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!"

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

Dan Wang — China, US and our Collective Future (EP.284) 10/02/2025

Alex Danco — Speeches and Spells for the Kings and Priests (EP.283) 09/25/2025

Sangeet Paul Choudary — AI and our System Reshuffle (EP.282) 09/18/2025

Michael Dean — The Architecture of Essays (EP.281) 09/11/2025

Michael Dean — The Architecture of Essays (EP.281) Michael Dean — architect-turned-writer, O’Shaughnessy Fellow, and creator of Essay Architecture — joins the show to explore the hidden structures beneath nonfiction and why essays, like buildings, can be designed with patterns rather than left to inspiration. We discuss the origins of Essay Architecture, Michael’s 27-pattern framework that maps essays across Idea, Form, and Voice, and how to make craft teachable and AI feedback useful without replacing the writer. Along the way, we dive into architecture school critiques, why publishable doesn’t mean perfect, how editing rewires thinking, and the cultural risks if we keep treating writing as vibes instead of patterns. 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: The Architecture of Essays: from Design School to Writing Frameworks The Pattern Language: Idea, Form, and Voice Local Nuance vs Global Stylekits Fundamentals before Breaking Rules: Joyce, Picasso, the Beatles Quality Without a Name Leveling the College Playing Field The Two Sandboxes of Fundamentals and Amplification Gamification, Play and Motivation Beyond the Five-paragraph Essay: Emerson and AI in Education Scoring Great Essays: Why David Foster Wallace takes Three Top Spots How Writing Colonized the brain Editing as Belief-rewiring: Why Writers Avoid It and Why Math Helps The King of Biases: Confirmation Bias Michael as Emperor of the World Books Mentioned: Works on Wall Street; Jim O’Shaughnessy Essay Architecture (in progress) ; by Michael Dean A Pattern Language; by Christopher Alexander The Best American Essays 2024 Anthology; by Wesley Morris and Kim Dana Kupperman Consider the Lobster; by David Foster Wallace The White Album; by Joan Didion Shooting an Elephant; by George Orwell Portrait of an Artist as a Young Man; by James Joyce Finnegan’s Wake; by James Joyce Towards a Golden Age; Paul Graham The Limits of Scientific Reasoning; by David Faust The WEIRDest People in the World; by Joseph Henrich /episode/index/show/infiniteloops/id/38149550

Roon — On Shape Rotators, AGI & Tenet (Infinite Loops CLASSICS) 09/04/2025

Gurwinder Bhogal's Guide to Modern Survival (Infinite Loops CLASSICS) 08/28/2025

Gurwinder Bhogal's Guide to Modern Survival (Infinite Loops CLASSICS) Hello everyone, Jim here. We're taking a brief two-week break from new episodes to spotlight a couple of golden oldies from the Infinite Loops archive. Years later, these remain some of my favorite conversations. We’ll be back soon with fresh episodes, but in the meantime, enjoy this trip back to August 2024, when we welcomed the one and only Gurwinder Bhogal. _________________ “We have created for ourselves a world that we didn't evolve for.” Gurwinder Bhogal is, for my money, one of the most independent, original and insightful thinkers you’ll find in our corner of the internet. He returns to discuss how willpower and good old-fashioned human agency can help us reclaim our mental sovereignty and escape the “constant avalanche of concerns that are being vomited over us through our laptop screens, our phones, our TV screens, and in conversations.” For the full transcript, episode takeaways, and bucketloads of other stuff designed to make you go, “Hmm, that’s interesting!” check out our . Important Links: Show Notes: “We have created for ourselves a world we didn’t evolve for” The dogged persistence of our stubborn beliefs Gamification; generational differences in agency The societal impact of the education system’s changing priorities How to zombify a population Skin in the game: Gurwinder’s guide to reclaiming agency LLMs, bullshit, and the atomization of culture How to play better games Willpower is the bottleneck Gurwinder as emperor of the world MORE! Books Mentioned: ; by Gurwinder Bhogal Think Again: The Power of Knowing What You Don't Know; by Adam Grant The Status Game: On Human Life and How to Play It; by Will Storr The True Believer: Thoughts on the Nature of Mass Movements; by Eric Hoffer ; by Jonathan Haidt (After Babel) ; by Tyler Austin Harper (The Atlantic) ; by Ben Hunt (Epsilon Theory) The Emperor’s New Clothes; by Hans Christian Andersen ; by Robin Hanson (Overcoming Bias) The Enlightenment Trilogy; by Jed McKenna The Weirdest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous; by Joseph Henrich /episode/index/show/infiniteloops/id/37988675

