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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 — 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 hold
Recent Episodes
322
July 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 — 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 hold
321
July 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 - 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 writ
320
June 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 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
319
June 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 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
318
June 11, 2026
Revan Lazarus - How AI is Rebuilding the Creator Economy (Ep. 318)
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/
317
June 4, 2026
Brian London, Marisa Adler & Eric Stubin - The Hidden Economy of Recycled Clothes (Ep. 317)
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 worl
316
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, 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 t
315
May 21, 2026
Chelsea Follett - Why Progress Is the Exception, Not the Rule (Ep. 315)
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
314
May 14, 2026
Mykhailo Marynenko - AI Tools That Give Creators More Control (Ep. 314)
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 th
313
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 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 sha
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About the Host
Jim O'Shaughnessy
Jim O'Shaughnessy built O'Shaughnessy Asset Management (OSAM) into a Wall Street powerhouse, managing billions before its successful acquisition. Now, he's embarked on a new venture: O'Shaughnessy Ventures (OSV), a creative investment firm empowering visionaries across business, tech, science, art, media, and literature.
Hailed as a "legendary investor" by Barron's, Jim authored the New York Times bestseller What Works on Wall Street among his four influential books. His expertise spans quantitative analysis, portfolio management, and investment strategy.
Beyond finance, Jim has served as former chair of the Chamber Music Society of Lincoln Center and host of the popular Infinite Loops podcast. He shares eclectic insights on everything from philosophy to quantum mechanics via his active Twitter presence (@jposhaughnessy). Jim resides in Connecticut with his wife Melissa, surrounded by the joyful chaos of their three children and six grandchildren.