Infinite Loops

Jim O'Shaughnessy

  • 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
  • 1 hour 45 minutes
    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/

    8 January 2026, 11:00 am
  • 1 hour 37 minutes
    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

    1 January 2026, 11:00 am
  • 2 hours 2 minutes
    Guy Spier — Wealth, Wisdom & Enlightenment (Infinite Loops CLASSICS)

    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:

    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
    25 December 2025, 11:00 am
  • 1 hour 35 minutes
    Vik Muniz — The Art of Perception (EP.294)

    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/

    17 December 2025, 11:00 am
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