Your Money Guide on the Side

Jaksot

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  The Greatest Financial Advisor You Never Knew You Had 14.09.2026 46min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠⁠tylergardner.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: Caldera+ Lab⁠ → If you've been meaning to take better care of your skin, head to CalderaLab.com/TYLER and use code TYLER for 20% off your first order. DeleteMe⁠ → joindeleteme.com/tyler20⁠ Use code Tyler20 for up to 20% off! Thrive Market⁠ → Use link thrivemarket.com/tyler to get $30 off your first two orders. You cannot get this deal on the website — it's only through my link. And that right there covers your membership fee, so sign up now before this exclusive offer ends Gelt → ⁠⁠joingelt.com/tyler⁠ because Q3 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. The best financial advisor Tyler has ever worked with charges almost nothing, never calls during dinner, and automatically fires its own losers. It’s the S&P 500. In this episode, Tyler revisits the case for simple index investing—and tackles the arguments that usually come next: What about concentration?What about international diversification?What about investor behavior?And what exactly are you paying an advisor to do? In this episode, Tyler covers: How the S&P 500’s profitability and inclusion rules create a built-in quality filter Why the index automatically removes declining companies and replaces them with stronger ones The case that large U.S. companies already provide meaningful international exposure Why today’s market concentration is a real risk—but not necessarily a reason to abandon the index The enormous long-term advantage of low fees and tax efficiency Tyler’s three-bucket framework for matching investment risk to when you actually need the money Whether behavioral coaching really justifies a 1% advisory fee How AI, primary-source verification, and hourly or flat-fee professionals can handle more complex planning questions The core idea: You don’t necessarily need someone continuously managing your investments. You need a simple structure you understand, enough friction to stop yourself panicking, and targeted expertise when the problem actually requires it. The S&P 500 won’t hold your hand. But for the job of growing long-term savings cheaply and automatically, it’s remarkably difficult to beat. 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.
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  How to Build the Perfect Portfolio - Part 2 of 2 07.09.2026 38min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠⁠tylergardner.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: Anthropic⁠ → ⁠⁠⁠claude.ai/tyler⁠ ⁠to experience AI for minds that don't stop at good enough.⁠ Facet⁠ → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! Bilt⁠ → ⁠⁠⁠joinbilt.com/tyler⁠⁠⁠ So you can choose the card that fits your lifestyle without missing out on points and exclusive benefits. ⁠⁠⁠⁠⁠⁠⁠⁠⁠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. And on to the show notes!! There is no single perfect portfolio. There is only the portfolio that is right for you. In Part 2, Tyler looks at five more of the greatest investing thinkers of the last century before pulling all ten together into a practical framework for building a portfolio that can actually survive real life. In this episode, Tyler covers: Robert Merton on building around the income you actually need Martin Leibowitz and why your capacity for risk matters more than a questionnaire Robert Shiller on valuations, behavioral finance, and global diversification Charles Ellis on winning by avoiding mistakes, not making brilliant moves Jeremy Siegel on stocks, long time horizons, and dollar-cost averaging Why TIPS repeatedly appear as the preferred long-term risk-off asset The five principles that emerge when all ten thinkers are compared The conclusions are surprisingly simple: Keep costs low. Know yourself. Diversify broadly. Protect against inflation. And stay the course. The perfect portfolio isn’t the one with the cleverest allocation. It’s the one built around your life, your risk tolerance, and your goals—and simple enough that you won’t abandon it when markets get ugly. 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.
