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Infinite Loops

Podcast Infinite Loops
Jim O'Shaughnessy
In a rapidly changing world, it's too easy to get trapped by the existing models. New problems are met with old solutions, leading to infinite loops of inaction...

Available Episodes

5 of 252
  • Sahil Bloom — A Multitude of Wealth (EP.251)
    Sahil Bloom, a prolific creator, founder and investor, has mastered the art of translating complex ideas about wealth and success into wisdom that resonates with millions. His newsletter, The Curiosity Chronicle, grew from just 100 readers to over 800,000 subscribers in three years - a testament to his ability to cut through the noise with clarity and insight. His upcoming book, "The 5 Types of Wealth," challenges our conventional understanding of what it means to be truly wealthy, arguing that financial success is just one piece of a much larger puzzle. Here's what makes Sahil fascinating - he's built his empire not through traditional paths (he left his high paying private equity job), but by following his curiosity and sharing what he learns along the way. Today, we'll explore the frameworks that have helped him impact millions, why traditional definitions of success might be holding us back, and how Sahil’s relationship with time reshaped the way he thinks about wealth, wisdom, and the pursuit of a meaningful life. 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: Sahil’s Website Sahil’s Twitter Sahil’s Blog Show Notes: The Ripple Effect of spreading good ideas Sahil’s Origin Story The Finite Impermanence of Time Would you trade lives with Warren Buffett? The Loneliness Epidemic The Paradox of setting Big Goals and needing Small Steps to get there Why waking up at 5am can rewire your brain Why do people chase the wrong things? Jim and Sahil’s Memento Mori Factoring in the 5 Types of Wealth when making a decision What makes A Wonderful Life? Money As a Byproduct of Pursuing Purpose Sahil’s Message As World Emperor Books Mentioned: Zorba the Greek; by Nikos Kazantzakis Adventures of a Bystander; by Peter Drucker The Anxious Generation; by Jonathan Haidt Tao Te Ching; by Lao Tzu Collective Illusions; by Todd Rose The Psychology of Money; by Morgan Housel
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  • Seth Stephens-Davidowitz — Who Makes the NBA? (EP.250)
    Seth Stephens-Davidowitz, a data scientist and bestselling author, is known for his brilliant use of data to upend conventional wisdom - often with humorous, surprising, and occasionally shocking results. His latest book, Who Makes the NBA, uses data to interrogate some of basketball’s biggest questions, consistently yielding unexpected insights. Here’s the kicker - he wrote the entire book in just 30 days after discovering Code Interpreter. Unsurprisingly for a former quant, I had a blast chatting to Seth. Topics discussed include why so many NBA players are called Chris, whether basketball is due for a Moneyball moment, and why so many of us misunderstand the rags-to-riches story. 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: Seth’s Website Twitter Show Notes: Author, data scientist… comedian? Using Code Interpreter to write a book in 30 days The trait that makes it incredibly easy to become an NBA player Why the best NBA player in history isn’t who you think it is Is basketball due a Moneyball moment? Why are so many NBA players named Chris? What people get wrong about the rags-to-riches story The hidden magic of data storytelling Finding your audience The danger of glamour Keep it simple, stupid Why the standard interview sucks Doppelgangers & the power of A/B testing The overdue revolution in health data Why Google should be worried Stated vs revealed preferences The power of enormous data sets Seth as World Emperor Books Mentioned: Who Makes the NBA?: Data-Driven Answers to Basketball's Biggest Questions; by Seth Stephens-Davidowitz Don't Trust Your Gut: Using Data to Get What You Really Want in Life; by Seth Stephens-Davidowitz Everybody Lies: Big Data, New Data, and What the Internet Can Tell Us About Who We Really Are; by Seth Stephens-Davidowitz What Works on Wall Street: A Guide to the Best-Performing Investment Strategies of All Time; by Jim O’Shaughnessy
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  • Julian Gough — The Egg and The Rock (EP.249)
    Julian Gough sums up his career as follows: “I just sit in my room and write.” Well, I think being an acclaimed children’s author, novelist, stage playwright, poet and top-ten Irish musician is a little more impressive than he’s letting on… Oh, and I didn’t even mention that he wrote the ending to the computer game Minecraft! His current project, The Egg and The Rock, puts all of this to shame. This book, which Julian is writing in public on Substack, seeks to do no less than redescribe the universe, arguing that is not some random, dead, purposeless sack of chemicals, but instead a living, evolving organism. Julian joins me to discuss why the arc of human evolution bends towards man-made black holes, the hidden catastrophe at the heart of materialist science, the strange life of subterranean ice aliens, and MUCH more! This was such an interesting conversation - I can’t wait for you to hear it. 