The WIN Podcast, What’s Important Now

Money feels permanent, but the way it’s made has changed constantly. In this episode of WIN: What’s Important Now, we explore how the U.S. Mint was created, how American currency evolved from metal to modern money, and why trust—not gold or paper—is what really makes money work.

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The money rules many of us grew up with were shaped by a very different economic world. In this episode of What’s Important Now, we look at where that advice came from and why it worked so well for our parents’ generation. Then we ask the harder question: Does it still work today? We explore what needs updating, what still matters, and how investors can apply tim...

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

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, 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.

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 th...

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.

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 movem...

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: ...

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.

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 massi...

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 dri...

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.

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 ...

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, l...

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 ...

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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We’ve all believed things that aren’t quite true—like the idea that ostriches bury their heads in the sand or that goldfish forget everything in three seconds. In this episode, we unpack five common myths people believe without question and explore the surprising ways they connect to financial behavior. From ignoring your budget like an ostrich to reacting emotionally to market “red” like a chargi...

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 stori...