Episodes

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 has become unmanageable, how thousand-page rulebooks discourage individual judgment, why infrastructure projects can take decades to approve, and how public institutions end up costing more while delivering less.

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 and Chinese AI models, creative “exhaust,” changing career paths, and how to compete when the rules of the game are constantly being rewritten. Important Links: Learn more about Sangeet and Reshuffle here: https://reshufflebook.com/ Read more about the Platform Revo...

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, NPCs, and the Hero’s Journey, they discuss what it means to stop drifting through life and start hol...

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 journalism school, how he convinced Bernie Madoff to grant him a prison interview, and his process for wri...

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 during pass pages), her 5:30 AM writing routine, and why "know thyself" remains the foundation of a...

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's tastiest berries, and the troubled development of The Princess Bride. Important Links: Learn mo...

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 content itself. Important Links: Learn more about Jamie AI: https://www.jamie-ai.com/

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. We discuss how the industry works, why fast fashion has made the problem harder, why 70% of the world u...

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 his philosophy around survival, resilience, and the “Cockroach Portfolio.” He and Jim explore why ...

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 doomsday predictions keep failing, and how freedom, innovation, and open inquiry helped create the moder...

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 creators without replacing them, why privacy and data ownership matter, and what it means to design tools ...

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 conversation explores what grief really feels like. With extraordinary honesty and grace, Danielle sh...

Saloni Dattani, author of the Scientific Discovery Substack and founding editor of 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...

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 harms and diffuse benefits.

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 creates cultural power, and what it means to remain fully human in the age of AI. Important Links:...

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 future may depend on revisiting forgotten ideas from the past. Important Links: Learn more about Sam h...

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 “seeker” may matter even more in the age of AI. The episode moves from Plato and Caesar to founders, my...

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 identity, media bias, and the hidden motivations driving success, this conversation is a deep dive into h...

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. We also discuss why science should get weirder, how to fight credentialism, and the dangers of prof...

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 evaluate founder psychology, why difficult conversations are essential in business, and why resili...

In this episode of Infinite Loops, Jim O’Shaughnessy sits down with Professor Angus Fletcher, a neuroscientist and storytelling expert at Ohio State University and author of Primal Intelligence. Fletcher’s research challenges one of the most widely accepted ideas in modern culture: that the human brain works like a computer. Drawing on his work with U.S. Army Special Operations, Fletcher argues that humans think not in equations, but in actions and stories—and that modern education systems are ...

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 epidemic. These recovering addicts became like older siblings to them. What began with one man in a sma...

Fresh off releasing 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...

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: https://www.notboring.co/p/optimism The Internet Contrarian: https://www.osam.com/pdfs/research/The%2...