Infinite Loops

Jim O'Shaughnessy
  • 4.6 (168)
  • TECHNOLOGY
  • UPDATED WEEKLY
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!"

  1. 4H AGO

    Natasha Joukovsky — On Recursion, Status Games & Manufactured Nonchalance (EP.268)

    Strategy consultant turned writer Natasha Joukovsky joins me to discuss why bourgeois comfort is more conducive to writing than you think, why choice-plots make for better fiction, the eyerolling prevalence of manufactured nonchalance, our shared distaste for Atlantis Bahamas, 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: Natasha’s Website Natasha’s Substack The Portrait of a Mirror Show Notes: “You can do everything, just not at the same time” It’s Recursion All the Way Down Pretending to Read vs Actually Reading Manufactured Nonchalance as a Status Signal Counter-Signalling, Fake-Famous & Jim’s Cursed Trip to Atlantis Bahamas On No-Choice Plots & Writing in Service of Beauty The Self-Deception of Status Hunting Why Bourgeois Comfort is More Conducive to Art Than You Think Natasha’s Next Book “We don’t do auctions” Natasha as World Empress Books Mentioned: The Portrait of a Mirror; by Natasha Joukovsky The novels of Jane Austen Status Anxiety; by Alain de Botton The Love Song of J. Alfred Prufrock (poem); by T.S. Eliot Class: A Guide Through the American Status System; by Paul Fussell Gödel, Escher, Bach: An Eternal Golden Braid; by Douglas R. Hofstadter Ulysses; by James Joyce Metamorphosis; by Franz Kafka Beloved; by Toni Morrison In Search of Lost Time (Remembrance of Things Past); by Marcel Proust Collective Illusions; by Todd Rose The Status Game; by Will Storr Anna Karenina; by Leo Tolstoy The Theory of the Leisure Class; by Thorstein Veblen A Little Life; by Hanya Yanagihara

    1h 32m

  2. MAY 8

    Tiago Forte — Unlocking the Power of the Annual Review (Ep. 267)

    I’ve said before that one of the best parts of hosting Infinite Loops is the chance to connect with people who consistently make me think differently — and few do that quite like Tiago Forte. Tiago Forte joins Infinite Loops for the first time, and within minutes we closed the door on his best-selling “Building A Second Brain” and were off to the races: from digitizing 50,000+ words of personal data to build an AI-powered life coach, to the emotional intelligence hiding inside envy, to the surprising lessons he learned walking through a tiny historical museum in Coconut Grove. We also dig into the messy magic of identity shifts, how fit dads triggered a personal transformation, and why letting go of productivity-as-performance might be the most productive thing you can do. Plus: the power of NotebookLM, building AI-native systems of self-awareness, and why the future will belong to those who embrace the one-way door. Unsurprisingly, this was a fun one. 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: Tiago Forte’s Website Tiago Forte on X Tiago Forte on LinkedIn Tiago Forte’s Annual Reviews Building A Second Brain Book The PARA Method Book I Replaced my $700/hour Coach with NotebookLM — Here’s What Happened (YouTube) What I Learned About the Future By Reading 100 Science Fiction Books Show Notes: Closing the Door on Second Brain The Power of the Annual Review Tiago's Family: Incredibly Vibrant, Visual, Auditory Incorporating AI Into Work & Life Joe Hudson: Mentorship and Emotional Intelligence Miami: The Most Introspective Place on Earth Irreversible Decisions Archival Material: Underrated Forcing Function The Future of Book Publishing The Hard Truth on Performance Reviews AI Skepticism & Building Moats AI-First Mentality for Early Adopters Learning From Sci-Fi Books Cumulative Cultural Evolution Tiago as Emperor of the World Books Mentioned: Building A Second Brain: A Proven Method to Organize Your Digital Life and Unlock Your Creative Potential; by Tiago Forte The PARA Method: Simplify, Organize, and Master Your Digital Life; by Tiago Forte How Emotions are Made: The Secret Life of the Brain; by Lisa Feldman Barrett Tiny Experiments: How to Live Freely in a Goal-Obsessed World; by Anne-Laure Le Cunff Why Greatness Cannot Be Planned; by Kenneth O. Stanley and Joel Lehman Molecules Of Emotion: The Science Behind Mind-Body Medicine; by Candace B. Pert What Works on Wall Street; by Jim O’Shaughnessy The Beginning of Infinity; by David Deutsch One Summer: America, 1927; by Bill Bryson White Mirror; by Tinkered Thinking The Forever War; by Joe Halderman

    1h 37m

  3. MAY 1

    Nir Eyal — The Psychology of Addictive Products (EP.266)

