Latest Episode
Derek Sivers - Living Many Lives: Parenting, Moving Countries & AI (Ep. 329)
Derek Sivers, author, entrepreneur, TED speaker, and founder of CD Baby, joins Jim O'Shaughnessy on Infinite Loops to talk about parenting a teenager who is ready to leave home, why he moves countries on purpose and plans to live in Bangalore and Shanghai next, the certainty slider, and how AI can make you less dependent on big tech, not more. It is his first podcast after more than a year of saying no to every request.
Show Notes
Derek Sivers & Jim O'Shaughnessy
Derek Sivers: Author, entrepren
Recent Episodes
329
Sept. 24, 2026
Derek Sivers - Living Many Lives: Parenting, Moving Countries & AI (Ep. 329)
Derek Sivers, author, entrepreneur, TED speaker, and founder of CD Baby, joins Jim O'Shaughnessy on Infinite Loops to talk about parenting a teenager who is ready to leave home, why he moves countries on purpose and plans to live in Bangalore and Shanghai next, the certainty slider, and how AI can make you less dependent on big tech, not more. It is his first podcast after more than a year of saying no to every request. Show Notes Derek Sivers & Jim O'Shaughnessy Derek Sivers: Author, entrepren
328
Sept. 17, 2026
Brent Seales - How AI Is Reading the Only Library That Survived Antiquity (Ep. 328)
Dr. Brent Seales, computer scientist at the University of Kentucky and co-founder of the Vesuvius Challenge, joins guest host Nick Tawil on Infinite Loops to explain how synchrotron X-rays and machine learning are making unopenable ancient scrolls readable, and why the work has now shifted from engineering to reading. This summer in Naples, his team presented results from three sealed Herculaneum scrolls, including the first read end to end. Show Notes Brent Seales & Nick Tawil Dr. Brent Seale
327
Sept. 10, 2026
Ryan Resch - How Data Changed the NBA and What AI Changes Next (Ep. 327)
Ryan Resch, former Assistant General Manager and VP of Basketball Operations for the Phoenix Suns, joins guest host Jimmy Soni on Infinite Loops to explore what happens to competitive advantage when every team has the same data, and why the real edge comes from the questions you ask of it. Ryan traces his path from a cold email to Baylor coach Scott Drew to nearly a decade in the Suns front office and his current work leading data and AI in private equity. Show Notes Ryan Resch & Jimmy Soni Rya
326
Sept. 3, 2026
Brian Chau - How AI is Reinventing Investigative Journalism (Ep. 326)
Brian Chau, founder of Effort News, joins Infinite Loops to explore how AI could fundamentally reshape investigative journalism—not by writing articles, but by searching, analyzing, and connecting millions of legal, financial, and government records that humans could never examine manually. Show Notes Brian Chau & Effort News Effort News — Brian Chau’s document-led investigative journalism publication, using AI to search and analyze large datasets while keeping the reporting and final writing
Aug. 27, 2026
Julian Gough — The Egg and The Rock (Infinite Loops Classics)
Julian Gough sums up his career as follows: “I just sit in my room and write.” Well, I think being an acclaimed children’s author, novelist, stage playwright, poet and top-ten Irish musician is a little more impressive than he’s letting on… Oh, and I didn’t even mention that he wrote the ending to the computer game Minecraft! His current project, The Egg and The Rock, puts all of this to shame. This book, which Julian is writing in public on Substack, seeks to do no less than redescribe the un
Aug. 20, 2026
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 b
Aug. 13, 2026
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
Aug. 6, 2026
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 hi
325
July 30, 2026
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.na
324
July 23, 2026
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.
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About the Host
Jim O'Shaughnessy
Jim O'Shaughnessy built O'Shaughnessy Asset Management (OSAM) into a Wall Street powerhouse, managing billions before its successful acquisition. Now, he's embarked on a new venture: O'Shaughnessy Ventures (OSV), a creative investment firm empowering visionaries across business, tech, science, art, media, and literature.
Hailed as a "legendary investor" by Barron's, Jim authored the New York Times bestseller What Works on Wall Street among his four influential books. His expertise spans quantitative analysis, portfolio management, and investment strategy.
Beyond finance, Jim has served as former chair of the Chamber Music Society of Lincoln Center and host of the popular Infinite Loops podcast. He shares eclectic insights on everything from philosophy to quantum mechanics via his active Twitter presence (@jposhaughnessy). Jim resides in Connecticut with his wife Melissa, surrounded by the joyful chaos of their three children and six grandchildren.