

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

May 30, 2023 • 1h 15min
Nat & Martha Sharpe — The Conflict between Agency & Community (EP.163)
 Nat & Martha Sharpe have been a creative team for over a decade. Nat was a film school graduate and Martha a storytelling enthusiast. They fell in love while filming a musical parody of "Beowulf" with their friends. After another comedy and two documentaries, they started having children. Focus shifted from art to survival. Together, they learned to code, got off food stamps, and traveled around America in an RV. Today, Nat and Martha homeschool their 5 kids and are eager to explore alternative education, expand their comfort zones, and—as always—make movies. Nat & Martha were the first recipients of an O'Shaughnessy Fellowship, which is a one-year program for ambitious people who want to build something great. Fellows receive a $100,000 grant and access to OSV's network of founders, investors and experts to support them in bringing their projects to life. Nat & Martha are using their fellowship grant to study and make documentary films of alternative childhood education schools. Important Links:  The O'Shaughnessy Fellowships Nat & Martha's Website  Nat & Martha's Twitter Nat & Martha's O'Shaughnessy Fellowship Application Video Nat & Martha's YouTube Channel OSV's investment in Synthesis School  Show Notes:  Nat & Martha's origin story How education is connected to community "Kids want to survive, they want to thrive, they want to learn" Education vs indoctrination Screen time isn't the problem & why unschooled children become entrepreneurs The magic blue bus Finding the others What caused the rise in helicopter parenting? The conflict between agency & community It can be hard to give people money Learning by doing; in-demand learning How can we monetize the best teachers in the world? How AI is going to transform education What's next? MUCH more!  Books Mentioned:  One Summer: America, 1927; by Bill Bryson  

43 snips
May 25, 2023 • 1h 12min
Jason Crawford — The Roots of Progress (EP.162)
 Jason Crawford is the founder & president of The Roots of Progress, a nonprofit dedicated to establishing a new philosophy of progress for the 21st century. Jason has written well over 100 essays on the history of technology and the philosophy of progress, and given numerous talks and interviews on the same. He joins the show to discuss whether humans deserve progress, how to make progress cool, the two types of optimism, and more! Important Links:  The Roots of Progress Jason's Website  Jason's Twitter Discourse on the Arts and Sciences; by Jean-Jacques Rousseau Triumph of the Nerds  Why I'm a proud solutionist  Show Notes:  Why do we need progress studies? Are humans conditioned to resist progress? Increasing the burden of safety What the Roots of Progress is seeking to achieve How can we make progress cool? Pessimism of the intellect; optimism of the will Do we deserve progress? Progress & politics Steelmanning the case against progress How can we defend against bad actors? Calibrating our approach to risk MUCH more!  Books Mentioned:  Frankenstein; by Mary Shelley Erewhon; by Samuel Butler Darwin Among The Machines; by Samuel Butler The Beginning of Infinity: Explanations That Transform the World; by David Deutsch The Ultimate Resource; by Julian L. Simon The Collapse of the Common Good: How America's Lawsuit Culture Undermines Our Freedom; by Philip K. Howard The Hitchhiker's Guide to the Galaxy; by Douglas Adams The Jungle; by Upton Sinclair One Summer: America, 1927; by Bill Bryson  

16 snips
May 18, 2023 • 1h 7min
David Pinsof — Everything is Bullshit (EP.161)
 David Pinsof is an evolutionary social scientist and a co-creator of the game Cards Against Humanity. He holds a PhD in Psychology from UCLA, where he studied the evolutionary origins of political bullshit, and has written a handful of academic papers, one of which has been cited 152 times and another of which was quoted in the New York Times. David is the author of the 'Everything Is Bullshit' Substack, which aims to poke holes in the stories we tell ourselves. He joins the show to discuss why happiness & morality are bullshit, the difference between bullshit & lying, why we conceal the status monkey, and more! Important Links:  David's Twitter David's Substack; Everything is Bullshit Cards Against Humanity The Execution Hypothesis; by Richard Wrangham Discordianism Our podcast with George Mack Our podcast with Will Storr  Show Notes:  What is bullshit? The difference between bullshitting and lying Why moralizing is bullshit Concealing the status monkey The origins of Cards Against Humanity How are status games changing? Why happiness is bullshit Happiness as a status symbol How can we escape bullshit? Why we're driven by negative emotions How to become more positive The role of humor in calling out bullshit MUCH more!  Books Mentioned:  On Bullshit; by Harry G. Frankfurt Propaganda; by Edward Bernays Influence: Science and Practice; by Robert Cialdini The Moral Animal: Why We Are The Way We Are; by Robert Wright The Status Game: On Social Position and How We Use It; by Will Storr The Lucifer Principle: A Scientific Expedition Into the Forces of History; by Howard Bloom Why Buddhism is True: The Science and Philosophy of Meditation and Enlightenment Happy; by Derren Brown Tao Te Ching; by Lao Tzu Gödel, Escher, Bach; by Douglas Hofstadter  

