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!"

Saloni Dattani - The Hidden Bottleneck Holding Back the Future of Medicine (Ep. 312) 04/30/2026

Brian Potter - How to Fix America’s Building Problem 04/23/2026

Alex Petkas - What Ancient Greece Can Teach Us About AI and the Future (Ep. 310) 04/16/2026

Sam Arbesman - Why Future Belongs to Curious People (Ep. 309) 04/09/2026

Johnathan Bi - Why the Best Founders Might Need a Little Delusion (Ep. 308) 04/02/2026

Polina Pompliano - What Truly Drives Successful People (Ep. 307) 03/26/2026

Adam Mastroianni - Why Creativity Feels Like It's Dying (Ep. 306) 03/19/2026

Arkady Kulik - The Psychology of Self-Deception (Ep. 305) 03/12/2026

Angus Fletcher - The Biggest Mistake We Made About Intelligence (Ep. 304) 03/05/2026

Jonathan Tepper - Growing Up in the Heroin Capital of Europe (Ep. 303) 02/26/2026

Paul Millerd & Jimmy Soni — The Creative Opportunities of a Boring Life (EP. 302) 02/19/2026

Paul Millerd & Jimmy Soni — The Creative Opportunities of a Boring Life (EP. 302) 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 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 Taoist approach to growing an audience, how to navigate financial uncertainty while raising a family, and why seemingly boring daily routines fuel extraordinary creative work. I hope you enjoy this conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, "Hmm, that's interesting!," check out our . Important Links: Show Notes: Make Books Beautiful Why Paul Turned Down Penguin Creative Work Should Inspire More Creative Work Cynicism at Scale in the Publishing Industry The Long Tail of Book Marketing Why Paul Launched a Hardcover Pathless Path Dre, Spielberg & Chappelle: Design Your Own System Playing Probabilistic Games How to Live a Pathless Life With a Family The Creative Perks of a Boring Life "What If I Do Less?” Books Are Win-Win Paul as World Emperor Books Mentioned: The Pathless Path: Imagining a New Story for Work and Life; by Paul Millerd Good Work: Reclaiming Your Inner Ambition; by Paul Millerd The Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley; by Jimmy Soni What Works on Wall Street; by Jim O'Shaughnessy How to Retire Rich; by Jim O'Shaughnessy Walden (Steel Brothers reimagined edition); by Henry David Thoreau Why Greatness Cannot Be Planned: The Myth of the Objective; by Kenneth O. Stanley The Work Is the Win; by Billy Oppenheimer (forthcoming) ; by Paul Millerd (essay) Tiny Experiments: How to Live Freely in a Goal-Obsessed World; by Anne-Laure Le Cunff The Chronic; by Dr. Dre (album) Tao Te Ching (Dao De Jing); by Lao Tzu /episode/index/show/infiniteloops/id/40153960

Packy McCormick - How Writing Shapes Companies (Ep. 301) 02/12/2026

Jean-Marc Daecius - The Last Human Chief of Staff (Ep. 300) 02/05/2026

John Wang - The Man Who Built The Queens Night Market (Ep. 299) 01/29/2026

Cliff Asness - Surviving the Meme Stock Bubble (Ep. 298) 01/22/2026

Tomás Pueyo — Explaining the World Through Geography, History and Data (EP. 297) 01/15/2026

