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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

34:04

Ep 19 - The 10 Rules of Not Getting Screwed When...

Your Money Guide on the Side ·

2025/06/09

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’...

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40:02

Ep 18 - Mady Mills - Why Billionaires Panic, What Men...

Your Money Guide on the Side ·

2025/06/02

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...

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33:18

Ep 17 - How I Would Invest $1,000,000 - 3 Approaches,...

Your Money Guide on the Side ·

2025/05/26

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...

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37:34

Ep 16 - Andrew Tobias - The Only Investment Interview...

Your Money Guide on the Side ·

2025/05/19

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,...

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29:35

Ep 15 - Should You Hire a Financial Advisor? (And 7...

Your Money Guide on the Side ·

2025/05/12

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 ...

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30:53

Ep 14 - Dan Brigham - On Faith, Finance, and First...

Your Money Guide on the Side ·

2025/05/05

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...

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28:08

Ep 13 - The Truth About Debt: How to Use It, Beat It,...

Your Money Guide on the Side ·

2025/04/28

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: ✅ ...

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30:42

Ep 12 - Andy Schneider - The Educator’s Guide to...

Your Money Guide on the Side ·

2025/04/21

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 ...

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26:22

Ep 11 - The 3-Step Framework for Solving Any...

Your Money Guide on the Side ·

2025/04/14

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 ...

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40:31

Ep 10 - Victoria Ferguson - On Money, Meaning, and...

Your Money Guide on the Side ·

2025/04/07

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 ...

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27:34

Ep 9 - On Playing to Win (The Asymmetry of Opportunity)

Your Money Guide on the Side ·

2025/03/31

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 small failures, and how our fear of loss keeps us from seeing the upside that could change everything. Tyler takes you from Disney’s acquisition of Pixar to Jeff Bezos’ “regret minimization framework,” unpacks the psychology of loss aversion, and explains why Monte Carlo simulations, the Kelly Crite...

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41:03

Ep 8 - Jessica Inskip - On Leaving Wall Street,...

Your Money Guide on the Side ·

2025/03/24

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 trader desk, and you may have seen her breaking down complex strategies alongside Jim Cramer, or offering sharp, accessible takes on CNBC, Fox Business, Schwab Network, and Yahoo Finance. In this episode, we unpack her journey from nearly becoming an engineer to becoming a nationally recognized v...

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13:24

Ep 7 - Killing Sacred Cows of Personal Finance, Or,...

Your Money Guide on the Side ·

2025/03/17

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 cases, dangerously misleading? In today’s episode, I take a hard look at why bonds are overrated, the risks most investors overlook, and whether they deserve a spot in your portfolio at all. While bonds can serve a purpose, blindly following the 60/40 portfolio mantra without questioning its effect...

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42:24

Ep 6 - Mike Taormina - Cutting Through Crypto Noise,...

Your Money Guide on the Side ·

2025/03/10

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 become a powerhouse in fintech, co-founding Vault, CommonBond, and Alluvial, with a Wharton MBA and a CFA to back it up. But credentials aside, what sets Mike apart is his ability to break down complex crypto and finance topics into something actually useful. In this episode, we dive into decentraliz...

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19:26

Ep 5 - Political Nonsense, the Integrity of Markets,...

Your Money Guide on the Side ·

2025/03/03

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 external "noise," and it is noise to me, is nonsense; I only change investing habits when my own life or financial needs have changed. Emphasizing and drawing upon historical data, the show explores the market's long term patterns of growth, regardless of who is in office. In short, the market transce...

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30:19

Ep 4 - Patrick Wetherille - Managing Detractors,...

Your Money Guide on the Side ·

2025/02/28

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 from and alongside business minds at every level. As the episode progresses, Patrick shares his thoughts on the importance of being able to work from anywhere and how that very freedom can often bring teams together and create optimized work cultures and production.

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17:32

Ep 3 - TikTok "Bans," Email Musts, and Building...

Your Money Guide on the Side ·

2025/02/28

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 same walk. When the TikTok "ban" occurred, I was left wondering why so many creators, all of whom discuss the power and importance of diversification on a daily basis, had not diversified their digital assets, as well, and considered their content as part of their overall portfolio.

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17:29

Ep 2 - Market Crashes, Awkward Neighbors, and...

Your Money Guide on the Side ·

2025/02/28

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 volatility first-hand through experience. I attempt to highlight the importance of thinking slightly differently and distantly about the markets and taking a walk when we need to escape from the relentless noise that is encouraging us to panic and make choices that we will, ultimately, regret when the wa...

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9:00

Ep 1 - Starting With Why

Your Money Guide on the Side ·

2025/02/28

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 help add value to your life. This episode is primarily highlighting what this endeavor will aim to achieve and how each episode might help you move closer to where you need to be with your personal finances, your attitude towards money, and your ability to learn more each and every day and ultimatel...

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39 results

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