Infinite Loops

Jim O'Shaughnessy
  • 4.8 (18)
  • 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. 2 DAYS AGO

    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

  2. 20 MAR

    Jason Carman — Filmmaking at the Frontier (EP.260)

    The relentlessly prolific Jason Carman is making the films our culture needs: optimistic, inspiring and positioned at the frontiers of modern tech and science. In under two years, he has shipped more than 70 high-quality mini-documentaries exploring the startups shaping the future, racking up over 130,000 YouTube subscribers along the way. His new venture, Story Company, premiered “New Space”, its 100+ minute-long exploration of the modern space industry, to a packed San Francisco theater this year. Story Company has multiple projects in the pipeline, including a full-length sci-fi feature. Ultimately, he intends to create a new generation of sci-fi films: a Star Wars for the 21st century. I love Jason’s ambition, drive and enthusiasm (not to mention his filmmaking chops), which is why we awarded him a $100k O’Shaughnessy Fellowship last year. 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: Jason on X Story Company on X Story Company on Youtube Story Company’s Website “New Space” Frontier Film Jason’s Fellowship Show Notes: How Jason fell in love with filmmaking Laziness as an edge How to build a good team How to fix Hollywood Frontier Films: a new category of movie From science-fact to science-fiction Finding the right infinite loops The roots of the idea of America A Complete Unknown: Jason’s slideshow & Bob Dylan’s anti-authoritarianism Getting woo on Tenet’s Sator square How do you know when a movie is finished? The fragility of the artist We are all co-creators Jason as World Emperor MORE! Books Mentioned: I Am a Strange Loop; by Douglas Hofstadter The Genius of the Beast: A Radical Re-Vision of Capitalism; by Howard Bloom One Summer: America 1927; by Bill Bryson The Hypomanic Edge: What Built America; by John D. Gartner The Hitchhiker's Guide to the Galaxy; by Douglas Adams Movies Mentioned: New Space (directed by Jason Carman) Flow (directed by Gints Zilbalodis) My Dinner With Andre (directed by Louis Malle) Star Wars (directed by George Lucas) A Complete Unknown (directed by James Mangold) Tenet (directed by Christopher Nolan) Dune: Part Two (directed by Denis Villeneuve)

    1h 46m

  3. 13 MAR

    Anne-Laure Le Cunff — Experiment Your Way to a Better Life (EP.259)

    My guest today is Anne-Laure Le Cunff, founder of Ness Labs and author of Tiny Experiments: How to Live Freely in a Goal-Obsessed World. On paper, Anne-Laure had it all: top grades, a high-flying job at Google, and a life that seemed to hit all the markers of success. But something was off. No matter how “traditionally” successful she became, she felt… “empty.” So, she decided to do something about it. A neuroscience PhD, 100,000+ newsletter subscribers, and a newly published book later, she’s developed a new model of success — one built around conducting “tiny experiments” that help her build a life on her own terms. She joins me to discuss how we get trapped in cognitive scripts, the hidden dangers of productivity culture, how we can experiment our way to a better life 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: Anne-Laure’s Twitter/X Ness Labs Tiny Experiments Book Show Notes: How do you know you are bored out? People who love us the most might turn out to be our biggest blockers Don't confuse activity with effectiveness We will do virtually anything to gain what is really an illusion of control The map is not the territory, the menu is not the meal. And yet, words are magic spells. The Winner’s Script and the Loser’s Script "You got to run at the top speed if you just want to stay in place.” Let go of the linear and replace it with the loop- a more cyclical approach for growth Can you sit alone in a room for 15 minutes? Procrastination is just a signal from your brain that something is not quite working right now We know nothing AI is a rocket ship for the mind In 100 years, nobody will remember you Books Mentioned: Why Greatness Cannot Be Planned; by Ken Stanley Thinking in Bets; by Annie Duke Collective Illusions; by Todd Rose Maybe Logic; by Robert Anton Wilson Beginning of Infinity; by David Deutsch Science and Sanity: An Introduction to Non-Aristotelian Systems and General Semantics; by Alfred Korzybski The Science of Storytelling: Why Stories Make Us Human and How to Tell Them Better; by Will Storr

