaches: how to draw down your money without running out, losing sleep, or overpaying in taxes. Accumulation is mostly math and discipline. Decumulation is judgment, flexibility, and understanding tradeoffs. This is a practical walkthrough of dynamic retirement income strategies — not rigid rules — and why the approach your parents used probably doesn’t work anymore. In this episode, Tyler breaks down: Why retirement drawdown is harder than saving — and why there’s no single “right” rule The three main income strategies in retirement: selling growth assets, living off dividends, and fixed income How the 4% rule actually works — and why it shouldn’t be followed blindly The pros and cons of dividend-focused portfolios, including tax implications When bonds, ladders, and annuities can make sense as income stabilizers Why inflation is the silent risk most retirees underestimate The most tax-efficient order to withdraw from accounts How Roth conversions, low tax brackets, and timing can save real money Along the way, Tyler explains why flexibility beats optimization, why peace of mind matters as much as returns, and why most retirees end up using a blend of all three strategies, not just one. This episode isn’t about squeezing every last dollar out of your portfolio. It’s about making your money last long enough to enjoy it — and knowing how to adapt as markets, taxes, and life change. If you’re approaching retirement, thinking about early retirement, or just want to understand how the endgame actually works, this episode gives you a solid framework to start from. And if the show has been helpful, leaving a quick review on Apple Podcasts or Spotify genuinely helps. As always, hope this gives you something worth thinking about this week.
• 5 Things the Insurance Industry Doesn't Want You to Know 26.01.2026 35min

  This week's episode is brought to you by: Facet. They provide you with access to a team of fiduciary CFP® professionals who gets paid to help you—not to sell you whole life insurance to fund their boat payment. New year, new financial plan that actually makes sense. Learn more at joinfacet.com/tyler. Copilot Money. The only finance app I've ever recommended to friends unprompted. Three finance professionals signed up, all three stuck around—which tells you everything. If you want to actually organize your money without turning it into a part-time job, check it out at try.copilot.money/tyler. Gelt. I spent six months doing everything right in my business—automated savings, proper accounting, the works—except I forgot to get a tax strategist. Rookie move. Should've been the first call, not an afterthought. If you're running a small business or a high earner, don't make my mistake. Check out joingelt.com/tyler. And on to the show notes! Most of what the insurance industry sells falls somewhere between unnecessary and borderline predatory. That’s not hyperbole. That’s the point of this episode. Here, Tyler breaks down what insurance is actually for, what you truly need, and why so many popular policies are aggressively oversold, misunderstood, or designed to benefit everyone except the person buying them. This is a blunt, behind-the-scenes look at how insurance really works — informed by Tyler’s time inside the finance industry — and why mixing insurance with investing is almost always a mistake. In this episode, Tyler covers: What insurance is meant to do — protect against catastrophic loss, not build wealth The short list of insurance most people actually need Why whole life insurance is a bad deal for nearly everyone How indexed and variable life policies repackage the same problems with more complexity and fees When annuities can make sense, and when they don’t Why HSAs are one of the most powerful financial tools available, if you’re eligible Along the way, Tyler explains how commissions shape “financial advice,” why bad products stick around, and how to spot sales tactics dressed up as planning. This episode isn’t anti-insurance. It’s about using insurance for what it’s good at — transferring risk — and avoiding products that pretend to be investments. And if the show has helped you avoid a mistake — or ask better questions — leaving a quick review on Apple Podcasts or Spotify genuinely helps. Hope this gives you something useful to think about this week.
• The 3-Day Workweek Blueprint: How to Buy Back 104 Days a Year | Andy Hill 19.01.2026 44min

  This week's endeavor in free financial literacy for all, brought to you by: LMNT: You can have all the money in the world, but if you don't feel good physically, none of it matters. For years, I'd finish my morning workout and be foggy-headed with a headache by 1 PM—turns out I was chronically under-hydrated and needed actual electrolytes, not just water. LMNT has 1,000mg sodium, 200mg potassium, 60mg magnesium, and zero sugar that keeps me sharp all day. My routine: one during my workout, then a Sparkling LMNT around 4 PM (Mango Chili is the move). Right now they're offering a free sample pack with any purchase at drinklmnt.com/tyler. Bilt: I spent my late 20s throwing thousands at rent in Vermont while maxing out retirement accounts, feeling like I was getting nothing back. ⁠Bilt⁠ fixes that by turning rent and mortgage payments into actual rewards—flights, hotels, fitness classes, or Amazon purchases. Join at ⁠joinbilt.com/Tyler⁠ and make money you're already spending work harder. Facet: Every January we prioritize physical health like it's the New Year's resolution Olympics, but why don't we give our financial health that same energy? I get hundreds of messages weekly asking for personalized advice, and while I want to help, I can't responsibly address your specific situation in a podcast. That's why I partner with ⁠Facet⁠: you get dedicated CFP® professionals who build actual financial plans tailored to your life, charging a flat fee instead of a percentage of assets. Connect with Facet at ⁠facet.com/tyler⁠ and start 2026 with both your health and your wealth dialed in. And on to the Show Notes! Somewhere between "retire at 30" and "work until 70," there's a middle path. Tyler talks with Andy Hill, host of Marriage, Kids and Money and author of Own Your Time, about how he and his wife reshaped their financial life to work 20–25 hours a week while staying financially secure—without winning the lottery or selling a tech company. This isn't a FIRE hype episode. It's a grounded conversation about tradeoffs, mistakes, marriage tension, and building a life that doesn't feel like a trap. Tyler and Andy discuss why extreme FIRE often breaks down in family life, how "Coast FIRE" creates a realistic middle ground, why income growth matters as much as cost-cutting, how money conversations can go wrong in marriage, and what it actually took to leave corporate work without blowing up financial security. Andy shares three concrete starting steps for anyone who feels stuck or burned out and wants to reclaim control over their time. This episode isn't about escaping work—it's about finding work you don't need to escape from. If the show has been helpful, leaving a quick review on Apple Podcasts or Spotify genuinely helps more people find it.