The WIN Podcast, What’s Important Now

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 Happynes...

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 n...

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 t...

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....

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...

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...

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 a guide, we break down how volatility, preparation,...

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 experiences at the right time? We tie it back to What’s Important Now? —looking at experiences that expire, whether or not there is a risk of over-saving, and how to better align your money with th...

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 what it teaches us about i...

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 Now isn’t more effort — it’s better systems. From money automation to life design, this episode...

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 episode captures the ideas that mattered most. These aren’t...

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. Along the way, we share the remarkable true story of Peter the Eagle , a bald eagle who lived inside the Philadelphia M...

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 timeless principles in a modern finan...

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 how you plan. R esources Corey’s Book Conne...

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 T...

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. We also draw clear parallels to personal f...

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 t...

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 , we unpack the psychology of regret — why we feel it, what it’s trying to teach us, and how to use it to...

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 movements of today, we trace how values e...

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: how modern design, tech, and abundan...

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. We connect paddles to portfolios, exploring what...

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 massive consequences. Then, they tie it...

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. Just as language infl...

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 down what they can teach us about r...