
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!"
Latest episodes

38 snips
Apr 13, 2023 • 1h 21min
Gurwinder Bhogal — Certainty is the Death of Thought (EP.155)
Gurwinder Bhogal is a writer and programmer who writes about the myriad ways in which technology and psychology conspire to fool us and how we can withstand the covert assault on our senses. Gurwinder is known for his epic Twitter ‘Megathreads’ which set out a series of powerful concepts for understanding the world. He joins the show to discuss our tendency to narrativize information, how to overcome the bandwidth tax, why Wikipedia is the world’s largest source of misinformation, and MUCH more! Important Links: Megathread: Feb 7, 2020 (53,000 likes) Megathread: Feb 11, 2022 (62,000 likes) Megathread: March 18, 2023 (most recent) Gurwinder's Substack Gurwinder's Twitter The Toxoplasma of Rage Show Notes: Megathreads & the Woozle effect AI, the Encyclopedia Disinformatica, and cultivating a garden of Mithridates Capturing the nuance between dishonesty and lying The Toxoplasma of Rage Overcoming the bandwidth tax Brandishing the golden hammer; why we can’t comprehend large numbers Tribalism & intersubjectivity The purity spiral Are we facing a lost generation? We are programmed to like complex explanations Narrativizing information “Certainty is the death of thought” Climbing the thinking ladder MUCH more! Books Mentioned: The Fifth Science; by Exurb1a Talking to Strangers; by Malcolm Gladwell Tao Te Ching; by Lao Tzu What's Our Problem?: A Self-Help Book for Societies; by Tim Urban

9 snips
Apr 6, 2023 • 1h 17min
Ed Latimore — The Difference Between Being Liked and Being Respected (EP.154)
This week, we’re delighted to welcome Ed Latimore back for his second Infinite Loops appearance. Ed is a best-selling author, former professional heavyweight boxer, competitive chess player, Physics graduate, father, and husband. He joins us to discuss stoicism, progress & pain, demonstrating authenticity, being liked vs. being respected, and a whole lot more. Important Links: Ed’s Twitter Ed’s website Ed’s Substack Ed’s first Infinite Loops appearance Show Notes: New child; new house; new book How Ed’s new book has developed Humor and progress Understanding addiction Being liked vs being respected “Stoicism found me” Is progress possible without pain? “Humans are very bad at the future” Demonstrating authenticity Being cast as a father figure What’s next for Ed Ed’s three step process for self-improvement “I don't think any situation has ever gotten worse because someone has good manners.” Books Mentioned: The Founders: The Story of PayPal and the Entrepreneurs who Shaped Silicon Valley; by Jimmy Soni The Art of Learning: An Inner Journey to Optimal Performance; by Josh Waitzkin Can't Hurt Me: Master Your Mind and Defy the Odds; by David Goggins The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life; by Mark Manson

Mar 30, 2023 • 1h 27min
Edward Rooster — I Did My Best. I Gave My All. I Was Here. (EP.153)
Edward Rooster is one of our favourite writers. His themes include the future, mythology, time and history. He has written two books, Box of Stars and Harvest, and he is currently working on a third. Edward joins the show to discuss embracing uncertainty, avoiding becoming Icarus, unsticking yourself from time, and MUCH more! Important Links: Edward’s Mirror Edward’s Substack Edward’s Typeshare Edward’s Twitter The Days Dad Started Over Leaving Eternity’s Parking Lot You Do Not Have to Be Perfect Looking Back from the Future Show Notes: The Days Dad Started Over: Why Edward started writing Edward’s book writing process Unsticking yourself from time Sources of storytelling inspiration Embracing uncertainty Avoiding the content trap The ‘create you own adventure’ approach to writing [Finding inspiration in music] Storytelling & common knowledge Writing as found art Not as much matters as we think it does How can we avoid becoming Icarus? Editing; Editors The opportunities of generative AI MUCH more! Books Mentioned: Stray Reflections; by Jawad Mian Box of Stars; by Edward Rooster Harvest; by Edward Rooster Retrieve; by Edward Rooster What Works on Wall Street: A Guide to the Best-Performing Investment Strategies of All Time; by Jim O’Shaughnessy Cloud Atlas; by David Mitchell The Great Gatsby; by F. Scott Fitzgerald American Gods; by Neil Gaiman Reality Hunger; by David Shields Zen and the Art of Motorcycle Maintenance; by Robert Pirsig Looking Backward; by Edward Bellamy

