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PODCAST

Your Money Guide on the Side

Your go-to podcast for mastering money and investing. Hosted by Tyler Gardner, a trusted influencer with over 2.5M 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.

business investing

All Episodes

37:45

The DIY Investor's Guide to Building Your Own Index...

Your Money Guide on the Side ·

2025/10/27

What if you could skip the index fund and build your own? In theory, you can. In practice…well, it’s a bit like building your own refrigerator. You’ll learn a lot, and maybe even get a working model, but you’ll also discover why the factory-made version is so efficient in the first place. In this episode, we dive into the peculiar urge to “DIY” the market, and why the exercise can be incredibly educational—even if you never actually follow through. Along the way, you’ll learn: The 11 Sectors ...

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28:48

4 Tax Moves That Can Save You 6 Figures - Part 2 of 2

Your Money Guide on the Side ·

2025/10/20

Your 50s are a tax-planning sweet spot—a decade when smart strategies can save you tens or even hundreds of thousands over the course of retirement. In this episode, Part Two of our two-part series, we explore four advanced but practical moves to keep more of your money compounding where it belongs. Here’s what we cover in this episode: The HSA Triple Play: Why this account is the most underrated retirement tool, and how to turn it into a stealth IRA with triple tax benefits.Social Security T...

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26:18

4 Tax Moves That Can Save You 6 Figures - Part 1 of 2

Your Money Guide on the Side ·

2025/10/13

Taxes in your 50s may not be cocktail party conversation, but they can make or break your retirement plan. In this episode, I kick off a two-part series on the smartest tax moves to make once the kids are (hopefully) off your payroll and you’re staring down retirement. In Part One, we cover four essential strategies: Roth Conversions: Why your 50s and early 60s may be the perfect window to pay taxes on your terms, not Uncle Sam’s.Withdrawal Sequencing: The order in which you raid your taxable...

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29:27

10 Ways Investors Lose Money Without Knowing It

Your Money Guide on the Side ·

2025/10/06

Most portfolios don’t implode in one dramatic crash; they leak slowly. A percent here, a hidden fee there, and before you know it, your retirement fund has been funding someone else’s yacht. (Cough, cough...your advisor's...) In this episode, I shine a light on ten common wealth leaks that quietly drain portfolios, plus practical fixes for each one. We’ll cover: How a “tiny” 1% fee can cost you a third of your returns.Why overtrading turns your portfolio into Swiss cheese.The real silent kill...

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29:21

The Only Asset Allocation Guide You’ll Ever Need

Your Money Guide on the Side ·

2025/09/29

Your portfolio’s performance isn’t about finding the next hot stock; it’s about how you slice the pie. In this episode, I break down the real math behind compounding, why losses hurt more than wins help, and three simple allocation models you can actually follow without losing sleep. We’ll cover: Why “average returns” are misleading and compounding is what matters.How diversification really works (hint: it’s not about guessing winners).Three practical allocation strategies for different level...

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40:55

The Secret Art of Finding Work You Love and Funding...

Your Money Guide on the Side ·

2025/09/22

Guest: Chris Hutchins, host of All the Hacks Episode theme: Building wealth with meaning—how to design a career (and life) you actually want, while optimizing the money side. What we cover: Meaning > money-first: Chris didn’t start out chasing wealth; he chased options. Early jobs in consulting/banking felt misaligned (little meritocracy, lots of “performance”). That tension pushed him toward work that creates—startups, product, and eventually a podcast. From layoff to leverage: A 2008 ...

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25:05

How I Invest My Own Money in 2025

Your Money Guide on the Side ·

2025/09/15

Please take a moment to complete this brief survey so I can learn more about YOU and what it is YOU want from this show! I promise, it will take no longer than 97 seconds, and it will help me continue to make the show better for you. There’s a strange YouTube genre called “What’s in My Bag?” where people pull out chapstick like it’s a state secret. This episode is basically that…except the bag is my financial life. And instead of chapstick, it’s index funds and money markets. Not sexy. ...

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28:04

Trump vs. Obama: Whose 401(k) Made You Richer?

Your Money Guide on the Side ·

2025/09/08

Before you hit play: I’ve put a quick listener survey together for listeners. It takes less time than finding your password for your old 401(k), and it helps me shape future episodes around what you actually care about. Please take a moment to fill out this 3 minute listener survey here. This week I’m wading into a swamp I usually avoid like lukewarm gas-station sushi: money and politics. Talking about 401(k) policy across administrations feels like trying to explain cricket at Thanksgiv...

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28:59

What If More Money Still Doesn’t Feel Like Enough?

Your Money Guide on the Side ·

2025/09/01

What if the biggest financial surprise in your life isn’t running out of money—but realizing that “having enough” doesn’t feel anything like you thought it would? In this episode, I explore the hidden side of wealth: the regrets, letdowns, and quiet disappointments that often surface after you’ve hit your financial goals. From savers who can’t spend, to retirees who waited too long for joy, to high achievers who retired from something but not to something, we unpack why reaching your number d...

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25:09

How Do I Make My Kid Filthy Rich (Without Going Broke)?

Your Money Guide on the Side ·

2025/08/25

In case you missed it, check out last week's episode of Your Money Guide on the Side that answers the question How Do I Manage My Own Investments? This Week...Your kid thinks money comes from your phone. Or maybe a magical debit card named Mom. Taxes? Rent? The economics of movie popcorn? Foreign concepts. This episode isn’t about turning your child into a trust fund caricature. It’s about giving them the tools, education, and compounding head start so they have choices—whether that’s ta...