Joe Hudson — The Art of Accomplishment (EP.280) 08/21/2025

Joe Hudson — The Art of Accomplishment (EP.280) What happens when a self-described "not very good" venture capitalist discovers he has an extraordinary gift for coaching the world's most successful CEOs? Joe Hudson joins Infinite Loops to share his unconventional journey from Alaska fishing boats to Hollywood directing to Silicon Valley boardrooms, ultimately finding his calling in helping high-performers unlock their deepest potential. This conversation dives deep into Joe's revolutionary three-center approach to human development—working with the head, heart, and nervous system simultaneously to create lasting transformation, and MORE! 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: Sign up for a complimentary transformation guide: Listen to the Art of Accomplishment Podcast on Listen to the Art of Accomplishment Podcast on Joe Hudson's Joe Hudson's Show Notes: Opening Joe's Unconventional Coaching Philosophy The Artist in the Art The "Should" Trap & The Trash Can Experiment Game Rules & Emotional Decision-Making The Curiosity Override The Big Five & CEO Personality Patterns The Three-Center System The Disinterested Observer & Emotional Suppression John Sarno & The Mind-Body Connection Fear & Gratitude Escaping the Logic Box Invest in Great Entrepreneurs The Tennis Ball & Quarter Analogy Micro Expressions & Unconditional Love Buddhist Monks & The last Taboo Trustafarians & Multi-Generational Wealth AI, Wandering & The Rat Park Joe as Emperor of the World Authors & Books Mentioned: Prometheus Rising; by Robert Anton Wilson Quantum Psychology; by Robert Anton Wilson Zen and the Art of Motorcycle Maintenance; by Robert Pirsig Mind Over Back Pain; by John Sarno Molecules of Emotion; by Candace Pert Adventures of a Bystander; by Peter Drucker The Love Song of J. Alfred Prufrock; by T.S. Eliot The Enlightened Brain; by Andrew Newberg /episode/index/show/infiniteloops/id/37886360

Michael Gibson & Danielle Strachman — The 1517 Rebellion (EP.279) 08/14/2025

Michael Gibson & Danielle Strachman — The 1517 Rebellion (EP.279) Michael Gibson and Danielle Strachman, co-founders of 1517 Fund, join the show to discuss their rebellion against higher education, why universities stifle creativity, why IQ doesn't correlate with innovation, and how betting on "misfit toys" is the way to go—plus we explore Girardian mimesis, the perishable nature of creativity, the laziness of pessimistic storytelling and MORE! 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: Why 1517 Fund Rebels Against Higher Education Giving Individuals a Shot “It’s cool to be building stuff, it’s not cool to be a Thiel Fellow” The ‘ATM Founder’ and ‘Rich Too Early’ Syndrome The Power of Predictive Character Traits Flipping Credentialist Thinking "How do we become Spielberg? How do we do something truly great?" Simple Memes and Powerful Narratives Avoiding a Monoculture of Misfits The Incestuous Universities Scene Choosing Your Own Path People Contain Multitudes Michael and Danielle as World Emperor and Empress Books & Essays Mentioned: A Mind at Play: How Claude Shannon Invented the Information Age; by Jimmy Soni and Rob Goodman Collective Illusions: Conformity, Complicity, and the Science of Why We Make Bad Decisions; by Todd Rose "A Gift for My Daughter"; by Harry Browne () Paper Belt on Fire; by Michael Gibson The Idea Factory: Bell Labs and the Great Age of American Innovation; by Jon Gertner The Right Stuff; by Tom Wolfe The Status Game; by Will Storr The Two Cultures; by C.P. Snow What Works on Wall Street; by Jim O'Shaughnessy White Mirror: Stories; by Tinkered Thinking Zero to One; by Peter Thiel The Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley; by Jimmy Soni Rome's Last Citizen: The Life and Legacy of Cato, Mortal Enemy of Caesar; by Jimmy Soni and Rob Goodman How I Found Freedom in an Unfree World; by Harry Browne /episode/index/show/infiniteloops/id/37806720