115 snips
Mar 23, 2023 • 1h 44min
Venkatesh Rao — The Art of Gig (EP.152)
Venkatesh Rao is a writer, consultant, and author. He has been writing about indie consulting for years and has recently published The Art of Gig, Volumes 1 & 2, which together take an in-depth look at the gig economy. Venkatesh joins the show to discuss tragic luck, becoming slightly nonsensical, the advantages of mediocrity, and a whole lot more! Important Links: Venkatesh's Website Venkatesh's Blog Venkatesh's Substack Venkatesh's Twitter The Art of Gig The Art of Gig: our synthesis The Gervais Principle Show Notes: Origins of The Art of Gig Paycheck People Learning how to take risks Is there a risk-taking gene? The case for fixed-point futurism Finding meaning Personality types, narrative, and becoming a courageous thinker Don’t get tragically lucky Generational agency Sparring, pressure and meaning-making Be slightly nonsensical Teaching others to appreciate randomness Towards infinite games; be mediocre Understanding divergentism MUCH more! Books Mentioned: The Art of Gig: Volumes 1 & 2; by Venkatesh Rao The 4-Hour Work Week: Escape the 9-5, Live Anywhere and Join the New Rich; by Tim Feriss Free Agent Nation: The Future of Working for Yourself; by Daniel H. Pink The Pathless Path: Imagining a New Story For Work and Life; by Paul Millerd Tempo: timing, tactics and strategy in narrative-driven decision-making; by Venkatesh Rao The Redemptive Self: Stories Americans Live By; by Dan P. McAdams Finite and Infinite Games: A Vision of Life As Play and Possibility; by James Carse Getting Things Done: The Art of Stress-free Productivity; by David Allen

Mar 16, 2023 • 1h 27min
Ananyo Bhattacharya — John von Neumann: The Man from the Future (EP.151)
Ananyo Bhattacharya is the author of The Man from the Future: The Visionary Life of John von Neumann, a brilliant biography of one of the most prolific and influential scientists to have ever lived. He joins the show to discuss von Neumann’s contributions to quantum physics, game theory, the Manhattan Project, and much more! Important Links: Ananyo’s Twitter The Man from the Future Show Notes: How did John von Neumann even exist? Would von Neumann’s discoveries have happened without him? The Martians of Hungary The migrant mentality Innovation in the face of extinction Science, genius & the herd mentality Von Neumann’s contribution to quantum physics Game theory, Minimax and zero-sum games von Neumann: quant in the streets; romantic in the sheets The eccentricity of brilliance Von Neumann and the Manhattan Project The godfather of the open-source movement Von Neumann as a project manager How writing the book changed Ananyo’s understanding of von Neumann Ananyo’s next projects MUCH more! Books Mentioned: The Man from the Future: The Visionary Life of John von Neumann; **by **Ananyo Bhattacharya The Beginning of Infinity: Explanations That Transform the World; by David Deutsch The Genius of the Beast: A Radical Re-Vision of Capitalism; by Howard Bloom Theory of Games and Economic Behaviour; by John von Neumann and Oskar Morgenstern

Mar 9, 2023 • 51min
Michael Breitenbach — On Crypto, AI & Cynicism (EP.150)
Michael Breitenbach is Senior Vice President within the Chief Investment Office at Bank of America Global Wealth and Investment Management, where he is responsible for leading development of quantitative infrastructure and machine learning models for evaluating both internally and externally covered investment offerings. He is also the man behind an extremely popular anonymous Twitter account that many of you will be familiar with (see if you can guess which one…) Michael joins the show to discuss the FTX fallout, the current state of the crypto industry, the rise of AI compliance, and MUCH more! Important Links: Michael’s LinkedIn Michael’s (personal) Twitter Show Notes: FTX: grift or systemic failure? The decline of old media AI compliance & regulation Crypto: use cases, privacy & regulation The end of privacy Dealing with new and better problems Scale vs anti-scale Cynicism can be a comparative advantage Against binary thinking Time binding & cultural evolution Consider taxation Books Mentioned: The Power Law: Venture Capital and the Art of Disruption; by Sebastian Mallaby Time-Binding: The General Theory; by Alfred Korzybski

33 snips
Mar 2, 2023 • 1h 34min
Visakan Veerasamy - On Creativity, Introspection & Being a Good Reply Guy (EP.149)
Visakan Veerasamy is a prolific thinker, writer & creator. As well as being the author of the books ‘Introspect’ and ‘Friendly Ambitious Nerd’, he is known for weaving huge, interconnected Twitter threads and for his mission to build “the greatest social graph of friendly, ambitious nerds that the world has ever seen.” Important Links: Visa's Website Visa's Twitter Visa's Youtube Show Notes: The origins of Friendly Ambitious Nerd “The most heroic thing you can do is not hate yourself” Confronting the minotaur Introspection & Maslow’s hierarchy of needs Overriding human OS Humor is the cure How to demonstrate the power of humor Dealing with judgment & criticism Responding to requests for help Enforcing a no-assholes rule "Focus your time and energy on what you want to see more of” “School is bullshit” Question defaults & screw around MUCH more! Books Mentioned: Friendly Ambitious Nerd; by Visakan Veerasamy Introspect; by Visakan Veerasamy The Science of Storytelling; by Will Storr The Status Game: On Social Position and How We Use It; by Will Storr The Hero with a Thousand Faces; by Joseph Campbell Shantaram; by Gregory David Roberts The Art of War; by Sun Tzu The Tao Te Ching; by Laozi The Lord of the Rings; by J. R. R. Tolkien

