Jim O'Shaughnessy

Infinite Loops

A Technology , Business and Entrepreneurship podcast Explicit

#64 in Technology · 🇵🇰 #95 in Technology · 🇿🇦

About the 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!"

Newest episodes

Jun Kwak - AI Agents and the Future of Commerce (Ep. 335)

Nov 12, 2026 1 hr 42 min

Jun Kwak, co-founder and CTO of Overjoy, joins Jim O'Shaughnessy on Infinite Loops to talk about why he believes every B2B SaaS company will have to become a service business, how Overjoy went from selling software to delivering sales outcomes for consumer brands, why tangled data is the strongest moat against the frontier labs, how AI agents could weaken wholesale marketplaces, why brands need websites AI agents can read, why small brands chasing big box stores often abandon their most profitable channel, whether agents will turn premium products into commodities, and what three national debate championships taught him about running a company. Show Notes Jun Kwak & Jim O'Shaughnessy Jun Kwak: Co-founder and CTO of Overjoy. Connect on LinkedIn Overjoy: The AI-powered wholesale growth platform Jun co-founded with Alex Han. Overjoy Overjoy on X: Follow Overjoy on X Jim O'Shaughnessy: Host of Infinite Loops, founder and CEO of O'Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter Books & Ideas Mentioned Zen and the Art of Motorcycle Maintenance by Robert M. Pirsig: The source of Jim's story about a friend outraged that his BMW motorcycle was fixed with a scrap of aluminum can. Zen and the Art of Motorcycle Maintenance Influence by Robert Cialdini: The classic text on persuasion Jim cites when asking whether AI will master it. Influence Sebastian Barry: The Irish novelist whose McNulty book A Temporary Gentleman Jim discussed with his AI agent. Sebastian Barry Consumer Reports: Jim's model for a trusted product-rating source in a world of AI shopping agents. Consumer Reports Collapse of Silicon Valley Bank: The 2023 bank run that locked up Overjoy's seed funding. Collapse of Silicon Valley Bank Faire: The wholesale marketplace Jun cites as the market leader. Faire Electronic data interchange (EDI): Th...

Infinite Loops Classics | Mike Maples, Jr. — How To Become a Pattern-Breaking Founder

Nov 5, 2026 1 hr 35 min

This week, we're re-upping one of my favorite episodes from the archives: my chat with Mike Maples, Jr., from September 2024. Normal scheduling will resume next week. Enjoy! *** Mike Maples, Jr., co-founding partner of the VC firm Floodgate, is the veteran seed investor behind some of the 21st century's great success stories, including Twitter, Twitch, and Applied Intuition. His book, Pattern Breakers (co-authored with Peter Ziebelman), articulates a new model of foundership, one built on the simple premise that transformative startups upend rather than improve current practices. I had a blast quizzing Mike on the nuts and bolts of pattern-breaking foundership, from finding true believers to waging asymmetric war on the status quo. Important Links: Pattern Breakers: Why Some Start-Ups Change the Future; by Mike Maples, Jr & Peter Ziebelman Twitter Substack (Starting Greatness) Floodgate LinkedIn Show Notes: Seagull mode: an unexpected founder paradigm How to wage asymmetric war on the present Evading the comparison trap Finding your people: how to build a movement Why we should continually seek the truth The customer isn't always right, but the ones living in the future are Why disagreeableness is undervalued How to fix a pitch Frankendeck Don't use jargon as a substitute for clear thinking How to find the true believers How to live in the future How founders are like trainspotters Why wanting to be a founder is a bad reason to start a company Reading habits of a pattern-breaker The unreliability of memory Mike as emperor of the world MORE! Books Mentioned: Jonathan Livingston Seagull: A story; by Richard Bach The Genius of the Beast: A Radical Re-Vision of Capitalism; by Howard Bloom The Beginning of Infinity: Explanations that Transform The World; by David Deutsch What Works on Wall Street; by Jim O'Shaughnessy Poor Charlie's Almanack: The Essential Wit and Wisdom of Charles T. Munger; by Charles T. Munger

Tren Griffin - How To Write, Publish & Sell A Book In The AI Era (Ep. 334)

