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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 3M 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. Let’s get you one step closer to where you need to be.
Latest Episodes
The most recent episodes — sign up to get AI-powered summaries of each one.
- Yesterday33 min
Why the S&P 500 is the Best (And Worst) Thing to Ever Happen to Investors
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: 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.
- 1 weeks ago31 min
Why I Will Never Retire. And Why the Premise Itself Might Be Wrong.
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: 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.
- 2 weeks ago30 min
The 80% Problem: Why Wealthy People Don't Save for a Rainy Day
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.
- 3 weeks ago39 min
The 5 Best (And Worst) Cars You Could Ever Buy (Financially Speaking, Of Course)
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.
- 4 weeks ago42 min
How to Divorce-Proof Your Finances (Whether You're Married, Divorced, or Somewhere In Between)
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.
- May 11, 202645 min
What I'd Do If $1,000,000 Landed in My Account Tomorrow: 3 Moves, 3 Mistakes, 3 Red Flags
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: → try.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.
- May 4, 202642 min
My Interview with Burton Malkiel (That You Will Never Hear)
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.
- Apr 27, 202641 min
The 0% Tax Bracket Most Retirees Walk Right Past
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.
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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 3M 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. Let’s get you one step closer to where you need to be.
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