February 19, 2026
Author Paul Millerd discusses rejecting a traditional publishing deal to forge a 'Pathless Path,' embracing creative freedom and entrepreneurship.
February 12, 2026
Packy McCormick shares how writing clarifies thinking and builds companies. He discusses the power of optimism, embracing failure, and innovation.
February 5, 2026
Jean-Marc Daecius on being the last human chief of staff, using AI to eliminate corporate bullshit, transform agriculture, and foster creativity.
January 29, 2026
How an ex-Yale lawyer built the Queens Night Market, a joyful civic hack championing diversity, affordability, and community entrepreneurship.
January 22, 2026
Cliff Asness on surviving market manias, the psychology of loss, private equity's "volatility laundering," and adapting quant models to AI.
January 15, 2026
Tomás Pueyo on how geography shapes history, our flawed intuition for exponential change, and how AI will radically reshape democracy and work.
January 8, 2026
Annie Duke explains why we misinterpret data. We jump from description to flawed explanation. Learn to interrogate info & think probabilistically.
January 1, 2026
Reinventing publishing: A deep dive into fixing a broken industry with A/B testing, targeted marketing, and author-centric strategies.
December 25, 2025
Guy Spear & Jim O'Shaughnessy on the inner journey, cultural nuances between the US & Europe, and why writing down your goals is magical.
December 11, 2025
Artist Marc Dennis discusses his unique blend of 17th-century technique with modern humor, the power of meta-narratives, and going all-in.
December 4, 2025
Art advisor Ariel Meyerowitz demystifies collecting. Focus on personal connection over investment, immerse yourself in galleries, and trust your gut.
November 27, 2025
Artisan cheese expert Adam Moskowitz discusses his journey from rapper to cheese guru, championing passion, purpose, and creative entrepreneurship.
November 20, 2025
Todd Rose's journey from dropout to Harvard prof reveals why rejecting the 'average' and embracing individuality is key to fulfillment and success.
November 13, 2025
Treat life as a video game to build agency. Break goals into levels, optimize your metrics, and cultivate curiosity to win.
November 6, 2025
Author Mike Perry joins Jim O'Shaughnessy to discuss writing, Midwestern pragmatism, unlikely mentors, and why kindness is not weakness.
October 23, 2025
Elle Griffin and Jim O'Shaughnessy explore rebuilding the middle class via broad-based ownership, new capitalism models, and tax incentives.
October 9, 2025
In the age of AI, startups must operate as 'experimentation machines,' where 10x founders leverage AI to compress learning cycles and win on velocity.
October 2, 2025
America's 'lawyerly society' excels at blocking, while China's 'engineering state' excels at building. How can the US build again?
