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Your Money Guide on the Side: Daily Summaries Delivered
by Tyler Gardner
Your go-to podcast for mastering money and investing. Hosted by Tyler Gardner, a trusted influencer with over 6M followers, Your Money Guide on the Side simplifies the complex, adds nuance to what seems simple, and connects you with the brightest minds in finance, investing, and business. Whether you’re just starting or leveling up, this is your one-stop resource to navigate your own finances with clarity, confidence, and a bit of fun.
Latest Episodes
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- 6 days ago46 min
The Greatest Financial Advisor You Never Knew You Had
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.
- 1 weeks ago38 min
How to Build the Perfect Portfolio - Part 2 of 2
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.
- 2 weeks ago35 min
How to Build the Perfect Portfolio - Part 1 of 2
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.
- 3 weeks ago44 min
The 4 Greatest Money (And Life) Lessons I Have Ever Learned
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.
- Aug 17, 202640 min
The $4.2 Million Man Who Couldn't Spend His Own Money
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.
- Aug 10, 202644 min
The Subtle Art of Doing Nothing (And Making More Money While Doing It)
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: 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.
- Aug 3, 202641 min
The $250,000 Mistake Most Retirees Never Know They Made
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 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.
- Jul 27, 202643 min
The Withdrawal Order Nobody Taught You (And How to Save 10% on Taxes Annually in Retirement)
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: 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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About Your Money Guide on the Side
Your go-to podcast for mastering money and investing. Hosted by Tyler Gardner, a trusted influencer with over 6M followers, Your Money Guide on the Side simplifies the complex, adds nuance to what seems simple, and connects you with the brightest minds in finance, investing, and business. Whether you’re just starting or leveling up, this is your one-stop resource to navigate your own finances with clarity, confidence, and a bit of fun.
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