    Author, speaker, founder, investor and behavioral design maestro Nir Eyal joins me for his second appearance on the show. Today, we dig into Nir’s first book, “Hooked: How to Build Habit-Forming Products.” We also discuss the difference between coercion and persuasion, AI’s use case as our personal Jiminy Cricket 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: Nir’s personal blog Nir’s LinkedIn Nir’s Twitter Nir’s YouTube channel Nir’s Habit Tracking Tool Nir’s Schedule Maker Tool Show Notes: What Makes Silicon Valley’s Tech Products So Sticky? The Morality of Manipulation The Perils of Legalized Gambling Twitter is for Journalists and Nerds AI for Behavioural Design Believing in our own Agency On Labels and Limiting Identities Pills Don’t Teach Skills The Power of an Internal Locus of Control Escaping Discomfort & Getting Hooked AI as a Self-Directed Personal Tutor Nir As Emperor of the World Books Mentioned: Hooked: How to Build Habit-Forming Products; by Nir Eyal Influence; by Robert Cialdini Sick Souls, Healthy Minds: How William James Can Save Your Life; by John Kaag

    1h 3m

  4. APR 24

    Nathan Baschez — On AI Writing, Thought Design & Solo Foundership (EP.265)

    Nathan Baschez is the cofounder and CEO of Lex, an AI word-processor. He also cofounded Every, was the first employee at Substack AND co-created Product Hunt. Suffice to say, Nathan knows a thing or two about building on the internet. He joins the show to discuss how AI is changing writing, why it’s time to rethink the article, the rise of solo founders 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: Lex Twitter Substack LinkedIn Show Notes: Lex: Your Spotter In the Writing Gym Letting People Into Your Creative Process Collaboration-as-a-Service Creation Is Fundamentally About Choices What Will Become of the AI Holdouts? AI Is Like the Internet In 1995 Can AI U****k the Government? Blindspots While Working In Organizations Rethinking The ‘Article’ As A Medium Memes Are Dense Information Packets It’s Time for Solo Founders Why Learning About Cumulative Cultural Evolution Is Vital What’s Next for Lex? Writing As A Way To Design Thoughts Nathan As World Emperor Books Mentioned: A Swim in a Pond in the Rain: In Which Four Russians Give a Master Class on Writing, Reading, and Life; by George Saunders The WEIRDest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous; by Joseph Henrich The Secret of Our Success: How Culture Is Driving Human Evolution, Domesticating Our Species, and Making Us Smarter; by Joseph Henrich

    1h 31m

  5. APR 17

    Tommy Potter — Building the CIA for Entrepreneurs (EP.264)

    Young, polymathic, and full of energy — Tommy Potter is on a quest to build a “CIA for Entrepreneurs.” He calls it “The Power Hour” — a startup community in Michigan that hosts dropouts, undergrads and PhDs across many industries: enterprise, consumer, CPG, aviation, gaming, robotics and AR/VR, as they work together to build cool projects. I had a great time chatting with Tommy as we spoke about non-linear career paths, embracing authenticity, working with dazzling, delusional people and 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: X/Twitter Linkedin Powerhour: The CIA For Entrepreneurship Show Notes: Tommy’s Origin Story Using The Third Door Lessons from Documenting the Homeless Can We Ever Be Our Authentic Self? What Traits Tommy Looks for in People Bringing Delusional People Together The East Coast - West Coast Bubbles Being a ‘Weirdo Broker’ Process Over Outcomes. Serendipity Over Itinerary. Different Personalities in Public vs. Private Markets The Importance of Learning People Life Isn’t a Highlight Reel - Live It All Tommy As World Emperor Books Mentioned: The Third Door: The Mindset of Success; by Alex Banayan One-upmanship; by Stephen Potter Class: Style and Status in the USA; by Paul Fussell Dignity: Seeking Respect in Back Row America; by Chris Arnade The Science of Getting Rich; by Wallace D. Wattles The Act of Creation; by Arthur Koestler

    1h 46m

  6. APR 10

    Alex Danco — On Strollers, Slop & Citizen Kane (EP.263)

