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

About this episode

Jennifer Shahade discusses her new book and shares insights on decision-making and creativity through the lens of chess and poker.

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…

People in this episode

Host: Ben Johnson

Guest: Jennifer Shahade

Topics covered

• cheating in chess
• decision-making
• AI in learning
• psychology
• chess strategies
• creativity

Keywords

• chess
• AI
• decision-making
• creativity
• Einstellung Effect
• cheating
• poker

Mentioned in this episode

Organizations: US Chess, Netflix

Books & works: Thinking Sideways: How to Think Like a Chess Player and Win at Life

More episodes of Perpetual Chess Podcast

• EP 486: James Black Jr. on Going from Scholastic Star to Chess Mentor · June 9, 2026 · 1h 1m
• EP 485: GM Simon Williams on Mistakes, Revival, and the Future of Chesspublishing · June 2, 2026 · 58 min
• EP 484: Jordan Himelfarb on Interregnum and the Drama of the 2024 Candidates Cycle · May 26, 2026 · 44 min
• EP 483- Paulo SantAnna: What Happens When a Retired Adult Treats Chess Like a Full-Time Job? · May 19, 2026 · 1h 9m
• EP 482- GM Ivan Sokolov on Talent, Training and Modern Chess · May 12, 2026 · 54 min
• EP 481- IM Greg Shahade: Inside His Incredible Jeopardy Run · May 5, 2026 · 1h 21m