Oct 29, 2026 1 hr 45 min

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 public, the Charlie Munger lesson that changed his life during the dot-com boom, whether serious reading is really dying, and how to find a passion worth following. Show Notes Tren Griffin & Jim O'Shaughnessy Tren Griffin: Investor, writer, and author of the 25iq blog. Read 25iq Charlie Munger: The Complete Investor: Tren's book on how Munger approached investing and life. Charlie Munger: The Complete Investor Tren on X: Follow Tren on X Infinite Books: Jim's publishing company. Infinite Books Tren's earlier conversation: Welcome to the Tren-verse, Ep. 86. Watch Jim O'Shaughnessy: Host of Infinite Loops, founder and CEO of O'Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter Books & Ideas Mentioned The Psychology of Money by Morgan Housel: Tren's example of how stories sell nonfiction. The Psychology of Money Runnin' Down a Dream by Bill Gurley: The book Tren recommends on turning passions into a career. Runnin' Down a Dream Kelly criterion: The bet-sizing formula Tren calls one of the hardest ideas to explain simply. Kelly criterion Why Greatness Cannot Be Planned by Kenneth Stanley and Joel Lehman: Jim's case for taking unexpected opportunities seriously. Kenneth Stanley 1,000 True Fans by Kevin Kelly: The essay behind Tren's advice to build a community of super fans. 1,000 True Fans Duncan Watts on social influence: Why bestsellers emerge from people copying what others buy. Duncan J. Watts Mimetic desire: René Girard's idea that we want what others want. Mimetic theory Influence by Robert Cialdini: Th...

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All episodes

The newest 50 of 347 episodes

Jun Kwak - AI Agents and the Future of Commerce (Ep. 335)

Nov 12, 2026 1 hr 42 min

Infinite Loops Classics | Mike Maples, Jr. — How To Become a Pattern-Breaking Founder

Nov 5, 2026 1 hr 35 min

Tren Griffin - How To Write, Publish & Sell A Book In The AI Era (Ep. 334)

Oct 29, 2026 1 hr 45 min

Spencer Greenberg - 106 Self-Help Books Distilled Into 12 Strategies (Ep. 333)

Oct 22, 2026 1 hr 46 min

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 the law of attraction can backfire, how to design hiring interviews that predict performance, and what his team found replicating new studies from top psychology journals. Show Notes Spencer Greenberg & Jim O'Shaughnessy Spencer Greenberg: Mathematician and entrepreneur, founder of ClearerThinking.org and Spark Wave, and host of the Clearer Thinking podcast. Clearer Thinking The 12 Levers: Spencer and Jeremy Stevenson's evidence-based toolkit for improving your life. The 12 Levers Clearer Thinking podcast: Spencer's interview show, where Jim has been a guest. Listen Transparent Replications: Spencer's project that randomly picks and re-runs new studies from top psychology journals. Transparent Replications Importance hacking: Spencer's essay on the problem his replications uncovered. Read the essay Jim O'Shaughnessy: Host of Infinite Loops, founder and CEO of O'Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter Books & Ideas Mentioned Reality tunnels: Robert Anton Wilson's idea that everyone perceives a different version of reality. Reality tunnel The Challenger memory study: Research showing how far people's memories of a major event drift over time. Flashbulb memory Spaced repetition: Spencer's recommended method for remembering what matters. Spaced repetition My Dinner with Andre: The film that shaped how Jim designed Infinite Loops. My Dinner with Andre Behavioral activation: The evidence-based depression technique Spencer describes. Behavioral activation Daniel Kahneman: Whose work for the Israeli mil...

Ed William - Writing A Biography That Reads Like Fiction (Ep. 332)

Oct 15, 2026 1 hr 19 min

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 nights in the homeless shelter. Drive-by shootings. Strangers in overalls dragging his mother away. As his world collapsed, David lost hope. No one was coming to save him. But he could save himself. When basketball threw him a lifeline, David grabbed it. So began an unlikely journey, one that carried him from living in a Volkswagen Jetta onto the courts of Division I, through the halls of the Naval Academy, into the corridors of national intelligence, and under the watchtowers of Guantánamo Bay. At last, scalpel in hand, David reached the operating room, where he could become the man his family needed. Ed William, a former lawyer, spent several days interviewing David and spoke to dozens of people from his life. The result is Ed's first book, No One's Coming to Save You: The Escape of David Rhoiney, out from Infinite Books on 8 December and now available for pre-order: https://infinitebooks.com/products/no-ones-coming-to-save-you "A powerful and deeply moving account of a boy forced to grow up too soon and the man he fought to become." —Rob Henderson, bestselling author of Troubled Ed joins Jim to discuss: The time David was forced to fight a schoolyard bully in front of his family. David's unusual experience of the Rodney King riots. The note David wrote to God every night. The English teacher who changed David's life in one hour. The prep school coach who cancelled David's credit cards. How a five-foot-three kid ended up playing Division I basketball. David as a role model for young men. The guilt underpinning David's success. The single word that describes David. Why Ed's interview plan fell apart in the first 5 minutes. Why Ed was inspired by Into...

