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Infinite Loops

Jim O'Shaughnessy
Infinite Loops
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313 episoder

  • Infinite Loops

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

    05.03.2026 | 1 t. 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/
  • Infinite Loops

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

    26.02.2026 | 1 t. 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/
  • Infinite Loops

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

    19.02.2026 | 1 t. 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-Obsessed World; by Anne-Laure Le Cunff
    The Chronic; by Dr. Dre (album)
    Tao Te Ching (Dao De Jing); by Lao Tzu
  • Infinite Loops

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

    12.02.2026 | 1 t. 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/
  • Infinite Loops

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

    05.02.2026 | 1 t. 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

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Om Infinite Loops

Every Thursday, join Jim O'Shaughnessy and his favorite people as they arm you with the tools & fresh perspectives required to upgrade your HumanOS and thrive in our messy, probabilistic world. Visit our Substack at newsletter.osv.llc for full transcripts, highlights, weekly doses of timeless wisdom, and a bounty of other goodies designed to make you go, "Hmm that's interesting!"
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