Infinite Loops

Jim O'Shaughnessy
  • 4.6 (169)
  • TECHNOLOGY
  • UPDATED WEEKLY

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. 1H AGO

    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 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-Obsessed World; by Anne-Laure Le Cunff The Chronic; by Dr. Dre (album) Tao Te Ching (Dao De Jing); by Lao Tzu

    1h 30m

  2. 6D AGO

    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 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/

    1h 33m

  3. FEB 5

    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 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

    1h 49m

  4. JAN 29

    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 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/

    1h 20m

  5. JAN 22

    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 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

    1h 58m
  6. Tomás Pueyo — Explaining the World Through Geography, History and Data (EP. 297)

    JAN 15

    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, 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

    1h 39m
  7. Annie Duke — Why We Make the Wrong Decisions (Ep. 296)

    JAN 8

    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 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/

    1h 45m

  8. JAN 1

    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 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

    1h 37m
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Hosts & Guests

4.6
out of 5
169 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
    309
  • Rating
    Explicit
  • Show Website
    Infinite Loops

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