Emma Camp - Why Gen Z Is Afraid of Rejection: Dating, Therapy Culture & Housing (Ep. 331)

Oct 8, 2026 1 hr 21 min

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 for the housing shortage is more housing, and why she invites everyone she's met to every party. She also previews her forthcoming essay collection on Gen Z and risk aversion. Show Notes Emma Camp & Jim O'Shaughnessy Emma Camp: Senior newsletter editor at Free Expression, The Wall Street Journal's opinion newsletter, and former Reason magazine editor. Read Free Expression Emma's breakout essay: Her reflection on the 2022 New York Times op-ed that started her career. After My Big Break Jim O'Shaughnessy: Host of Infinite Loops, founder and CEO of O'Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter Books & Ideas Mentioned The Grim Old Days by Chelsea Follett: Emma's reference for how hard life was for the average person before modern markets. Chelsea Follett The Genius of the Beast by Howard Bloom: Jim's reference for what capitalism achieved that earlier systems couldn't. The Genius of the Beast Jefferson Literary and Debating Society: The University of Virginia society where Emma threw a party every Friday. Jefferson Society Partiful: The app Emma uses to invite everyone to every party. Partiful Sally Rooney: The novelist Emma writes about in her essays on modern relationships. Sally Rooney Attachment theory: Emma's frame for why a secure marriage lets her take more social risks. Attachment theory NAR 2025 Profile of Home Buyers and Sellers: The data on first-time buyers reaching a record median age of 40. Coverage

Julie Fredrickson - The Right to Compute: AI Agents, Nuclear Power & Human Data (Ep. 330)

Oct 1, 2026 1 hr 28 min

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 chatbots keep recommending the same sunscreen, and what 2,089 days of daily public writing taught her about being wrong. It is her second Infinite Loops conversation, three years after Episode 181. Show Notes Julie Fredrickson & Jim O'Shaughnessy Julie Fredrickson: Managing Partner of Chaotic Capital, an early-stage venture fund, and a former founder in e-commerce and beauty. Chaotic Capital Julie on X: Julie's preferred way to be reached. Follow Julie on X Julie's daily writing: More than 2,000 consecutive days of public writing, started January 1, 2021. Read Julie's blog Jim O'Shaughnessy: Host of Infinite Loops, founder and CEO of O'Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter Julie's Work & Projects Montana's Right to Compute Act: The first state law protecting people's right to own and use computers and AI tools, which Julie advocated for. Read the Right to Compute Act Valar Atomics: The small modular reactor company founded by Isaiah Taylor, where Julie invested. Valar Atomics Julie's first Infinite Loops episode: Episode 181, "Circumstances change. Humanity doesn't. Plan accordingly." Watch Episode 181 Books & Ideas Mentioned The Beginning of Infinity by David Deutsch: Jim's reference for why no one in 1900 could have predicted the internet. The Beginning of Infinity Carlota Perez: The economist whose work on technology booms and build-outs shapes Julie's view that AI is still in its invention phase. Carlota Perez Rainbows End by Vernor Vinge: The novel Julie cites for a future where people ear...

Derek Sivers - Living Many Lives: Parenting, Moving Countries & AI (Ep. 329)

Sep 24, 2026 1 hr 44 min

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 can make you less dependent on big tech, not more. It is his first podcast after more than a year of saying no to every request. Show Notes Derek Sivers & Jim O'Shaughnessy Derek Sivers: Author, entrepreneur, and TED speaker, and founder of CD Baby, once the largest seller of independent music online. Derek's website Derek on X: Where Derek shares his writing. Follow Derek on X Derek's TED talks: Including "How to Start a Movement," his most popular talk. Watch Derek's talks Jim O'Shaughnessy: Host of Infinite Loops, founder and CEO of O'Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter Derek's Books & Projects Useful Not True: Derek's book on skepticism and choosing beliefs because they are useful, not because they are true. Useful Not True How to Live: 27 conflicting answers on how to live, which Derek calls his masterpiece. How to Live Hell Yeah or No: Simple mental models for deciding what's worth doing. Hell Yeah or No Anything You Want: Derek's bestselling book of 40 lessons from starting, building, and selling CD Baby. Anything You Want Tech Independence: Step-by-step instructions and a setup script for running your own server and email instead of depending on big tech. Tech Independence Books & Ideas Mentioned Personal Development for Smart People by Steve Pavlina: The book whose idea about seeking surprise sent Derek around the world. Derek's notes China's World View by David Daokui Li: Derek's pick for understanding the Chinese government's point of view. Derek's notes Maverick by Ricardo Semle...

Brent Seales - How AI Is Reading the Only Library That Survived Antiquity (Ep. 328)

Sep 17, 2026 54 min

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 engineering to reading. This summer in Naples, his team presented results from three sealed Herculaneum scrolls, including the first read end to end. Show Notes Brent Seales & Nick Tawil Dr. Brent Seales: Stanley and Karen Pigman Chair of Heritage Science at the University of Kentucky and co-founder of the Vesuvius Challenge. Brent Seales at the University of Kentucky Vesuvius Challenge: The open competition Brent co-founded with Nat Friedman and Daniel Gross to read the carbonized Herculaneum scrolls. Vesuvius Challenge The June 2026 breakthrough: The announcement in Naples of new texts, titles, and authors recovered from the scrolls. The day the Herculaneum scrolls began speaking again Nick Tawil: Guest host and head of Infinite Films. Connect with Nick The Scrolls & the Discoveries The Herculaneum library: Roughly 1,800 scrolls carbonized by Mount Vesuvius in 79 AD, the only library from antiquity that survived. Vesuvius Challenge: the scrolls Philodemus, On Gods, Book 8: A title and author read from a sealed scroll, establishing that the work ran to at least eight books. CNN on the discovery The En-Gedi scroll: The burned Torah scroll Brent's team read without opening, containing one of the oldest known copies of the first two chapters of Leviticus in the canonical Masoretic text. Vesuvius Challenge on En-Gedi The $1 million prize: The open competition to fully unroll and read one of the remaining sealed scrolls. Current prizes Films & Coverage Mentioned The Vesuvius Challenge: The upcoming documentary from Infinite Films and Scott Free, in partnership with Calliope Pictures, narrated by Guy Pearce. Deadline announcement Secrets of the Dead: The Herculaneum Scr...

