Saving – The WIN Podcast

The Weight of Maybe: Why We Freeze (EP. 95)

By The-WIN-Podcast | December 9, 2025

In this episode of The WIN Podcast, we dive into the hidden weight of indecision and explore why the word “maybe” quietly drains our energy, momentum, and opportunity. From historical missteps to modern-day moments of analysis paralysis, we unpack the psychological forces that keep us stuck and the surprising cost of delaying even the smallest decisions.

We also draw clear parallels to personal finance, showing how hesitation can erode wealth just as easily as it stalls personal growth. With practical frameworks and real-world examples, this conversation gives you the tools to move from uncertainty to confident action. If you’ve been parked in neutral—mentally, emotionally, or financially—this episode will help you shift into gear and move forward with purpose.

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The Echo in the Well: How Past Voices Shape Today’s Decisions (EP. 92)

By The-WIN-Podcast | October 28, 2025

Every generation believes they’re raising their children differently — better — than the last. But what if every rebellion simply sets the stage for the next correction? In this episode of The WIN Podcast: What’s Important Now, we explore how the voices of our past shape the way we parent, lead, and live. From strict Victorian discipline to the free-range movements of today, we trace how values echo across generations — and how awareness helps us break, or balance, those cycles in our families, careers, and finances.

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The Comfort Trap: How Convenience and Choice Quietly Control Us (EP. 91)

By The-WIN-Podcast | October 14, 2025

In a world that promises to make everything effortless — from one-click shopping to instant streaming — our decisions should feel easier. Yet somehow, we’re more overwhelmed, less satisfied, and financially less disciplined than ever. In this episode of The WIN Podcast: What’s Important Now, we explore the hidden costs of convenience and the paradox of choice: how modern design, tech, and abundance quietly shape our behavior and wealth. You’ll learn why our brains crave simplicity but struggle with too much of it — and how to reclaim control by reintroducing intentional friction and strategic constraints in life, money, and mindset.

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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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Laying Up or Going for It: Risk, Reward, and the Green Ahead (EP. 78)

By The-WIN-Podcast | April 15, 2025

Fresh off The Masters, we dive into the high-stakes decision every golfer faces on a par 5—lay up or go for the green—and explore how that same risk/reward choice shows up in personal finance. Whether you’re building a nest egg or eyeing a bold investment move, knowing when to play it safe and when to take a calculated shot is key. Tune in as we break down the parallels between smart course management and sound financial planning.