Jim O'Shaughnessy

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!"

Author

Jim O'Shaughnessy

Category

Technology

Podcast website

infiniteloopspodcast.com

Latest episode

Jul 9, 2026

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Episodes

Jameson Olsen - Becoming the Main Character (Ep. 322) 09.07.2026

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 — a way to study agency, ambition, empathy, failure, courage, and change without having to live every consequence yourself. Through Hamlet, Frankenstein, Sherlock Holmes, Lord of the Rings, training montages, N...

David Gelles - The Stories that Shape Business (Ep. 321) 02.07.2026

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 - and the reporting behind major stories on Bernie Madoff, Jack Welch, Boeing's 737 Max crashes, and Patagonia's Yvon Chouinard. David explains how he broke a front-page story five weeks into journal...

Gretchen Rubin - How Curiosity Becomes a Calling (Ep. 320) 25.06.2026

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 fuel her work. They cover her transition from law to writing Power Money Fame Sex , why she often ends up writing the book before the proposal, the art of editing until the final hour (even...

Ben Cohen - The Hidden Art of Making Things Better (Ep. 319) 18.06.2026

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 shaped a generation of journalists, the peanut butter and jelly crisis in the Warriors locker room, why ASML is the most important company you've never heard of, the strange story of Driscoll...

Revan Lazarus - How AI is Rebuilding the Creator Economy (Ep. 318) 11.06.2026

AI is no longer just a tool creators use to make content faster. It is beginning to reshape the entire creator economy. Revan Lazarus is the founder of Jamie, an AI platform for podcast networks and digital sales teams. He joins Infinite Loops, guest-hosted by Nick Tawil, to discuss how AI is changing podcasting, media sales, audience analytics, creator monetization, brand deals, and the future of...

Brian London, Marisa Adler & Eric Stubin - The Hidden Economy of Recycled Clothes (Ep. 317) 04.06.2026

What actually happens after you donate a bag of clothes? Most people assume it gets sold locally to someone in need, but the reality is much bigger, stranger, and more global. In this episode of Infinite Loops, hosted by OSV's Nick Tawil , we sit down for a roundtable on the hidden global economy of secondhand textiles with Brian London , Marisa Adler , and Eric Stubin , all experts in the field....

Jason Buck - Faith, Failure, and Finance (Ep. 316) 28.05.2026

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, and taught him one of the hardest lessons in markets: being right is not the same thing as making money. Jason explains how he went from real estate developer to volatility trader and eventually built...

Chelsea Follett - Why Progress Is the Exception, Not the Rule (Ep. 315) 21.05.2026

Chelsea Follett joins Infinite Loops to explain why the "good old days" were far darker than most people imagine — and why progress should never be taken for granted. Chelsea is the managing editor of Human Progress and author of Centers of Progress and the forthcoming The Grim Old Days. We discuss why humans are so drawn to nostalgia, what life was really like in the preindustrial past, why dooms...

Mykhailo Marynenko - AI Tools That Give Creators More Control (Ep. 314) 15.05.2026

Mykhailo Marynenko joins Infinite Loops for for a fascinating conversation about the future of AI, creative tools, privacy, and data ownership.  From growing up in his father's phone repair shop in Ukraine to building experimental AI systems today, Mykhailo has spent his life taking things apart, figuring out how they work, and rebuilding them in unexpected ways.  We explore how AI can help creato...

Danielle Crittenden - Dispatches from Grief (Ep. 313) 07.05.2026

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 joins  Infinite Loops  to discuss her luminous memoir,  Dispatches from Grief , which unflinchingly traces the strange afterlife of grief with precision, restraint, and unexpected humor. This...

Saloni Dattani - The Hidden Bottleneck Holding Back the Future of Medicine (Ep. 312) 30.04.2026

Saloni Dattani, author of the Scientific Discovery Substack and founding editor of Works in Progress magazine, joins Infinite Loops to discuss why medical innovation is often much slower than it needs to be. We explore why so much research still begins in animal models, how poor data distorts our understanding of disease, why clinical trials are one of the biggest bottlenecks in medicine, and how...

Brian Potter - How to Fix America's Building Problem 23.04.2026

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 there are no easy fixes to America's building problem. We discuss Katerra, California's anti-growth turn, and the deeper logic behind local opposition to growth: concentrated ha...