Ryan Resch - How Data Changed the NBA and What AI Changes Next (Ep. 327)

Sep 10, 2026 1 hr 42 min

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 traces his path from a cold email to Baylor coach Scott Drew to nearly a decade in the Suns front office and his current work leading data and AI in private equity. Show Notes Ryan Resch & Jimmy Soni Ryan Resch on LinkedIn: Former Suns Assistant GM and VP of Basketball Operations, now leading data and AI at 1949 Capital Partners. Connect with Ryan Beyond the Dashboard: Ryan's Harvard Business School interview with Boris Groysberg on optical tracking, dashboards, and AI. Read the interview Shore Capital Partners: The private equity firm founded by Justin Ishbia, where Ryan helped roll out AI tools. Shore Capital Partners Jimmy Soni on X: Guest host, bestselling author, and editor-in-chief of Infinite Books. Connect with Jimmy Teams, Leaders & Data Discussed James Jones: The 2020-21 NBA Executive of the Year, whose Suns rebuild started with raising the floor. Executive of the Year Scott Drew: The Baylor head coach who answered Ryan's cold email and later had him build lineup data. Scott Drew at Baylor SportVU: The camera system that brought optical tracking to every NBA arena in 2013-14. SportVU and the NBA Second Spectrum: The machine learning platform that turned tracking data into tagged plays and dashboards teams across the league use. Second Spectrum and the NBA Hawk-Eye: Sony's 3D tracking system, used across the NBA since 2023-24. Hawk-Eye and the NBA Books, Shows & AI Tools Mentioned Moneyball by Michael Lewis: The 2003 book on the Oakland A's that frames how analytics moved from baseball into basketball. Moneyball Hyperion by Dan Simmons: The first book in the sci-fi series Ryan is reading, and a window into how earlier writers imagined AI. Hyperion The Fo...

Brian Chau - How AI is Reinventing Investigative Journalism (Ep. 326)

Sep 3, 2026 1 hr 46 min

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 Notes Brian Chau & Effort News Effort News — Brian Chau's document-led investigative journalism publication, using AI to search and analyze large datasets while keeping the reporting and final writing human-reviewed. Effort News About Effort News — More on Brian's approach to AI-assisted investigative reporting and the publication's editorial principles. About Effort News Effort's Null Results — Investigations where Effort searched the available evidence but found no newsworthy result. Null Results Brian Chau on X — @brianchau57. Follow Brian on X Investigations Discussed The $1.2B Refugee Services Program that Funds Pro-Asylum Religious Groups — Effort's investigation into federal refugee-resettlement grants and the organizations receiving them. Read the investigation The 19th-Century Family Fortunes Funding Degrowth — Effort's investigation tracing funding for Partners for a New Economy through donor-side disclosures and the Swiss Philanthropy Foundation. Read the investigation Partners for a New Economy (P4NE) — The philanthropic fund discussed in Brian's explanation of tracing obscured donor funding. P4NE Swiss Philanthropy Foundation — The organization that hosts P4NE's pooled philanthropic fund. Swiss Philanthropy Foundation on P4NE How to Go Viral on the New X Algorithm — Effort's analysis of X's open-source recommendation algorithm, which Jim references near the end of the conversation. Read the investigation Freedom Fuel Network — Brian discusses Effort's then-upcoming investigation into the mysterious network of discounted gas stations in Pennsylvania and New Jersey. Effort has since published its findings, Who Supplies Freedom Fuel?, on its site. Effort New...

