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    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!”

    Advertise
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    Latest Episodes:
    Jesse Michels — American Alchemy (Infinite Loops Classics) Aug 06, 2026
    Show notes Hi everyone, Jim here. We're taking a short pause on new episodes through the end of August. In the meantime, we're digging out some of our favorite conversations from the archive. This one is from February 2023, so a few of the references have aged since (mine included), but the ideas have only gotten better. Enjoy this one with the wonderfully heretical Jesse Michels.

    Jesse Michels is an investor at Thiel Capital and the creator and host of 'American Alchemy', a Youtube channel dedicated to highlighting the most heretical thinkers and ideas of our time.

    He joins the show to discuss the transmission theory of consciousness, whether mushrooms are aliens, the reawakening of the Boomers and MUCH more!

    Important Links:

    - American Alchemy - https://www.youtube.com/@JesseMichels/about - Jesse's Twitter - https://twitter.com/alchemyamerican

    Books Mentioned:

    - The Half-Life of Facts: Why Everything We Know Has an Expiration Date; by Samuel Arbesman - The User Illusion: Cutting Consciousness Down to Size; by Tor Norretranders - Gödel, Escher, Bach: an Eternal Golden Braid; by Douglas Hofstadter - The Beginning of Infinity: Explanations That Transform the World; by David Deutsch - The Immortality Key : The Secret History of the Religion with No Name; by Brian C. Muraresku - The New Inquisition: Irrational Rationalism and the Citadel of Science; by Robert Anton Wilson - How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression and Transcendence; by Michael Pollan - Chaos: Charles Manson, the CIA, and the Secret History of the Sixties; by Tom O'Neill - Weird Scenes Inside the Canyon: Laurel Canyon, Covert Ops & the Dark Heart of the Hippie Dream; by David McGowan - Prometheus Rising; by Robert Anton Wilson - Quantum Psychology: How Brain Software Programs You & Your World; by Robert Anton Wilson - The Cosmic Trigger trilogy; by Robert Anton Wilson - Communion: A True Story; by Whitley Strieber


    Nat Eliason - The High School That Guarantees You'll Make $1 Million (Ep. 325) Jul 30, 2026
    Show notes

    Nat Eliason joins guest host Jimmy Soni to discuss Founders School, a new high school for entrepreneurs that guarantees students will generate $1 million in gross profit by graduation or get their tuition refunded. We explore how AI is changing what teenagers can build, why traditional entrepreneurship education falls short, and what happens when we take young people seriously. Important Links: Learn more about Founders School: https://founders.school/ Read more from Nat here: https://www.nateliason.com/


    Philip Howard - How to Bring Common Sense Back to America (Ep. 324) Jul 23, 2026
    Show notes

    Philip Howard joins Infinite Loops to explain how America's legal and regulatory system became too complicated to function effectively—and how we can rebuild it around judgment, accountability, and human agency.

    We discuss why government has become unmanageable, how thousand-page rulebooks discourage individual judgment, why infrastructure projects can take decades to approve, and how public institutions end up costing more while delivering less.


    Sangeet Choudary - How AI Will Reshape the Knowledge Economy (Ep. 323) Jul 16, 2026
    Show notes

    Sangeet Choudary joins Infinite Loops to explain why AI's greatest impact will not be automating today's work, but rebuilding the structures beneath it. They discuss AI-native companies, the future of knowledge work, the American and Chinese AI models, creative "exhaust," changing career paths, and how to compete when the rules of the game are constantly being rewritten. Important Links: Learn more about Sangeet and Reshuffle here: https://reshufflebook.com/ Read more about the Platform Revolution here: https://platformthinkinglabs.com/materials/platform-revolution


    Jameson Olsen - Becoming the Main Character (Ep. 322) Jul 09, 2026
    Show notes

    What if the great stories were more than just stories?

