Tag: Guidance
Win the Match, Not the Point (EP. 114)

Win the Match, Not the Point (EP. 114)

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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 works much the same way. Markets will have bad days, difficult years, and periods when a strategy simply doesn’t go as planned. In this episode, we use tennis and Federer’s extraordinary career to explore the importance of patience, perspective, and keeping your eyes on the long-term goal. You don’t have to win every point—you just have to win the match.

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The Great Wealth Transfer (EP. 113)

The Great Wealth Transfer (EP. 113)

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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 families and investors.

But transferring wealth is about more than simply passing along money. We discuss the importance of preparation, communication, estate planning, and teaching the next generation how to handle what they receive. Because building wealth is only half the journey—the real challenge may be making sure the next generation is ready for the handoff.

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Know When to Hold ‘Em (EP. 112)

Know When to Hold ‘Em (EP. 112)

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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 the World Series of Poker and uncover the surprising lessons it offers investors.

From bankroll management and expected value to knowing when to take calculated risks, poker and investing have more in common than you might think. Join us as we discuss why success isn’t about winning every hand—it’s about making smart decisions over time and staying in the game long enough for the odds to work in your favor.

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The Long Game (EP. 111)

The Long Game (EP. 111)

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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 the knockout rounds, every match offers a lesson in preparation, patience, discipline, and resilience.

Just like investing, championships aren’t won with one spectacular play—they’re earned through consistency, smart decisions, and the ability to stay in the game when the pressure is highest. Whether you’re a lifelong soccer fan or have never watched a match, you’ll discover why the principles that lead to lifting the World Cup trophy are the very same principles that can help you achieve lasting financial success.

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The Pursuit (Ep. 110)

The Pursuit (Ep. 110)

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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 told in The Pursuit of Happyness. Along the way, we examine why the things we choose to chase often reveal more about us than the things we eventually achieve.

Whether it’s wealth, success, security, knowledge, or purpose, every pursuit comes with tradeoffs. Join us as we discuss the difference between chasing what is merely interesting and pursuing what is truly important. Because in the end, a meaningful life isn’t defined only by what we attain—it’s shaped by what we choose to pursue.

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The Myth of the Magic Number (EP. 109)

The Myth of the Magic Number (EP. 109)

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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.

From lucky numbers and cultural beliefs to retirement targets and net worth goals, we’ll examine why numbers often carry more emotional weight than practical meaning. Most importantly, we’ll discuss why a successful retirement isn’t determined by a single figure in an account balance, but by the relationship between your resources, your lifestyle, and the life you want to live.

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Selling Shovels in the Digital Age (EP. 108)

Selling Shovels in the Digital Age (EP. 108)

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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 that remains just as relevant today.

In this episode, we explore what the Gold Rush can teach us about the modern AI revolution and why the biggest opportunities are not always where the crowd is looking. From pickaxes and shovels to chips, cloud computing, and digital infrastructure, we’ll examine how every boom creates winners—and why those who support the opportunity often outperform those chasing it.

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The Maintenance Myth: Why Success Is Never Finished (EP. 107)

The Maintenance Myth: Why Success Is Never Finished (EP. 107)

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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 care of themselves.

We’ll discuss the hidden cost of deferred maintenance, why people naturally avoid upkeep, and how small overlooked issues often become major problems over time. Because in the end, success isn’t something we achieve once — it’s something we protect intentionally.

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The Thin Line Between Winning and Losing (EP. 106)

The Thin Line Between Winning and Losing (EP. 106)

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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 events no one can fully control.

We discuss why “this time is different” is one of the most dangerous phrases in finance, how discipline matters more than prediction, and why successful investors — like championship teams — stay committed to the process even when the bounces don’t go their way.

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The Danger of Playing the Wrong Game (EP. 105)

The Danger of Playing the Wrong Game (EP. 105)

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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 wrong metrics in money, life, and decision-making.

Because in the end, the real risk isn’t losing—it’s winning a game that was never worth playing.

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