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Jim O'Shaughnessy · Philosophy

Infinite Loops

Every Thursday, join Jim O'Shaughnessy and his favorite people as they arm you with the tools & fresh perspectives required to upgrade your HumanOS and thrive in our messy, probabilistic world. Visit our Substack at newsletter.osv.llc for full transcripts, highlights, weekly doses of timeless wisdom, and a bounty of other goodies designed to make you go, "Hmm that's interesting!"

Episodes

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Annie Duke — Why We Make the Wrong Decisions (Ep. 296)

08 Jan 2026
1h 45m
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Annie Duke, a former world-class poker player and decision-making expert, discusses her upcoming book, emphasizing the importance of interrogating data to improve decision quality. She highlights that most people aren't intentionally lying or misleading, but rather misinterpreting data due to biases and a lack of prope...

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Jimmy Soni — The Publishing System is Broken (EP. 295)

01 Jan 2026
1h 37m
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Guy Spier — Wealth, Wisdom & Enlightenment (Infinite Loops CLASSICS)

25 Dec 2025
2h 2m
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Vik Muniz — The Art of Perception (EP.294)

17 Dec 2025
1h 35m
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Marc Dennis — Painting the Punchline (EP.293)

11 Dec 2025
1h 58m
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Ariel Meyerowitz — Navigating the Art World (EP. 292)

04 Dec 2025
1h 36m
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Adam Moskowitz — The Way of the Cheesemonger (EP.291)

27 Nov 2025
1h 14m
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Todd Rose — Escaping the Trap of the Standard Path (EP.290)

20 Nov 2025
2h 3m
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George Mack — The Game of Life (Infinite Loops CLASSICS)

13 Nov 2025
1h 43m
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Michael Perry — Improbable Mentors and the Art of Midwestern Storytelling (EP. 289)

06 Nov 2025
1h 52m
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Kenneth Stanley — The Trap of the Objective (EP.288)

30 Oct 2025
1h 25m
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Elle Griffin — Rethinking Ownership and the Future of Work (EP. 287)

23 Oct 2025
1h 38m
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Jay Yang — The Power of Permissionless Action (EP. 286)

16 Oct 2025
1h 23m
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Jeff Bussgang — The Experimentation Machine (EP.285)

09 Oct 2025
1h 19m
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Dan Wang — China, US and our Collective Future (EP.284)

02 Oct 2025
1h 37m
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Alex Danco — Speeches and Spells for the Kings and Priests (EP.283)

25 Sep 2025
1h 20m
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Sangeet Paul Choudary — AI and our System Reshuffle (EP.282)

18 Sep 2025
1h 39m
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In this episode of Infinite Loops, Jim O'Shaughnessy interviews Sangeet Paul Choudary, author of "Platform Revolutions" and "Reshuffle," about his thesis on AI's impact on the economy. Choudary argues that AI's primary effect will be rewiring the economy through coordination, not just speeding up tasks. They discuss ho...

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Michael Dean — The Architecture of Essays (EP. 281)

11 Sep 2025
1h 34m
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Roon — On Shape Rotators, AGI & Tenet (Infinite Loops CLASSICS)

04 Sep 2025
1h 6m
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Gurwinder Bhogal's Guide to Modern Survival (Infinite Loops CLASSICS)

28 Aug 2025
1h 41m
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