Julian Gough — The Egg and The Rock (Infinite Loops Classics)

Aug 27, 2026 1 hr 47 min

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 top-ten Irish musician is a little more impressive than he's letting on… Oh, and I didn't even mention that he wrote the ending to the computer game Minecraft! His current project, The Egg and The Rock, puts all of this to shame. This book, which Julian is writing in public on Substack, seeks to do no less than redescribe the universe, arguing that is not some random, dead, purposeless sack of chemicals, but instead a living, evolving organism. Julian joins me to discuss why the arc of human evolution bends towards man-made black holes, the hidden catastrophe at the heart of materialist science, the strange life of subterranean ice aliens, and MUCH more! This was such an interesting conversation - I can't wait for you to hear it. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, "Hmm, that's interesting!", check out our Substack. Important Links: Julian's Website The Egg and The Rock Julian's Twitter Show Notes: "I just sit in my room and write" Why write a book in public? Materialism & science's hidden catastrophe "The scientific method is in conflict with human nature" The faulty assumption at the heart of cosmology Big bangs, supermassive black holes & Darwinian evolution: A ~30 minute masterclass in cosmological natural selection "I'm predicting very, very large amounts of life in this universe" The strange life of subterranean ice aliens Could we spot man-made black holes? Bringing consciousness into physics Pulling back the curtain Julian as World Emperor MORE! Books & Articles Mentioned: The New Inquisition: Irrational Rationalism and the Citadel of Science; by Robert Anton Wilson Against Method: Outline o...

Dr. Julie Gurner — Ultra Successful (Infinite Loops Classics)

Aug 20, 2026 1 hr 33 min

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 performance coach to top percentile executives, primarily in finance and technology. She is also the proprietor of the Ultra Successful newsletter, which delivers a weekly challenge pulled from global business leaders and designed to "help you unleash your power." Dr. Gurner joins the show to discuss the merits of being unreasonable, why your business should not be your identity, why niceness is overrated, and more! Important Links: - Substack - https://drgurner.substack.com - Twitter - https://twitter.com/drgurner?s=21&t=kpNZMw5M-jHHMC0vAkndPg - Website - https://www.drgurner.com/consulting/ Show Notes: 0:00:00 Intro 0:01:24 Main podcast 0:02:20 Dr. Gurner's origin story 0:05:07 How forensic psychology experience can help executive coaching 0:07:11 Leaning into the 1% 0:15:23 Why psychological tests are flawed 0:19:26 The common traits of successful founders 0:29:12 High performance & bottlenecks 0:30:38 Why your business should not be your identity 0:41:01 How Dr. Gurner applies her strategies in her own life 0:44:17 Don't be nice 0:46:48 Be unreasonable 0:51:18 Social validation is not important 0:56:22 How can you improve someone's communication skills 1:01:43 How Dr. Gurner would teach executive coaching 1:03:36 The "no Plan B" mentality 1:06:48 Can high energy be detrimental? 1:10:21 How to unpack charisma 1:15:57 How to turn down work 1:20:01 Dr. Gurner's greatest satisfaction 1:22:31 How has leadership changed in the last 20 years? 1:25:40 Dr. Gurner as Empress of the World 1:31:18 End screen Books Mentioned: - The Art of War; by Sun Tzu

Lulu Cheng Meservey — Going Direct: What Founders can learn from K-Pop, Crypto, and the Early Christians (Infinite Loops Classics)

Aug 13, 2026 1 hr 37 min

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 gotten better. Enjoy this conversation with Lulu Cheng Meservey. Lulu Cheng Meservey is the Chief Communications Officer and Executive Vice President of Corporate Affairs at Activision Blizzard. She joins Infinite Loops to provide us with a masterclass in communications for startups. A must-listen for current and aspiring founders. Important Links: • Lulu's Twitter • Lulu's Substack • Episode summary from Podcasts Recapped Show Notes: • Why people write hit pieces • The insurgency framework • How to access your audience's neural real estate • How to develop a spontaneous elevator pitch • Tips for becoming better at reading the room • Speak directly and take the hits • Defining business objectives • Learning from other industries • Personalising your message • Overcoming resistance to the unknown, what Christianity can teach us about comms • Escaping corporate jargon • How comms resembles rugby • Taking ownership of comms • Moving to a new model of comms • "Don't let things happen to you. Go and happen to things." Books Mentioned: • The Network State: How To Start a New Country; by Balaji S. Srinivasan • The Hero with a Thousand Faces; by Joseph Campbell

Jesse Michels — American Alchemy (Infinite Loops Classics)

Aug 6, 2026 1 hr 25 min

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 gotten better. Enjoy this one with the wonderfully heretical Jesse Michels. Jesse Michels is an investor at Thiel Capital and the creator and host of 'American Alchemy', a Youtube channel dedicated to highlighting the most heretical thinkers and ideas of our time. He joins the show to discuss the transmission theory of consciousness, whether mushrooms are aliens, the reawakening of the Boomers and MUCH more! Important Links: - American Alchemy - https://www.youtube.com/@JesseMichels/about - Jesse's Twitter - https://twitter.com/alchemyamerican Books Mentioned: - The Half-Life of Facts: Why Everything We Know Has an Expiration Date; by Samuel Arbesman - The User Illusion: Cutting Consciousness Down to Size; by Tor Norretranders - Gödel, Escher, Bach: an Eternal Golden Braid; by Douglas Hofstadter - The Beginning of Infinity: Explanations That Transform the World; by David Deutsch - The Immortality Key : The Secret History of the Religion with No Name; by Brian C. Muraresku - The New Inquisition: Irrational Rationalism and the Citadel of Science; by Robert Anton Wilson - How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression and Transcendence; by Michael Pollan - Chaos: Charles Manson, the CIA, and the Secret History of the Sixties; by Tom O'Neill - Weird Scenes Inside the Canyon: Laurel Canyon, Covert Ops & the Dark Heart of the Hippie Dream; by David McGowan - Prometheus Rising; by Robert Anton Wilson - Quantum Psychology: How Brain Software Programs You & Your World; by Robert Anton Wilson - The Cosmic Trigger trilogy; by Robert Anton Wilson - Communion: A True Story; by Whitley Stri...