    Jameson Olsen, host of Becoming the Main Character, joins guest host Liberty to explore fiction as a kind of operating system for life — a way to study agency, ambition, empathy, failure, courage, and change without having to live every consequence yourself. Through Hamlet, Frankenstein, Sherlock Holmes, Lord of the Rings, training montages, NPCs, and the Hero's Journey, they discuss what it means to stop drifting through life and start holding the pen of your own story. Important Links: Listen to Jameson's podcast here: https://www.becomingmain.com/


    David Gelles - The Stories that Shape Business (Ep. 321) Jul 02, 2026
    Show notes

    David Gelles joins guest host Jimmy Soni to discuss his career covering business for The New York Times. They talk about his books - Mindful Work, The Man Who Broke Capitalism, and Dirtbag Billionaire - and the reporting behind major stories on Bernie Madoff, Jack Welch, Boeing's 737 Max crashes, and Patagonia's Yvon Chouinard.

    David explains how he broke a front-page story five weeks into journalism school, how he convinced Bernie Madoff to grant him a prison interview, and his process for writing books while working full-time. They also discuss raising kids who read for hours every day and why meditation helps him stay sane.


    Gretchen Rubin - How Curiosity Becomes a Calling (Ep. 320) Jun 25, 2026
    Show notes

    Gretchen Rubin joins guest host and Infinite Books CEO Jimmy Soni to discuss her journey from Supreme Court clerk to bestselling author, the creative obsessions that shaped her career, and the daily habits that fuel her work. They cover her transition from law to writing Power Money Fame Sex, why she often ends up writing the book before the proposal, the art of editing until the final hour (even during pass pages), her 5:30 AM writing routine, and why "know thyself" remains the foundation of all her books - from 40 Ways to Look at Winston Churchill to Life in Five Senses.

    Important Links:

    Learn more about Gretchen: https://gretchenrubin.com/

    Read more of Gretchen's work: https://gretchenrubin.com/books

    Listen to Gretchen's podcast: https://gretchenrubin.com/happier/


    Ben Cohen - The Hidden Art of Making Things Better (Ep. 319) Jun 18, 2026
    Show notes

    Wall Street Journal columnist Ben Cohen joins guest host Jimmy Soni, CEO of Infinite Books, to explore the hidden art of making things better. They explore the hot hand phenomenon in basketball, why Moneyball shaped a generation of journalists, the peanut butter and jelly crisis in the Warriors locker room, why ASML is the most important company you've never heard of, the strange story of Driscoll's tastiest berries, and the troubled development of The Princess Bride. Important Links: Learn more about Ben here: https://www.wsj.com/news/author/ben-cohen Read The Science of Success: https://www.wsj.com/news/types/science-of-success Read The Hot Hand: https://www.harpercollins.com/pages/hothand


    Revan Lazarus - How AI is Rebuilding the Creator Economy (Ep. 318) Jun 11, 2026
    Show notes

    AI is no longer just a tool creators use to make content faster. It is beginning to reshape the entire creator economy.

    Revan Lazarus is the founder of Jamie, an AI platform for podcast networks and digital sales teams.

    He joins Infinite Loops, guest-hosted by Nick Tawil, to discuss how AI is changing podcasting, media sales, audience analytics, creator monetization, brand deals, and the future of content itself. Important Links: Learn more about Jamie AI: https://www.jamie-ai.com/


    Brian London, Marisa Adler & Eric Stubin - The Hidden Economy of Recycled Clothes (Ep. 317) Jun 04, 2026
    Show notes

    What actually happens after you donate a bag of clothes? Most people assume it gets sold locally to someone in need, but the reality is much bigger, stranger, and more global.

    In this episode of Infinite Loops, hosted by OSV's Nick Tawil, we sit down for a roundtable on the hidden global economy of secondhand textiles with Brian London, Marisa Adler, and Eric Stubin, all experts in the field. We discuss how the industry works, why fast fashion has made the problem harder, why 70% of the world uses secondhand clothing, what AI can and can't solve, and why turning an old shirt into a new shirt is still much harder than it sounds.

    Substack: https://newsletter.osv.llc/


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