Goals – The WIN Podcast

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

By The-WIN-Podcast | May 12, 2026

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)

By The-WIN-Podcast | April 28, 2026

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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Why the Road to Wealth Isn’t Straight (EP. 104)

By The-WIN-Podcast | April 14, 2026

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, strong financial foundations, and ongoing adjustments all play a role in building lasting wealth. If your financial path feels unpredictable, this episode will help you see why that might be exactly what it’s supposed to look like.

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Die with Zero (EP. 103)

By The-WIN-Podcast | March 31, 2026

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 the life you actually want to live.

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Are You the Hero… or the Bottleneck? (EP. 101)

By The-WIN-Podcast | March 3, 2026

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 challenges you to stop managing chaos and start building structure. Because real success isn’t about being needed… it’s about creating something that works even when you’re not in the room.

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The 100 Lessons Project (EP. 100)

By The-WIN-Podcast | February 17, 2026

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 just highlights — they’re principles we’ve seen play out in real lives, real markets, and real decisions.

Reaching 100 episodes is a milestone we don’t take lightly. Most podcasts never get here, and we’re grateful for every listener who has joined the journey. In this special episode, Corey and Zed go back and forth, sharing the lessons that have defined WIN — and what will guide the next 100. If you want a condensed blueprint for what truly matters now, this is the episode to hear.

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What Our Parents Got Right—and Wrong—About Money (EP 98)

By The-WIN-Podcast | January 20, 2026

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 financial landscape—focusing on what’s truly important now.

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From Calendar Chaos to Financial Clarity (EP. 97)

By The-WIN-Podcast | January 6, 2026

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.

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Removing the Blindfold: Why Money Feels Hard (EP. 96)

By The-WIN-Podcast | December 23, 2025

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: What’s Important Now, we talk about why money is so unintuitive, the common mistakes almost everyone makes, and what changes once you finally understand the rules. This isn’t about perfection or timing—it’s about removing the blindfold, playing intentionally, and quietly doing better than most people over the long run.

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The Weight of Maybe: Why We Freeze (EP. 95)

By The-WIN-Podcast | December 9, 2025

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 finance, showing how hesitation can erode wealth just as easily as it stalls personal growth. With practical frameworks and real-world examples, this conversation gives you the tools to move from uncertainty to confident action. If you’ve been parked in neutral—mentally, emotionally, or financially—this episode will help you shift into gear and move forward with purpose.