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  How to Build the Perfect Portfolio - Part 1 of 2 31.08.2026 35min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠⁠tylergardner.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: Copilot Money → ⁠⁠⁠www.copilot.money/tyler⁠⁠⁠ — use code TYLER2 for two free months.⁠ Caldera+ Lab⁠ → If you've been meaning to take better care of your skin, head to CalderaLab.com/TYLER and use code TYLER for 20% off your first order. DeleteMe⁠ → joindeleteme.com/tyler20⁠ Use code Tyler20 for up to 20% off! Momentous⁠ → ⁠⁠livemomentous.com⁠ Use code Tyler for up to 35% off your first order! And on to the show notes!! In Pursuit of the Perfect Portfolio, Part 1 Is there such a thing as the perfect portfolio? Yes. And no. In this episode, Tyler steps back from his own investing philosophy and looks at how five of the most influential thinkers in modern finance approached the same question. Drawing from In Pursuit of the Perfect Portfolio, Tyler explores where their ideas overlap, where they disagree, and what individual investors can actually use. In this episode, Tyler covers: Harry Markowitz and why correlation and diversification changed investing forever William Sharpe on balancing market risk with safer assets Eugene Fama and the case for efficient markets, broad indexing, and factor tilts Jack Bogle’s obsession with low costs, simplicity, and staying invested Myron Scholes on tail risk, market concentration, and the limits of passive investing Why risk tolerance, taxes, time horizon, and life stage matter more than finding a universal allocation The common ground is surprisingly simple: Diversify. Keep costs low. Understand the risks you can actually tolerate. And don’t add complexity unless it solves a real problem. There may not be one perfect portfolio for everyone. But there are a handful of principles that keep appearing whenever serious people study the question. Next week, Tyler looks at five more investing thinkers before bringing all ten together into a practical framework. 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.
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  The 4 Greatest Money (And Life) Lessons I Have Ever Learned 24.08.2026 44min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠⁠tylergardner.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: Factor → factormeals.com/tylerg50off and use code tylerg50off to get 50% off and one free breakfast item per box for one year while supplies last until 10/31/2026. 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. And on to the show notes!! Personal finance is usually very good at answering how. How to invest.How to save.How to retire. The harder question is what any of it is actually for. In this episode, Tyler steps away from the technical side of money to share four lessons that have shaped how he thinks about work, time, happiness, and wealth. In this episode, Tyler explores: Why having more free time means little if you don’t know what to do with it Why work itself isn’t the enemy—the wrong work, people, and structure are The myth of the “heroic week,” and why meaningful progress is built on ordinary weekdays Why money really can buy happiness—if you spend it on what genuinely matters to you How to use your own spending as data through the Path Dividend Why the financial plan should always serve the life, not become the life The core idea: Money is a means, not an end. The goal isn’t simply more wealth, more freedom, or more time. It’s knowing what kind of days, work, people, and experiences you actually want those things to make possible. 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.
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  The $4.2 Million Man Who Couldn't Spend His Own Money 17.08.2026 40min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠⁠tylergardner.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: DeleteMe⁠ → joindeleteme.com/tyler20⁠ Use code Tyler20 for up to 20% off! Gelt → ⁠⁠joingelt.com/tyler⁠ because Q3 is where strategic businesses make game-changing tax moves. If you're a business or a high-net worth individual, time to make moves. Caldera+ Lab⁠ → If you've been meaning to take better care of your skin, head to CalderaLab.com/TYLER and use code TYLER for 20% off your first order. Facet⁠ → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! And on to the show notes!! You can have enough money and still be afraid to spend it. That’s the final problem. In Part 5 of the Art of Decumulation series, Tyler moves beyond withdrawal rates, tax brackets, and portfolio mechanics to the harder question: How do you actually become a spender after spending forty years becoming a saver? Because the transition isn’t really financial. It’s an identity shift. In this episode, Tyler covers: Why saving becomes part of your identity—not just a behavior The real cost of oversaving in retirement Why permission to spend has to come from you How to front-load experiences whose value declines with age Why retirees should explicitly define what the money is for The case for giving money away while you’re still alive to see what it changes Why real wealth is ultimately about control over your time The core idea: The portfolio exists to fund the life. The life does not exist to preserve the portfolio. Spend on the experiences that won’t wait. Give while you can witness the impact. And use the money to buy back the hours you actually care about. This is Part 5 and the final episode of the Art of Decumulation series. 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.
