Finances – The WIN Podcast

From Calendar Chaos to Financial Clarity (EP. 97)

By The-WIN-Podcast | January 6, 2026

Not everyone’s New Year starts on January 1—and neither does smart financial planning. In this episode, we explore Calendar Chaos: how different cultures mark time, why calendars don’t always align, and what that means for your money. From the lunar New Year to fiscal years, we break down how understanding when you plan can be just as important as how you plan.

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Removing the Blindfold: Why Money Feels Hard (EP. 96)

By The-WIN-Podcast | December 23, 2025

Most people feel behind when it comes to money—but that feeling isn’t a failure, it’s a blindfold. We were never taught how the financial game actually works, our instincts push us toward the wrong decisions, and the system quietly rewards spending over patience. When you combine psychology, brutal math, and constant noise, it’s no surprise money feels confusing and stressful.

In this episode of The WIN Podcast: What’s Important Now, we talk about why money is so unintuitive, the common mistakes almost everyone makes, and what changes once you finally understand the rules. This isn’t about perfection or timing—it’s about removing the blindfold, playing intentionally, and quietly doing better than most people over the long run.

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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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Blind Spots: Why We Miss What’s Right in Front of Us (EP. 94)

By The-WIN-Podcast | November 25, 2025

Blind spots aren’t a sign of ignorance — they’re part of being human. In this episode, we explore the unseen forces that quietly shape how we think, behave, and make decisions. From generational overcorrections to psychological patterns like confirmation bias, we break down where blind spots come from and why they’re so difficult to recognize in ourselves. We also share practical tools to reveal those hidden assumptions so you can make clearer, more intentional choices in your life, relationships, and financial future.

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If Only… Why Regret Is the Emotion That Teaches the Hardest Lessons (EP. 93)

By The-WIN-Podcast | November 11, 2025

We all carry a few “what ifs.” The job we didn’t take, the person we didn’t call, the risk we were too scared to try. Regret isn’t just emotional baggage — it’s data. A built-in feedback mechanism that tells us what truly matters to us.

In this episode of The WIN Podcast: What’s Important Now, we unpack the psychology of regret — why we feel it, what it’s trying to teach us, and how to use it to make better decisions moving forward. From the stories of famous inventors and investors who learned from their biggest missteps, to everyday moments we all replay in our minds, we’ll explore how looking back can actually help us move forward.

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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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From Courts to Capital: What Pickleball Teaches Us About Investing (EP. 90)

By The-WIN-Podcast | September 30, 2025

Pickleball has exploded from a backyard game into the fastest-growing sport in America, and its journey offers valuable lessons for investors. In this episode of The WIN Podcast, Corey and Zed look at how the sport’s rapid rise mirrors trends in finance, from spotting opportunities early to understanding the importance of having a reliable partner.

We connect paddles to portfolios, exploring what pickleball teaches us about patience, risk, strategy, and long-term thinking. Whether you’re on the court or in the market, the principles are the same: play smart, stay adaptable, and focus on the bigger picture.

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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.