

Infinite Loops
Jim O'Shaughnessy
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!"
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!"
Episodes
Mentioned books

Apr 27, 2023 • 1h 24min
Jimmy Soni & Liberty RPF — Unleashing the Future of Publishing (EP.157)
Friend-of-the-show (and new O'Shaughnessy Ventures team member) Liberty RPF joins Jim and fellow friend-of-the-show Jimmy Soni to discuss the current state of the publishing industry and the new opportunities emerging for current and aspiring authors. Important Links: Jimmy's Website Jimmy's Twitter Liberty's Newsletter Liberty's Twitter 10 Reasons Why I'm Publishing My Next Book on Substack Kurt Vonnegut: Unstuck in Time Show Notes: How has the publishing industry changed? Reinventing the audiobook The living book Towards new book pricing models Why the traditional publishing industry is becoming unsustainable The tragedy of unwritten books A rejection from a traditional publisher is meaningless What do traditional publishers do well? The importance being invested in the success of a product Leveraging AI & other tools in the writing process Why the publishing industry is successful Increasing the power of individual creators Change, prestige & disruption Playing the right kind of status games Aligning quality with meritocracy MUCH more! Books Mentioned: The Founders; by Jimmy Soni A Mind at Play; by Jimmy Soni & Rob Goodman Rome's Last Citizen: The Life and Legacy of Cato, Mortal Enemy of Caesar; by Jimmy Soni & Rob Goodman What Works on Wall Street; by Jim O'Shaughnessy Invest Like The Best; by Jim O'Shaughnessy Can't Hurt Me: Master Your Mind and Defy the Odds; by David Goggins The Psychology of Money; by Morgan Housel The 4-Hour Work Week: Escape the 9-5, Live Anywhere and Join the New Rich; by Tim Feriss Harry Potter; by J. K. Rowling Reality Hunger; by David Shields $100M Offers: How To Make Offers So Good People Feel Stupid Saying No; by Alex Hormozi The Status Game: On Social Position and How We Use It; by Will Storr

6 snips
Apr 20, 2023 • 48min
Alex Danco — On Self-Delusion, Sancho Panza, Safe Words & Seinfeld (EP.156)
Alex Danco returns for his seventh (yes, SEVENTH) appearance on Infinite Loops to discuss, as usual, pretty much everything other than the topics we had prepared in advance. This week, we discuss: The two types of lawyers, what Alex learned from reading Don Quixote, Elon the Reply Guy, the psychology of Seinfeld, the best Wall Street Movies, and much more. Important Links: Twitter: https://twitter.com/Alex_Danco Website: https://alexdanco.com/ Newsletter: https://danco.substack.com/ Show Notes: The two kinds of lawyers Medicine, placebo, Don Quixote & theatre Heroes, villains & main characters Elon the Reply Guy Safe words, scams & narrative collapse Self-deception is multiplayer The psychology of Seinfeld To what extent are great innovations already baked into the systems? Margin Call: The two schools of thought The best Wall Street movies MUCH more! Books Mentioned: The Theory And Practice Of Gamesmanship Or The Art Of Winning Games Without Actually Cheating; by Stephen Potter Don Quixote; by Miguel de Cervantes The Fifth Science; by Exurb1a The Status Game: On Human Life and How to Play It; by Will Storr The Lucifer Principle: A Scientific Expedition into the Forces of History; by Howard K. Bloom Games People Play: The Psychology of Human Relationships; by Eric Berne Mendel's Dwarf; by Simon Mawer The Big Short: Inside the Doomsday Machine; by Michael Lewis The Bonfire of the Vanities; by Tom Wolfe The Smartest Guys in the Room: The Amazing Rise and Scandalous Fall of Enron; by Peter Elkind & Bethany McLean

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

41 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