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: Julian’s Website The Egg and The Rock Julian’s Twitter Show Notes: “I just sit in my room and write” Why write a book in public? Materialism & science’s hidden catastrophe “The scientific method is in conflict with human nature” The faulty assumption at the heart of cosmology Big bangs, supermassive black holes & Darwinian evolution: A ~30 minute masterclass in cosmological natural selection “I'm predicting very, very large amounts of life in this universe” The strange life of subterranean ice aliens Could we spot man-made black holes? Bringing consciousness into physics Pulling back the curtain Julian as World Emperor MORE! Books & Articles Mentioned: The New Inquisition: Irrational Rationalism and the Citadel of Science; by Robert Anton Wilson Against Method: Outline of an Anarchistic Theory of Knowledge; by Paul Feyerabend What the Tortoise Said to Achilles; by Lewis Carroll The Life of the Cosmos; by Lee Smolin What Is Life? The Physical Aspect of the Living Cell; by Erwin Schrödinger Isis Unveiled: A Master-Key to the Mysteries of Ancient and Modern Science and Theology; by Helena Petrovna Blavatsky The Bhagavad Gita Did the Universe evolve?; by Lee Smolin The Great Filter - Are We Almost Past It?; by Robin Hanson
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  • Ben Reinhardt — Speculative Technologies (EP.248)
    Ben Reinhardt is the founder of Speculative Technologies “a nonprofit industrial research lab that’s working to unlock a wonderful, abundant future through technologies that don’t have a home in other institutions.” He has previously worked at NASA and Bay Area startups/VC firms, founded a startup building robotics for eldercare, and helped entrepreneurs start companies in Singapore. Oh, and he has a Ph.D. in space robotics from Cornell University and is one of the few people with a B.Sc. in history! Ben, who brings his expertise in emerging technologies to the OSV advisory council, joins the show to discuss why tech people don’t do philanthropy, when to trust a credential, why there aren’t more government moonshot programs, why academia is beholden to the new, and MUCH more! 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: Speculative Technologies Ben’s Twitter Ben’s LinkedIn Show Notes: Speculative Technologies: the four-stage roadmap How early VC funding can affect incentives From ‘eureka!’ to getting it out into the world Market failure & institutional consolidation Where are the moonshot programs? The skills needed to run a research program Why tech people don’t do philanthropy Turning philanthropy into a status game The hidden importance of materials & manufacturing When to trust a credential Agency & American culture Lean ideas vs. fat ideas Why academia is beholden to novelty Ben as World Emperor MORE! Books Mentioned: What Works on Wall Street, Fourth Edition: The Classic Guide to the Best-Performing Investment Strategies of All Time; by Jim O’Shaughnessy The Beginning of Infinity: Explanations that Transform the World; by David Deutsch The Road; by Cormac McCarthy The Hypomanic Edge: The Link Between (A Little) Craziness and (A Lot of) Success in America; by John D. Gartner The Coffee Can portfolio; by Robert G. Kirby
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  • Jay Reno — Making A Point (EP.247)
    My guest on Infinite Loops this week knew he wanted to be an entrepreneur from the time he was buying and selling things on eBay. Jay Reno claims he didn’t know what the word ‘arbitrage’ meant back then, but if you tug on the colourful threads of his career, you’d reveal the kind of tenacity and resourcefulness that allows special founders like him to repeatedly find value in places that have long been deserted by everybody else. If you listen in on today’s episode, it will become apparent why O’Shaughnessy Ventures invested in Jay and his current venture. Jay is the CEO and Founder of Pointhound, which helps people find amazing deals on flights and travel using their credit card points and miles. He’s also a partner at 645 ventures. Among other fun pursuits, he’s spent the last ten years building all sorts of cool things; like a same-day grocery delivery service, a craft coffee company, a restaurant and bar reservation app, and a furniture rental service for city dwellers. We spent our conversation talking about his advice for first-time founders; his learnings from building Pointhound; the whimsical world of credit card point programmes; his thoughts on consumer psychology; and much more! 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: Jay’s Twitter Jay’s LinkedIn 645 Ventures Pointhound HQ Show Notes: How To Bring Your Idea To Life The Virtues of the Y-Combinator Model Picking the Right Investor Pointhound & The Points Game On Consumer Psychology and Trying New Things Removing the Invisible Barrier Product Cycles and User Feedback Slow Down to Speed Up The Common Pitfalls in Building Consumer Products The Credit Card Prestige Factor The Cashback Conundrum The Future of Pointhound Jay, The Emperor of The World Books & Articles Mentioned: My Inventions: The Autobiography of Nikola Tesla; by Nikola Tesla Mistakes were Made. (And, Yes, by Me.); by Jim O’Shaughnessy
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About Infinite Loops

In a rapidly changing world, it's too easy to get trapped by the existing models. New problems are met with old solutions, leading to infinite loops of inaction. We're here to change that. By exploring ideas ranging from the Tao Te Ching to cutting-edge advances in AI, we will arm you with the tools & fresh perspectives required to upgrade your HumanOS and thrive in our messy, probabilistic world. Infinite Loops is part of Jim’s new company, O'Shaughnessy Ventures. For in-depth syntheses of our guests' ideas, as well as for additional ideas that make you go Hmm that’s interesting!, subscribe to our Substack at https://infiniteloops.substack.com. Powered by O’Shaughnessy Ventures.
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