Infinite Loops

Polina Pompliano, newsletter writer and author of Hidden Genius who profiles high performers, shares patterns behind top thinkers. She discusses mental models like creativity, practical rationality, and betting on yourself. Conversations cover profiling techniques, media bias, storytelling’s role in empathy, and how identity and hidden motivations shape success.

Adam Mastroianni, experimental psychologist and cultural critic, explores why creativity feels like it is fading. He discusses rising cultural sameness, the decline of deviant risk-taking, and how prosperity and the internet reshape innovation. He proposes small, rule-light institutions like 'science houses' and practical ways for outsiders to do and replicate science.

Arkady Kulik, a venture capitalist and trained physicist focused on deep tech and founder psychology. He talks about resilience as adaptability, how self-deception undermines founders, the importance of hard conversations and ownership, and signals—like rituals and hiring choices—that reveal true motivation.

Angus Fletcher, professor and storytelling researcher who wrote Primal Intelligence and consults for U.S. Army Special Operations, argues humans think in actions and stories, not like computers. He explores how movement and walking boost creativity. He discusses training imagination for real-world decision making, the limits of standardized schooling, and why adventurous, possibility-driven thinking matters.

Jonathan Tepper, author and investor who grew up in Madrid where his missionary parents started a drug rehab, recounts a childhood among recovering addicts. He discusses growing up in San Blas, the rise of a grassroots rehab movement, the arrival of AIDS, writing and revising his memoir, and how those experiences shaped his outlook on grief, empathy, and investing.

Jimmy Soni, writer, publisher, and CEO of Infinite Books, who rethinks publishing models. Paul Millerd, author of The Pathless Path, who experiments with self-publishing and creative living. They probe broken incentives in traditional publishing. They discuss building durable creative careers, designing beautiful hardcovers, online audience-building, balancing family finances, and why boring routines fuel big creative work.

Packy McCormick, writer and founder of Not Boring known for long-form tech and investing essays. He explains how writing forces clearer thinking. They discuss turning conversations into paid essays, recovering from public mistakes, why rational optimism follows meeting builders, AI’s impact on creative work, and investing in hard-tech and vertical integration.

Jean-Marc Dacius, artist-programmer and OSV's Chief of Staff who builds AI-first workflows. He explains automating email and protecting deep work. They explore AI-driven publishing experiments, agriculture with robotic food forests, personalized recommendations over ads, and AI curators that cut cultural spam.

John Wang, founder of the Queens Night Market, left a legal career to build a $6-capped, culturally diverse food market. He discusses starting the market from childhood market memories, the two-vendor-per-country curation, how it incubates micro businesses, operational realities like sales variability, and the challenge of keeping food affordable amid rising costs.

Cliff Asness, co-founder and chief investment officer at AQR Capital Management, shares his insights into market psychology and the nature of investing. He explains how losses affect behavior more than wins and draws comparisons between the dot-com bubble and today's meme stock frenzy. They discuss the risks of gamified trading, the often misunderstood use of leverage, and how modern finance resembles gambling. Cliff also highlights the impact of machine learning in quant investing, cautioning about its opacity and limitations in spotting bubbles.