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

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

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 …

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

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

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 …

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

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

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 …

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

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

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, …

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

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

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 …

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

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

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 …

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

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

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. …

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

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

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 …

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

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

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 …

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