Big ideas, followed all the way down.
Infinite Loops favors patient, intellectually restless conversations over tidy lessons. Recent episodes move from ancient Greece and AI to creativity, founder delusion, self-deception, heroin addiction, and the uneasy machinery behind success.
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Infinite Loops is a long-form interview show organized around curiosity, ambition, and the strange mechanics of human judgment. It is not a neat advice program. The conversations roam. Recent episodes move from Aristotle’s idea of zeal to artificial intelligence, from Greek city-states and mesh networks to institutional drift, from founder delusion to the psychology of action. The show is especially interested in people who think across boundaries. Sam Arbesman talks about curiosity, wonder, walking, and the selection criteria for unusual minds. Johnathan Bi argues through founders, delusion, materialism, and the limits of introspection. Polina Pompliano looks at success by watching for the moment a public mask drops. Adam Mastroianni brings creativity, deviance, youth culture, and cultural convergence into the same frame. Arkady Kulik pushes on self-deception, responsibility, truth-seeking mechanisms, and contact with the market. Angus Fletcher treats story as part of the operating system of human intelligence, especially as AI reshapes the question of what humans do best. Jonathan Tepper’s episode turns more personal, using his book about childhood in Madrid’s San Blas neighborhood to explore addiction, family, memory, and moral formation. Infinite Loops works because it lets abstract ideas stay attached to concrete lives. A question about the future can lead backward to Plutarch, Gutenberg, Leonardo da Vinci, propaganda, quantum physics, grantmaking, or a walk through a city. The tone is warm but not soft. It can be playful, grave, skeptical, and openly fascinated within the same hour. Listeners looking for quick summaries may find it winding. Listeners who like to hear smart people test definitions, revise premises, and follow a thought past its first clean stopping point will find the sprawl useful. Its recurring subject is not simply success, technology, or culture. It is how people decide what is real, what matters, and what is worth doing.
Made for: For listeners who enjoy long, searching conversations about intelligence, ambition, history, technology, creativity, and human behavior. Best for people who prefer nuanced thinking to quick prescriptions.
What sets it apart: Infinite Loops connects self-improvement to philosophy, history, science, and lived experience without flattening the conversations into takeaways. Its strength is giving guests enough room to reveal how they think, not just what they believe.
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!"
Based on 6 episodes we listened to · September 2026
Jim O'Shaughnessy turns wide-ranging guest conversations into close examinations of ambition, belief, curiosity, and the institutions surrounding individual lives.
Infinite Loops gives Jim O'Shaughnessy room to follow a guest's governing idea until it reaches questions about how people live together. Todd Rose's rejection of standardized paths becomes a conversation about trust and social fear, while Alex Petkas connects ancient Greece,…
Ancient Greece, artisan cheese, and founder delusion all earn a page in your notebook.
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Short reviews from the PlayNext desk, based on the episodes we processed.
A classical look at the future, built from zeal, networks, and the long reach of history.
Jim and Alex Petkass use ancient Greece as a way to think through the future, moving from Aristotle's idea of zeal to heroic stories, rhetoric, and the warning that new inventions can seem able to do everything.
A thoughtful conversation that treats curiosity as a practice, not a slogan.
The episode covers a lot of ground without losing its center. It moves from the history of computing and the paths not taken into institutions, grantmaking, and the difference between being odd and doing something worth paying attention to.
A philosophical conversation about founders, blind spots, and the psychology that drives action.
This episode keeps returning to a blunt idea: some of the sharpest builders may also be the least self-aware, and part of their edge could come from blind spots they never quite face.
A grounded conversation about success, character, and the cost of ambition.
The episode works best when it treats success as something you can see in behavior, not branding. It keeps circling the gap between a polished public mask and the quieter habits, hesitations, and tradeoffs underneath it, and Hidden Genius gives that idea a clear frame through…
A memoir of faith, family, and addiction set against a childhood in Madrid's hardest-hit neighborhood.
Jonathan Tepper's story starts in San Blas, Madrid, where a Christian missionary family settled because the rent was cheap and the neighborhood had the highest rate of heroin use in Europe.
A cheese obsession becomes a loose, funny study of craft, lineage, and attention.
Adam Moskowitz and Jim O'Shaughnessy turn artisan cheese into more than a niche interest: it becomes a story about family business, camp nicknames, and a rapper turned cheese insider who sounds entirely at ease in the obsession.
A sharp, wide-ranging case against sameness that keeps returning to fit, fear, and the limits of the average.
Todd Rose and Jim O'Shaughnessy make a clear case against conformity. The standard path can become a trap, and the idea of an average person can hide more than it explains.