    Shopify Product Director Alex Danco returns for his NINTH appearance on the show — and he comes in hot. As you’ll hear, I didn’t even get a chance to introduce him before he launched into his take on what everyone gets wrong about Citizen Kane. We also unpack the performance art of parenting, why dinner parties are the new status signals, the difference between meme and slop culture and MUCH more. Unsurprisingly, this was a fun one. 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: Twitter: https://twitter.com/Alex_Danco Substack: https://danco.substack.com Website: https://alexdanco.com/ Previous episode: https://newsletter.osv.llc/p/finding-method-in-the-madness?utm_source=publication-search Show Notes: What EVERYONE gets wrong about Citizen Kane Jim’s hardest interview question Elon & Lutnick: clash of the cartoons The status hierarchy of baby strollers What happened to Yuval Noah Harari? (With a diversion via digital girlfriends and North Korean crypto hackers) Dinner parties as status signals Parenting as performative art History’s greatest memers Infinite Jest: the sequel (an Alex Danco & Jim O’Shaughnessy production) GIF culture vs AI slop From “code is capital” to “code is labour” “Did I mention that I dropped out of Stamford?” From Clint Eastwood to Cloud Atlas MORE! Books, Articles & Films Mentioned: Two Thoughts: A Timeless Collection of Infinite Wisdom; by Jim O'Shaughnessy and Vatsal Kaushik Finnegans Wake; by James Joyce Invest Like the Best; by Jim O'Shaughnessy Sapiens: A Brief History of Humankind; by Yuval Noah Harari Underwriters of the United States: How Insurance Shaped the American Founding; by Hannah Farber The Magic Mountain; by Thomas Mann The Gervais Principle; by Venkatesh Rao Scarcity & Abundance in 2025; by Alex Danco Cloud Atlas; by David Mitchell Citizen Kane; directed by Orson Welles F for Fake; directed by Orson Welles My Dinner with Andre; directed by Louis Malle Letters from Iwo Jima; directed by Clint Eastwood Million Dollar Baby; directed by Clint Eastwood Fawlty Towers (TV show) Absolutely Fabulous (TV Show)

    1h 42m

  7. APR 3

    Vizi Andrei — The Way of the Tinkerer (EP.262)

    My guest today is my former teammate Vizi Andrei, founder of The Sovereign Artist program and author of Sovereign Artist: Meditations on Lifestyle Design. Vizi’s journey has been anything but conventional. After dabbling in various creative projects, he realized that the internet offers a unique opportunity: the freedom to take countless small risks without catastrophic consequences. He built The Sovereign Artist program to help creators step away from the toxic hustle culture and build sustainable, meaningful lives rooted in creativity, deep work, and sacred leisure. His insights into Slow Living, the Sicilian Dream, and embracing experimentation over optimization can help one break free from comparison traps. He joins me to discuss the dangers of chasing unrealistic benchmarks of success, the myths of modern productivity, how to unlock creative freedom, 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: Website Instagram The Sovereign Artist KronArête (Community) Gumroad X The Great Reshuffle Show Notes: Is procrastination a signal for something bigger? The Sicilian Dream: challenging the hustle culture The Pursuit of Busyness The rise of the pseudo-entrepreneur Are we taking the internet for granted? The outlier obsession can kill your creative potential Are your goals your own? or borrowed from prepackaged societal narratives? Drunk with too many choices Crossing the bridge of nihilism The art of boredom: slow living might just be the answer Knowledge is existential; energy is everything MORE! Books Mentioned: Sovereign Artist: Meditations on Lifestyle Design; by Vizi Andrei The Pathless Path: Imagining a New Story for Work and Life; by Paul Millerd Status Anxiety; by Alain de Botton The Soul of the World; by Roger Scruton Escolios to an Implicit Text; by Nicolás Gómez Dávila Antifragile: Things That Gain from Disorder; by Nassim Taleb The Infinity of Lists; by Umberto Eco The Myth of the Eternal Return; by Mircea Eliade Happy: Why More or Less Everything is Absolutely Fine; by Derren Brown

    1h 20m

  8. MAR 27

    Barry Ritholtz — Make Fewer Errors, Make More Money (EP.261)

    My friend Barry Ritholtz has spent his career being an astute market observer, investigating behavioral finance and data analytics. He runs Ritholtz Wealth Management which has been named ETF Advisor of the Year, Financial Times Top 300 Advisors, and one of America’s fastest-growing RIAs. He’s also the host of Masters in Business, Bloomberg Radio’s most popular podcast (50+ million streams/downloads), which he started way back in 2014. In his new book, How Not To Invest, Barry emphasizes how avoiding rookie mistakes can significantly help you do better financially. He blends engaging stories with data-driven insights, and explores overlooked aspects of behavioral finance, psychology and the market. Reading his book is like having a casual drink with an experienced, wise, and honest friend. 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: Blog Twitter LinkedIn Ritholtz Wealth Management Show Notes: How Amateurs Win Managing Emotions When the Market Goes Down If You Can't Afford a Financial Advisor Yet… Notable Financial Innovations Barry’s Transition from a Trader to an Investor Varieties of Investor Personas What To Do When Randomness Derails Your Plans Finding Your Own Maintainable Processes Having Reliable Information Sources Barry As World Emperor Books Mentioned: How Not to Invest: The Ideas, Numbers, and Behaviors That Destroy Wealth - And How to Avoid Them; by Barry Ritholtz Winning the Loser’s Game; by Charley Ellis How We Know What Isn't So: The Fallibility of Human Reason in Everyday Life; by Thomas Gilovich

    1h 28m
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Hosts & Guests

4.6
out of 5
168 Ratings

About

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!"

Information

  • Creator
    Jim O'Shaughnessy
  • Years Active
    2019 - 2025
  • Episodes
    269
  • Rating
    Explicit
  • Show Website
    Infinite Loops

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