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/

Jimmy Soni, CEO and editor in chief of Infinite Books, is back on Infinite Loops. We discuss what's broken in traditional publishing and how we're fixing it. We also dig into Jimmy's forthcoming book on Kobe Bryant, why the world needs more "problem authors," and why our goal is to make our authors millionaires.

We explore why most industries optimize for prestige instead of outcomes, how digital distribution has reshaped attention, and why authors — and creators more broadly — have more leverage than they realize.

Important Links:

Infinite Books: https://www.infinitebooks.com/

Jimmy's X: https://x.com/jimmyasoni

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

Books Mentioned:

The Founders by Jimmy Soni

A Mind at Play by Jimmy Soni

The Dao of Kobe by Jimmy Soni (Upcoming)

What Works on Wall Street by Jim O'Shaughnessy

Invest Like the Best by Jim O'Shaughnessy

How to Retire Rich by Jim O'Shaughnessy

The 4-Hour Workweek by Tim Ferriss

The Almanac of Naval Ravikant by Eric Jorgenson (transcribed as "Naval Akan")

Dispatches from Grief (Upcoming)

Mamba Mentality by Kobe Bryant

Slow Horses by Mick Herron

The Boys in the Boat by Daniel James Brown

Happy Holidays! We're taking a short break from new episodes this week so you can focus on finishing that Christmas dinner. We'll be back next Thursday with something new. In the meantime, why not tuck into this conversation with Guy Spier from January 2024, which remains one of my favorites. Enjoy!

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Guy Spier runs the Aquamarine Fund, an "investment partnership closely modeled on the original Buffet Partnerships." He is also a podcast host, YouTube creator, author of The Education of a Value Investor and the host of the annual investment gathering VALUEx. He describes his life's project as "a quest for wealth, wisdom and enlightenment."

Guy joins the show to discuss the differences between Switzerland and the US, how to unlock the British class system, what he learned from Warren Buffett, and MUCH more!

Important Links:

• Guy's Website
• Guy's Twitter
• Guy's YouTube Channel
• 3Blue1Brown (YouTube Channel)
• Numberphile (YouTube Channel)

Show Notes:

• The Differences Between New York, Switzerland & Paris
• Exploring the Dark Underbelly of New York Nightlife
• Psychedelics, Guns & Regulation
• The Advantages of Swiss Democracy
• Don't Short the United States
• The Branding Skill of the Royal Family
• Unlocking the Rules of the Class System
• Life Paths & Premeditation
• Luck, Opportunity & Non-Canonical Science
• Jim's Music Taste
• Mathematical Shenanigans
• Guy as Emperor of the World
• MORE!

Books Mentioned:

• How to Change Your Mind: What the New Science of Psychedelics Teaches Us about Consciousness, Dying, Addiction, Depression, and Transcendence; by Michael Pollan
• The Hypomanic Edge: The Link Between (a Little) Craziness and (a Lot Of) Success in America; by John Gartner
• Write It Down, Make It Happen: Knowing What You Want and Getting It; by Henriette Anne Klauser
• Invest Like The Best; by Jim O'Shaughnessy
• Outside, the Sky is Blue: The story of a family told with searing honesty, humour and love; by Christina Patterson