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  The Subtle Art of Doing Nothing (And Making More Money While Doing It) 10.08.2026 44min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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: ⁠⁠⁠⁠⁠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. Copilot Money → ⁠⁠www.copilot.money/tyler⁠⁠ — use code TYLER2 for two free months.⁠ Anthropic⁠ → ⁠⁠claude.ai/tyler ⁠to experience AI for minds that don't stop at good enough.⁠ Bilt⁠ → ⁠⁠joinbilt.com/tyler⁠⁠ So you can choose the card that fits your lifestyle without missing out on points and exclusive benefits. And on to the show notes!! A market crash doesn’t usually destroy a retirement. Panic does. In Part 4 of the Art of Decumulation series, Tyler explores how retirees can survive market downturns without turning temporary losses into permanent ones. Because the financial news reports the weather. Your retirement plan needs to be built for the climate. In this episode, Tyler covers: Why the first five years of retirement carry the greatest sequence-of-returns risk How a larger cash buffer can prevent forced selling during downturns Why a rising equity glide path may make more sense than becoming increasingly conservative with age How the Guyton-Klinger guardrails adjust spending in good and bad markets Why modest spending cuts can support a higher sustainable withdrawal rate The behavioral cost of panic selling—and why knowledge alone rarely prevents it How writing a decision plan in advance can protect you when markets turn Why almost every apparent catastrophe eventually proves to be ordinary market weather The core idea: The most valuable skill in retirement investing is often the ability to do nothing. Use the cash buffer.Adjust spending when the guardrails require it.Trust the plan you made while thinking clearly. Then let the storm pass. This is Part 4 of the Art of Decumulation series. Next week, the final episode: how to move from saver to spender and give yourself permission to enjoy what you 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.
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  The $250,000 Mistake Most Retirees Never Know They Made 03.08.2026 39min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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 Q3 is where strategic businesses make game-changing tax moves. If you're a business owner or a high-net worth individual, time to make moves! Facet → ⁠⁠⁠facet.com/tyler⁠⁠ for an exclusive $550 kickstart offer! Schedule your intro call today! Fabric → ⁠⁠meetfabric.com/tyler⁠⁠ because if someone depends on your income, term life insurance is the next item on your financial agenda! ⁠⁠⁠⁠⁠⁠⁠⁠⁠Thrive Market⁠ → ⁠⁠thrivemarket.com/tyler⁠ for $20 off your first three orders plus you’ll get a FREE $60 gift! And On To the Show Notes! A traditional IRA can look like your money. But part of it belongs to the IRS. In Part 3 of the Art of Decumulation series, Tyler tackles three of the most important—and expensive—pieces of retirement tax planning: Roth conversions, RMDs, and IRMAA. Because the goal isn’t to avoid taxes entirely. It’s to control when you pay them and at what rate. In this episode, Tyler covers: Why the years between retirement and RMDs can be your biggest tax-planning opportunity How Roth conversions work—and when they can save significant money Why filling lower tax brackets deliberately can matter more than minimizing income How required minimum distributions (RMDs) can push retirees into higher brackets later Why IRMAA is a cliff, not a normal marginal tax bracket The importance of planning for the widow’s penalty Why retirement tax planning should become an annual practice, not a one-time decision The core idea: Your traditional IRA is a future tax bill. The question is whether you choose when to pay it—or let the IRS choose for you. This is Part 3 of the Art of Decumulation series. Next week: market downturns, sequence-of-returns risk, and when to actually change the plan. 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.
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  The Withdrawal Order Nobody Taught You (And How to Save 10% on Taxes Annually in Retirement) 27.07.2026 43min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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: Caldera+ Lab⁠: → If you've been meaning to take better care of your skin, head to CalderaLab.com/TYLER and use code TYLER for 20% off your first order. This has been a game-changer for me. ⁠⁠⁠⁠Copilot Money: → ⁠⁠www.copilot.money/tyler⁠⁠ — use code TYLER2 for two free months, and learn why this is the only budgeting app that makes it into our group texts. Momentous⁠: → ⁠⁠livemomentous.com⁠ Use code Tyler for up to 35% off your first order! ⁠⁠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. And On to the Show Notes! Most retirement advice gives you a simple withdrawal order: Taxable.Traditional.Roth. Useful? Yes. Always right? Not even close. In Part 2 of the Art of Decumulation series, Tyler digs into what actually determines where your retirement income should come from each year — taxes, healthcare, market conditions, account type, and the life you’re trying to fund. Because retirement withdrawals aren’t a problem you solve once. They’re a decision you revisit every year. In this episode, Tyler covers: Why the “taxable → traditional → Roth” rule is only a starting point How to use low tax brackets strategically instead of simply minimizing withdrawals Why asset location matters just as much as asset allocation How sequence-of-returns risk changes the early years of retirement Monthly vs. annual withdrawals — and why the mathematically “best” answer may not be the best life answer When ACA subsidies and Roth conversions should override the usual withdrawal order Why the Roth is often best preserved for last The core idea: The best withdrawal strategy changes with the year in front of you. Do the math carefully. But remember what the math is for. This is Part 2 of the Art of Decumulation series. Next week: Roth conversions, RMDs, and IRMAA. 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.