Annie Duke — Why We Make the Wrong Decisions (Ep. 296) 01/08/2026

Jimmy Soni — The Publishing System is Broken (EP. 295) 01/01/2026

Guy Spier — Wealth, Wisdom & Enlightenment (Infinite Loops CLASSICS) 12/25/2025

Guy Spier — Wealth, Wisdom & Enlightenment (Infinite Loops CLASSICS) Happy Holidays! We’re taking a short break from new episodes this week so you can focus on finishing that Christmas dinner. We’ll be back next Thursday with something new. In the meantime, why not tuck into this conversation with Guy Spier from January 2024, which remains one of my favorites. Enjoy! _________________ Guy Spier runs the Aquamarine Fund, an “investment partnership closely modeled on the original Buffet Partnerships.” He is also a podcast host, YouTube creator, author of The Education of a Value Investor and the host of the annual investment gathering VALUEx. He describes his life’s project as “a quest for wealth, wisdom and enlightenment.” Guy joins the show to discuss the differences between Switzerland and the US, how to unlock the British class system, what he learned from Warren Buffett, and MUCH more! Important Links: (YouTube Channel) (YouTube Channel) Show Notes: The Differences Between New York, Switzerland & Paris Exploring the Dark Underbelly of New York Nightlife Psychedelics, Guns & Regulation The Advantages of Swiss Democracy Don’t Short the United States The Branding Skill of the Royal Family Unlocking the Rules of the Class System Life Paths & Premeditation Luck, Opportunity & Non-Canonical Science Jim’s Music Taste Mathematical Shenanigans Guy as Emperor of the World MORE! Books Mentioned: How to Change Your Mind: What the New Science of Psychedelics Teaches Us about Consciousness, Dying, Addiction, Depression, and Transcendence; by Michael Pollan The Hypomanic Edge: The Link Between (a Little) Craziness and (a Lot Of) Success in America; by John Gartner Write It Down, Make It Happen: Knowing What You Want and Getting It; by Henriette Anne Klauser Invest Like The Best; by Jim O’Shaughnessy Outside, the Sky is Blue: The story of a family told with searing honesty, humour and love; by Christina Patterson /episode/index/show/infiniteloops/id/39481555

Vik Muniz — The Art of Perception (EP.294) 12/17/2025

Marc Dennis — Painting the Punchline (EP.293) 12/11/2025

Ariel Meyerowitz — Navigating the Art World (EP. 292) 12/04/2025

Adam Moskowitz — The Way of the Cheesemonger (EP.291) 11/27/2025

Todd Rose — Escaping the Trap of the Standard Path (EP.290) 11/20/2025

Todd Rose — Escaping the Trap of the Standard Path (EP.290) From a 0.9 GPA in rural Utah to the faculty of Harvard, Todd Rose’s life is a testament to the idea that the "standard path" is a myth. In this return appearance on Infinite Loops, Todd opens up about the gritty, unvarnished reality of his origin story—a journey that includes ten minimum wage jobs, a stint administering enemas for a living, and the life-changing intervention of a department secretary named Marilyn Diamond. We dive deep into the "Dark Horse" mindset and why the pursuit of fulfillment, rather than the pursuit of excellence, is actually the most reliable driver of success. We also bond over our mutual disdain for Frederick Taylor, explore the devastating impact of "average-based" thinking on human potential, and discuss why dignity is the bedrock of a free society—illustrated by a heartbreaking personal encounter with a jar of chunky peanut butter. If you’ve ever felt like a square peg in a round hole, or if you’re looking for a roadmap to navigate the coming cultural shifts in the age of AI, this conversation is essential listening. I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack. Show Notes: The 0.9 GPA and the "Correct Answer Machine" Ten minimum wage jobs and the advice to "get longer gloves" Marilyn Diamond: The improbable mentor who saved Todd's education The "No Average Brain" discovery in neuroscience Why we both despise Frederick Taylor and Scientific Management Dark Horses: Ignoring the destination to find the path Degrees of Freedom: How Todd hacked the GRE The "Chunky Peanut Butter" story and the importance of dignity Resentment, trust, and the future of AI The "Rainy Day Club" and how paradigms actually shift Books Mentioned: Collective Illusions; Todd Rose The End of Average; Todd Rose Dark Horse; Todd Rose Improbable Mentors; Mike Perry The Principles of Scientific Management; Frederick Taylor The Structure of Scientific Revolutions; Thomas Kuhn The Wealth of Nations; Adam Smith Man’s Search for Meaning; Viktor Frankl Dignity; Chris Arnade Capitalism, Socialism and Democracy; Joseph Schumpeter /episode/index/show/infiniteloops/id/39106640

George Mack — The Game of Life (Infinite Loops CLASSICS) 11/13/2025

Michael Perry — Improbable Mentors and the Art of Midwestern Storytelling (EP. 289) 11/06/2025

