In this episode, host Travis Chappell and producer Eric break down missed opportunities, painful losses, and fraud-adjacent stories to show how real-world investors actually think through risk. Using everything from crypto FOMO to Shark Tank misses and Ponzi-style funds, they explore how to build a rational investing framework that can survive both wins and wipeouts.​

On this episode we talk about:

Passing on early opportunities like crypto and what that really cost over time

Famous “missed deals” like Ring and other Shark Tank passes that later exploded

How to emotionally process investments that go to zero—even when they seemed “safe”

Why trying to “beat the market” usually backfires for non-professional investors

The blackjack analogy for setting clear investing rules and sticking to them

Angel investing math: why most startups fail and what that means for your checks

A real story of an investor-turned-felon running a quasi‑Ponzi fund

How seemingly smart people slide from aggressive bets into outright fraud

Why Travis shifted from big swings to boring, low‑risk, long‑term investments

Top 3 Takeaways

Losses are inevitable, so you need rules before you need returns. Approaching investing like blackjack—accepting losses as part of the game and sticking to a predetermined strategy—keeps you from going on emotional “tilt” after a bad beat.

Most private deals will fail, even with “strong” founders. Angel and alternative investments should be treated as high‑risk, small‑allocation bets—not as the foundation of your net worth.

Boring usually wins over time. For long‑term wealth, broad, diversified, low‑chance‑of‑zero investments (like major index funds) are a far more reliable base than chasing the next Uber or crypto rocket ship.

Notable Quotes

“You have to set rules and then stick to the rules—because losses are part of the game.”

“You’re not going to beat the market. Ray Dalio can’t consistently beat the market, and he’s the best in the world.”

“There’s no truly ‘no‑risk’ investment. If someone promises that, they’re either lying or they’re going to prison.”​

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