Latest Episode 
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!
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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
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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
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Brent Seales - How AI Is Reading the Only Library That Survived Antiquity (Ep. 328)
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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.