Nat Eliason - The High School That Guarantees You'll Make $1 Million (Ep. 325)

Jul 30, 2026 1 hr 36 min

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 entrepreneurship education falls short, and what happens when we take young people seriously. Important Links: Learn more about Founders School: https://founders.school/ Read more from Nat here: https://www.nateliason.com/

Philip Howard - How to Bring Common Sense Back to America (Ep. 324)

Jul 23, 2026 1 hr 16 min

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 - How AI Will Reshape the Knowledge Economy (Ep. 323)

Jul 16, 2026 1 hr 48 min

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

Jameson Olsen - Becoming the Main Character (Ep. 322)

Jul 9, 2026 1 hr 34 min

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 - The Stories that Shape Business (Ep. 321)

Jul 2, 2026 1 hr 10 min

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 - How Curiosity Becomes a Calling (Ep. 320)

Jun 25, 2026 1 hr 23 min

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/

Ben Cohen - The Hidden Art of Making Things Better (Ep. 319)

Jun 18, 2026 1 hr 20 min

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

Revan Lazarus - How AI is Rebuilding the Creator Economy (Ep. 318)

Jun 11, 2026 54 min

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/

Brian London, Marisa Adler & Eric Stubin - The Hidden Economy of Recycled Clothes (Ep. 317)

Jun 4, 2026 1 hr 7 min

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 - Faith, Failure, and Finance (Ep. 316)

May 28, 2026 2 hr 1 min

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 - Why Progress Is the Exception, Not the Rule (Ep. 315)

May 21, 2026 1 hr 29 min

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 - AI Tools That Give Creators More Control (Ep. 314)

May 15, 2026 1 hr 43 min

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

Danielle Crittenden - Dispatches from Grief (Ep. 313)

May 7, 2026 1 hr 52 min

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 - The Hidden Bottleneck Holding Back the Future of Medicine (Ep. 312)

Apr 30, 2026 1 hr 25 min

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/

Brian Potter - How to Fix America's Building Problem (Ep. 311)

Apr 23, 2026 1 hr 13 min

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, California's anti-growth turn, and the deeper logic behind local opposition to growth: concentrated harms and diffuse benefits. Important Links: Read Brian's newsletter Construction Physics here: https://www.construction-physics.com/ Read Brian's book The Origins of Efficiency here: https://press.stripe.com/origins-of-efficiency Learn more about Brian here: https://ifp.org/author/brian-potter

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

Apr 16, 2026 1 hr 36 min

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 fear that writing would become a tool for forgetting, the real lesson of Icarus, why decentralization creates cultural power, and what it means to remain fully human in the age of AI. Important Links: Learn More about The Cost of Glory: www.costofglory.com Check out Alex's Youtube Channel: https://www.youtube.com/@costofglory Alex's Twitter: https://x.com/costofglory The Cost of Glory Substack: https://costofglory.substack.com/

Sam Arbesman - Why Future Belongs to Curious People (Ep. 309)

Apr 9, 2026 1 hr 46 min

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 open-mindedness more than intelligence, why science works even though scientists are imperfect, and why the future may depend on revisiting forgotten ideas from the past. Important Links: Learn more about Sam here: https://arbesman.net/ Read Sam's latest book: https://www.hachettebookgroup.com/titles/samuel-arbesman/the-magic-of-code Sam's Substack: https://arbesman.substack.com/about Neal Stephenson's Innovation Starvation: https://www.wired.com/2011/10/stephenson-innovation-starvation/ David Deutsch's The Beginning of Infinity: https://www.thebeginningofinfinity.com/

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

Apr 2, 2026 1 hr 39 min

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 America encourages megalomania, what happens when materialism starts to feel incomplete, and why the "seeker" may matter even more in the age of AI. The episode moves from Plato and Caesar to founders, mystics, near-death experiences, and the future of human creativity. Important Links: Johnathan's Youtube Channel: https://www.youtube.com/@bi.johnathan Johnathan's Substack: https://substack.com/@johnathanbi

Polina Pompliano - What Truly Drives Successful People (Ep. 307)