Ed Mylett interviews entrepreneurs, athletes, and leaders about the moments that changed everything.
Asian Efficiency's Tan Pham and Brooks Duncan on time management, habits, and AI tools.
Alex Petkas, host of Cost of Glory and co-founder of the Classical Society, uses Aristotle’s The Rhetoric to argue that zeal, or emulation, is a positive force for excellence while envy is destructive.
Sam returns for a loose, curious conversation that starts with rational optimism and the way pessimism can pass for seriousness.
Third time, and still not tidy.
Polina Pompliano starts with the mask.
This episode explores the decline of creativity and cultural convergence, featuring an interview with experimental psychologist Adam Mastroianni about how reduced deviance in youth behavior might impact innovation and societal trends.
Jim O'Shaughnessy interviews Arkady Kulik about the psychology of self-deception, personal responsibility, and how truth-seeking mechanisms drive civilization-level progress.
This episode features a conversation with Angus Fletcher about human intelligence, the interplay between probability and possibility in the brain, and how stories serve as the operating system for human cognition.
The conversation starts in San Blas.
An interview with author Paul Millerd about his self-publishing journey and new book 'Good Work', discussing the challenges and beauty of independent publishing.
Jim O'Shaughnessy interviews Paki McCormick about his journey from a newsletter to a paid publication and fund, emphasizing the importance of writing and optimism in entrepreneurship.
Jim O'Shaughnessy interviews Jean-Marc Dacius about his role as an AI-first chief of staff and the impact of AI on reducing cognitive load.
John Wang shares his journey from being a Yale-trained lawyer to founding the Queens Night Market, discussing his career transition and the market's impact on New York City.
Cliff Asness discusses behavioral finance concepts like prospect theory and emotional responses to investment gains and losses in the context of surviving market bubbles.
Jim O'Shaughnessy interviews Thomas Pueyo about exponential growth, human intuition, and using data to understand the world.
Jim O'Shaughnessy interviews Annie Duke about her new book on decision-making, emphasizing that every decision involves a forecast and expected value.
Adam Moskowitz opens in artisan cheese myth mode.
Todd Rose pushes back against the standard path.
Jim O'Shaughnessy introduces the podcast's goal of helping listeners improve their thinking to avoid mental loops, then welcomes guest Alex Danko for his 10th appearance.
Jim O'Shaughnessy introduces a rerun episode featuring a conversation with an AI expert about technology and optimism.
This episode features a conversation with thinker Gurwinder Bhogal about modern survival strategies and resetting thinking patterns through a multidisciplinary lens.
Jim O'Shaughnessy interviews Nick Maggiuli about his new book, discussing investing, data, and behavioral finance.
Jim O'Shaughnessy introduces the podcast's goal of helping listeners reset their thinking to avoid infinite loops, then begins a conversation with Lawrence Yeo about trusting oneself.
Jim O'Shaughnessy introduces a break from new episodes to replay a classic conversation with author Will Storr about his book The Status Game.
Jim O'Shaughnessy introduces a classic episode from the Infinite Loops archive, emphasizing the show's goal to help listeners become better investors and more nuanced thinkers through multidisciplinary discussions.
Jim O'Shaughnessy interviews two OSB grantees who overcame great adversity and now help others, exploring themes of resilience and lifting others up.
Jim O'Shaughnessy introduces the podcast's goal of helping listeners improve their thinking and investing by exploring topics through multiple disciplines, then begins an interview with Dr.
Jim O'Shaughnessy interviews Todd Rose about collective illusions and individuality, aiming to help listeners think more nuancedly.
Jim O'Shaughnessy interviews Chuck Beams about his career in aerospace and technology, aiming to help listeners become better investors and thinkers.
Jim O'Shaughnessy interviews Natasha Joukovsky about her unique background spanning the art world and strategy consulting, her novel, and themes like recursion and status games.
This episode features an interview with Tiago Forte discussing his annual review methodology and productivity systems for organizing digital life and enhancing creative thinking.
Jim O'Shaughnessy discusses with Nir Eyal how to improve thinking and investing by avoiding infinite loops of thought.
Jim O'Shaughnessy introduces the podcast's mission to help listeners improve their thinking and investing by exploring topics through multiple lenses, then interviews Vizzy Andre about creative business models.
Jim O'Shaughnessy interviews Barry Ritholtz about investing, markets, and behavioral finance.
Jim O'Shaughnessy interviews Gabriel Kennedy about Robert Anton Wilson's life and ideas, aiming to help listeners break free from mental loops and think more nuancedly.
Jim O'Shaughnessy interviews Christine Bentz about her book on retirement, covering financial and psychological aspects of a happy retirement.