182 episodes

Become a more nuanced thinker.

In an era of uncertainty, the ability to think dynamically and avoid getting trapped in infinite loops of thought is more important than ever.

Whether we’re discussing ancient Chinese philosophy, the history of finance, or cutting-edge advances in artificial intelligence, our host Jim O'Shaughnessy’s passion, experience, and eclectic range of interests, combined with our extensive research into our podcast guests, always result in surprising conversations which substantively engage with our guests’ ideas.

Our aim: To equip you with the tools required to navigate through the Great Reshuffle that we are in.

Let’s start exploring.

Infinite Loops Jim O'Shaughnessy

    • Education
    • 4.6 • 153 Ratings

Become a more nuanced thinker.

In an era of uncertainty, the ability to think dynamically and avoid getting trapped in infinite loops of thought is more important than ever.

Whether we’re discussing ancient Chinese philosophy, the history of finance, or cutting-edge advances in artificial intelligence, our host Jim O'Shaughnessy’s passion, experience, and eclectic range of interests, combined with our extensive research into our podcast guests, always result in surprising conversations which substantively engage with our guests’ ideas.

Our aim: To equip you with the tools required to navigate through the Great Reshuffle that we are in.

Let’s start exploring.

    Julie Fredrickson — “Circumstances change. Humanity doesn't. Plan accordingly.”

    Julie Fredrickson — “Circumstances change. Humanity doesn't. Plan accordingly.”

    Julie Fredrickson is a former founder and the Managing Partner of Chaotic Capital, an “early stage fund for companies that adapt our lives and systems to the opportunities that chaos brings.”
    She joins the show to discuss the Great Weirding, becoming a playable character, how the market provides a muse, the power of preparation, and more!

    Important Links:
    Website Twitter LinkedIn Chaotic Capital The Great Weirding; by Venkatesh Rao The Thinker and The Prover Show Notes:
    Julie’s Origin Story The Difference Between Hippies and Tech “Circumstances change. Humanity does not. Plan accordingly.” The Great Weirding The Myth of the Perfect Past How to Become a Playable Character The Weirdo Lighthouse The Power of Showing Up How Julie Assesses Founders Talent Doesn’t Matter The Market is the Muse “In the beginning, there was the word” Preference Falsification vs. Revealed Preferences Julie’s Revealed Preferences “Prepare, and the opportunity will come” Silicon Valley Is an Idea, Not a Place The Open-Source Ethos Julie as Empress of the World Books Mentioned:
    Bad Predictions: 2000 Years of the Best Minds Making the Worst Forecasts; by Laura Lee The History of the Peloponnesian War; by Thucydides Republic; by Plato American Cycles of History: According to the Fourth Turning Generational Theory and The Boomer Soul 1946-2022; by William H. Van Marter Jr. William Blake vs the World; by John Higgs Julie, or the New Heloise; by Jean-Jacques Rousseau The End of History and the Last Man; by Francis Fukuyama The Peripheral; by William Gibson Neuromancer; by William Gibson The Fifth Science; by Exurb1a The Science of Storytelling: Why Stories Make Us Human, and How To Tell Them Better; by Will Storr Class: A Guide Through the American Status System; by Paul Fussell What Works on Wall Street: The Classic Guide to the Best-Performing Investment Strategies of All Time; by Jim O’Shaughnessy Singularity Sky; by Charles Stross Marxism and Modernism; by Eugene Lunn The Genius of the Beast: A Radical Re-Vision of Capitalism; by Howard Bloom

    • 1 hr 21 min
    Danny Miranda — Attracted to the Light

    Danny Miranda — Attracted to the Light

    Danny Miranda’s ambition is to sell out Madison Square Gardens for a live edition of his podcast. Now, on episode 402 (and counting), he is getting closer to that goal every week. He joins the show to discuss the art of interviewing, why he’s attracted to the light, his favorite questions, and more.

