Infinite Loops
by Jim O'Shaughnessy
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!"
Episodes
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Tren Griffin - How To Write, Publish & Sell A Book In The AI Era (Ep. 334)
Tren Griffin, author of Charlie Munger: The Complete Investor and the 25iq blog, joins Jim O'Shaughnessy on Infinite Loops to talk about why writing a book is rarely about money, how AI is reshaping writing and publishing, why every author is really starting a business, how to build a book in...
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Spencer Greenberg - 106 Self-Help Books Distilled Into 12 Strategies (Ep. 333)
Spencer Greenberg, mathematician, founder of Clearer Thinking, and co-author of The 12 Levers, joins Jim O'Shaughnessy on Infinite Loops to talk about which self-help techniques hold up to evidence, why memory works like autocomplete, how exposure therapy cured his lifelong social anxiety, why…
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Ed William - Writing A Biography That Reads Like Fiction (Ep. 332)
Pre-order No One's Coming to Save You today: https://infinitebooks.com/products/no-ones-coming-to-save-you David Rhoiney was five when his father walked out, forcing David to become the "man of the house." Compton, Oakland, Long Beach: no matter where they turned, fear and hunger waited. Long...
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Emma Camp - Why Gen Z Is Afraid of Rejection: Dating, Therapy Culture & Housing (Ep. 331)
Emma Camp, senior newsletter editor at The Wall Street Journal's Free Expression, joins Jim O'Shaughnessy on Infinite Loops to talk about why Gen Z is dating less and spending more time alone, how therapy culture and helicopter parenting can turn growing pains into permanent labels, why the fix…
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Julie Fredrickson - The Right to Compute: AI Agents, Nuclear Power & Human Data (Ep. 330)
Julie Fredrickson, Managing Partner of Chaotic Capital, rejoins Jim O'Shaughnessy on Infinite Loops to talk about Montana's Right to Compute Act, why verified human data may become one of the most valuable assets online, what nuclear power and the encryption wars teach about regulating AI, why...
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Derek Sivers - Living Many Lives: Parenting, Moving Countries & AI (Ep. 329)
Derek Sivers, author, entrepreneur, TED speaker, and founder of CD Baby, joins Jim O'Shaughnessy on Infinite Loops to talk about parenting a teenager who is ready to leave home, why he moves countries on purpose and plans to live in Bangalore and Shanghai next, the certainty slider, and how AI…
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Brent Seales - How AI Is Reading the Only Library That Survived Antiquity (Ep. 328)
Dr. Brent Seales, computer scientist at the University of Kentucky and co-founder of the Vesuvius Challenge, joins guest host Nick Tawil on Infinite Loops to explain how synchrotron X-rays and machine learning are making unopenable ancient scrolls readable, and why the work has now shifted from...
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Ryan Resch - How Data Changed the NBA and What AI Changes Next (Ep. 327)
Ryan Resch, former Assistant General Manager and VP of Basketball Operations for the Phoenix Suns, joins guest host Jimmy Soni on Infinite Loops to explore what happens to competitive advantage when every team has the same data, and why the real edge comes from the questions you ask of it. Ryan...
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Brian Chau - How AI is Reinventing Investigative Journalism (Ep. 326)
Brian Chau, founder of Effort News, joins Infinite Loops to explore how AI could fundamentally reshape investigative journalism—not by writing articles, but by searching, analyzing, and connecting millions of legal, financial, and government records that humans could never examine manually. Show...
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Julian Gough — The Egg and The Rock (Infinite Loops Classics)
We're digging out some of our favorite conversations from the archive. This one is from January 2025, with Julian Gough. Enjoy. Julian Gough sums up his career as follows: "I just sit in my room and write." Well, I think being an acclaimed children's author, novelist, stage playwright, poet and...
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Dr. Julie Gurner — Ultra Successful (Infinite Loops Classics)
Hi everyone, Jim here. We're taking a short pause on new episodes through the end of August. In the meantime, we're digging out some of our favorite conversations from the archive. This one is from August 2023, with Dr. Julie Gurner. Enjoy. Dr. Julie Gurner is a doctor of psychology and executive...
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Lulu Cheng Meservey — Going Direct: What Founders can learn from K-Pop, Crypto, and the Early Christians (Infinite Loops Classics)
Hi everyone, Jim here. We're taking a short pause on new episodes through the end of August. In the meantime, we're digging out some of our favorite conversations from the archive. This one is from November 2022, so a few of our references (and jobs!) are out of date, but the ideas have only…
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Jesse Michels — American Alchemy (Infinite Loops Classics)
Hi everyone, Jim here. We're taking a short pause on new episodes through the end of August. In the meantime, we're digging out some of our favorite conversations from the archive. This one is from February 2023, so a few of the references have aged since (mine included), but the ideas have only...
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Nat Eliason - The High School That Guarantees You'll Make $1 Million (Ep. 325)
Nat Eliason joins guest host Jimmy Soni to discuss Founders School, a new high school for entrepreneurs that guarantees students will generate $1 million in gross profit by graduation or get their tuition refunded. We explore how AI is changing what teenagers can build, why traditional...