Mar 26, 2026 1 hr 7 min

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 ourselves), and what it really takes to see the world differently. From creativity and rationality to identity, media bias, and the hidden motivations driving success, this conversation is a deep dive into how great thinkers actually operate. Important Links: Check out Polina's new book: https://www.amazon.com/Hidden-Genius-Thinking-Successful-People/dp/0593715604 More from Polina Pompliano — The Profile: https://theprofile.substack.com

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

Mar 19, 2026 1 hr 32 min

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 risk-averse, we may be unintentionally reducing the "deviance" that drives originality and breakthrough thinking. We also discuss why science should get weirder, how to fight credentialism, and the dangers of professionalization. Important Links: To learn more about Adam Mastroianni: https://www.adammastroianni.com/ Adam's Piece on the Decline of Deviance: https://www.experimental-history.com/p/the-decline-of-deviance Slime Mold Time Mold: https://slimemoldtimemold.com/ Our Conversation with Julian Gough: https://newsletter.osv.llc/p/the-egg-and-the-rock-ep-249

Arkady Kulik - The Psychology of Self-Deception (Ep. 305)

Mar 12, 2026 1 hr 31 min

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 stress, and why the biggest lie entrepreneurs tell is often to themselves. He also explains how investors evaluate founder psychology, why difficult conversations are essential in business, and why resilience is more about adaptability than stubbornness. Important Links: Listen to our last conversation with Arkady here: https://www.infiniteloopspodcast.com/arkady-kulik-bridging-science-entrepreneurship-ep193/ Arkady's deep tech venture fund, rpv global: https://rpv.global/

Angus Fletcher - The Biggest Mistake We Made About Intelligence (Ep. 304)

Mar 5, 2026 1 hr 36 min

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 most widely accepted ideas in modern culture: that the human brain works like a computer. Drawing on his work with U.S. Army Special Operations, he argues that humans think not in equations, but in actions and stories — and that modern education systems are failing to cultivate the kinds of intelligence needed to navigate the real world. Jim and Angus explore the difference between probability thinking and possibility thinking, why standardized education may be suppressing creativity, how stories shape strategy and leadership, and why the most successful innovators think like explorers rather than optimizers. Important Links: Read Angus' book — Primal Intelligence: The New Science of How We Think: https://www.amazon.com/Primal-Intelligence-New-Science-Think/dp/0593712974 Angus' Harvard Business Review Article — Your Brain Doesn't Work the Way You Think It Does: https://hbr.org/2025/01/your-brain-doesnt-work-the-way-you-think-it-does Learn more about Angus here: https://www.angusfletcher.co/

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

Feb 26, 2026 1 hr 12 min

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 brothers grew up alongside former bank robbers, prison survivors, and people living through the AIDS epidemic. These recovering addicts became like older siblings to them. What began with one man in a small apartment grew into a global movement operating in 20 countries. Jonathan's memoir, Shooting Up: A Memoir of Love, Loss, and Addiction, is out now and published in the US by Infinite Books and in the UK by Little, Brown Book Group. Important Links Buy Shooting Up: A Memoir of Love, Loss and Addiction: https://www.infinitebooks.com/books/products/shooting-up Read the first chapter for free: https://infiniteloops.substack.com/p/give-them-to-anyone-who-looks-like Learn more about Jonathan here: https://jonathan-tepper.com/

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

Feb 19, 2026 1 hr 30 min

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 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 Substack. Important Links: Paul's Website Paul's X Paul's Substack The Pathless Path Premium Hardcover Good Work Infinite Books Jimmy's X 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) Reclaim the Book; by Paul Millerd (essay) Tiny Experiments: How to Live Freely in a Goal-Obses...

Packy McCormick - How Writing Shapes Companies (Ep. 301)

Feb 12, 2026 1 hr 33 min

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 the internet punishes you for being early and wrong. Important Links: Packy McCormick on Optimism: https://www.notboring.co/p/optimism The Internet Contrarian: https://www.osam.com/pdfs/research/The%20Internet%20Contrarian.pdf Elliot Herschberg on GitLab Founder and Cancer: https://www.notboring.co/p/the-builder-cancer-problem Ben Thompson's Aggregation Theory: https://stratechery.com/aggregation-theory/

Jean-Marc Daecius - The Last Human Chief of Staff (Ep. 300)

Feb 5, 2026 1 hr 49 min

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 AI can remove meaningless cognitive load, protect deep work, and unlock creative leverage — from reshuffling priorities and filtering email, to reinventing publishing, agriculture, education, and even how we discover books, movies, and ideas. Important links: Substack: https://newsletter.osv.llc/ Jean Marc's "The Future of Food": https://newsletter.osv.llc/p/the-future-of-food

John Wang - The Man Who Built The Queens Night Market (Ep. 299)

Jan 29, 2026 1 hr 20 min

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 celebrated food markets in the world. From leaving a traditional legal career to imposing a strict price cap in one of the most expensive cities on earth, John shares how the market evolved into a cultural institution representing more than 100 countries through food. Important links: Substack: https://newsletter.osv.llc/ Queens Night Market: https://queensnightmarket.com/

