The Winner’s Curse: Why Smart People Lose Their Way | Alex Imas – EP 716

What if “winning” isn’t proof of intelligence, but evidence that something went wrong?

In this compelling episode of Passion Struck, behavioral economist Alex Imas joins John R. Miles to unpack The Winner’s Curse, a powerful concept from behavioral economics that explains why smart, capable people systematically overpay, overcommit, and double down on bad decisions.

Drawing from his research and his forthcoming book co-authored with Nobel Laureate Richard Thaler, Alex reveals how the Winner’s Curse shows up far beyond auctions and markets—shaping career choices, relationships, investments, leadership decisions, and even how we interact with AI-driven systems. When competition, uncertainty, and ego collide, the “winner” is often the person who misunderstood the situation the most.

John and Alex explore why human decision-making breaks down under uncertainty, how mental representation distorts the choices we think we’re making, and why loss aversion and sunk costs keep us chasing outcomes that no longer serve us. They also examine how modern technology and algorithms don’t correct these flaws but often amplify them.

At its core, this episode is about reclaiming agency in an irrational world: learning to recognize when confidence is misleading, when winning comes at too high a cost, and how better decisions begin not with smarter thinking, but with clearer framing. If you’ve ever wondered why success sometimes feels hollow, why “winning” creates regret, or why intelligent people repeat the same costly mistakes, this conversation will change how you see choice itself.

Passion Struck was recently ranked #1 on FeedSpot’s list of the Top Passion Podcasts on the Web, recognizing the show’s ongoing commitment to thoughtful, human-centered conversations like this one.

Check the full show notes here: https://passionstruck.com/the-winners-curse-alex-imas/

Download a Free Companion Workbook with reflection prompts tied to this episode.

All links gathered here, including books, Substack, YouTube, and Start Mattering apparel:

https://linktr.ee/John_R_Miles

Pre-order You Matter, Luma:

https://youmatterluma.com/

For more about Alex Imas:

https://www.chicagobooth.edu/faculty/directory/i/alex-imas

In this episode, you will learn

• Why the Winner’s Curse means the “winner” often made the biggest mistake
• How behavioral economics challenges the myth of rational decision making
• What mental representation is and how it distorts the choices we believe we’re making
• Why loss aversion and sunk costs keep us chasing bad outcomes
• How uncertainty, competition, and ego interact to produce overconfidence
• Why AI and algorithms often magnify human bias instead of correcting it
• Practical ways to slow down decisions and avoid costly “wins.”

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