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  The 6 Money Moves to Make Before You Retire 20.07.2026 43min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠DeleteMe⁠ → joindeleteme.com/tyler20⁠ Use code Tyler20 for up to 20% off! Caldera+ Lab⁠ → CalderaLab.com/TYLER and use code TYLER for 20% off your first order. ⁠Facet⁠ → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! Gelt → ⁠⁠joingelt.com/tyler⁠ because having the right tax strategist changes the game entirely. If you're a business or a high-net worth individual, you might want to check this one out today. And on to the show notes!! Most financial advice is about building wealth. Far less is about what comes next. In this episode, Tyler kicks off a five-part series on the art of decumulation—the transition from saving for retirement to confidently spending what you've spent decades building. Because retirement isn't just a financial shift. It's a life shift. In this episode, Tyler covers: Why the first year of retirement is often the most emotionally challenging How to build a 12–24 month cash buffer before leaving work What to do with your 401(k) when you retire How to think about Social Security and the healthcare gap before Medicare Why every retiree should review beneficiaries and prepare their spouse to manage the finances How to reposition your portfolio before retirement—not after The core idea: A successful retirement starts long before your last day at work. The more decisions you make in advance, the less likely you'll be forced into emotional ones later. This is Part 1 of Tyler's five-part series on retirement spending. Next week, he dives into one of the biggest decisions retirees face: which accounts to withdraw from first—and why the order matters. 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.
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  The $2 Million Portfolio: Two Funds, Three Funds, or Five? 13.07.2026 36min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Fabric⁠ → ⁠meetfabric.com/tyler⁠ Made for busy parents like you; all online, on your schedule, right from your couch. You could be covered in under 10 minutes, often with no health exam required. 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. ⁠⁠⁠Copilot Money → ⁠⁠www.copilot.money/tyler⁠⁠ — use code TYLER2 for two free months.⁠ ⁠Bilt⁠ → ⁠joinbilt.com/tyler⁠ So you can choose the card that fits your lifestyle without missing out on points and exclusive benefits. And on to the show notes!! Most investors think a better portfolio is a more complicated portfolio. It usually isn't. In this episode, Tyler revisits his retirement portfolio framework and answers one of the most common questions he's received: How many funds do you actually need? From a simple two-fund portfolio to more complex five-fund allocations, Tyler explains where diversification adds real value—and where it simply adds complexity. In this episode, Tyler covers: The differences between two-, three-, and five-fund portfolios Why simplicity often outperforms complexity over the long run The difference between bond funds and money market funds Whether international stocks are actually necessary When adding more funds becomes an active bet, not diversification Why rebalancing once a year is usually enough The behavioral advantage of owning a portfolio you can actually stick with The core idea: The best portfolio isn't the most sophisticated. It's the one you'll hold through the next bear market. Because long-term investing isn't won by finding the perfect allocation. It's won by keeping costs low, staying invested, and resisting the urge to tinker. 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.