Michael Perry — Improbable Mentors and the Art of Midwestern Storytelling (EP. 289) What happens when a shy farm kid from rural Wisconsin who never dreamed of being a writer becomes one of America's most beloved storytellers? Michael Perry joins Infinite Loops to share his remarkable journey from cleaning calf pens to pitching scripts at Universal Studios, all while maintaining his day job as a volunteer firefighter and EMT in his hometown. This conversation is a masterclass in authentic storytelling, practical wisdom, and the power of staying true to your roots while navigating an industry that often values credentials over character. Perry shares unforgettable stories about turning down Oprah (yes, really), why he sells hundreds of books to "people who don't read" at firefighter conventions, and how his nursing background taught him the most important skill for any writer: human assessment. We explore his philosophy of "kindness is not weakness," the difference between cash and cachet, and why sometimes the best career move is knowing when not to move at all. Whether you're a writer, entrepreneur, or simply someone who believes in the power of authentic storytelling, this episode will remind you that sometimes the best way forward is to embrace your own improbable path and never stand behind a sneezing cow. I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our . Important Links: Michael Perry’s - Michael Perry’s Voice Mail Michael’s / Twitter Michael Perry’s Show Notes: Connections with Mark Twain The NFL Friend & First Investment Mark Twain’s European Fame & American Diplomacy Blue Collar vs. Capital ‘A’ Art Flying Under the Radar Midwestern Wisdom & Family Stories Charity, Humility, & Fundamentalist Upbringing The Positive Side of Imposter Syndrome Happy Tangents vs. Detailed Blueprints Publishing Industry Frustrations EMT Requires Pulse & Driver's License The Oprah Story First Mover Disadvantage Brothers, Guns, & Material Sources Mortality & Perspective The Gimlet-Eyed Drive Visiting Tom The Reality of Writing Today Pragmatism & Adaptation Voltaire & Historical Perspective Mike as Emperor of the World Books Mentioned: A Tale of Two Cities; Charles Dickens Mark Twain; Ron Chernow Improbable Mentors and Happy Tangents; Michael Perry Population: 485; Michael Perry Visiting Tom; Michael Perry Truck: A Love Story; Michael Perry Million Billion; Michael Perry 40 Acres Deep; Michael Perry Montaigne in Barn Boots; Michael Perry The Peter Principle; Laurence J. Peter What Works on Wall Street; Jim O’Shaughnessy Invest Like the Best; Jim O’Shaughnessy How to Retire Rich; Jim O’Shaughnessy Greatness Cannot Be Planned; Ken Stanley The Bible All Quiet on the Western Front; Erich Maria Remarque Tao Te Ching; Laozi Gone With the Wind; Margaret Mitchell Serpico; Peter Maas Candide; Voltaire /episode/index/show/infiniteloops/id/38931285

Kenneth Stanley — The Trap of the Objective (EP.288) 10/30/2025

Kenneth Stanley — The Trap of the Objective (EP.288) Ken Stanley – AI researcher and author of "Why Greatness Cannot Be Planned" – joins me to explore why ambitious objectives can blind us to the stepping stones that make breakthroughs possible. Ken is the inventor of the novelty search algorithm and co-creator of Picbreeder, a crowdsourced evolutionary art experiment that has led to important insights about our objective-obsessed culture. This conversation covers everything from why vacuum tubes had to come before computers, how the path you take to success matters more than the success itself, the "fractured entangled representation" hypothesis, why grant applications kill innovation, how education beats the playground mentality out of children, and why "interesting" is the opposite of random. I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our . Important Links: Show Notes: Are We Deterministic Thinkers Living in a Probabilistic World? Evolving Complexity and the NEAT Algorithm The Origins of The Power of Novelty Search The Cultural Impact of Non-Objective Thinking Why Pursuing Interestingness is Not the Same as Being Random Mechanizing Serendipity via Stepping Stones The Allure of the Security Blanket The Omni-culture of NSF Funding What Makes an Innovator? The Fractured Entangled Representation Hypothesis What does it say about LLMs if They Are Fractured and Entangled? Path Dependency and Careers Ken as Emperor of the World Books Mentioned: Why Greatness Cannot Be Planned; by Kenneth Stanley (and Joel Lehman) The God Problem; by Howard Bloom The Lucifer Principle; by Howard Bloom Global Brain; by Howard Bloom The Beginning of Infinity; by David Deutsch Invest Like the Best; by Jim O'Shaughnessy A Mind At Play; by Jimmy Soni /episode/index/show/infiniteloops/id/38834930

