Infinite Loops

Hosted by Jim O'Shaughnessy

Business Entrepreneurship EducationInterviews guests

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336

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Aug 2026

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About the show

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!"

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60 recent

August 20, 20261 hr 33 min

Dr. Julie Gurner — Ultra Successful (Infinite Loops Classics)

Hi everyone, Jim here. We're taking a short pause on new episodes through the end of August. In the meantime, we're digging out some of our favorite conversations from the archive. This one is from August 2023, with Dr. Julie Gurner. Enjoy. 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 - https://drgurner.substack.com - Twitter - https://twitter.com/drgurner?s=21&t=kpNZMw5M-jHHMC0vAkndPg - Website - https://www.drgurner.com/consulting/ Show Notes: 0:00:00 Intro 0:01:24 Main podcast 0:02:20 Dr. Gurner's origin story 0:05:07 How forensic psychology experience can help executive coaching 0:07:11 Leaning into the 1% 0:15:23 Why psychological tests are flawed 0:19:26 The common traits of successful founders 0:29:12 High performance & bottlenecks 0:30:38 Why your business should not be your identity 0:41:01 How Dr. Gurner applies her strategies in her own life 0:44:17 Don't be nice 0:46:48 Be unreasonable 0:51:18 Social validation is not important 0:56:22 How can you improve someone's communication skills 1:01:43 How Dr. Gurner would teach executive coaching 1:03:36 The "no Plan B" mentality 1:06:48 Can high energy be detrimental? 1:10:21 How to unpack charisma 1:15:57 How to turn down work 1:20:01 Dr. Gurner's greatest satisfaction 1:22:31 How has leadership changed in the last 20 years? 1:25:40 Dr. Gurner as Empress of the World 1:31:18 End screen Books Mentioned: - The Art of War; by Sun Tzu

August 13, 20261 hr 37 min

Lulu Cheng Meservey — Going Direct: What Founders can learn from K-Pop, Crypto, and the Early Christians (Infinite Loops Classics)

Hi everyone, Jim here. We're taking a short pause on new episodes through the end of August. In the meantime, we're digging out some of our favorite conversations from the archive. This one is from November 2022, so a few of our references (and jobs!) are out of date, but the ideas have only gotten better. Enjoy this conversation with Lulu Cheng Meservey. Lulu Cheng Meservey is the Chief Communications Officer and Executive Vice President of Corporate Affairs at Activision Blizzard. She joins Infinite Loops to provide us with a masterclass in communications for startups. A must-listen for current and aspiring founders. Important Links: • Lulu's Twitter • Lulu's Substack • Episode summary from Podcasts Recapped Show Notes: • Why people write hit pieces • The insurgency framework • How to access your audience's neural real estate • How to develop a spontaneous elevator pitch • Tips for becoming better at reading the room • Speak directly and take the hits • Defining business objectives • Learning from other industries • Personalising your message • Overcoming resistance to the unknown, what Christianity can teach us about comms • Escaping corporate jargon • How comms resembles rugby • Taking ownership of comms • Moving to a new model of comms • "Don't let things happen to you. Go and happen to things." Books Mentioned: • The Network State: How To Start a New Country; by Balaji S. Srinivasan • The Hero with a Thousand Faces; by Joseph Campbell

August 6, 20261 hr 25 min

Jesse Michels — American Alchemy (Infinite Loops Classics)

Hi everyone, Jim here. We're taking a short pause on new episodes through the end of August. In the meantime, we're digging out some of our favorite conversations from the archive. This one is from February 2023, so a few of the references have aged since (mine included), but the ideas have only gotten better. Enjoy this one with the wonderfully heretical Jesse Michels. Jesse Michels is an investor at Thiel Capital and the creator and host of 'American Alchemy', a Youtube channel dedicated to highlighting the most heretical thinkers and ideas of our time. He joins the show to discuss the transmission theory of consciousness, whether mushrooms are aliens, the reawakening of the Boomers and MUCH more! Important Links: - American Alchemy - https://www.youtube.com/@JesseMichels/about - Jesse's Twitter - https://twitter.com/alchemyamerican Books Mentioned: - The Half-Life of Facts: Why Everything We Know Has an Expiration Date; by Samuel Arbesman - The User Illusion: Cutting Consciousness Down to Size; by Tor Norretranders - Gödel, Escher, Bach: an Eternal Golden Braid; by Douglas Hofstadter - The Beginning of Infinity: Explanations That Transform the World; by David Deutsch - The Immortality Key : The Secret History of the Religion with No Name; by Brian C. Muraresku - The New Inquisition: Irrational Rationalism and the Citadel of Science; by Robert Anton Wilson - How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression and Transcendence; by Michael Pollan - Chaos: Charles Manson, the CIA, and the Secret History of the Sixties; by Tom O'Neill - Weird Scenes Inside the Canyon: Laurel Canyon, Covert Ops & the Dark Heart of the Hippie Dream; by David McGowan - Prometheus Rising; by Robert Anton Wilson - Quantum Psychology: How Brain Software Programs You & Your World; by Robert Anton Wilson - The Cosmic Trigger trilogy; by Robert Anton Wilson - Communion: A True Story; by Whitley Strieber

