Infinite Loops

Jim O'Shaughnessy

  • 1 hour 7 minutes
    Polina Pompliano - What Truly Drives Successful People (Ep. 307)

    Polina Pompliano studies some of the most successful people in the world—and what she's found challenges how we think about success, creativity, and human behavior.

    In this episode of Infinite Loops, we explore the mental models behind high performers, why we misunderstand people (including 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

    26 March 2026, 12:15 pm
  • 1 hour 32 minutes
    Adam Mastroianni - Why Creativity Feels Like It's Dying (Ep. 306)

    In this episode of Infinite Loops, we speak with Adam Mastroianni—experimental psychologist and sharp critic of modern culture and science. We ask, why does creativity feel like it's fading? From endless remakes to cultural sameness, Adam argues that as society becomes more stable and 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

    19 March 2026, 12:15 pm
  • 1 hour 31 minutes
    Arkady Kulik - The Psychology of Self-Deception (Ep. 305)

    In this episode of Infinite Loops, we sit down with venture capitalist and physicist Arkady Kulikov to explore the psychology behind founders, responsibility, and self-deception. Kulik discusses why the hardest problems in business are almost always human problems, how great founders deal with 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/

    12 March 2026, 12:36 pm
  • 1 hour 36 minutes
    Angus Fletcher - The Biggest Mistake We Made About Intelligence (Ep. 304)

    In this episode of Infinite Loops, Jim O'Shaughnessy sits down with Angus Fletcher, Professor of Story Science at Ohio State University's Project Narrative and author of multiple books at the intersection of narrative theory, psychology, and brain science.

    Angus' research challenges one of the 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/

    5 March 2026, 1:15 pm
  • 1 hour 12 minutes
    Jonathan Tepper - Growing Up in the Heroin Capital of Europe (Ep. 303)

    In this episode of Infinite Loops, we sit down with author Jonathan Tepper to discuss his extraordinary childhood.

    In 1985, when Jonathan was seven, his missionary parents moved the family to San Blas — then the heroin capital of Europe — to start a drug rehabilitation center. Jonathan and his 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/

    26 February 2026, 1:15 pm
  • 1 hour 30 minutes
    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:

    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

    19 February 2026, 11:00 am
  • 1 hour 33 minutes
    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/

    12 February 2026, 1:20 pm
  • 1 hour 49 minutes
    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

    5 February 2026, 1:30 pm
  • 1 hour 20 minutes
    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/

    29 January 2026, 1:30 pm
  • 1 hour 57 minutes
    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

    22 January 2026, 1:30 pm
  • 1 hour 38 minutes
    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:

    15 January 2026, 11:00 am
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