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Your Money Guide on the Side

Your Money Guide on the Side
Author: Tyler Gardner
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© 2025 Your Money Guide on the Side
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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.
12 Episodes
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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 ...
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 ...
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 ...
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...
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...
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...
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...
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...
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.
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.
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...
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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