Annie Duke — former professional poker player, decision strategist, and bestselling author — joins us for a deep conversation about why smart people so often make bad decisions.

Annie explains why misinterpretation is more dangerous than misinformation, why data is often true but misleading, and how our brains are wired for certainty in a probabilistic world. From real-world media examples to investing, health decisions, and AI-generated insights, this episode explores how explanations feel satisfying — even when they’re wrong.

Important links:

Substack: https://newsletter.osv.llc/

Annie's website: https://www.annieduke.com/

TIMESTAMPS

0:00 — Intro
6:30 — Misinformation vs. Misinterpretation
11:28 — The Washington Post COVID Headline
17:00 — Explanatory Satisfaction
29:00 — Deterministic Minds in a Probabilistic World
35:28 — Probability vs. Possibility
51:17 — Luck vs. Decision Quality
1:03:01 — Communicating Uncertainty
1:13:02 — Base Rates, Language, and Framing
1:29:00 — Survivorship Bias & Self-Selected Samples