Infinite Loops

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 Revolution here: https://platformthinkinglabs.com/materials/platform-revolution

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 holding the pen of your own story. Important Links: Listen to Jameson's podcast here: https://www.becomingmain.com/

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 writing books while working full-time. They also discuss raising kids who read for hours every day and why meditation helps him stay sane.

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 all her books - from 40 Ways to Look at Winston Churchill to Life in Five Senses. Important Links: Learn more about Gretchen: https://gretchenrubin.com/ Read more of Gretchen's work: https://gretchenrubin.com/books Listen to Gretchen's podcast: https://gretchenrubin.com/happier/

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 more about Ben here: https://www.wsj.com/news/author/ben-cohen Read The Science of Success: https://www.wsj.com/news/types/science-of-success Read The Hot Hand: https://www.harpercollins.com/pages/hothand

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 uses secondhand clothing, what AI can and can't solve, and why turning an old shirt into a new shirt is still much harder than it sounds. Substack: https://newsletter.osv.llc/   

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 true diversification always feels uncomfortable, why human behavior is the most persistent source of market mistakes, and why investing beliefs often resemble religion. Important Links: Learn more about Mutiny Fund here: https://mutinyfund.com/ Listen to more from Jason here: https://mutinyfund.com/podcasts

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 modern world. Important Links: Learn More about Chelsea's upcoming book here: https://www.simonandschuster.com/books/The-Grim-Old-Days Read more of Chelsea's Human Progress work here: https://humanprogress.org/authors/chelsea-follett

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 that give people more control over complex information. Important Links More about Misha: https://linktr.ee/0x77dev?utm_medium=mykhailo.link

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 shares the physical pain, the loneliness of loss, and the slow work of carrying her daughter's memory forward.  Dispatches from Grief is out now: Infinite Books | Amazon Danielle's Substack: The Femsplainers With Danielle Crittenden

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 better systems could help promising treatments reach patients faster. Important Links: Read more from Saloni here: https://worksinprogress.co/our-authors/saloni-dattani And here: https://substack.com/@salonium And listen to Saloni's podcast "Hard Drugs" here: https://harddrugs.worksinprogress.co/

Why is hard work a form of laziness? Why should we be wary of short-term success? How can imagining parallel worlds help us make better decisions? Author, management advisor, and researcher Luca Dellanna joins us to discuss these questions and more! Important Links: Luca's Website Luca's Twitter Show Notes: Ergodicity: survival is king Why sample size matters The two types of competitors Teaching by signaling The parallel worlds approach to decision-making Racing to the bottom Why working hard can be a form of laziness The three things managers should prioritize Why desiring change isn't enough Fighting avoidance with actionable small steps "Mixed values produce mixed results" Thinking by writing What Luca has learned from living in multiple countries Luca as Emperor of the World MORE! Books Mentioned: Antifragile: Things that Gain from Disorder; by Nassim Nicholas Taleb What Works on Wall Street; by Jim O'Shaughnessy Ergodicity: Definition, Examples, And Implications, As Simple As Possible; by Luca Dellanna The Control Heuristic: The Nature of Human Behavior; by Luca Dellanna 100 Truths You Will Learn Too Late; by Luca Dellanna Tao Te Ching; by Lao Tzu

In this episode of Infinite Loops we spoke with Chris Sommers, CEO at Unhedged. We discuss: Sailing the world for 4 years without knowing how to sail Chris' experience at Greenlight Capital Shorting Lehman's stock in 2008 And much more… Follow Chris on Twitter (https://twitter.com/QuisitiveInvest) and learn more about Unhedged here (https://www.unhedged.com/).