July 30, 20261 hr 36 min

Nat Eliason - The High School That Guarantees You'll Make $1 Million (Ep. 325)

Nat Eliason joins guest host Jimmy Soni to discuss Founders School, a new high school for entrepreneurs that guarantees students will generate $1 million in gross profit by graduation or get their tuition refunded. We explore how AI is changing what teenagers can build, why traditional entrepreneurship education falls short, and what happens when we take young people seriously. Important Links: Learn more about Founders School: https://founders.school/ Read more from Nat here: https://www.nateliason.com/

July 23, 20261 hr 16 min

Philip Howard - How to Bring Common Sense Back to America (Ep. 324)

Philip Howard joins Infinite Loops to explain how America's legal and regulatory system became too complicated to function effectively—and how we can rebuild it around judgment, accountability, and human agency. We discuss why government has become unmanageable, how thousand-page rulebooks discourage individual judgment, why infrastructure projects can take decades to approve, and how public institutions end up costing more while delivering less.

July 16, 20261 hr 48 min

Sangeet Choudary - How AI Will Reshape the Knowledge Economy (Ep. 323)

Sangeet Choudary joins Infinite Loops to explain why AI's greatest impact will not be automating today's work, but rebuilding the structures beneath it. They discuss AI-native companies, the future of knowledge work, the American and Chinese AI models, creative "exhaust," changing career paths, and how to compete when the rules of the game are constantly being rewritten. Important Links: Learn more about Sangeet and Reshuffle here: https://reshufflebook.com/ Read more about the Platform Revolution here: https://platformthinkinglabs.com/materials/platform-revolution

July 9, 20261 hr 34 min

Jameson Olsen - Becoming the Main Character (Ep. 322)

What if the great stories were more than just stories? Jameson Olsen, host of Becoming the Main Character, joins guest host Liberty to explore fiction as a kind of operating system for life — a way to study agency, ambition, empathy, failure, courage, and change without having to live every consequence yourself. Through Hamlet, Frankenstein, Sherlock Holmes, Lord of the Rings, training montages, NPCs, and the Hero's Journey, they discuss what it means to stop drifting through life and start holding the pen of your own story. Important Links: Listen to Jameson's podcast here: https://www.becomingmain.com/

July 2, 20261 hr 10 min

David Gelles - The Stories that Shape Business (Ep. 321)

David Gelles joins guest host Jimmy Soni to discuss his career covering business for The New York Times. They talk about his books - Mindful Work, The Man Who Broke Capitalism, and Dirtbag Billionaire - and the reporting behind major stories on Bernie Madoff, Jack Welch, Boeing's 737 Max crashes, and Patagonia's Yvon Chouinard. David explains how he broke a front-page story five weeks into journalism school, how he convinced Bernie Madoff to grant him a prison interview, and his process for writing books while working full-time. They also discuss raising kids who read for hours every day and why meditation helps him stay sane.

June 25, 20261 hr 23 min

Gretchen Rubin - How Curiosity Becomes a Calling (Ep. 320)

Gretchen Rubin joins guest host and Infinite Books CEO Jimmy Soni to discuss her journey from Supreme Court clerk to bestselling author, the creative obsessions that shaped her career, and the daily habits that fuel her work. They cover her transition from law to writing Power Money Fame Sex , why she often ends up writing the book before the proposal, the art of editing until the final hour (even during pass pages), her 5:30 AM writing routine, and why "know thyself" remains the foundation of all her books - from 40 Ways to Look at Winston Churchill to Life in Five Senses . Important Links: Learn more about Gretchen: https://gretchenrubin.com/ Read more of Gretchen's work: https://gretchenrubin.com/books Listen to Gretchen's podcast: https://gretchenrubin.com/happier/

June 18, 20261 hr 20 min

Ben Cohen - The Hidden Art of Making Things Better (Ep. 319)

Wall Street Journal columnist Ben Cohen joins guest host Jimmy Soni, CEO of Infinite Books, to explore the hidden art of making things better. They explore the hot hand phenomenon in basketball, why Moneyball shaped a generation of journalists, the peanut butter and jelly crisis in the Warriors locker room, why ASML is the most important company you've never heard of, the strange story of Driscoll's tastiest berries, and the troubled development of The Princess Bride. Important Links: Learn more about Ben here: https://www.wsj.com/news/author/ben-cohen Read The Science of Success: https://www.wsj.com/news/types/science-of-success Read The Hot Hand: https://www.harpercollins.com/pages/hothand