Ed Latimore — The Art of Self-Transformation (EP.278) 08/07/2025

Sam Arbesman — Science, Complexity and Humanistic Computation (EP.277) 07/31/2025

Sam Arbesman — Science, Complexity and Humanistic Computation (EP.277) Sam Arbesman, complexity scientist, author of "The Magic of Code," and scientist in residence at Lux Capital, joins me for a wide-ranging exploration of how we navigate an increasingly complex world that often exceeds human comprehension. We dive into the oral traditions that preserve crucial scientific knowledge, why cognitive diversity trumps demographic diversity, the forgotten innovations hiding in technological history, and Sam's vision for "Maxis 2.0". This conversation had everything—from science fiction's cultural impact to the philosophy of intellectual humility. Sam and I discovered we're remarkably simpatico on how to think about complex systems, the importance of historical context, and why saying "I don't know" is the foundation of genuine learning. 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: Sam’s Sci-fi Origins The Oral Tradition in Science and Technology Cultivating the Unexpected Open-Endedness and Large Language Models “All Models Are Wrong, but Some Are Useful” Culture’s Role in Shaping Everything Patching Bugs in HumanOS Tech History and Forgotten Innovations A Tech Archaeology Fellowship Humility and Knowledge Learning Via Negativa The Complexity of Our World Sam’s Current Obsessions in Science and Gaming Sam As Emperor of the World Books Mentioned: Dune; by Frank Herbert Foundation trilogy; by Isaac Asimov Overcomplicated: Technology at the Limits of Comprehension; by Sam Arbesman The Half-Life of Facts; by Sam Arbesman When We Cease to Understand the World; by Benjamín Labatut White Mirror; by Tinkered Thinking Nonzero; by Robert Wright The Evolution of God; by Robert Wright God and Golem, Inc.; by Norbert Wiener The Road; by Cormac McCarthy The Guide for the Perplexed; by Moses Maimonides The Story of Civilization; by Will and Ariel Durant Mistakes Were Made, and Yes, by Me; by Jim O'Shaughnessy /episode/index/show/infiniteloops/id/37594735

Nick Maggiulli — Climbing the Wealth Ladder (EP.276) 07/24/2025

Lawrence Yeo — The Inner Compass (EP.275) 07/17/2025

Will Storr—The Status Game (Infinite Loops CLASSICS) 07/10/2025

Will Storr—The Status Game (Infinite Loops CLASSICS) Hello everyone, Jim here. We're taking a brief two-week break from new episodes to spotlight a couple of golden oldies from the archive. Years later, these remain some of my favorite conversations. We’ll be back soon with fresh episodes, but in the meantime, here's my September 2022 chat with the always interesting Will Storr. _________________ Will Storr is an award winning journalist and author. His book ‘The Status Game’ transforms our understanding of human nature by demonstrating how our unconscious desire for status ultimately drives our behaviour. Important Links: Twitter: Website: The Science of Storytelling: Show Notes: Will’s origin story The strange case of David Irving The fundamental nature of status games The Stanford prison experiment and dominance games The status games played by cults Luxury beliefs Why we are all moral hypocrites The importance of being funny Social status and socioeconomic status Human OS and the education system How status seeking leads to the “very best of human nature” The murderous nature of reputation destruction The post WW1 humiliation of Germany Loaded magazine Finding the true reason behind seemingly crazy beliefs The value of religion Trading status Spreading humility Why we could be wrong about our closest beliefs Books Mentioned: The Unpersuadables: Adventures with the Enemies of Science; by Will Storr The Lucifer Principle: A Scientific Expedition into the Forces of History; by Howard Bloom The Genius of the Beast: A Radical Re-Vision of Capitalism; by Howard Bloom The WEIRDest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous; by Joseph Henrich The Science of Storytelling; by Will Storr Slaughterhouse-Five; by Kurt Vonnegut Selfie: How We Became so Self-Obsessed and What It’s Doing to Us; by Will Storr The Status Game: On Social Position and How We Use It; by Will Storr /episode/index/show/infiniteloops/id/37348275

Rupert Sheldrake — On Scientism, Morphic Resonance and the Extended Mind (Infinite Loops CLASSICS) 07/03/2025