    1h 30m

  4. 6 MAR

    Gabriel Kennedy — The Life and Thought Crimes of Robert Anton Wilson (EP.258)

    If you’ve heard me speak for more than five minutes you’ve probably caught me dropping a Robert Anton Wilson reference (or several). Wilson is one of the most interesting (and underappreciated) writers I’ve ever come across — a Nostradamus for modern times. I was delighted to sit down with Gabriel Kennedy, author of the excellent biography Chapel Perilous: The Life and Thought Crimes of Robert Anton Wilson. I could talk about this stuff for days, and we had a blast discussing Wilson’s ideas, influence and impact. Consider it a beginner’s guide to avoiding cosmic schmuckery. 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: Chapel Perilous: The Life and Thought Crimes of Robert Anton Wilson; by Gabriel Kennedy The Thinker and the Prover; by Jim O’Shaughnessy Gabriel’s Substack Show Notes: The most interesting man of the last fifty years? How can we escape chapel perilous? The anti-determinist, rock & roll philosophy of Bob Wilson Tune in: a 30 minute masterclass on the influences, ideas and impact of Robert Anton Wilson How to avoid becoming a cosmic schmuck Who influenced Wilson the most? Why you should read Wilson Gabriel as World Emperor MORE! Books & Articles Mentioned: The Thinker and the Prover; by Jim O’Shaughnessy Chapel Perilous: The Life and Thought Crimes of Robert Anton Wilson; by Gabriel Kennedy Prometheus Unbound by Robert Anton Wilson Quantum Psychology: How Brain Software Programs You and Your World by Robert Anton Wilson The Illuminatus! Trilogy by Robert Anton Wilson and Robert Shea Cosmic Trigger Volume I: Final Secret of the Illuminati by Robert Anton Wilson The New Inquisition: Irrational Rationalism and the Citadel of Science by Robert Anton Wilson Prometheus Rising by Robert Anton Wilson Quantum Psychology: How Brain Software Programs You and Your World by Robert Anton Wilson The Waste Land by T. S. Eliot From Ritual to Romance by Jessie L. Weston Finnegans Wake by James Joyce Science and Sanity: An Introduction to Non-Aristotelian Systems and General Semantics by Alfred Korzybski On the Einstein Podolsky Rosen Paradox; by John S. Bell How the Hippies Saved Physics: Science, Counterculture, and the Quantum Revival by David Kaiser Character Analysis by Wilhelm Reich Man Meets Dog by Konrad Lorenz

    1h 27m

  5. 27 FEB

    The Art of Retirement — Christine Benz (EP.257)

    Christine Benz is the Director of Personal Finance and Retirement Planning at Morningstar, where she has spent over three decades helping investors navigate the complexities of financial planning. She is also the author of "How to Retire: 20 Lessons for a Happy, Successful, and Wealthy Retirement" and serves as the president of the John C. Bogle Center for Financial Literacy. Before focusing on retirement planning, Christine worked as a fund analyst, bringing a unique perspective that combines deep investment knowledge with practical financial wisdom. Christine joins the show to discuss why retirement isn't just about hitting your "magic number," how to overcome the psychological barriers to retirement spending, why keeping your inner circle vibrant is crucial for long-term happiness, the surprising power of lifetime giving, 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 Twitter LinkedIn Show Notes: Retirement Focus: Finances or Lifestyle? Bring Your Kids In The Loop Embrace the Challenges of Social Health A Day in The Life of a Retiree Defaulting People Into Saving Genesis of the FIRE Movement Horsemen of The Investment Apocalypse The Delicate Balance of Investment Buckets Dodging A Single Point of Failure How to Sniff Out Fishy Financial Advice The Saver vs the Investor Personality Type Keeping Up With Mr. Market Annuities: The Low-Risk Underdog Christine as World Emperor Books / Authors Mentioned: How to Retire: 20 Lessons for a Happy, Successful, and Wealthy Retirement; by Christine Benz The works of Jonathan Franzen

