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Infinite Loops

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Jim O'Shaughnessy

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!"

#300

Ariel Meyerowitz — Navigating the Art World (EP. 292)

Professional art advisor Ariel Meyerowitz joins Jim O'Shaughnessy to demystify the complex... more

04 Dec 2025

1 HR 36 MINS

1:36:08

04 Dec 2025

#299

Adam Moskowitz — The Way of the Cheesemonger (EP.291)

<a href= "https://www.adamjaymoskowitz.com" target="_blank" rel= "noopener">Adam Moskowitz... more

27 Nov 2025

1 HR 14 MINS

1:14:08

27 Nov 2025

#298

Todd Rose — Escaping the Trap of the Standard Path (EP.290)

From a 0.9 GPA in rural Utah to the faculty of Harvard, Todd Rose's life is a testament to... more

20 Nov 2025

2 HR 03 MINS

2:03:46

20 Nov 2025

#297

George Mack — The Game of Life (Infinite Loops CLASSICS)

Hello everyone, Jim here. We're taking a brief break from new episodes to spotlight a gold... more

13 Nov 2025

1 HR 43 MINS

1:43:33

13 Nov 2025

#296

Michael Perry — Improbable Mentors and the Art of Midwestern Storytelling (EP. 289)

What happens when a shy farm kid from rural Wisconsin who never dreamed of being a writer ... more

06 Nov 2025

1 HR 52 MINS

1:52:55

06 Nov 2025

#295

Kenneth Stanley — The Trap of the Objective (EP.288)

Ken Stanley – AI researcher and author of "Why Greatness Cannot Be Planned" – joins me to ... more

30 Oct 2025

1 HR 25 MINS

1:25:34

30 Oct 2025

#294

Elle Griffin — Rethinking Ownership and the Future of Work (EP. 287)

Writer, editor, and founder of The Elysian, Elle Griffin joins me on Infinite Loops to dis... more

23 Oct 2025

1 HR 38 MINS

1:38:47

23 Oct 2025

#293

Jay Yang — The Power of Permissionless Action (EP. 286)

What if the biggest barrier between you and your dreams isn't talent, connections, or luck... more

16 Oct 2025

1 HR 23 MINS

1:23:53

16 Oct 2025

#292

Jeff Bussgang — The Experimentation Machine (EP.285)

Jeff Bussgang — entrepreneur, venture capitalist, Harvard Business School professor, and c... more

09 Oct 2025

1 HR 19 MINS

1:19:34

09 Oct 2025

#291

Dan Wang — China, US and our Collective Future (EP.284)

Dan Wang, author of "Breakneck: China's Quest to Engineer the Future," joins me to explore... more

02 Oct 2025

1 HR 37 MINS

1:37:43

02 Oct 2025

#290

Alex Danco — Speeches and Spells for the Kings and Priests (EP.283)

It's Alex Danco's landmark 10th appearance on Infinite Loops! He joins the show to discuss... more

25 Sep 2025

1 HR 20 MINS

1:20:33

25 Sep 2025

#289

Sangeet Paul Choudary — AI and our System Reshuffle (EP.282)

Sangeet Paul Choudary, bestselling author of Platform Revolution and Reshuffle, and senior... more

18 Sep 2025

1 HR 39 MINS

1:39:44

18 Sep 2025

#288

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

Michael Dean — architect-turned-writer, O'Shaughnessy Fellow, and creator of Essay Archite... more

11 Sep 2025

1 HR 34 MINS

1:34:25

11 Sep 2025

#287

Roon — On Shape Rotators, AGI & Tenet (Infinite Loops CLASSICS)

Hello everyone, Jim here. We're taking a brief two-week break from new episodes to spotlig... more

04 Sep 2025

1 HR 06 MINS

1:06:17

04 Sep 2025

#286

Gurwinder Bhogal's Guide to Modern Survival (Infinite Loops CLASSICS)

Hello everyone, Jim here. We're taking a brief two-week break from new episodes to spotlig... more

28 Aug 2025

1 HR 41 MINS

1:41:22

28 Aug 2025

#285

Joe Hudson — The Art of Accomplishment (EP.280)

What happens when a self-described "not very good" venture capitalist discovers he has an ... more

21 Aug 2025

1 HR 33 MINS

1:33:17

21 Aug 2025

#284

Michael Gibson & Danielle Strachman — The 1517 Rebellion (EP.279)

Michael Gibson and Danielle Strachman, co-founders of 1517 Fund, join the show to discuss ... more

14 Aug 2025

1 HR 31 MINS

1:31:19

14 Aug 2025

#283

Ed Latimore — The Art of Self-Transformation (EP.278)

Ed Latimore: boxer, physicist, and author of Hard Lessons from the Hurt Business makes his... more

07 Aug 2025

1 HR 45 MINS

1:45:24

07 Aug 2025

#282

Sam Arbesman — Science, Complexity and Humanistic Computation (EP.277)

Sam Arbesman, complexity scientist, author of "The Magic of Code," and scientist in reside... more

31 Jul 2025