Tag: Guidance
Happy Accidents (EP. 83)

Happy Accidents (EP. 83)

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Velcro. Post-its. Potato chips. What do they have in common? None of them were part of the plan. In this episode of WIN, we dive into the world of accidental inventions—and how their surprise success offers a powerful lesson for investors and dreamers alike. Because sometimes, the best financial returns don’t come from predicting the future, but from being ready when it shows up.

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What Ostriches, Lightning, and Goldfish Can Teach You About Money (EP. 82)

What Ostriches, Lightning, and Goldfish Can Teach You About Money (EP. 82)

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We’ve all believed things that aren’t quite true—like the idea that ostriches bury their heads in the sand or that goldfish forget everything in three seconds. In this episode, we unpack five common myths people believe without question and explore the surprising ways they connect to financial behavior. From ignoring your budget like an ostrich to reacting emotionally to market “red” like a charging bull, we break down how these false beliefs can quietly derail your financial plan.

Sometimes, what costs us most isn’t what we don’t know—it’s what we think we know.

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Financial Fables: What a tortoise, a fox, and a golden goose can teach you about your wallet (EP. 81)

Financial Fables: What a tortoise, a fox, and a golden goose can teach you about your wallet (EP. 81)

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In this episode of WIN: What’s Important Now, we unpack five classic Fables—stories you may have heard as a child—and discover the powerful financial wisdom they hold for adults. From the slow-and-steady tortoise to the golden-egg-laying goose, these tales reveal truths about saving, investing, greed, preparation, and mindset. Join us as we connect ancient stories to modern money habits and ask: what’s your financial fable?

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Timeless Truths (EP. 79)

Timeless Truths (EP. 79)

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In Episode 79 of WIN: What’s Important Now, we explore five timeless truths about human behavior — and how they still shape our decisions today. Inspired by Morgan Housel’s Same as Ever, we examine surprising moments from history that reveal why some lessons never go out of style.

Through stories of risk, patience, and the power of incentives, we connect the past to the present, showing how what’s always been true still matters now. Whether you’re thinking about money, mindset, or meaning, this episode is a reminder that some of the most important things… don’t really change.

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Laying Up or Going for It: Risk, Reward, and the Green Ahead (EP. 78)

Laying Up or Going for It: Risk, Reward, and the Green Ahead (EP. 78)

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Fresh off The Masters, we dive into the high-stakes decision every golfer faces on a par 5—lay up or go for the green—and explore how that same risk/reward choice shows up in personal finance. Whether you’re building a nest egg or eyeing a bold investment move, knowing when to play it safe and when to take a calculated shot is key. Tune in as we break down the parallels between smart course management and sound financial planning.

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Bracketology & Bankrolls: The Madness of March & Markets (EP. 75)

Bracketology & Bankrolls: The Madness of March & Markets (EP. 75)

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March Madness isn’t just about basketball—it’s about risk, reward, and the unpredictable nature of both brackets and investing. In this episode of WIN: What’s Important Now, we break down the financial lessons hidden in the tournament, from the psychology of picking Cinderella teams to the importance of diversification in both your portfolio and your bracket. Plus, we explore the staggering impact March Madness has on workplace productivity. Whether you’re a hoops fan or a finance geek, this episode is a slam dunk!

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The Science of Knowing When to Say Yes (EP. 74)

The Science of Knowing When to Say Yes (EP. 74)

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How do you know when to stop searching and finally make a decision? Whether you’re picking a life partner, buying a house, or deciding when to invest, the fear of making the wrong choice can leave you stuck in indecision. In this episode, we explore Optimal Stopping Theory—a mathematical approach to decision-making that helps determine the perfect moment to act. Known as the 37% Rule, this principle provides a simple yet powerful way to balance exploration and commitment, so you don’t waste time searching forever or settle too soon.

From dating and job hunting to stock picking and real estate investing, this framework applies to almost every area of life. We’ll break down how it works, why perfection is a myth, and how using this strategy can help you make better, faster, and more confident decisions. Tune in to learn when to trust the process, take the leap, and stop second-guessing yourself!

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Presidents, Money, and the Stories They Tell (EP. 72)

Presidents, Money, and the Stories They Tell (EP. 72)

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In this episode of The WIN Podcast, we delve into the history books to uncover how U.S. presidents handled money, from George Washington’s savvy land investments to Lincoln’s creation of greenbacks during the Civil War. We’ll also explore Franklin D. Roosevelt’s bold departure from the gold standard and fun facts like presidential salaries.

Join us for a lighthearted yet insightful journey through history, where leadership and finance intersect in unexpected ways. Whether it’s lessons in diversification, adapting to change, or smart money management, these presidential stories prove that financial wisdom transcends time. Tune in and discover how the past can inspire your financial future!

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Flipping the Odds: Finding Success Amid Uncertainty (EP. 70)

Flipping the Odds: Finding Success Amid Uncertainty (EP. 70)

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In this special Christmas Eve episode, we explore how life’s uncertainties can still lead to incredible success. Drawing inspiration from stories like Walt Disney’s rise from failure and Heinz Berggruen’s journey from refugee to renowned art collector, we’ll discuss how focusing on what you can control—and letting go of what you can’t—can transform your mindset.

We’ll also dive into the art of picking your battles, whether during the holiday hustle or in your financial life. Join us for a thoughtful conversation about finding joy in the unknown, making intentional choices, and celebrating the moments that truly matter this season.

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The Hype and the Gap – Investing with Perspective (EP. 69)

The Hype and the Gap – Investing with Perspective (EP. 69)

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In this episode of WIN: What’s Important Now, we explore the Gartner Hype Cycle—a framework for understanding the lifecycle of new technologies—and its parallels to market trends and investor behavior. Using real-world examples like self-driving cars and 3D printing, we uncover lessons on recognizing hype and identifying sustainable opportunities.

We also examine the “behavior gap” to discuss how emotions often derail smart investing. Tune in for practical tips on navigating market hype, managing emotional decisions, and aligning investments with long-term goals.

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