Latest Episode 
Jun Kwak - AI Agents and the Future of Commerce (Ep. 335)
Jun Kwak, co-founder and CTO of Overjoy, joins Jim O'Shaughnessy on Infinite Loops to talk about why he believes every B2B SaaS company will have to become a service business, how Overjoy went from selling software to delivering sales outcomes for consumer brands, why tangled data is the strongest moat against the frontier labs, how AI agents could weaken wholesale marketplaces, why brands need websites AI agents can read, why small brands chasing big box stores often abandon their most profitab
Recent Episodes
335
Nov. 12, 2026
Jun Kwak - AI Agents and the Future of Commerce (Ep. 335)
Jun Kwak, co-founder and CTO of Overjoy, joins Jim O'Shaughnessy on Infinite Loops to talk about why he believes every B2B SaaS company will have to become a service business, how Overjoy went from selling software to delivering sales outcomes for consumer brands, why tangled data is the strongest moat against the frontier labs, how AI agents could weaken wholesale marketplaces, why brands need websites AI agents can read, why small brands chasing big box stores often abandon their most profitab
Nov. 5, 2026
Infinite Loops Classics | Mike Maples, Jr. — How To Become a Pattern-Breaking Founder
This week, we're re-upping one of my favorite episodes from the archives: my chat with Mike Maples, Jr., from September 2024. Normal scheduling will resume next week. Enjoy! *** Mike Maples, Jr., co-founding partner of the VC firm Floodgate, is the veteran seed investor behind some of the 21st century's great success stories, including Twitter, Twitch, and Applied Intuition. His book, Pattern Breakers (co-authored with Peter Ziebelman), articulates a new model of foundership, one built on the
334
Oct. 29, 2026
Tren Griffin - How To Write, Publish & Sell A Book In The AI Era (Ep. 334)
Tren Griffin, author of Charlie Munger: The Complete Investor and the 25iq blog, joins Jim O'Shaughnessy on Infinite Loops to talk about why writing a book is rarely about money, how AI is reshaping writing and publishing, why every author is really starting a business, how to build a book in public, the Charlie Munger lesson that changed his life during the dot-com boom, whether serious reading is really dying, and how to find a passion worth following. Show Notes Tren Griffin & Jim O'Shaughn
333
Oct. 22, 2026
Spencer Greenberg - 106 Self-Help Books Distilled Into 12 Strategies (Ep. 333)
Spencer Greenberg, mathematician, founder of Clearer Thinking, and co-author of The 12 Levers, joins Jim O'Shaughnessy on Infinite Loops to talk about which self-help techniques hold up to evidence, why memory works like autocomplete, how exposure therapy cured his lifelong social anxiety, why the law of attraction can backfire, how to design hiring interviews that predict performance, and what his team found replicating new studies from top psychology journals. Show Notes Spencer Greenberg &
332
Oct. 15, 2026
Ed William - Writing A Biography That Reads Like Fiction (Ep. 332)
Pre-order No One's Coming to Save You today: https://infinitebooks.com/products/no-ones-coming-to-save-you David Rhoiney was five when his father walked out, forcing David to become the "man of the house." Compton, Oakland, Long Beach: no matter where they turned, fear and hunger waited. Long nights in the homeless shelter. Drive-by shootings. Strangers in overalls dragging his mother away. As his world collapsed, David lost hope. No one was coming to save him. But he could save himself. When
331
Oct. 8, 2026
Emma Camp - Why Gen Z Is Afraid of Rejection: Dating, Therapy Culture & Housing (Ep. 331)
Emma Camp, senior newsletter editor at The Wall Street Journal's Free Expression, joins Jim O'Shaughnessy on Infinite Loops to talk about why Gen Z is dating less and spending more time alone, how therapy culture and helicopter parenting can turn growing pains into permanent labels, why the fix for the housing shortage is more housing, and why she invites everyone she's met to every party. She also previews her forthcoming essay collection on Gen Z and risk aversion. Show Notes Emma Camp & Jim
330
Oct. 1, 2026
Julie Fredrickson - The Right to Compute: AI Agents, Nuclear Power & Human Data (Ep. 330)
Julie Fredrickson, Managing Partner of Chaotic Capital, rejoins Jim O'Shaughnessy on Infinite Loops to talk about Montana's Right to Compute Act, why verified human data may become one of the most valuable assets online, what nuclear power and the encryption wars teach about regulating AI, why chatbots keep recommending the same sunscreen, and what 2,089 days of daily public writing taught her about being wrong. It is her second Infinite Loops conversation, three years after Episode 181. Show N
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
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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.