Your Money Guide on the Side

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Your Money Guide on the Side

Tyler Gardner

29 episodes

5 days ago

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 and asking: Does this still make sense for my life? You’ll walk away with 7 practical steps to audit your own portfolio, whether you DIY, use an advisor,...

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Entrepreneurship,

All content for Your Money Guide on the Side is the property of Tyler Gardner and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

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 and asking: Does this still make sense for my life? You’ll walk away with 7 practical steps to audit your own portfolio, whether you DIY, use an advisor,...

Show more...

Entrepreneurship,

Episodes (20/29)

Your Money Guide on the Side

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 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 and asking: Does this still make sense for my life? You’ll walk away with 7 practical steps to audit your own portfolio, whether you DIY, use an advisor,...

5 days ago

28 minutes

Your Money Guide on the Side

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, 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. 📚 ...

1 week ago

41 minutes

Your Money Guide on the Side

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 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,...

2 weeks ago

32 minutes

Your Money Guide on the Side

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 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 fi...

3 weeks ago

42 minutes

Your Money Guide on the Side

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 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 ...

1 month ago

33 minutes

Your Money Guide on the Side

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 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 wit...

1 month ago

33 minutes

Your Money Guide on the Side

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 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...

1 month ago

31 minutes

Your Money Guide on the Side

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, 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 Discu...

1 month ago

45 minutes

Your Money Guide on the Side

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 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...

2 months ago

27 minutes

Your Money Guide on the Side

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 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...

2 months ago

45 minutes

Your Money Guide on the Side

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 cash, I’ll walk you through the 10 timeless rules you must follow if you want to avoid getting taken for a ride—financially and emotionally. No guilt trips. No boomer advice. Just strategy, leverage, and power dynamics decoded. And full disclosure: I love cars. I lease new ones every few years. I’...

2 months ago

34 minutes

Your Money Guide on the Side

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 everything from surviving the 2016 election newsroom to navigating the terrifyingly personal world of money and relationships. Mady opens up about growing up around volatility — both financial and emotional — and how it fuels her empathy-first approach to financial journalism today. We talk about: Why...

2 months ago

40 minutes

Your Money Guide on the Side

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 theoretical asset allocation or textbook strategies. It’s about real lives, real goals, and real risk tolerance. We meet three investors—Chad, Nina, and Marge—each at very different life stages, each with a radically different approach to putting their wealth to work: Chad Slater, the thrill-seeking e...

2 months ago

33 minutes

Your Money Guide on the Side

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 political advocate, and the brilliant mind behind The Only Investment Guide You’ll Ever Need. His book was literally the first financial text I ever read, and it remains one of the few I return to over and over again—for its timeless principles, relatable tone, and surprising humor. In this conversation,...

3 months ago

37 minutes

Your Money Guide on the Side

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 not giving you a yes or no answer (sorry, not sorry). Instead, I’m walking you through a three-part framework to decide if you need an advisor—skill, will, and time—and then I’m sharing seven real-world filters for choosing the right one if you do. Because the truth is: Working with a financial ...

3 months ago

29 minutes

Your Money Guide on the Side

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 breath of fresh air. No paywalls. No “six-figure side hustle” webinars. Just brutally honest content, bite-sized math on notecards, and a contagious belief that you can take control of your money — excuses not included. In this episode of Your Money Guide on the Side, we dive into the moments tha...

3 months ago

30 minutes

Your Money Guide on the Side

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 shame, and leverage it as a tool for long-term wealth. Whether you’re currently drowning in high-interest credit cards, juggling student loans, or just debating whether to pay off your 3% mortgage early, this episode is your new north star for how to think clearly about debt. You’ll learn how to: ✅ ...

3 months ago

28 minutes

Your Money Guide on the Side

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 Schneider, a career educator and current CFO at an independent school, for a wide-ranging and deeply honest conversation about what we teach (and don’t teach) about money. Andy has worn a lot of hats—boarding school English teacher, PWC consultant, MBA grad, educational administrator—and he brings a ...

4 months ago

30 minutes

Your Money Guide on the Side

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 place? This solo episode is a follow-up to last week’s conversation with CFP® Victoria Ferguson, and it’s all about creating a personal framework that helps you stop spinning your wheels and finally make meaningful progress in your financial life. You’ll learn: Why most people never get past step ...

4 months ago

26 minutes

Your Money Guide on the Side

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. Victoria is a CERTIFIED FINANCIAL PLANNER® who left a traditional finance career to create educational content full-time. Why? Because she knew more people needed clear, honest money guidance—and that trust is built through storytelling, not spreadsheets. In this episode, we talk about: Why budgets ...

4 months ago

40 minutes