1799219049
Your Money Guide on the Side

Advertise on podcast: Your Money Guide on the Side

Rating
★★★★★
4.9
from
2947 reviews
This podcast has
90 episodes
Language
English
Publisher
Tyler Gardner
Explicit
No
Date created
2025/02/28
Latest episode
2026/10/19
Average duration
41 min.
Release period
7 days

Description

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. 

Unlock Your Money Guide on the Side podcast Email contact info,
Listeners & Audience details

Email contact information

Direct podcast contact details

Listeners

Audience numbers & engagement insights

Audience details

Podcast Insights

Podcast episodes

Check latest episodes from Your Money Guide on the Side podcast


The 5 Things You Need to Retire Tomorrow
2026/10/19
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! Facet⁠ → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! ⁠Copilot Money⁠ → ⁠www.copilot.money/tyler⁠ — use code TYLER2 for two free months. LMNT⁠ → drinklmnt.com/tyler⁠ Get a free 8-count Sample Pack of LMNT’s most popular drink mix flavors with any purchase at drinklmnt.com/tyler. And on to the show notes!! You’ve reached your retirement number. Now what’s going to get you out of bed on Monday? A healthy account balance can fund your freedom, but it can’t give your days a shape. In this episode, Tyler explores five needs behind a happy retirement: autonomy, relatedness, competence, desire and marked time. Drawing on psychological research and his own experience, he asks what happens when work stops supplying the people, progress and structure you barely noticed it provided. Even the colleague you found irritating may have been doing you some good. You’ll learn: Why autonomy means choosing worthwhile obligations, rather than having none. How everyday acquaintances provide connection your closest relationships can’t replace. Why getting better at something matters more than already being good. How an unfinished bucket list keeps anticipation alive. Why distinct experiences and annual rituals help make the years memorable. Build the life your money makes possible before your last working Monday arrives. If this episode gave you something to think about, please consider leaving a review on Apple or Spotify.
Why I Still Hate Bonds (With a Few Minor Concessions)
2026/10/12
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 → 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. 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. Anthropic⁠ → ⁠⁠claude.ai/tyler ⁠to experience AI for minds that don't stop at good enough. 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!! The “safe” part of a portfolio can still deliver a nasty surprise. Bonds have a job to do, but protecting against everything isn’t in the contract. In this episode, Tyler revisits his earlier argument against bonds with a sharper distinction between growth and ballast. He explores what fixed income actually protects, what it leaves exposed, and when certainty matters more than chasing a higher return. You’ll learn: How interest rates, inflation and opportunity cost challenge the idea that bonds are automatically safe. Why a bond fund is not a bond, and what duration reveals about potential price swings. The different jobs money markets, bond funds and TIPS can perform. When matching maturities to expenses and holding a retirement spending buffer make sense. Why pensions and other steady income belong in your whole financial picture. The useful question is safe from what? Judge each holding by the job it needs to do, rather than a reassuring label. If this episode helped, please consider leaving a review on Apple or Spotify.
The 5 Questions You Would Not Stop Asking Me in 2026
2026/10/05
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: Bilt → ⁠⁠joinbilt.com/tyler⁠⁠ So you can choose the card that fits your lifestyle without missing out on points and exclusive benefits. 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 Get a free 8-count Sample Pack of LMNT’s most popular drink mix flavors with any purchase at drinklmnt.com/tyler. Facet → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! And on to the show notes!! Most of the biggest money questions aren’t really about what to buy. They’re about how to think when the answer isn’t obvious. In this episode, Tyler answers the five questions listeners have asked most in 2026 — from pensions and politics to healthcare, market concentration, and long-term care — with an emphasis on what you can actually control. You’ll learn: How a pension and Social Security can change the way you think about portfolio risk Why being right about markets or politics still doesn’t mean you can time them How the return of the ACA subsidy cliff changes early-retirement planning What today’s S&P 500 concentration does — and doesn’t — tell you The four main ways to prepare for long-term care, including the risks of each The recurring lesson is that good planning rarely comes from predicting the future. It comes from understanding the whole picture, knowing what you own, and preparing for the decisions you can control. If the show’s been helpful, please consider leaving a review on Apple or Spotify.
5 Things I Will Never Spend Money On as a Multimillionaire (And 5 That Are Worth Every Penny)
2026/09/28
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: Momentous⁠ → ⁠⁠livemomentous.com⁠ Use code Tyler for up to 35% off your first order! 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. 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. And on to the show notes!! Most people spend decades learning how to make and save money. Far fewer learn how to spend it well. In this episode, Tyler shares two very personal lists: five things he’ll happily overpay for, and five things he refuses to spend money on again. Not because one list is objectively right. Because the point is figuring out your own list. In this episode, Tyler covers: Why many well-funded retirees still struggle to give themselves permission to spend Five things Tyler believes are genuinely worth the money, from generous tipping to buying back time Why a capsule wardrobe, books, house cleaning, and even leasing a car can make sense when they solve the right problem Five purchases he’s done with—including short-haul first class, expensive wine, and other versions of “luxury” that don’t actually improve his life Why outsourcing tasks you hate can increase happiness—but outsourcing things you enjoy can do the opposite How to separate spending that buys time, health, peace, or connection from spending that mostly buys an audience The exercise of building your own “worth it” and “never again” lists The core idea: The money was never the finish line. It’s a tool for buying more of what you already value. Spend generously where it meaningfully improves your life. And stop paying for things you only thought you were supposed to want. 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 Biggest Red Flags of Financial Advising
2026/09/21
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 Get a free 8-count Sample Pack of LMNT’s most popular drink mix flavors with any purchase at drinklmnt.com/tyler. ⁠Facet⁠ → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! Copilot Money → ⁠⁠⁠www.copilot.money/tyler⁠⁠⁠ — use code TYLER2 for two free months.⁠ And on to the show notes!! Hiring a financial advisor can be genuinely valuable. Hiring the wrong one can be extremely expensive. In this episode, Tyler breaks down five red flags to watch for when choosing an advisor—or evaluating the one you already have. Because the question isn’t whether financial advice has value. It’s whether this advisor is worth what you’re paying them. In this episode, Tyler covers: Why the traditional 1% assets-under-management fee can become enormously expensive over time The one question to ask every prospective advisor: “What would you do with $100,000 of my money?” Why real market experience—and humility—matters when things get ugly How to confirm your advisor is a fiduciary 100% of the time Why your investments should always be held with an independent third-party custodian How guarantees, deadlines, and high-pressure sales tactics reveal misaligned incentives What to watch for once you’re a client, including churning and unnecessary cash drag How to leave an advisor without creating an avoidable tax bill The core idea: Good financial advice can be worth paying for. But the price should reflect the service—not the size of your portfolio. Look for transparent pricing, boring investments, real planning expertise, aligned incentives, and someone willing to tell you exactly how they get paid. And remember: it’s your money, not theirs. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something useful to think about this week.
The Greatest Financial Advisor You Never Knew You Had
2026/09/14
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.
How to Build the Perfect Portfolio - Part 2 of 2
2026/09/07
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.
How to Build the Perfect Portfolio - Part 1 of 2
2026/08/31
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.
The 4 Greatest Money (And Life) Lessons I Have Ever Learned
2026/08/24
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.
The $4.2 Million Man Who Couldn't Spend His Own Money
2026/08/17
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.
The Subtle Art of Doing Nothing (And Making More Money While Doing It)
2026/08/10
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.
The $250,000 Mistake Most Retirees Never Know They Made
2026/08/03
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.
The Withdrawal Order Nobody Taught You (And How to Save 10% on Taxes Annually in Retirement)
2026/07/27
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.
The 6 Money Moves to Make Before You Retire
2026/07/20
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.
The $2 Million Portfolio: Two Funds, Three Funds, or Five?
2026/07/13
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.

