Jennifer Shahade is a two-time U.S. Women’s Champion, poker professional, commentator, and acclaimed author. This week, she returns to the pod to discuss her new book Thinking Sideways: How to Think Like a Chess Player and Win at Life. Drawing on chess, poker, and psychology, Jen shares practical tips and memorable stories about decision-making, creativity, and improvement.

We discuss:

Why she interviewed reformed chess cheaters and what their stories reveal about ambition
Helpful advice for remembering opening lines
The “Einstellung Effect” and how to avoid missing better ideas
How AI is changing the way we learn and think

We also catch up on Jen’s recent travels and upcoming events. There is a lot to learn and plenty of great stories along the way.

0:00- Intro-

Jen Shahade and US Chess announce a settlement:

https://x.com/KenneyBaden/status/2039375140534767852?s=20

0:02- Jen Shahade joins me. How did she find reformed chess cheaters to interview? What did she learn from talking with them for her book?

Mentioned: Netflix Untold Documentary about the Niemann-Carlsen story

https://www.netflix.com/title/81582391

0:10- What is “MTR”?

0:14- Working with legendary trainer IM Mark Dvoretsky

0:18- Lessons learned from interviewing a memory champion

Mentioned: Yanjaa Wintersoul, GM Sam Shankland

0:28- Jen’s experiences coding with Claude

Check out the links to the app she built here:

https://jenshahade.substack.com/p/spin-the-wheel-vibe-a-move

0:36- What is “the Einstellung effect”?

0:40- Jen’s chess-related conversation with legendary psychologist and author Daniel Kahneman

0:42- How chess master and Alpha Zero creator Demis Hassabas “thought sideways” to secure funding for his start up.

0:48- Observations from the recent Sloan sports analytic conference

0:50- What is “the sandwich method”?

0:51- Upcoming book events for Jen

0:52- If you will be in NYC on May 12 and want to support a good cause, come see Jen and I at this event.

You can buy tickets to the Chess in the Schools Poker/Chess Fundraiser here:

https://secure.givelively.org/event/chess-in-the-schools-inc/chess-in-the-schools-3rd-annual-charity-poker-tournament

0:54- Thanks to Jen for joining me again, here is where to order her book.

https://www.simonandschuster.com/books/Thinking-Sideways/Jennifer-Shahade/9798897100729

https://www.amazon.com/Thinking-Sideways-Think-Chess-Player/dp/B0FCDDB8XV

Photo in thumbnail by Maria Emelianova

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EP 477- Jennifer Shahade on Cheating, AI, and Thinking Like a Chess Player