The WIN Podcast, What’s Important Now

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 ca...

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 wron...

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-wo...

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 ti...

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 investing, p...

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 effor...

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 id...

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 t...

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...