    Important Links:
    Danny’s Twitter Danny’s Website Wisdom Unleashed Show Notes:
    Fancy a phone call? The power of human interaction What Danny has learned from 397 podcasts The Art of Interviewing Finding “the thing” How has Danny changed deciding his aim was to sell out Madison Square Garden? Danny’s research process “I’m attracted to the light” When did things go wrong? Podcasting as idea collecting In-person vs Zoom The ability to speak to anyone in the world Danny’s favorite questions The different types of podcast Why podcasts are like the printing press for audio The importance of connection What will podcasting look like in 2034? Always Be Closing Danny as emperor of the world MORE! Books Mentioned:
    How to Win Friends and Influence People; by Dale Carnegie Hidden Genius; by Polina Marinova Pompliano The Tao Te Ching; by Lao Tzu Jim’s “Exploring the Dark” Reading List: Meditations; by Marcus Aurelius Heart of Darkness; by Joseph Conrad The Human Animal: A Personal View of the Human Species; by Desmond Morris Exploring the Shadow: Understanding and Addressing the Dark Side of the Human Psyche; by John C. Friel and Linda D. Friel (Article) Man's Search for Meaning; by Viktor E. Frankl The Archetypes and the Collective Unconscious; by Carl Jung Memories, Dreams, Reflections: An Autobiography; by Carl Jung Beyond Good and Evil; by Friedrich Nietzsche The Lucifer Effect: Understanding How Good People Turn Evil; by Philip Zimbardo Meeting the Shadow: Hidden Power of the Dark Side of Human Nature; edited by Connie Zweig and Jeremiah Abrams

    • 1 hr 5 min
    Dror Poleg — The Future of Work

    Dror Poleg — The Future of Work

    Dror Poleg is an author, speaker, and researcher investigating technology’s impact on the way people work, live, and invest. He joins us to discuss the relationship between AI and remote work, how cities are going to change, the internet’s role as a matching engine, and MUCH more!

    Important Links:
    Dror’s Website Dror’s Twitter Our Great Reshuffle Series The Once and Future Liberalism; by Walter Russell Mead The Great Online Game; by Packy McCormick Show Notes:
    The relationship between AI & remote work How remote work & AI will change our cities What cities will succeed in the new world? Remote work vs. Back to the office Uncertainty & the death of the “job” How to cure zero-sum thinking The economy doesn’t need us all to be ambitious How work is going to change How AI will transform professions’ scalability; the internet as a matching engine How Dror uses AI Unbundling ideas from execution The value of Twitter The tragedy of the uncommon The great online game UBI & the need for new social systems Dror as emperor of the world. MORE! Books Mentioned:
    Rethinking Real Estate: A Roadmap to Technology’s Impact on the World’s Largest Asset Class; by Dror Poleg After Office: A Survival Guide For Cities, Humans And Companies; by Dror Poleg The Longer Long Tail: How Endless Choice is Creating Unlimited Demand; by Chris Anderson

    • 1 hr 34 min
    Trung Phan & Rob Henderson — Apocalypse Now

    Trung Phan & Rob Henderson — Apocalypse Now

    Our previous episode with Trung & Rob included the bombshell reveal that Rob had never watched Apocalypse Now.
    Nearly one year later, Rob and Trung make their triumphant return to the show to discuss the themes of the film, the lessons aspiring creators can draw from its troubled production history, the role of the Vietnam War in American cinema, and a whole lot more.

    Important Links:
    Rob’s Substack Rob’s Twitter Trung’s Substack Trung’s Twitter Our previous episode with Trung & Rob Show Notes:
    Rob’s homework assignment The two endings of Apocalypse Now Coppola’s disastrous production process Should Willard have taken Kurtz’ place? Draft dodgers: fear of death, or fear of social judgment? Different perspectives of American Empire The memory industry: Vietnam in film When condemning backfires The thin veneer of civilization Willard’s moral injury Is pacificism sustainable? Art as a response to social conditions Telling the story vs romanticizing it Be careful what you wish for: The McKenna take When Jim was Jedpilled When Rob was Jedpilled The creative process: feeding the black box, becoming the vessel, and summoning the muse George Lucas’ version of Apocalypse Now Cut scenes and time travel Trung & Rob as Emperors of the World MORE! Books Mentioned:
    The Enlightenment Trilogy; by Jed McKenna Heart of Darkness; by Joseph Conrad The Lucifer Principle; by Howard Bloom Howard Bloom hierarchies The Sympathizer; by Viet Thanh Nguyen The War of Art; by Steven Pressfield Moby-Dick; by Herman Melville The Tao Te Ching; by Lao Tzu The Creative Act: A Way of Being; by Rick Rubin Films, TV Shows & Podcasts Mentioned:
    Apocalypse Now; directed by Francis Ford Coppola Hearts of Darkness: A Filmmaker's Apocalypse; directed by Fax Bahr, George Hickenlooper & Eleanor Coppola The Vietnam War; directed by Ken Burns and Lynn Novick Platoon; directed by Oliver Stone The Wolf of Wall Street; directed by Martin Scorcese Wall Street; directed by Oliver Stone The Social Network; directed by David Fincher Born on the Fourth of July; directed by Oliver Stone The Deer Hunter; directed by Michael Cimino A Clockwork Orange; directed by Stanley Kubrick Patton; directed by Franklin J. Schaffner Full Metal Jacket; directed by Stanley Kubrick Saving Private Ryan; directed by Steven Spielberg The Godfather & The Godfather Part II; directed by Francis Ford Coppola The Matrix; directed by the Wachowskis Rick and Morty Do We Get To Win This Time? Tetragrammation with Rick Rubin