Cliff Asness - Surviving the Meme Stock Bubble (Ep. 298)

Jan 22, 2026 1 hr 57 min

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 than wins, how bubbles form, why modern investing increasingly resembles gambling, and what the dot-com era can teach us about today's markets. Important links: Substack: https://newsletter.osv.llc/ Cliff's Perspectives: https://www.aqr.com/Insights/Perspectives Cliff's X: https://x.com/CliffordAsness

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

Jan 15, 2026 1 hr 38 min

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, why the Luddites might have been right, the "social media politician" of the future, why education is mostly signaling, and how air conditioning and mosquito eradication could change the destiny of nations. Important Links: Tomas's Website X / Twitter LinkedIn Substack: Uncharted Territories YouTube Channel

Annie Duke — Why We Make the Wrong Decisions (Ep. 296)

Jan 8, 2026 1 hr 45 min

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 how our brains are wired for certainty in a probabilistic world. From real-world media examples to investing, health decisions, and AI-generated insights, this episode explores how explanations feel satisfying — even when they're wrong. Important links: Substack: https://newsletter.osv.llc/ Annie's website: https://www.annieduke.com/

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

Jan 1, 2026 1 hr 37 min

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 authors millionaires. We explore why most industries optimize for prestige instead of outcomes, how digital distribution has reshaped attention, and why authors — and creators more broadly — have more leverage than they realize. Important Links: Infinite Books: https://www.infinitebooks.com/ Jimmy's X: https://x.com/jimmyasoni Substack: https://newsletter.osv.llc/ Books Mentioned: The Founders by Jimmy Soni A Mind at Play by Jimmy Soni The Dao of Kobe by Jimmy Soni (Upcoming) What Works on Wall Street by Jim O'Shaughnessy Invest Like the Best by Jim O'Shaughnessy How to Retire Rich by Jim O'Shaughnessy The 4-Hour Workweek by Tim Ferriss The Almanac of Naval Ravikant by Eric Jorgenson (transcribed as "Naval Akan") Dispatches from Grief (Upcoming) Mamba Mentality by Kobe Bryant Slow Horses by Mick Herron The Boys in the Boat by Daniel James Brown

Guy Spier — Wealth, Wisdom & Enlightenment (Infinite Loops CLASSICS)

Dec 25, 2025 2 hr 2 min

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: Guy's Website Guy's Twitter Guy's YouTube Channel 3Blue1Brown (YouTube Channel) Numberphile (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

Vik Muniz — The Art of Perception (EP.294)

Dec 17, 2025 1 hr 35 min

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 be humanity's most important invention after fire. Born in São Paulo and now collected by major museums around the world, Muniz reflects on his own life journey — from growing up in a Brazilian favela to redefining what art can be — and explains why the artwork is only ever half complete. The viewer finishes it. #Art #Creativity #VicMuniz #Perception #Photography #Innovation #Documentary #Mindset #VisualArt #InfiniteLoops Important links: Substack: https://newsletter.osv.llc/ Vik's website: https://vikmuniz.net/

Marc Dennis — Painting the Punchline (EP.293)

Dec 11, 2025 1 hr 58 min

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 full-time artist with no plan B. They discuss why the "key to failure" is trying to please everyone, how humor acts as a survival mechanism, and the crucial difference between perception and reality. Marc also offers a masterclass on intention, explaining why he plants hidden stories within his paintings and sharing the profound realization that you cannot love others until you love yourself. This conversation is a deep dive into the creative mind, offering insights on resilience, identity, and the art of betting on yourself. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, "Hmm, that's interesting!", check out our Substack. #Art #Creativity #Hyperrealism #Philosophy #MentalModels #Resilience #Humor #Psychology Important Links: Substack: https://newsletter.osv.llc/ Marc's Website: http://www.marcdennis.com/ Marc's Instagram: https://www.instagram.com/darcmennis/ Books mentioned: Meditations by Marcus Aurelius The Twelve Caesars by Suetonius

Ariel Meyerowitz — Navigating the Art World (EP. 292)

Dec 4, 2025 1 hr 36 min

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 inner workings of galleries, auctions, and art fairs, contrasting the emotional value of art with the often-fickle investment market. Ariel also shares her philosophy on patronage, the psychology of collecting, and the profound, stress-reducing impact of living with art. This conversation is a perfect starting point for anyone looking to break into the art world, offering a clear path from intimidation to appreciation. #Art #ArtCollecting #Investing #Culture #Creativity #MentalModels #Innovation #Design #Psychology #Philosophy Important Links: Substack: https://newsletter.osv.llc/ Ariel's Website: https://www.arielmeyerowitz.com/ Books mentioned: The Painted Word by Tom Wolfe

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Podcast details

Created by: Jim O'Shaughnessy
Status: Active
Latest episode: Nov 12, 2026
Episodes: 347
Release period: Weekly
Avg. episode length: 1 hr 25 min
Explicit: Yes
Language: English

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