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Philip Howard - How to Bring Common Sense Back to America (Ep. 324)
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...
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Sangeet Choudary - How AI Will Reshape the Knowledge Economy (Ep. 323)
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…
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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...
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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,...
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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...
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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...
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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...
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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…
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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...
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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…
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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,...
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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...
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Saloni Dattani - The Hidden Bottleneck Holding Back the Future of Medicine (Ep. 312)
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...
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Brian Potter - How to Fix America's Building Problem
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,...
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Alex Petkas - What Ancient Greece Can Teach Us About AI and the Future (Ep. 310)
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...
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Sam Arbesman - Why Future Belongs to Curious People (Ep. 309)
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...
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Johnathan Bi - Why the Best Founders Might Need a Little Delusion (Ep. 308)
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...
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Polina Pompliano - What Truly Drives Successful People (Ep. 307)
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...
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Adam Mastroianni - Why Creativity Feels Like It's Dying (Ep. 306)
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…
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Arkady Kulik - The Psychology of Self-Deception (Ep. 305)
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...
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Angus Fletcher - The Biggest Mistake We Made About Intelligence (Ep. 304)
In this episode of Infinite Loops, Jim O'Shaughnessy sits down with Angus Fletcher, Professor of Story Science at Ohio State University's Project Narrative and author of multiple books at the intersection of narrative theory, psychology, and brain science. Angus' research challenges one of the…
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Jonathan Tepper - Growing Up in the Heroin Capital of Europe (Ep. 303)
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...
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Paul Millerd & Jimmy Soni — The Creative Opportunities of a Boring Life (EP. 302)
Fresh off releasing one of the most beautiful 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...
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Packy McCormick - How Writing Shapes Companies (Ep. 301)
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...
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Jean-Marc Daecius - The Last Human Chief of Staff (Ep. 300)
What happens when you design a company assuming AI should do everything it possibly can? Jean-Marc Daecius, OSV's Chief of Staff, joins Infinite Loops to explain what it means to be "AI first" — and why he believes he may be the company's last human chief of staff. The conversation explores how…
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John Wang - The Man Who Built The Queens Night Market (Ep. 299)
The Queens Night Market is one of New York City's most beloved institutions — but it was never supposed to last more than a year. John Wang, founder of the Queens Night Market, joins Infinite Loops to explain how a side project with a "terrible business model" unexpectedly became one of the most...
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Cliff Asness - Surviving the Meme Stock Bubble (Ep. 298)
Cliff Asness — co-founder, managing principal, and chief investment officer at AQR Capital Management — is one of the most influential quantitative investors of the last 30 years. He's also one of the most candid. In this conversation, Cliff joins Infinite Loops to talk about why losses hurt more...
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Tomás Pueyo — Explaining the World Through Geography, History and Data (EP. 297)
Tomás Pueyo, the French-Spanish engineer and writer behind the successful "Uncharted Territories" Substack, joins us to dismantle the invisible forces that shape our history and future. We cover why humans are horrible at understanding exponential change, the geographical advantages of the U.S…
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Annie Duke — Why We Make the Wrong Decisions (Ep. 296)
Annie Duke — former professional poker player, decision strategist, and bestselling author — joins us for a deep conversation about why smart people so often make bad decisions. Annie explains why misinterpretation is more dangerous than misinformation, why data is often true but misleading, and...
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Jimmy Soni — The Publishing System is Broken (EP. 295)
Jimmy Soni, CEO and editor in chief of Infinite Books, is back on Infinite Loops. We discuss what's broken in traditional publishing and how we're fixing it. We also dig into Jimmy's forthcoming book on Kobe Bryant, why the world needs more "problem authors," and why our goal is to make our…
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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....
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Vik Muniz — The Art of Perception (EP.294)
What if the invention that truly made us human wasn't the wheel, language, or even agriculture — but art? In this episode of Infinite Loops, we sit down with internationally renowned artist Vik Muniz to explore a radical and deeply human idea: that art — the ability to represent the world — may…
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Marc Dennis — Painting the Punchline (EP.293)
Artist Marc Dennis joins Jim O'Shaughnessy to explore the intersection of hyper-realism, humor, and the "meta-narrative." Marc shares his incredible non-linear journey—from accidentally starting a forest fire at age seven to becoming a tenured professor and eventually betting it all to become a...
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Ariel Meyerowitz — Navigating the Art World (EP. 292)
Professional art advisor Ariel Meyerowitz joins Jim O'Shaughnessy to demystify the complex world of art. Ariel provides an essential guide for aspiring collectors, explaining where to begin, how to develop your eye, and why buying what you love is the most important first step. They explore the...
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Adam Moskowitz — The Way of the Cheesemonger (EP.291)
Adam Moskowitz is the King of Cheese—but his path to the throne was anything but straight. In this delicious episode of Infinite Loops, Adam shares his wild journey from a failed rap career and a battle with addiction to becoming one of the most influential figures in cheese and the host of A...
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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…
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About this show
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!"
Hosted by
Jim O'Shaughnessy
Categories