Podcast reviews

Read Your Money Guide on the Side podcast reviews


4.9 out of 5
2947 reviews
★★★★★
Big deal explained 2026/10/20
Retirement is a big deal
Tyler explains planning for retirement in the exact way I need.
★★★★★
*TJ16* 2026/10/20
Practical and entertaining
Tyler gives all the things you need and nothing that you don’t. I have been listening off and on for about a year. Tyler has helped me think holistica...
★★★★★
prefabshout 2026/10/19
Beyond the money!
While I was initially here for building practical investment knowledge, I keep coming back for Tyler taking us beyond the money to explore more of the...
★★★★★
SGR1961 2026/10/19
Excellent, simple explanations of issues
My brother recommended Tyler’s podcast, and I’m happy he did. I find Tyler’s style to be easy going, his explanations of sometimes confusing financial...
★★★★★
HighlandsHome 2026/10/19
Clear and intelligible conversations about the right things
I started listening to Tyler earlier this year, drawn in by his shorts on Facebook. I read and listen quite a bit to books about retirement but still ...
★★★★★
Jack the Bears 2026/10/19
My favorite podcast
This endeavor is worth it. You are doing good.
★★★★★
Glichy on an off 2026/10/18
Learning from the content
Tyler makes a lot of sense. I’ve only just discovered him. I wish I had discovered him a couple years ago.
★★★★★
Larry M Photo 2026/10/18
Real world practical advice
First ran across Tyler on YouTube watching his shorts. Then wandered over to his podcast for his long form content. What I love about his episodes is ...
★★★★★
TheHappyFlosser 2026/10/18
Appreciation
I really appreciate and value this podcast. Tyler does a remarkable job at taking things that seem complex and scary and making them easier to underst...
★★★★★
Toadboy 135 2026/10/16
Excellent content
I have been following Tyler on facebook for awhile . His information is always well thought out. Great common sense financial analysis. Thank you
check all reviews on apple podcasts

Podcast sponsorship advertising

Start advertising on Your Money Guide on the Side relevant audience podcasts


What do you want to promote?