Rupert Sheldrake — On Scientism, Morphic Resonance and the Extended Mind (Infinite Loops CLASSICS) Hello everyone, Jim here. We're taking a brief two-week break from new episodes to spotlight a couple of golden oldies from the Infinite Loops archive. Years later, these remain some of my favorite conversations. We’ll be back soon with fresh episodes, but in the meantime, enjoy this trip back to February 2024, when we welcomed the one and only Rupert Sheldrake. _________________ Rupert Sheldrake is a biologist and author of 9 books and over 100 scientific papers. A critic of what he sees as the scientific establishment’s dogmatic dedication to materialism, he is perhaps best known for his theory of “morphic resonance,” via which information and activity can be transferred across space and time. Rupert joins the show to discuss being branded a heretic, how to test for telepathy, his advice for young scientists, and MUCH more! Important Links: ; by Rupert Sheldrake ; by Rupert Sheldrake ; by Rupert Sheldrake ; by Rupert Sheldrake (Journal of Consciousness Studies) Show Notes: The Apostate of Scientism The Origins of Scientism How to Achieve a Phase Change in the Sciences Testing for Telepathy & Incentivizing Intuition Structural Resistance to Panpsychism When Science Gets Personal Loosening the Grip of Determinism Advice for Young Scientists Rupert as Emperor of the World MORE! Books & Articles Mentioned: The Science Delusion; by Rupert Sheldrake New Science of Life; by Rupert Sheldrake Dogs That Know When Their Owners Are Coming Home: And Other Unexplained Powers of Animals; by Rupert Sheldrake Is The Sun Conscious?; by Rupert Sheldrake The New Inquisition: Irrational Rationalism and the Citadel of Science; by Robert Anton Wilson Rationality: What It Is, Why It Seems Scarce, Why It Matters; by Steven Pinker The Blank Slate: The Modern Denial of Human Nature; by Steven Pinker Entangled Life: How Fungi Make Our Worlds, Change Our Minds and Shape Our Futures; by Merlin Sheldrake The End of Faith; by Sam Harris The Fifth Science; by Exurb1a What the Tortoise Said to Achilles; by Lewis Carroll Zen and the Art of Motorcycle Maintenance; by Robert M. Pirsig The (Mis)Behaviour of Markets: A Fractal View of Risk, Ruin and Reward; by Benoit B. Mandelbrot & Richard L. Hudson The Structure of Scientific Revolutions; by Thomas Kuhn /episode/index/show/infiniteloops/id/37257195

Aaron Stupple & Logan Chipkin — The Sovereign Child: Liberating Kids from the Tyranny of Rules 06/26/2025

Aaron Stupple & Logan Chipkin — The Sovereign Child: Liberating Kids from the Tyranny of Rules What if everything we think we know about raising children is not just wrong, but actively harmful? Aaron Stupple and Logan Chipkin, authors of "The Sovereign Child," join Infinite Loops to make a case so compelling and radical that it challenges the very foundation of modern parenting and education. From birth, we're told that children need rules, structure, and authority to thrive. But what if this approach is crushing their natural creativity, problem-solving abilities, and authentic self-development? Stupple and Chipkin argue that children are people—full stop. They have reasons, preferences, and the capacity to make decisions about their own lives, yet we systematically ignore this reality in favor of compliance and control. We dive deep into their concept of the "foul four"—the four devastating ways that imposing non-consensual rules damages children's relationships with themselves, their parents, problem-solving itself, and their understanding of how to navigate the world. From the arbitrary nature of bedtimes to the deeper psychological damage of forcing gratitude and politeness, this conversation will make you question every "because I said so" moment in your childhood and parenting. Whether you're a parent, educator, or simply someone interested in human flourishing, this episode offers a radically different lens through which to view childhood, autonomy, and what it means to raise great adults. Important Links: Show Notes: Opening & The Radical Quote The Childhood Inversion Problem False Dichotomy: Control vs. Neglect AI Steel-manning the Opposition Edge Cases and Prohibition Parallels Podcast Host Reactions & Food Wars Evolutionary Food Arguments Raising Great Adults Scaling Challenges & Sleep Dilemmas Market Opportunities & Historical Context Why Alternative Schools Didn’t Scale The Foul Four Explained Game Rules vs. Imposed Rules Etiquette, Manners & Sibling Conflicts The Bully Problem & Popper’s Paradox Class and Economics Arguments Rules Built on Sand Falsification & Moral Philosophy Conformity, Culture & Progress Emotional Intelligence & Propaganda Self-Silencing & Social Dynamics The School Persona Revelation Emperor of the World Matilda & Closing Thoughts Books Mentioned: The Sovereign Child: How a Forgotten Philosophy Can Liberate Kids and Their Parents (Aaron Stupple with Logan Chipkin) Influence: The Psychology of Persuasion (Dr. Robert Cialdini) The Open Society and Its Enemies (Karl Popper) What the Tortoise Said to Achilles (Lewis Carroll) No Country for Old Men (Cormac McCarthy) One Summer: America 1927 (Bill Bryson) Alice in Wonderland (Lewis Carroll) Matilda (Roald Dahl) Authors Mentioned: Jed McKenna Jonathan Haidt Edward Bernays Robert Solomon David Deutsch /episode/index/show/infiniteloops/id/37148320

