For generations, Americans have spent decades building wealth through homes, businesses, investments, and retirement accounts. Now, much of that wealth is beginning to move to the next generation. In this episode, we explore The Great Wealth Transfer—how we got here, why trillions of dollars are expected to change hands, and what that could mean for …
Every summer, thousands of players gather in Las Vegas with one goal: winning the World Series of Poker. While luck may determine the outcome of a single hand, the world’s best players know that long-term success is built on discipline, probability, patience, and making consistently good decisions. In this episode, we explore the history of …
Every four years, the FIFA World Cup captures the attention of billions, but the lessons extend far beyond the soccer pitch. In this episode, we explore what makes the world’s most popular sporting event so captivating and uncover the surprising parallels between winning a championship and building long-term financial success. From the group stage to …
What are you pursuing? It’s a simple question, but one that has shaped lives, careers, and civilizations throughout history. In this episode, we explore the meaning and origins of the word pursuit—from its historical roots to its appearance in phrases like “the pursuit of happiness,” the classic board game Trivial Pursuit, and the inspiring story …
For years, we’ve been told that reaching a certain number—often $1 million—is the key to a successful retirement. But is there really a magic number that guarantees financial security? In this episode, we explore why humans are naturally drawn to round numbers, milestones, and even superstitions, and how those tendencies can influence the way we …
In 1849, hundreds of thousands of people rushed west in search of gold, hoping to strike it rich. While a few found fortunes in the mines, many of the greatest and most lasting fortunes were built by the people selling the tools, supplies, transportation, and infrastructure that supported the boom. The California Gold Rush offers …
Success isn’t usually destroyed by one catastrophic mistake — it slowly erodes through years of neglected maintenance. In this episode, Corey and Zed explore why the most important parts of life and wealth require constant attention, even after we’ve worked hard to build them. From finances and health to relationships and personal growth, the things …
The Stanley Cup Playoffs remind us that the thin line between winning and losing is often measured in inches — a puck off the post, a fortunate bounce, or one split-second decision under pressure. In this episode of The WIN Podcast, we explore how hockey’s chaos and unpredictability mirror the world of investing, where short-term …
What if winning isn’t the goal—but the problem? In this episode of The WIN Podcast: What’s Important Now, we explore the strange world of Guinness World Records to uncover a deeper truth: you can optimize for almost anything—even when it doesn’t actually matter. Through extreme examples, we highlight how easy it is to chase the …
Most people expect the path to wealth to be a straight line—but just like the roads we drive every day, it’s anything but. In this episode, we explore why curves, bridges, and changing conditions aren’t flaws in the journey—they’re intentional design features that keep us moving forward safely and efficiently. Using real-world road engineering as …