Infinite Loops

Jim O'Shaughnessy
  • 4.6 (173)
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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!"

  1. 12h ago

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

    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

  2. Oct 29

    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 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: The reciprocity principle behind Jim's warning about manipulation. Influence Reflexivity: George Soros's idea from The Alchemy of Finance, which shaped Tren's thinking on feedback loops. Reflexivity Benoit Mandelbrot: Whose The (Mis)Behavior of Markets Jim credits with shaping the models he built to pick stocks. Benoit Mandelbrot Gödel, Escher, Bach by Douglas Hofstadter: Jim's example of a hard book that AI could open up to more readers. Gödel, Escher, Bach Clarke's third law: "Sufficiently advanced technology is indistinguishable from magic." Clarke's three laws Cabo Wabo: Sammy Hagar's tequila, Tren's example of a founder bringing a ready-made community to a product. Cabo Wabo Menlo Ventures consumer AI survey (2025): About 3% of AI users pay, in line with Tren's point that most people use AI for free. Read the release

  3. Oct 22

    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 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 military showed which interview methods actually predict performance. Daniel Kahneman Pre-mortem: The technique of imagining a plan has failed and working out why. Pre-mortem Replication crisis: The finding that many published psychology results don't hold up when re-run. Replication crisis John Sarno: The NYU physician whose work on the mind's role in chronic pain Jim credits with curing his frozen neck. John E. Sarno Molecules of Emotion by Candace Pert: Jim's reference on how emotions show up physically in the body. Candace Pert Mirror box therapy: The phantom limb treatment Spencer uses to show the brain can reinterpret a pain signal. Mirror box

  4. Oct 15

    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 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 the Wild and Raiders of the Lost Ark. How Ed captured David's voice. Much more! Show Notes Ed William & Jim O'Shaughnessy Ed William: Writer, editor, former lawyer and author of No One's Coming to Save You. Read Rough Cuts The book: No One's Coming to Save You: The Escape of David Rhoiney, out December 8, 2026. Pre-order Infinite Books: The publishing imprint behind the book. Infinite Books 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, Films & Ideas Mentioned Into the Wild: The film Ed compares to the Houston chapter, where David almost stops to rest. Into the Wild Raiders of the Lost Ark: Spielberg's "no boring bits" approach that set the book's pace. Raiders of the Lost Ark Mad Max: Fury Road: Ed's model for a story that never stops moving. Mad Max: Fury Road The Pursuit of Happyness and Good Will Hunting: The stories Ed sees as the book's closest film parallels. The Pursuit of Happyness / Good Will Hunting What Works on Wall Street: Jim's book, which David challenged him on in their first conversations. What Works on Wall Street Behaviorism: The mid-century "give me a baby and I'll make it anything" school Jim cites in the nature-versus-nurture debate. Behaviorism

  5. Oct 8

    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 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

  6. Oct 1

    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 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 earn a living doing small tasks only humans can do. Rainbows End Snow Crash by Neal Stephenson: Julie's reference for how ideas spread like a virus through programmers. Snow Crash Fall; or, Dodge in Hell by Neal Stephenson: The novel Julie describes, in which Americans mourn victims of a nuclear attack that never happened. Fall; or, Dodge in Hell The WEIRDest People in the World by Joseph Henrich: Jim's reference on how long cultures take to adapt to new technology. The WEIRDest People in the World Nineteen Eighty-Four by George Orwell: Jim's starting point for cognitive security and invented history. Nineteen Eighty-Four From Googlebot to GPTBot: Cloudflare's report on the rise in AI crawler traffic that Julie cites. Cloudflare report The Vesuvius Challenge: The project reading the Herculaneum scrolls, subject of a documentary from Infinite Films. Vesuvius Challenge Agrippa's trilemma: Jim's reference for why chasing a claim to its source often ends in sand. Agrippa's trilemma

  7. Sep 24

    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 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 Semler: The book behind Derek's short-lived profit-sharing plan at CD Baby. Maverick Why Greatness Cannot Be Planned by Kenneth O. Stanley and Joel Lehman: Jim's reference on why new vantage points change where you want to go. Why Greatness Cannot Be Planned The Beginning of Infinity by David Deutsch: The book Jim calls a definitive look at how he sees the world. The Beginning of Infinity Nothing & Everything by Val N. Tine: The book on nihilism Derek recommends, with his advice to read only the first half. Derek's notes

  8. Sep 17

    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 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 Scrolls: The PBS episode following Brent inside the Villa of the Papyri. Watch on PBS Cost of Glory: The Roman history podcast Brent and Nick reference while discussing what might still be buried. Cost of Glory Dead Poets Society: The source of "carpe diem," one of the two ideas Brent would give the world. Dead Poets Society

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Hosts & Guests

4.6
out of 5
173 Ratings

About

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!"

Information

  • Creator
    Jim O'Shaughnessy
  • Years Active
    2019 - 2026
  • Episodes
    346
  • Rating
    Explicit
  • Show Website
    Infinite Loops

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