May 16, 2023 • 57min
Dylan O'Sullivan — Essayful (EP.160)
 Dylan O'Sullivan is a writer and media specialist based in Cork, Ireland. Dylan's work has been published in magazines such as The Spectator and Areo. He is also the creator of Essayful, a Substack dedicated to becoming "a new home for writing." Following his participation in David Perell's Write of Passage course last year, Dylan joined us as an intern at O'Shaughnessy Ventures. He joins the show to discuss the problem with traditional education, the blurry border between fiction & nonfiction, how AI is going to impact writing, why Ireland has such cultural influence, and more! Important Links:   Dylan's Twitter  Essayful  Write of Passage  Show Notes:  Losing the O's The collapse of the old institutions An introduction to Essayful "There's nothing new under the sun." The blurry border between fiction & nonfiction Rebuilding the Tower of Babel A book as a living thing How is AI going to impact writing? Why Dylan took Write of Passage Why are academic papers so hard to read? Why does Ireland have such cultural influence? What's next? More!  Books Mentioned:  Old God's Time; by Sebastian Barry Unflattening; by Nick Sousanis The Island of Saints and Scholars; Sean McMahon Ulysses; by James Joyce  

May 11, 2023 • 1h 20min
John Sills — The Human Experience (EP.159)
 After starting his career on a market stall in Essex, John Sills has spent the last twenty-five years working to make the world a better place for customers. John is the Managing Partner at the customer-led growth company The Foundation, and his writing has also been featured in publications such as The Guardian and Management Today. He joins the show to discuss his thought-provoking and timely new book The Human Experience: How to make life better for your customers and create a more successful organization. Important Links:  John's Website John's Twitter John's Substack  Show Notes:  John's time working on an Essex market stall Human vs functional customer experience What's blocking the human experience? Why do leaders stay away from the frontline? Escaping Vogonization Does the human experience scale? The benefits of starting from first principles Why companies should empower their staff The link between curiosity, creativity & customer experience Why aren't companies changing & why aren't more startups disrupting? Are frictionless customer experiences desirable? The myth of customer loyalty Tech upgrades & immersion MUCH more!  Books Mentioned:  The Human Experience: How to make life better for your customers and create a more successful organization; by John Sills The Genius of the Beast: A Radical Re-Vision of Capitalism; by Howard Bloom The Customer Copernicus: How to be Customer-Led; by Charlie Dawson The Hitchhiker's Guide to the Galaxy; by Douglas Adams  

21 snips
May 4, 2023 • 1h 3min
Billy Oppenheimer — On Curiosity, Creativity & Conceptual Ancestors (EP.158)
 Billy Oppenheimer is a researcher for Ryan Holiday. He is also known for his  viral long-form tweets and Six at 6 on Sunday newsletter. Billy is insatiably curious. He is a master at drawing lessons from anecdotes from the worlds of sports, music, comedy, business, and more. He joins the show to discuss how to cultivate good taste, whether everything is a remix, why he learns through introjection, and a whole lot more. Important Links:  Six at 6 on Sunday  Billy's Twitter Billy's website Our episodes with David Senra (1, 2)  'A Bicycle of the Mind' - Steve Jobs on the Computer  Our episode with Edward Rooster  To His Coy Mistress; by Andrew Marvell  Kubla Khan; by Samuel Taylor Coleridge  Show Notes:  Focus on doing the thing SIX at 6's origin story Learning through introjection Developing taste & cultivating curiosity "People don't have ideas, ideas have people" How Billy practices his scales Fiction vs non-fiction Repetition, repetition, repetition Should we study more failures? Process compounds "Care, but don't care too much" Has anyone succeeded without persistence? Conceptual ancestors Everything's a remix Taste, tools, markets & feedback Finding your pain points MUCH more!  Books Mentioned:  Trust Me, I'm Lying; by Ryan Holiday Psychology of Money; by Morgan Housel Atomic Habits; by James Clear The Immortality Key : The Secret History of the Religion with No Name; by Brian C. Muraresku Reality Hunger; by David Shields The Power of Myth; by Joseph Campbell & Bill Moyers Cloud Atlas; by David Mitchell The Great Gatsby; by F. Scott Fitzgerald The Da Vinci Code; by Dan Brown  

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  


