The WIN Podcast, What’s Important Now

Most decisions in life come with a second chance—you can adjust, change course, or try again. But some of life’s biggest financial moments don’t offer the same flexibility. Retirement, helping aging parents, receiving an inheritance, selling a business, and preparing an estate can represent decisions where much of the important work needs to happen long before the moment itself arrives.

In this episode, we explore...

Have you ever spent hours assembling a piece of furniture only to feel strangely proud of the finished product? There may actually be a psychological reason for that. In this episode, we explore the history of IKEA and the fascinating phenomenon known as the “IKEA Effect”—our tendency to place greater value on things simply because we helped create them.

But the IKEA Effect extends far bey...

As the U.S. Open takes center stage and Roger Federer enters the International Tennis Hall of Fame, we look back at one remarkable statistic from his legendary career: Federer won only about 54% of the points he played, yet won 82% of his matches. It’s a powerful reminder that success doesn’t require winning every single point—it requires staying focused on the bigger objective.

Investing ...

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 ...

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 epi...

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 f...

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...

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 think about money and retirement.

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 a fascinating lesson about wealth, opportunity, and human behavior tha...

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 that matter most rarely take car...

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 outcomes are often driven by volatility, emotion, and even...

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 ho...

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.

In this episode, we explore the key ideas from Die with Zero and challenge the traditional mindset of saving for “someday.” What if the goal isn’t to die rich, but to use your money to create meaningful experienc...

What’s the most important phone call ever made? It may have been the very first one. In 1876, Alexander Graham Bell spoke the words, “Mr. Watson, come here — I want to see you,” proving for the first time that the human voice could travel through a wire.

In this episode of The WIN Podcast: What’s Important Now, we explore how that simple moment changed communication—and w...

Are you the hero… or the bottleneck? In this episode of The WIN Podcast, we explore how constantly saving the day in your business, finances, or family might actually be holding you back. Hustle and heroics work in the beginning — but if everything depends on you, growth has a ceiling.

What’s Important N...

Episode 100 is here — and we’re celebrating by distilling 100 conversations into the Top 10 lessons that have shaped how we think about money, mindset, leadership, and purposeful living. From Olympic-level preparation and strategic financial planning to the domino effect of small habits and becoming the “coffee bean” under pressure, this...

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.

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 c...