Alex Petkas - What Ancient Greece Can Teach Us About AI and the Future (Ep. 310) 16.04.2026

What can Aristotle, Plato, Prometheus, and the Greek city-states teach us about AI, innovation, and the future of human flourishing? Alex Petkas joins the show to explore how old myths still matter in a world shaped by technology. We talk about Prometheus as the foundational myth of tech, Plato's fear that writing would become a tool for forgetting, the real lesson of Icarus, why decentralization...

Sam Arbesman - Why Future Belongs to Curious People (Ep. 309) 09.04.2026

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 about why pessimism is often mistaken for sophistication, why AI may reward open-mindedness more than intelligence, why science works even though scientists are imperfect, and why the fut...

Johnathan Bi - Why the Best Founders Might Need a Little Delusion (Ep. 308) 02.04.2026

Johnathan Bi returns to Infinite Loops for a conversation about founders, delusion, America, religion, mysticism, and the strange tension between truth and action. We explore why some of the most effective builders may be the least introspective, why societies often run on useful fictions, how America encourages megalomania, what happens when materialism starts to feel incomplete, and why the "see...

Polina Pompliano - What Truly Drives Successful People (Ep. 307) 26.03.2026

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 mental models behind high performers, why we misunderstand people (including ourselves), and what it really takes to see the world differently. From creativity and rationality to identi...

Adam Mastroianni - Why Creativity Feels Like It's Dying (Ep. 306) 19.03.2026

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 sameness, Adam argues that as society becomes more stable and risk-averse, we may be unintentionally reducing the "deviance" that drives originality and breakthrough thinking....

Arkady Kulik - The Psychology of Self-Deception (Ep. 305) 12.03.2026

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 almost always human problems, how great founders deal with stress, and why the biggest lie entrepreneurs tell is often to themselves. He also explains how investors...

Angus Fletcher - The Biggest Mistake We Made About Intelligence (Ep. 304) 05.03.2026

In this episode of  Infinite Loops , Jim O'Shaughnessy sits down with Angus Fletcher , Professor of Story Science at Ohio State University's Project Narrative and author of multiple books at the intersection of narrative theory, psychology, and brain science.  Angus' research challenges one of the most widely accepted ideas in modern culture: that the human brain works like a computer. Drawing on...

Jonathan Tepper - Growing Up in the Heroin Capital of Europe (Ep. 303) 26.02.2026

In this episode of Infinite Loops, we sit down with author Jonathan Tepper to discuss his extraordinary childhood. In 1985, when Jonathan was seven, his missionary parents moved the family to San Blas — then the heroin capital of Europe — to start a drug rehabilitation center. Jonathan and his brothers grew up alongside former bank robbers, prison survivors, and people living through the AIDS epid...

Paul Millerd & Jimmy Soni — The Creative Opportunities of a Boring Life (EP. 302) 19.02.2026

Fresh off releasing one of the most beautiful hardcover books we've ever seen, Paul Millerd returns alongside Infinite Books CEO Jimmy Soni for a deep dive into the broken incentives of traditional publishing, why the industry breeds  "cynicism at scale," and how the internet is powering a second Renaissance for creators. We get into what it means to build a creative life on your own terms, the Ta...

Packy McCormick - How Writing Shapes Companies (Ep. 301) 12.02.2026

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 optimism becomes rational when you spend time with people actually building things, and what happens when the internet punishes you for being early and wrong.   Important Links: Packy McCormick on Optimism: ht...

Jean-Marc Daecius - The Last Human Chief of Staff (Ep. 300) 05.02.2026

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" — and why he believes he may be the company's last human chief of staff. The conversation explores how AI can remove meaningless cognitive load, protect deep work, and unlock creative leverage — from reshuf...

John Wang - The Man Who Built The Queens Night Market (Ep. 299) 29.01.2026

The Queens Night Market is one of New York City's most beloved institutions — but it was never supposed to last more than a year. John Wang, founder of the Queens Night Market, joins Infinite Loops to explain how a side project with a "terrible business model" unexpectedly became one of the most celebrated food markets in the world. From leaving a traditional legal career to imposing a strict pric...

Cliff Asness - Surviving the Meme Stock Bubble (Ep. 298) 22.01.2026

Cliff Asness — co-founder, managing principal, and chief investment officer at AQR Capital Management — is one of the most influential quantitative investors of the last 30 years. He's also one of the most candid. In this conversation, Cliff joins Infinite Loops to talk about why losses hurt more than wins, how bubbles form, why modern investing increasingly resembles gambling, and what the dot-co...

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