    1h 13m

  6. 20 FEB

    Luke Fehily — Ireland's Innovation Playbook (EP.256)

    Luke Fehily is the Director of Innovation Policy at Progress Ireland — an independent think tank backed by the likes of the Collison brothers — that’s on a mission to connect Ireland to proven policy solutions from around the world. Before joining Progress Ireland, Luke cut his teeth in both public and private sectors, developing a unique perspective on how to navigate bureaucratic challenges while maintaining ambitious visions for change. His current work spans housing, infrastructure, and innovation policy, with a particular emphasis on meta-scientific approaches to research funding and development. In this episode we discuss why Ireland should embrace techno-optimism, how to beat the NIMBY challenge with win-win solutions, why young scientists need more research funding, and MUCH more. Plus, we even touch on drone coffee deliveries (happening now in Dublin) and the things needed to unleash Ireland's entrepreneurial spirit. 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: Progress Ireland Website Twitter LinkedIn Show Notes: The Irish GDP Boom The Origins of Progress Ireland The Path Past Bureaucratic Barriers Where the State Meets the Street How Bad Political Vibes Can Seep in Where the Creme De La Creme Goes in State Projects Innovation Amidst EU’s Strict Restrictions National EU Friction Densification Dilemmas Balancing Efficiency and Equity in Public Procurement How to Handle NIMBYs Pushing Past Infrastructural Comfort Zones Fostering Cultural Shifts What is Metascience? Recalibrating Success Metrics The Irish Brain Drain Books Mentioned: Where the State Meets the Street by Bernardo Zacka

    1h 11m

  7. 13 FEB

    Rudy Havenstein — How to Fix America’s Accountability Crisis (EP.255)

    Rudy Havenstein is a writer and satirist known for his sharp critiques of America’s sprawling institutions and the elites who run them. He joins the show to discuss the accountability crisis in America — how it manifests across political life and, most importantly, what we can do to fix it. Important Links: Rudy’s Twitter Rudy’s Substack Show Notes: Why we should fear hyperinflation “The Fed is Congress’ drug dealer” The Great Financial Crash & America’s accountability crisis How to disagree agreeably How democracy REALLY works Why we should bring back Glass-Steagall The problem of cluelessness Solutions to the accountability crisis What has happened to investigative journalism? Why partisanship is overstated Rudy as World Emperor MORE! Books Mentioned: Yellen: The Trailblazing Economist Who Navigated an Era of Upheaval; by Jon Hilsenrath Deterring Democracy; by Noam Chomsky The Rule of Nobody: Saving America from Dead Laws and Broken Government; by Philip K. Howard

    1h 40m

  8. 6 FEB

    Mark Daniel — How to Find a Kaleidoscopic Alien (EP.254)

    Mark Daniel is the co-founder and managing partner of the investment firm Digital, whose portfolio extends across accelerated computing, gaming, crypto, social networking, AI, extended reality, cybersecurity, creator tools, spatial computing, and immersive learning. Back in 2013, he was also one of the very first recipients of a Thiel Fellowship. This was a fun one. Mark joins the show to discuss why podcasts are dangerous (😬), why content creators should have a 10 post limit, how he identifies kaleidoscopic aliens to invest in, 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: Digital Mark’s Twitter Mark’s LinkedIn Show Notes: Why podcasts are dangerous Why content creators should be limited to 10 posts Advice is simple; life is hard How to find a kaleidoscopic alien How to win the great game Mania-immune investing Jim’s “I’m a sports guy” algorithm What beliefs would you die for? What have you unlearned in the past year? The fragility of morality Passion as a forcing function Movie recommendations: My Dinner With Andre & Elevator to Gallows Mark as World Emperor MORE! Books & Articles Mentioned: How to Be Successful; by Jim O’Shaughnessy How to Win Friends and Influence People; by Dale Carnegie

    1h 27m
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    Hosts & Guests

    4.8
    out of 5
    18 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
      262
    • Rating
      Explicit
    • Show Website
      Infinite Loops

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