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  5 Money Milestones and the Lie Each One Tells 06.07.2026 43min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Thrive Market⁠: → ⁠⁠thrivemarket.com/tyler for⁠ $20 off your first three orders plus you’ll get a FREE $60 gift! ⁠Gelt: → ⁠⁠⁠joingelt.com/tyler⁠⁠ because Q3 is where strategic businesses make game-changing tax moves before the yearis over. If you're a business or a high-net worth individual, check out Gelt today. Anthropic⁠: → ⁠⁠claude.ai/tyler ⁠to experience AI for minds that don't stop at good enough. ⁠Facet⁠⁠: → ⁠⁠⁠facet.com/tyler⁠⁠ for an exclusive $550 kickstart offer! And on to the show notes!! We spend a lot of our lives chasing financial milestones. A six-figure salary. Coast FIRE. Retirement. The next big achievement. But what if those milestones were never meant to make us feel complete? In this episode, Tyler steps away from spreadsheets and investment strategies to explore what literature can teach us about money, ambition, and the illusion that one more milestone will finally make everything click. Drawing on works by C.P. Cavafy, Samuel Johnson, Kazuo Ishiguro, and David Foster Wallace, Tyler reflects on why so many financial goals feel strangely empty once we reach them—and what that means for how we should build our lives. In this episode, Tyler explores: Why a six-figure salary often changes less than we expect What Coast FIRE really gives us—and what it doesn't The hidden myth at the heart of retirement planning Why major achievements rarely deliver lasting fulfillment The importance of always having another "Ithaca" on the horizon The one financial milestone that genuinely does transform people's lives: getting out of high-interest debt The core idea: Financial milestones matter—but not because they complete us. They give us direction. The real value isn't in arriving. It's in the person you become on the way there. 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.
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  How to Build an Inflation-Proof Portfolio (And 3 Mistakes to Avoid) 29.06.2026 39min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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: 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. Wispr Flow: → wisprflow.ai/tyler for one free month of Wispr Flow Pro free! ⁠⁠⁠⁠⁠Copilot Money⁠⁠: → ⁠⁠www.copilot.money/tyler⁠⁠ — use code TYLER2 for two free months.⁠ ⁠⁠Fabric⁠⁠: → ⁠⁠meetfabric.com/tyler⁠⁠ because if someone depends on your income, term life insurance is the next step you should take today. And on to the show notes!! Inflation doesn't usually destroy wealth overnight. It does it slowly. A little bit each year. A little less purchasing power. A little more expensive to maintain the same lifestyle. And over a long retirement, those small changes add up. In this episode, Tyler breaks down how investors can build portfolios that are designed to keep pace with inflation, rather than slowly fall behind it. Because protecting your money isn't just about growing it. It's about preserving what it can actually buy. In this episode, Tyler covers: Why inflation is one of the biggest long-term risks retirees face The asset classes that have historically done the best job of outpacing rising prices Why stocks remain the most powerful long-term inflation hedge How TIPS (Treasury Inflation-Protected Securities) work The role of real estate and infrastructure in an inflation-resistant portfolio Why traditional bond-heavy portfolios can struggle when inflation rises The hidden cost of holding too much cash How overreacting to inflation headlines can hurt returns more than inflation itself Tyler also walks through three increasingly sophisticated portfolio approaches, ranging from a simple stock-and-TIPS allocation to a more diversified strategy incorporating real assets. The core idea: Inflation isn't a market event. It's a permanent feature of the system. The goal isn't to predict it. The goal is to build a portfolio that's prepared for 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.
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  13 Money Moves They're Betting You Won't Make 22.06.2026 38min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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: 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. ⁠⁠Bilt⁠: → ⁠joinbilt.com/tyler⁠ to find the card that fits your lifestyle! ⁠⁠⁠⁠⁠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. And on to the show notes!! Most people assume the listed price is the real price. It often isn't. In this episode, Tyler shares a collection of practical money-saving strategies he's used himself — from negotiating internet bills to appealing property tax assessments — and explains why so many financial opportunities come down to one simple skill: Asking. Because companies routinely offer discounts, credits, and incentives that never appear on their websites. In this episode, Tyler covers: Why calling the retention department can save hundreds per year How often to shop auto insurance for the best results The medical bill strategy that can dramatically reduce healthcare costs Why HSAs may be the most underrated retirement account available How Roth conversions can create major tax savings in low-income years The surprisingly effective property tax appeal process Hidden consumer tricks involving credit cards, Costco pricing, and price protection policies Why unclaimed property databases are worth checking at least once The common thread through all of these strategies is simple: Most savings opportunities aren't hidden because they're complicated. They're hidden because most people never ask. The companies know it. The people who save money know it. And now you do too. 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.
