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.
Episodes (32)
Trump vs. Obama: Whose 401(k) Made You Richer?
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...
What If More Money Still Doesn’t Feel Like Enough?
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...
How Do I Make My Kid Filthy Rich (Without Going Broke)?
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...
Ep 29 - The Portfolio Sanity Check: 7 Steps to Vet Your Own Investments Like a Pro (Without Having a Nervous Breakdown)
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...
Ep 28 - Taylor Sohns - 3 (Rational) Reasons to Take Social Security at 62 (Or: How to Stop Deferring an Already Deferred Life)
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,...
Ep 27 - 5 Ways to Make ChatGPT Your (Free) Financial Advisor (Without Getting Sued or Sold a Timeshare)
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...
Ep 26 - Tess Waresmith - 3 Silent Wealth Killers Hiding in Plain Sight (Or Small Print)
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...
Ep 25 - The ONLY 6 Accounts You Will Ever Need (And How to Use Each of Them Strategically)
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...
Ep 24 - Bill Perkins - How to Die With Zero (and Actually Live First)
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...
Ep 23 - The 3 Reasons You’ll Never Beat the Market (And Why That’s Okay)
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...
Ep 22 - Wendy Li - The Secret Strategies of Billion-Dollar Portfolios
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,...
Ep 21 - How Much Can I Spend in Retirement? Why the 4% Rule Gets it Wrong
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...
Ep 20 - JL Collins - The Simple Path to F-You Money (And Why You Need to Ask Your Boss for a Paid Leave Today)
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...
Ep 19 - The 10 Rules of Not Getting Screwed When Buying or Leasing a New Car
Car buying has become one of the most financially dangerous consumer experiences in modern life. In today’s episode, we’re flipping the script. Whether you’re buying or leasing, trading in or paying...
Ep 18 - Mady Mills - Why Billionaires Panic, What Men Need to Hear, and the One Account that Buys Your Financial Freedom
She’s been on Bloomberg. The New York Times. Yahoo Finance. But Mady’s real talent? Translating the chaos of markets and money into stories that make you feel seen. In this episode, we dive into...
Ep 17 - How I Would Invest $1,000,000 - 3 Approaches, 3 Stories, and 1 Question to Simplify Your Life
You've hit the million-dollar mark—now what? In this episode of Your Money Guide on the Side, we tackle the deceptively simple question: how should you invest a million dollars? This isn’t about...
Ep 16 - Andrew Tobias - The Only Investment Interview You Will Ever Need (And How Money CAN Buy Happiness)
What if the only investment guide you ever needed... actually was? This week, I sit down with personal finance legend Andrew Tobias—bestselling author, Harvard Business School grad, long-time...
Ep 15 - Should You Hire a Financial Advisor? (And 7 Things to Look For If You Do)
This might be the most common money question I get, and maybe even the most important: Should I hire a financial advisor? And right behind it: If so, how do I find a good one? In today’s episode, I’m...
Ep 14 - Dan Brigham - On Faith, Finance, and First Principles
He paid off $100K in debt and isn’t trying to sell you a thing — meet Dan the Budget Man. In a financial world cluttered with gurus, grifters, and gatekeepers, Dan Brigham (@budgeters_anonymous) is a...
Ep 13 - The Truth About Debt: How to Use It, Beat It, and Stop Feeling Bad About It
Is All Debt Bad? What the Wealthy Know That Most People Don’t Debt doesn’t have to be your enemy—and in this solo episode, Tyler Gardner breaks down how to make smarter decisions about debt, ditch...
Ep 12 - Andy Schneider - The Educator’s Guide to Money, College, and Real-World Finance
What happens when a former English teacher becomes a CFO—and decides to teach everyone around him how money actually works? In this episode, Tyler sits down with longtime friend and campmate Andy...
Ep 11 - The 3-Step Framework for Solving Any Financial Problem (That's Actually Worth Solving)
Have you ever said, “I’m just bad with money”? Yeah—me too. But what if the real issue isn’t your spending or saving or investing strategy... but your ability to name the actual problem in the first...
Ep 10 - Victoria Ferguson - On Money, Meaning, and Saying No to Budgets
What do you get when you combine a financial planner with the heart of a teacher and the boldness of a creator? You get Victoria Ferguson—today’s guest and a true money guide for the modern world....
Ep 9 - On Playing to Win (The Asymmetry of Opportunity)
Most people spend their lives trying not to lose. The wealthy? They play to win. In this solo episode, Tyler Gardner breaks down the asymmetry of opportunity—why one big win can outweigh dozens of...
Ep 8 - Jessica Inskip - On Leaving Wall Street, Fighting Misinformation, and Redefining Financial Education
This week on Your Money Guide on the Side, I’m joined by the incredible Jessica Inskip—one of the sharpest, most grounded voices in modern investing. Jessica was the first female on Fidelity’s active...
Ep 7 - Killing Sacred Cows of Personal Finance, Or, Why I (Really) Don't Love Bonds
Bonds have been a staple in portfolios for decades, often hailed as the “safe” investment that brings stability and protects wealth. But what if I told you that this belief is outdated, and in many...
Ep 6 - Mike Taormina - Cutting Through Crypto Noise, and a Case for Active Portfolio Management
Back in 2003, I met Mike Taormina at the London School of Economics, never expecting we'd stay in touch—let alone spend decades debating finance and traveling together. Fast forward, and Mike has...
Ep 5 - Political Nonsense, the Integrity of Markets, and Broken Clocks as Great Investors
In this week's episode, we explore our common tendency to react emotionally to political elections and their perceived impact on the stock market. I argue that changing investing habits based on...
Ep 4 - Patrick Wetherille - Managing Detractors, Working from Anywhere, and Optimizing our Finances and our Lives
My guest this week, Patrick Wetherille, shares a little bit about his experience with optimizing life, managing empathy through start-up culture, and taking advantage of every opportunity to learn...
Ep 3 - TikTok "Bans," Email Musts, and Building Resilience for the Inevitable Storm
In this episode, I explore the power of diversifying communication channels, income streams, and the irony of many people knowing they should diversify and yet their not quite being able to walk the...
Ep 2 - Market Crashes, Awkward Neighbors, and Overcoming Angel's Landing
In this episode, I do my best to touch on the absolute musts of investing and controlling our emotions. Not only controlling our emotions, but knowing our emotions and our reactions to market...
Ep 1 - Starting With Why
I am thrilled to offer a brief glimpse into the "why" behind building out the podcast. The ability to add nuance, engage other minds, and learn from multiple voices intrigues me and hopefully will...
About this Podcast
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© 2025 Your Money Guide on the Side
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