    • 1 hr 11 min
    Frederik Gieschen — On Agility, Agreeableness, Alchemy & the Arena

    Frederik Gieschen — On Agility, Agreeableness, Alchemy & the Arena

    "Who is America’s best-known banker? That would be Jamie Dimon.
    But who is the richest? That would be Andy Beal, with an estimated net worth of $9 billion."

    Friend-of-the-show Frederik Gieschen joins us for an impromptu conversation about his article on the life and work of Andy Beal, the richest banker in America.

    Important Links:
    High Roller: Lessons from America’s Richest Banker Frederik’s Twitter Frederik’s Substack Frederik’s previous episode The Internet Contrarian Show Notes:
    The Arena, the Maze, and the Labyrinth Why do myths endure? “You can’t do a good deal with a bad person” America’s richest banker: the Andrew Beal story Agreeableness, contrarianism, and accountability Thinking like a banker vs. thinking like an investor The random buzz generator: How to fight linear thinking The alchemy of success Bubbles: When heterogeneity becomes homogeneity “The higher you rise in a hierarchy, the less good the information you get.” Deterministic vs. probabilistic thinking The difference between being an investor and being in the investing business The return of Andrew Beal The importance of agility MORE! Books Mentioned:
    The Cosmic Trigger trilogy; by Robert Anton Wilson Aesop’s Fables; by Aesop Breath: The New Science of a Lost Art; by James Nestor The Professor, the Banker, and the Suicide King: Inside the Richest Poker Game of All Time; by Michael Craig What Works on Wall Street; by Jim O’Shaughnessy The Snowball: Warren Buffett and the Business of Life; by Alice Schroeder

    • 1 hr 14 min
    Dr. Julie Gurner — Ultra Successful

    Dr. Julie Gurner — Ultra Successful

    Dr. Julie Gurner is a doctor of psychology and executive performance coach to top percentile executives, primarily in finance and technology. She is also the proprietor of the Ultra Successful newsletter, which delivers a weekly challenge pulled from global business leaders and designed to ”help you unleash your power.”


    Dr. Gurner joins the show to discuss the merits of being unreasonable, why your business should not be your identity, why niceness is overrated, and more!
    Important Links:
    Substack Twitter Website Show Notes:
    Dr. Gurner’s origin story How forensic psychology experience can help executive coaching Leaning into the 1% Why psychological tests are flawed The common traits of successful founders High performance & bottlenecks Why your business should not be your identity Data vs. emotion How Dr. Gurner applies her strategies in her own life Don’t be nice Be unreasonable Social validation is not important How can you improve someone’s communication skills? How Dr. Gurner would teach executive coaching The “no Plan B” mentality Can high energy be detrimental? How to unpack charisma How to turn down work Dr. Gurner’s greatest satisfaction How has leadership changed in the last 20 years? Dr. Gurner as Empress of the World MORE! Books Mentioned:
    The Art of War; by Sun Tzu

    • 1 hr 19 min

Customer Reviews

4.6 out of 5
153 Ratings

153 Ratings

DaveNKait ,

Psychedelics for chronic pain

Loved your interview with Brom! Started a newco developing psychedelic NCEs for chronic pain (Cacti Therapeutics) so especially appreciated the bit about mind/body connection. Big believer in taking a holistic approach and combining healing modalities to optimize outcomes. Personalized and precision medicine takes many forms! Truly enjoyable interview!

t.8 ,

Let the guests talk

Jim has really interesting people on but he talks far more than they do. Sometimes he barely let's them get more than a couple words in before starting another monologue.

Yoodleyou ,

Such a gem of a show

Love most of the content and excellent guests. Jim can be a little preachy sometimes but with zero doubt he only means well for the world at large and has a focus on objective truth.

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