Podcast · 65 episodes
Your Money Guide on the Side
by Tyler Gardner · English
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. Let’s get you one step closer to where you need to be.
Latest episodes
5 Things I Will Never Spend Money On as a Multimillionaire (And 5 That Are Worth Every Penny)A personal, “money is for what you value” episode arguing spending is a different skill than saving/investing.28 Sep 2026 · 36 min
The 5 Biggest Red Flags of Financial AdvisingHow to vet financial advisors and avoid five “red flags” that signal you’re overpaying, being steered, or lacking real fiduciary protection.21 Sep 2026 · 37 min
The Greatest Financial Advisor You Never Knew You HadTyler Gardner argues the S&P 500 functions like a “financial advisor you never knew you had,” outperforming most active managers mainly due to low costs, built-in quality filters, automatic…14 Sep 2026 · 46 min
All episodes
5 Things I Will Never Spend Money On as a Multimillionaire (And 5 That Are Worth Every Penny)A personal, “money is for what you value” episode arguing spending is a different skill than saving/investing.28 Sep 2026 · 36 min · 11 chapters
The 5 Biggest Red Flags of Financial AdvisingHow to vet financial advisors and avoid five “red flags” that signal you’re overpaying, being steered, or lacking real fiduciary protection.21 Sep 2026 · 37 min · 14 chapters
The Greatest Financial Advisor You Never Knew You HadTyler Gardner argues the S&P 500 functions like a “financial advisor you never knew you had,” outperforming most active managers mainly due to low costs, built-in quality filters, automatic…14 Sep 2026 · 46 min · 19 chapters
How to Build the Perfect Portfolio - Part 2 of 2How to build a “perfect” long-term investment portfolio (Part 2 of 2), synthesizing 10 academic/investing thinkers into a usable framework: prioritize low costs, use TIPS as an inflation-protected…7 Sep 2026 · 38 min · 14 chapters
How to Build the Perfect Portfolio - Part 1 of 2Building the “perfect portfolio” using academic research (Part 1 of 2), emphasizing diversification, low costs, and matching risk to personal circumstances; also addressing tail risks of passive…31 Aug 2026 · 35 min · 12 chapters
The 4 Greatest Money (And Life) Lessons I Have Ever LearnedFour money (and life) lessons arguing that financial decisions should serve a designed life: time structure, autonomy in chosen work, consistent “unheroic” habits, and spending to match your own…24 Aug 2026 · 45 min · 11 chapters
The $4.2 Million Man Who Couldn't Spend His Own MoneyWhy “having enough” doesn’t lead to spending in retirement—Edward’s $4.2M case—and how to spend intentionally by rebuilding identity, avoiding oversaving, front-loading high-decay experiences,…17 Aug 2026 · 41 min · 16 chapters
The Subtle Art of Doing Nothing (And Making More Money While Doing It)How to handle market downturns in retirement by distinguishing “weather” (short-term headlines) from “climate” (long-run returns), understanding sequence-of-returns risk, using a rising equity glide…10 Aug 2026 · 44 min · 19 chapters
The $250,000 Mistake Most Retirees Never Know They MadeHow retirees should use Roth conversions during the “conversion window” (retirement to RMD start) to reduce lifetime taxes; explains traditional IRAs as a “wrapped tax bomb,” how RMDs force…3 Aug 2026 · 41 min · 15 chapters
The Withdrawal Order Nobody Taught You (And How to Save 10% on Taxes Annually in Retirement)Retirement decumulation strategy focused on the “withdrawal order” (taxable vs traditional IRA vs Roth), arguing the optimal order changes every year and is driven by tax-bracket “terrain,” ACA…27 Jul 2026 · 43 min · 17 chapters
The 6 Money Moves to Make Before You RetireOrientation for retirement “decumulation”: six pre-retirement decisions (cash buffer, 401k move, Social Security timing, healthcare bridge to 65, beneficiary/spousal planning, and portfolio…20 Jul 2026 · 44 min · 15 chapters
The $2 Million Portfolio: Two Funds, Three Funds, or Five?How to build a $2 million retirement portfolio using 2, 3, or 5 funds; argues that more funds usually add complexity and behavioral risk without improving long-run returns.13 Jul 2026 · 36 min · 17 chapters
5 Money Milestones and the Lie Each One TellsThe episode argues that financial “milestones” (six figures, Coast FIRE, retirement, and a capstone like a book/sale) often deliver little emotional change because the real value is the “becoming”…6 Jul 2026 · 44 min · 16 chapters
How to Build an Inflation-Proof Portfolio (And 3 Mistakes to Avoid)How to build an inflation-proof portfolio and avoid three common investor mistakes that reduce real, after-tax returns.29 Jun 2026 · 40 min · 16 chapters
13 Money Moves They're Betting You Won't Make“13 Money Moves They’re Betting You Won’t Make” argues most savings exist in the gap between advertised prices and what companies will do if you ask.22 Jun 2026 · 38 min · 16 chapters
Why the S&P 500 is the Best (And Worst) Thing to Ever Happen to InvestorsThe “tyranny of the benchmark” created by S&P 500 index funds—how it psychologically pushes investors to chase beating the market, even though matching it (cheaply, patiently) is the best realistic…15 Jun 2026 · 34 min · 15 chapters
Why I Will Never Retire. And Why the Premise Itself Might Be Wrong.The episode argues that “retirement” as a finish line is outdated and can harm mental health and well-being; instead of aiming to stop work, listeners should build autonomy, leverage, and purpose so…8 Jun 2026 · 31 min · 12 chapters
The 80% Problem: Why Wealthy People Don't Save for a Rainy DayArgues that “save for a rainy day” is a virtue trap for most people; wealthy people don’t rely on cash savings as their main safety strategy.1 Jun 2026 · 30 min · 13 chapters
The 5 Best (And Worst) Cars You Could Ever Buy (Financially Speaking, Of Course)Financially evaluating car purchases using total cost of ownership (depreciation, insurance, fuel, maintenance, financing), not monthly payments, and ranking the five worst and five best cars to buy.25 May 2026 · 40 min · 15 chapters
How to Divorce-Proof Your Finances (Whether You're Married, Divorced, or Somewhere In Between)How to “divorce-proof” finances through prevention (while married), protection (technical/legal steps), and a post-divorce “financial freeze” to avoid bad decisions.18 May 2026 · 43 min · 18 chapters
What I'd Do If $1,000,000 Landed in My Account Tomorrow: 3 Moves, 3 Mistakes, 3 Red FlagsWhat to do if $1,000,000 hits your account tomorrow—3 immediate moves, 3 mistakes/red flags, and 3 behaviors to watch.11 May 2026 · 45 min · 20 chapters
My Interview with Burton Malkiel (That You Will Never Hear)A narrative history of index investing, centered on Burton Malkiel and Jack Bogle, arguing that after fees it’s extremely hard for active managers to beat the market, and that the real challenge is…4 May 2026 · 42 min · 17 chapters
The 0% Tax Bracket Most Retirees Walk Right PastHow retirement withdrawal rates and taxes are inseparable; five tax considerations for a retiree drawing from a $2M portfolio (pre-tax, Roth, taxable), using 2026 tax numbers.27 Apr 2026 · 42 min · 15 chapters
I Moved to Arizona for the Winter: The 5 Things Nobody Tells You About SnowbirdingThe host’s first-time “snowbirding” experience (Vermont to Sedona, AZ) and five money/life lessons tied to relocation, time-saving, housing decisions, spending adaptation, community building, and…20 Apr 2026 · 40 min · 14 chapters