Personal Finance – The WIN Podcast

The Domino Effect: How One Small Choice Can Change Your Future (EP. 89)

By The-WIN-Podcast | September 16, 2025

Sometimes it’s not the big decisions that shape history—it’s the small ones. Ronald Wayne’s decision to sell his 10% stake in Apple for $800 cost him over $100 billion in missed gains. Even NASA’s choice of a simple pencil reshaped safety in space.

In this episode, Corey and Zed explore how tiny decisions—both famous and forgotten—set off domino chains with massive consequences. Then, they tie it back to money: how everyday choices like starting a savings plan, skipping one payment, or investing a single dollar at 25 can determine your financial future.

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The Long Tail of Fads: When Today’s Trend is Tomorrow’s Prank (EP. 88)

By The-WIN-Podcast | September 2, 2025

Why do we fall in love with fads? From hula hoops to Beanie Babies to meme stocks, history is filled with crazes that capture our imagination—and our wallets—before vanishing almost overnight. They make us laugh, they make us hope, and sometimes they cost us big. In this episode, Corey and Zed explore why fads are so powerful, what they reveal about human behavior, and how the same forces that drive silly cultural trends also fuel risky financial manias.

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Language Evolution: From Dialects to Domain Names (EP. 87)

By The-WIN-Podcast | August 19, 2025

From ancient campfires to current-day slang, language has always shaped the way humans think, act, and connect. In this episode, Corey and Zed trace the journey of language through history—how early tribes relied on clarity for survival, how the printing press standardized communication, and how the digital age introduced memes, slang, and financial jargon at lightning speed.

Just as language influences culture, the words we use around money influence how we invest, save, and plan for the future. The hosts explore why misunderstanding terms like APY, diversification, or volatility can lead to costly mistakes, and how mastering the “language of wealth” creates confidence and clarity.

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Why We Love Underdogs: The Hidden Cost of Betting on Hope (EP. 86)

By The-WIN-Podcast | August 5, 2025

Everyone loves an underdog. From the Jamaican bobsled team to Seabiscuit, we’re drawn to the grit, heart, and improbable rise of those who weren’t “supposed” to win. But when emotion takes the wheel — especially in investing — it can lead us into risky bets masked as hopeful stories.

In this episode, Corey and Zed unpack three powerful underdog stories and break down what they can teach us about risk, value, and decision-making. Why do we root for long shots? When does hope help — and when does it cloud judgment? And how do we separate an inspiring story from a sound investment?

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Same Water Different Outcomes (EP. 85)

By The-WIN-Podcast | July 22, 2025

When life heats up, how do you respond? This episode explores the powerful parable from The Coffee Bean—a story of a carrot that softens, an egg that hardens, and a coffee bean that transforms its environment. Through real-life examples of Elizabeth Holmes, Howard Hughes, and Viktor Frankl, we examine how people react under pressure—and what it means for life, leadership, and financial decisions. Are you letting adversity shape you, or are you shaping the outcome? Discover how to build resilience, stay grounded, and become the kind of person who changes the water around them.

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Independent Thinking in a Dependent World (EP. 84)

By The-WIN-Podcast | July 8, 2025

In a world flooded with trends, opinions, and financial noise, independent thinking has never been more essential — or more difficult. In this special July 4th-themed episode, we explore what it means to declare your own financial independence. We’ll draw parallels between the American Revolution and modern money choices, offer practical tools to help you think for yourself in a dependent world, and sprinkle in some fun Fourth of July facts that just might shift your mindset.

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Happy Accidents (EP. 83)

By The-WIN-Podcast | June 24, 2025

Velcro. Post-its. Potato chips. What do they have in common? None of them were part of the plan. In this episode of WIN, we dive into the world of accidental inventions—and how their surprise success offers a powerful lesson for investors and dreamers alike. Because sometimes, the best financial returns don’t come from predicting the future, but from being ready when it shows up.

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Financial Fables: What a tortoise, a fox, and a golden goose can teach you about your wallet (EP. 81)

By The-WIN-Podcast | May 27, 2025

In this episode of WIN: What’s Important Now, we unpack five classic Fables—stories you may have heard as a child—and discover the powerful financial wisdom they hold for adults. From the slow-and-steady tortoise to the golden-egg-laying goose, these tales reveal truths about saving, investing, greed, preparation, and mindset. Join us as we connect ancient stories to modern money habits and ask: what’s your financial fable?

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If a Tree Falls… and a Cart is Left Behind (EP. 80)

By The-WIN-Podcast | May 13, 2025

What do a falling tree, a shopping cart, and your retirement account have in common? In this episode, we explore the unseen choices that shape our lives—from acts of everyday integrity to the quiet discipline of long-term investing. Inspired by the Grocery Cart Theory and the age-old forest riddle, this conversation is a reminder that what’s important now isn’t always visible—but it always matters.

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Timeless Truths (EP. 79)

By The-WIN-Podcast | April 29, 2025

In Episode 79 of WIN: What’s Important Now, we explore five timeless truths about human behavior — and how they still shape our decisions today. Inspired by Morgan Housel’s Same as Ever, we examine surprising moments from history that reveal why some lessons never go out of style.

Through stories of risk, patience, and the power of incentives, we connect the past to the present, showing how what’s always been true still matters now. Whether you’re thinking about money, mindset, or meaning, this episode is a reminder that some of the most important things… don’t really change.