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Podcast

Infinite Loops

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!"

Episodes

250

Infinite Loops · Aug 6, 2026

Jesse Michels — American Alchemy (Infinite Loops Classics)

Hi everyone, Jim here. We're taking a short pause on new episodes through the end of August. In the meantime, we're digging out some of our favorite conversations from the archive. This one is …

1:25:01

Infinite Loops · Jul 23, 2026

Philip Howard - How to Bring Common Sense Back to America (Ep. 324)

Philip Howard joins Infinite Loops to explain how America's legal and regulatory system became too complicated to function effectively—and how we can rebuild it around judgment, accountability, and human agency. We discuss why government …

1:16:06

Infinite Loops · Jul 16, 2026

Sangeet Choudary - How AI Will Reshape the Knowledge Economy (Ep. 323)

Sangeet Choudary joins Infinite Loops to explain why AI's greatest impact will not be automating today's work, but rebuilding the structures beneath it. They discuss AI-native companies, the future of knowledge work, the American …

1:48:42

Infinite Loops · Jul 9, 2026

Jameson Olsen - Becoming the Main Character (Ep. 322)

What if the great stories were more than just stories? Jameson Olsen, host of Becoming the Main Character, joins guest host Liberty to explore fiction as a kind of operating system for life — …

1:34:14

Infinite Loops · Jul 2, 2026

David Gelles - The Stories that Shape Business (Ep. 321)

David Gelles joins guest host Jimmy Soni to discuss his career covering business for The New York Times. They talk about his books - Mindful Work, The Man Who Broke Capitalism, and Dirtbag Billionaire …

1:10:59

Infinite Loops · Jun 25, 2026

Gretchen Rubin - How Curiosity Becomes a Calling (Ep. 320)

Gretchen Rubin joins guest host and Infinite Books CEO Jimmy Soni to discuss her journey from Supreme Court clerk to bestselling author, the creative obsessions that shaped her career, and the daily habits that …

1:23:43

Infinite Loops · Jun 18, 2026

Ben Cohen - The Hidden Art of Making Things Better (Ep. 319)

Wall Street Journal columnist Ben Cohen joins guest host Jimmy Soni, CEO of Infinite Books, to explore the hidden art of making things better. They explore the hot hand phenomenon in basketball, why Moneyball …

1:20:14

Infinite Loops · May 28, 2026

Jason Buck - Faith, Failure, and Finance (Ep. 316)

Jason Buck, founder and CIO of Mutiny Funds, joins Infinite Loops to tell the painful and darkly funny story of how the 2007–2008 crash destroyed his real estate business, wiped out his paper wealth, …

2:01:50

Infinite Loops · May 7, 2026

Danielle Crittenden - Dispatches from Grief (Ep. 313)

On a February morning, Danielle Crittenden's world cleaved in two: the life before her daughter Miranda was found dead in her Brooklyn apartment, and the life after. Two years and three months later, Danielle …

1:52:28

Infinite Loops · Apr 23, 2026

Brian Potter - How to Fix America's Building Problem

Why has America become so bad at building housing, infrastructure, and major projects? Brian Potter, author of The Origins of Efficiency and writer of Construction Physics, explains why prefab housing keeps failing and why …

1:13:00

Infinite Loops · Apr 9, 2026

Sam Arbesman - Why Future Belongs to Curious People (Ep. 309)

Scientist and writer Sam Arbesman joins us for a wide-ranging conversation on AI, optimism, science, education, archives, science fiction, and why the history of computing still has so much to teach us. We talk …

1:46:29

Infinite Loops · Mar 26, 2026

Polina Pompliano - What Truly Drives Successful People (Ep. 307)

Polina Pompliano studies some of the most successful people in the world—and what she's found challenges how we think about success, creativity, and human behavior. In this episode of Infinite Loops, we explore the …

1:07:08

Infinite Loops · Mar 19, 2026

Adam Mastroianni - Why Creativity Feels Like It's Dying (Ep. 306)

In this episode of Infinite Loops, we speak with Adam Mastroianni—experimental psychologist and sharp critic of modern culture and science. We ask, why does creativity feel like it's fading? From endless remakes to cultural …

1:32:42

Infinite Loops · Mar 12, 2026

Arkady Kulik - The Psychology of Self-Deception (Ep. 305)

In this episode of Infinite Loops, we sit down with venture capitalist and physicist Arkady Kulikov to explore the psychology behind founders, responsibility, and self-deception. Kulik discusses why the hardest problems in business are …

1:31:23

Infinite Loops · Feb 12, 2026

Packy McCormick - How Writing Shapes Companies (Ep. 301)

Packy McCormick is one of the most thoughtful writers in tech and investing. In this episode of Infinite Loops, we talk about why writing is still the most powerful way to think clearly, how …

1:33:13

Infinite Loops · Feb 5, 2026

Jean-Marc Daecius - The Last Human Chief of Staff (Ep. 300)

What happens when you design a company assuming AI should do everything it possibly can? Jean-Marc Daecius, OSV's Chief of Staff, joins Infinite Loops to explain what it means to be "AI first" — …

1:49:24

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