Elle Griffin — Rethinking Ownership and the Future of Work (EP. 287) 10/23/2025

Elle Griffin — Rethinking Ownership and the Future of Work (EP. 287) Writer, editor, and founder of The Elysian, Elle Griffin joins me on Infinite Loops to discuss her vision for participatory capitalism, a world where ownership, reputation, and creativity are shared more broadly across society. We explore the evolution of capitalism from the industrial era to the networked age, how broad-based ownership could rebuild the middle class, why optimism is revolutionary, and how storytelling shapes our collective imagination. We also discuss how reputation is becoming a new form of capital and how writers can become architects of meaning in a world reshaped by AI and automation. I hope you enjoy this conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, "Hmm, that's interesting!," check out our . Important Links: Show Notes: The New GI Bill for Stock Ownership Rethinking ESOPs, RSUs, and Equity for All The Founder’s Dilemma: Risk, Ownership & Exit Tax Incentives for Employee Ownership A Tale of Two Experiments The Ownership Czar for the Day The Future of Work The State with Baby Bonds The Problem with Worth and Deserving The Power of Utopian Fiction The Currency of Belief and Reputation Empress of the World Question Books and References Mentioned: Obscurity; by Elle Griffin The Elysian; by Elle Griffin The Beginning of Infinity; by David Deutsch The Lessons of History; by Will & Ariel Durant The History of Civilization; by Will & Ariel Durant Why Greatness Can’t Be Planned; by Kenneth O. Stanley Looking Backward; by Edward Bellamy Herland; by Charlotte Perkins Gilman Les Misérables; by Victor Hugo Frankenstein; by Mary Shelley The Republic; by Plato Das Kapital; by Karl Marx The Count of Monte Cristo; by Alexandre Dumas 20,000 Leagues Under the Sea; by Jules Verne A Tale of Two Cities; by Charles Dickens White Mirror Stories; by Infinite Books /episode/index/show/infiniteloops/id/38745720

Jay Yang — The Power of Permissionless Action (EP. 286) 10/16/2025

Jay Yang — The Power of Permissionless Action (EP. 286) What if the biggest barrier between you and your dreams isn't talent, connections, or luck— but simply the belief that you need permission to act? Jay Yang joins Infinite Loops to challenge one of the most limiting assumptions of our time: that opportunities must be handed to us rather than created by us. At just 16, Jay cold-emailed the CEO of Beehiiv with a concrete plan that led to an internship. At 17, he sent Noah Kagan a 19-page audit of his email funnel with ready-to-ship assets, ultimately becoming head of content and helping put "Million Dollar Weekend" on the New York Times bestseller list. His secret? Understanding that preparation beats bravado, that most doors don't even have locks, and that the fastest way to get what you want is to do the work upfront and make saying "yes" a no-brainer for others. This conversation dives deep into Jay's philosophy of permissionless action, exploring why most people accept the "standard pace" when there's actually no speed limit, how to reprogram limiting beliefs through small wins, and why high agency people focus on outputs while low agency people get trapped tracking inputs. I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our . Important Links: Jay Yang's Jay Yang's Jay Yang's Jay Yang's Book, Jay Yang's Show Notes: The Philosophy of Permissionless Action Breaking Free from Era-Defining Ideas Overcoming Limiting Beliefs Starting Small: Building Confidence Through Micro-Actions Inner vs. Outer Orientation Inputs vs. Outputs: The Agency Divide Failure as Feedback The Power of Persistence Curiosity and Cognitive Diversity AI and the Future of Work The Busy-ness Trap Signal vs. Noise in the AI Era People You Learn From Don't Have Huge Following The TAG Method Explained The New Way of Hiring Learning from the Greats Motivation vs. Clarity Jay’s North Star and Anti-Goals Viktor Frankl and Finding Your Why Working in Public The Second Book Preview The Emperor Question Closing & Contact Information Books Mentioned: You Can Just Do Things: The Power of Permissionless Actions (Jay Yang) Million Dollar Weekend by Noah Kagan The Tao of Kobe (forthcoming 2026, Jimmy Soni) Greatness Cannot Be Planned (Ken Stanley) Man's Search for Meaning (Viktor Frankl) /episode/index/show/infiniteloops/id/38596955

Jeff Bussgang — The Experimentation Machine (EP.285) 10/09/2025

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