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  Why the S&P 500 is the Best (And Worst) Thing to Ever Happen to Investors 15.06.2026 33min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠tylergardner.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: ⁠⁠⁠⁠⁠Superpower: → superpower.com⁠ Use code Tyler for $20 off your membership! And remember, wealth means nothing without your health. Facet⁠: → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! ⁠⁠Copilot Money⁠: → ⁠www.copilot.money/tyler⁠ — use code TYLER2 for two free months.⁠ ⁠Fabric⁠: → ⁠meetfabric.com/tyler⁠ because if someone depends on your income, term life insurance is the next step you should take today. And on to the show notes!! Most investors spend their lives trying to beat the market. The problem? The market is already made up of millions of people trying to do the exact same thing. In this episode, Tyler explores what he calls "the tyranny of the benchmark" — the idea that comparing ourselves to the S&P 500 often creates more anxiety, more mistakes, and worse outcomes than simply owning the market in the first place. Because for most investors, matching the market isn't mediocrity. It's success. In this episode, Tyler covers: How index funds changed investing forever Why the S&P 500 became a benchmark that many investors misunderstand The hidden psychological cost of constantly comparing performance Why beating the market is mathematically harder than most people realize What you're really competing against when you try to outperform The behavioral mistakes that consistently hurt returns Why missing just a handful of the market's best days can dramatically reduce long-term wealth How fees, overconfidence, and market timing quietly work against investors Tyler also explains why the greatest threat to most portfolios isn't Wall Street. It's the person checking the portfolio. The core idea: The goal isn't to outsmart the market. It's to stop getting in your own way. Own it cheaply. Hold it patiently. Let time do the heavy lifting. Because the most remarkable investing outcomes often come from the most unremarkable investing stories. 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.
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  Why I Will Never Retire. And Why the Premise Itself Might Be Wrong. 08.06.2026 31min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠tylergardner.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: ⁠⁠Square⁠⁠⁠: → ⁠⁠⁠⁠⁠⁠square.com/go/tyler⁠ Get up to $200 off Square hardware and run your business smarter today. ⁠Wispr Flow: → wisprflow.ai/tyler for one free month of Wispr Flow Pro free! Momentous⁠: → ⁠⁠livemomentous.com⁠ Use code Tyler for up to 35% off your first order!⁠ ⁠Anthropic⁠: → ⁠⁠claude.ai/tyler ⁠to experience AI for minds that don't stop at good enough. And on to the show notes!! We’ve been sold a very specific version of success: Work for forty years.Retire at sixty-five.Finally enjoy your life. But what if retirement, at least as we think about it, is the wrong goal entirely? In this episode, Tyler makes the case that the wealthiest people don’t retire — they redesign work. Because the real goal isn’t escaping your life. It’s building one you don’t constantly want to escape from. In this episode, Tyler covers: Why retirement is a relatively modern invention — and why the system was built for a different world What people like Warren Buffett, John D. Rockefeller, and Jeff Bezos have in common Why autonomy, purpose, and meaningful work matter more than most financial plans acknowledge The hidden traps of lifestyle inflation and “golden handcuffs” Why so many people stay in jobs they dislike (even when they know it) The difference between trading time for money and building assets that buy time back Why purpose matters just as much as portfolio size Tyler also shares a more personal reflection on leaving a stable career to build something of his own — and why uncertainty, while uncomfortable, can be worth it. The core idea: Real wealth isn’t retiring from your life. It’s building one you don’t need to retire from. Because the goal was never the finish line. It was finding a game worth playing for a very long time. 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.
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  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 ⁠⁠tylergardner.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.
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  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 ⁠tylergardner.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.
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  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 tylergardner.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.
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  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 ⁠tylergardner.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.
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  My Interview with Burton Malkiel (That You Will Never Hear) 04.05.2026 42min

  Pre-order Tyler's book, Real Wealth, at tylergardner.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.