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28:51

How Do I Manage My Own Portfolio? 7 Steps to Start

Your Money Guide on the Side ·

2025/08/18

In case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question: When Should I take Social Security? This week on Your Money Guide on the Side, we’re tackling one of the questions I used to get more than any other—right after “Should I buy gold?” and “Is my advisor secretly bad at this?” We’re talking about how to vet your own portfolio. Not how to invest—that’s for another episode. This is about taking the pulse of your current investments ...

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41:44

Ep 28 - Taylor Sohns - 3 (Rational) Reasons to Take...

Your Money Guide on the Side ·

2025/08/11

How secure is your future benefit and what should you actually do about it? Taylor Sohns is a Certified Financial Planner™ and co-founder of Life Goal Wealth Advisors. Before starting his own firm, Taylor spent over a decade inside some of Wall Street’s biggest investment shops — the ones that build the ETFs, mutual funds, and hedge funds you’ve probably been pitched. Now he works on the other side of the table, helping everyday investors align their portfolios with their real-world goals. 📚

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32:00

Ep 27 - 5 Ways to Make ChatGPT Your (Free) Financial...

Your Money Guide on the Side ·

2025/08/04

What if your smartest financial sidekick never sleeps, never judges, and doesn’t charge 1% AUM? In this episode of Your Money Guide on the Side, Tyler Gardner explores how to use ChatGPT—not as your stock-picking guru, but as your emotionally-stable, algorithmic thought partner. One that can help you think better about money, values, timelines, and fees—without selling you a whole life policy disguised as “peace of mind.” We break it down into five key ways AI can help you think more clearly,...

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42:29

Ep 26 - Tess Waresmith - 3 Silent Wealth Killers...

Your Money Guide on the Side ·

2025/07/28

Tess Waresmith is a financial educator, speaker, and investor known for helping people reach financial independence with simple investing. She’s the founder of Wealth With Tess, where she helps women build wealth and confidence through investing. Tess has been featured by CNBC, Business Insider, and Fox 5 NY, and is a self-made millionaire focused on helping others avoid the mistakes that cost her… well let’s not go there. 📚 What We Discuss with Tess Waresmith: 🔍 03:15 — Early mistakes and

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33:30

Ep 25 - The ONLY 6 Accounts You Will Ever Need (And...

Your Money Guide on the Side ·

2025/07/21

In this solo episode, Tyler breaks down the only six financial accounts you’ll ever truly need—and more importantly, how to actually use them. Whether you’re just getting started or managing a more complex portfolio, this is your streamlined, nonsense-free guide to designing a system that works. No more chasing every new fintech app or wondering if you’re missing something. If you’ve ever felt overwhelmed by the alphabet soup of financial tools, Tyler’s here to cut through the noise and give ...

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33:57

Ep 24 - Bill Perkins - How to Die With Zero (and...

Your Money Guide on the Side ·

2025/07/14

Is Future Planning Ruining Your Future? What if your financial advisor told you to spend your money now? To give away your inheritance early? To go on more vacations? To prioritize experience over investment? What if they told you the only inflation-protected asset is experience? Bill Perkins is a hedge fund manager, poker player, and author of the bestseller Die With Zero. On this week’s episode, he breaks down why money is just a means — and experience is the end. 📚 What We Discuss

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31:28

Ep 23 - The 3 Reasons You’ll Never Beat the Market...

Your Money Guide on the Side ·

2025/07/07

Let’s be honest: you’re not going to beat the stock market. And that’s not an insult — it’s a liberation. In this episode of Your Money Guide on the Side, Tyler Gardner unpacks one of the most misunderstood goals in investing: trying to “win” against the market. Drawing on decades of investing experience (and more than a few Peloton mistakes), Tyler explains why comparing yourself to the S&P 500 is often irrelevant, how hedge funds and high-frequency traders have rigged the game against r...

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45:12

Ep 22 - Wendy Li - The Secret Strategies of...

Your Money Guide on the Side ·

2025/06/30

Wendy Li managed billions for New York’s top institutions — here’s what she thinks individual investors can (and should) steal from the pros. After leading portfolios for the Met Museum, UJA-Federation, and the Mother Cabrini Health Foundation, Wendy now serves as CIO at Ivy Invest. She’s spent decades on the inside — and in this episode she’s walking us through how institutional investors actually make decisions, where regular people go wrong, and what it means to manage risk. 📚What We

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27:24

Ep 21 - How Much Can I Spend in Retirement? Why the...

Your Money Guide on the Side ·

2025/06/23

What if the most common retirement rule was never meant to be a rule at all? In this episode, we unpack the origins, flaws, and overlooked nuances of the 4% rule—and why it might not be the best way to plan your financial future. From its fear-based beginnings to its rigid application in a dynamic world, Tyler breaks down 5 key reasons to rethink the 4% rule altogether. You’ll learn: Where the 4% rule actually came from (hint: worst-case scenario thinking) What the Trinity Study really showed...

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45:44

Ep 20 - JL Collins - The Simple Path to F-You Money...

Your Money Guide on the Side ·

2025/06/16

Today’s guest is someone whose work has quietly and profoundly shaped how a generation thinks about money. JL Collins is the author of The Simple Path to Wealth, a personal finance classic that has empowered hundreds of thousands to think differently about investing, independence, and freedom. In this conversation, JL and I explore the real meaning behind financial independence — not retiring early, but reclaiming your ability to say no. We go back to the moments that shaped his life philosop...

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39 results

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