Nadia Asparouhova — An Antimemetic Rollercoaster 06/19/2025

Miyoba Hamuhuma and Israel Balogun — Grassroots Solutions for Africa’s Impoverished Youth (EP.272) 06/12/2025

Dr. Diane Hennacy Powell — Speculations in Post-Materialism (EP.271) 06/05/2025

Todd Rose — Are We Living in the Truman Show? (EP.270) 05/29/2025

Charles Beames — Welcome to the Second Space Race (EP.269) 05/22/2025

Natasha Joukovsky — On Recursion, Status Games & Manufactured Nonchalance (EP.268) 05/15/2025

Tiago Forte — Unlocking the Power of the Annual Review (Ep. 267) 05/08/2025

Tiago Forte — Unlocking the Power of the Annual Review (Ep. 267) I’ve said before that one of the best parts of hosting Infinite Loops is the chance to connect with people who consistently make me think differently — and few do that quite like Tiago Forte. Tiago Forte joins Infinite Loops for the first time, and within minutes we closed the door on his best-selling “Building A Second Brain” and were off to the races: from digitizing 50,000+ words of personal data to build an AI-powered life coach, to the emotional intelligence hiding inside envy, to the surprising lessons he learned walking through a tiny historical museum in Coconut Grove. We also dig into the messy magic of identity shifts, how fit dads triggered a personal transformation, and why letting go of productivity-as-performance might be the most productive thing you can do. Plus: the power of NotebookLM, building AI-native systems of self-awareness, and why the future will belong to those who embrace the one-way door. Unsurprisingly, this was a fun one. 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: (YouTube) Show Notes: Closing the Door on Second Brain The Power of the Annual Review Tiago's Family: Incredibly Vibrant, Visual, Auditory Incorporating AI Into Work & Life Joe Hudson: Mentorship and Emotional Intelligence Miami: The Most Introspective Place on Earth Irreversible Decisions Archival Material: Underrated Forcing Function The Future of Book Publishing The Hard Truth on Performance Reviews AI Skepticism & Building Moats AI-First Mentality for Early Adopters Learning From Sci-Fi Books Cumulative Cultural Evolution Tiago as Emperor of the World Books Mentioned: Building A Second Brain: A Proven Method to Organize Your Digital Life and Unlock Your Creative Potential; by Tiago Forte The PARA Method: Simplify, Organize, and Master Your Digital Life; by Tiago Forte How Emotions are Made: The Secret Life of the Brain; by Lisa Feldman Barrett Tiny Experiments: How to Live Freely in a Goal-Obsessed World; by Anne-Laure Le Cunff Why Greatness Cannot Be Planned; by Kenneth O. Stanley and Joel Lehman Molecules Of Emotion: The Science Behind Mind-Body Medicine; by Candace B. Pert What Works on Wall Street; by Jim O’Shaughnessy The Beginning of Infinity; by David Deutsch One Summer: America, 1927; by Bill Bryson White Mirror; by Tinkered Thinking The Forever War; by Joe Halderman /episode/index/show/infiniteloops/id/36467885

Nir Eyal — The Psychology of Addictive Products (EP.266) 05/01/2025

Nathan Baschez — On AI Writing, Thought Design & Solo Foundership (EP.265) 04/24/2025

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