37 snips
Feb 23, 2023 • 1h 46min
David Senra & Liberty RPF — Unleashing the Scenius (EP.148)
Friends-of-the-show David Senra & Liberty RPF return for a characteristically wide-ranging conversation. Enjoy! Important Links Founders Podcast Founders on Colossus David’s Twitter Liberty’s Substack Liberty’s Twitter David Bowie Predicts the Impact of the Internet on Newsnight Show Notes: David’s lunch with Sam Zell Optimizing for freedom Information can build a fortune Persist, persist, persist Burning the ships Customising education Where are the Teddy Roosevelt’s of today? Embracing our evangelical side “Art is not what you see, but what you make others see” Fighting fear of technological development Is anything truly ‘new’? "Properly understood technology is just a better way to do something” Towards positive sum games How to cultivate voluntary engagement Unleashing the scenius Finding better explanations Risk-taking and the origins of the USA The explore and create framework Read biographies MUCH more! Books Mentioned: Am I Being Too Subtle?: Straight Talk From a Business Rebel; by Sam Zell The River of Doubt: Theodore Roosevelt's Darkest Journey; by Candice Millard Hero of the Empire: The Boer War, a Daring Escape, and the Making of Winston Churchill; by Candice Millard Cinema Speculation; by Quentin Tarantino Christopher Nolan: The Iconic Filmmaker and His Work; by Ian Nathan The WEIRDest People in the World; by Joseph Henrich Zero to One: Notes on Startups, or How to Build the Future; by Peter Thiel The Autobiography of Andrew Carnegie; by Andrew Carnegie All I Want To Know Is Where I'm Going To Die So I'll Never Go There: Buffett & Munger - A Study in Simplicity and Uncommon, Common Sense; by Peter Bevelin The Almanack of Naval Ravikant: A Guide to Wealth and Happiness; by Eric Jorgenson Enzo Ferrari 2018: Power, Politics and the Making of an Automobile Empire; by Luca Dal Monte The Beginning of Infinity: Explanations That Transform the World; by David Deutsch One Summer: America, 1927; by Bill Bryson

27 snips
Feb 16, 2023 • 1h 36min
Dwarkesh Patel — Podcasting, Talent & Innovation (EP.147)
Dwarkesh Patel is the host of The Lunar Society podcast, where he interviews scientists, historians, economists, intellectuals, & founders about their ideas. He also writes about tech, progress, talent, science, and the long-term over at his Substack. Dwarkesh has been described as “one of the best young podcasters alive”, and his Substack has been praised by the likes of Jeff Bezos, Paul Graham and Tyler Cowen. Important Links: The Lunar Society Dwarkesh’ Twitter The Mystery of the Miracle Year Popularizers are intellectual market makers Scouting talent as buying options Show Notes: How to become a better podcaster The importance of curiosity Disagreement & problem solving “Computer programs are written by humans for other humans to read, and only incidentally for computers to execute” The difference between podcasting & essay writing Investing in public and private companies; human OS Premeditation & decision-making The mystery of the miracle year How much innovation is baked into the cake? How to cultivate young talent AI & education The importance of intellectual market makers Scouting talent as buying options Interviewing Sam Bankman-Fried Effective altruism & virtue signalling If you do everything, you will win Books Mentioned: The Years of Lyndon Johnson; by Robert Caro What Works on Wall Street: A Guide to the Best-Performing Investment Strategies of All Time; by Jim O’Shaughnessy Little Soldiers: An American Boy, a Chinese School, and the Global Race to Achieve; by Lenora Chu Outliers: The Story of Success; by Malcolm Gladwell One Summer: America, 1927; by Bill Bryson The Lessons of History; by Will & Ariel Durant The Story of Civilization; by Will & Ariel Durant Fallen Leaves: Last Words on Life, Love, War, and God; by Will Durant

17 snips
Feb 9, 2023 • 56min
David Ha — AI & Evolution: Learning to do More with Less (EP.146)
David Ha is the Head of Strategy at Stability AI, and one of the top minds working in AI today. He previously worked as a research scientist in the Brain team at Google. David is particularly interested in evolution and complex systems, and his research explores how intelligence may emerge from limited resource constraints. He joins the show to discuss the advantages of open-source models, modelling AI as an emergent system, why large language models are bad at maths and MUCH more! Important Links: David’s website David’s Twitter Teaching Machines to Draw (2017) Weight Agnostic Neural Networks (2019) Show Notes: Why David joined Stability AI The advantages of open-source models We cannot predict the inventions of tomorrow Making memes with generative AI The centaur approach to AI An introduction to large language models The relationship between complex systems and resource constraints Large language models are bad at maths Modelling AI as an emergent system Understanding different perspectives MUCH more! Books Mentioned: The Beginning of Infinity: Explanations That Transform the World; by David Deutsch Why Greatness Cannot Be Planned: The Myth of the Objective; by Kenneth Stanley and Joel Lehman