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Infinite Loops

Infinite Loops

Written by: Jim O'Shaughnessy
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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!" Economics Leadership Management & Leadership
Episodes
  • Jason Buck - Faith, Failure, and Finance (Ep. 316)
    May 28 2026

    Jason Buck, founder and CIO of Mutiny Funds, joins Infinite Loops to tell the painful and darkly funny story of how the 2007–2008 crash destroyed his real estate business, wiped out his paper wealth, and taught him one of the hardest lessons in markets: being right is not the same thing as making money.

    Jason explains how he went from real estate developer to volatility trader and eventually built his philosophy around survival, resilience, and the "Cockroach Portfolio." He and Jim explore why true diversification always feels uncomfortable, why human behavior is the most persistent source of market mistakes, and why investing beliefs often resemble religion.

    Important Links:

    Learn more about Mutiny Fund here: https://mutinyfund.com/

    Listen to more from Jason here: https://mutinyfund.com/podcasts

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    2 hrs and 2 mins
  • Chelsea Follett - Why Progress Is the Exception, Not the Rule (Ep. 315)
    May 21 2026

    Chelsea Follett joins Infinite Loops to explain why the "good old days" were far darker than most people imagine — and why progress should never be taken for granted.

    Chelsea is the managing editor of Human Progress and author of Centers of Progress and the forthcoming The Grim Old Days. We discuss why humans are so drawn to nostalgia, what life was really like in the preindustrial past, why doomsday predictions keep failing, and how freedom, innovation, and open inquiry helped create the modern world.

    Important Links:

    Learn More about Chelsea's upcoming book here: https://www.simonandschuster.com/books/The-Grim-Old-Days

    Read more of Chelsea's Human Progress work here: https://humanprogress.org/authors/chelsea-follett

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    1 hr and 30 mins
  • Mykhailo Marynenko - AI Tools That Give Creators More Control (Ep. 314)
    May 15 2026

    Mykhailo Marynenko joins Infinite Loops for for a fascinating conversation about the future of AI, creative tools, privacy, and data ownership.

    From growing up in his father's phone repair shop in Ukraine to building experimental AI systems today, Mykhailo has spent his life taking things apart, figuring out how they work, and rebuilding them in unexpected ways.

    We explore how AI can help creators without replacing them, why privacy and data ownership matter, and what it means to design tools that give people more control over complex information.

    Important Links

    More about Misha: https://linktr.ee/0x77dev?utm_medium=mykhailo.link

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    1 hr and 44 mins
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