

Infinite Loops
Jim O'Shaughnessy
Every Thursday, join Jim O'Shaughnessy and his favorite people as they arm you with the tools & fresh perspectives required to upgrade your HumanOS and thrive in our messy, probabilistic world.
Visit our Substack at newsletter.osv.llc for full transcripts, highlights, weekly doses of timeless wisdom, and a bounty of other goodies designed to make you go, "Hmm that's interesting!"
Visit our Substack at newsletter.osv.llc for full transcripts, highlights, weekly doses of timeless wisdom, and a bounty of other goodies designed to make you go, "Hmm that's interesting!"
Episodes
Mentioned books
Jan 29, 2026 • 1h 20min
John Wang - The Man Who Built The Queens Night Market (Ep. 299)
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.

59 snips
Jan 22, 2026 • 1h 58min
Cliff Asness - Surviving the Meme Stock Bubble (Ep. 298)
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.
66 snips
Jan 15, 2026 • 1h 39min
Tomás Pueyo — Explaining the World Through Geography, History and Data (EP. 297)
Tomás Pueyo, a French-Spanish engineer and writer known for his insightful essays on COVID-19, dives deep into how geography and data shape our lives. He explores why humans struggle with exponential change and how this affects decision-making. Pueyo critiques the limitations of modern democracies and suggests innovative governance methods. He discusses geographical advantages that favor nations like the U.S., and proposes practical solutions like air conditioning to improve development. His predictions about the future of politics also highlight the intersection of social media and citizen engagement.

172 snips
Jan 8, 2026 • 1h 45min
Annie Duke — Why We Make the Wrong Decisions (Ep. 296)
Annie Duke, a former professional poker player and decision strategist, dives deep into the art of decision-making. She explains how misinterpretation can be riskier than misinformation and emphasizes the importance of distinguishing between true data and misleading conclusions. Annie shares insights on teaching probabilistic thinking, the pitfalls of deterministic reasoning, and how to ask the right questions about data. She also discusses the role of luck versus decision quality, urging listeners to adopt decision hygiene practices for better outcomes.
45 snips
Jan 1, 2026 • 1h 37min
Jimmy Soni — The Publishing System is Broken (EP. 295)
Jimmy Soni, CEO of Infinite Books and author, dives deep into the broken systems of traditional publishing while highlighting his upcoming book on Kobe Bryant. He discusses the importance of A/B testing in cover designs, arguing that authors now hold unprecedented leverage in the industry. Soni emphasizes the shift toward data-driven marketing and the need for long-term strategies rather than a quick promotional push. He also encourages writers to embrace their creativity across genres and aims to transform authors into millionaires.

66 snips
Dec 25, 2025 • 2h 2min
Guy Spier — Wealth, Wisdom & Enlightenment (Infinite Loops CLASSICS)
Guy Spier, a value investor behind the Aquamarine Fund and author of The Education of a Value Investor, dives into fascinating contrasts between life in New York, Zurich, and Paris. He reflects on the vibrant street culture of NYC and its dark nightlife, shares insights on Swiss democracy, and discusses the intricacies of the British class system. Spier also opens up about his experiences with psychedelics, the art of making luck, and the mind-body connection in healing, all while advocating for a blend of wisdom and wealth in personal development.
13 snips
Dec 17, 2025 • 1h 35min
Vik Muniz — The Art of Perception (EP.294)
Vik Muniz, a Brazilian-born visual artist celebrated for his unconventional photographic works and the documentary 'Wasteland', discusses the profound role of art in shaping human experience. He argues that art may be humanity's most significant invention after fire, emphasizing that a piece of art is only complete when viewers engage with it. Vik shares his journey from a São Paulo favela to major museums, explores the challenges of modern representation, and highlights art's potential to drive social change and foster empathy.
29 snips
Dec 11, 2025 • 1h 59min
Marc Dennis — Painting the Punchline (EP.293)
Marc Dennis, a contemporary painter known for his blend of hyper-realism and humor, shares his unconventional journey from a tenured professor to a full-time artist. He discusses starting a forest fire as a child, the role of humor in survival, and the difference between perception and reality. Marc explores his artistic intent, creating narratives within his paintings, and the importance of self-love in one's creative journey. Engagingly, he highlights the impact of childhood inspirations and offers insights on identity through his work, including the provocative 'Three Jews Walk Into a Bar' series.
10 snips
Dec 4, 2025 • 1h 36min
Ariel Meyerowitz — Navigating the Art World (EP. 292)
Ariel Meyerowitz, an art advisor from New York, guides collectors in navigating the complex art world. She emphasizes starting with what you love to develop a personal collection. Ariel discusses how galleries can feel intimidating and the influence of social dynamics on art collecting. She shares insights on the emotional benefits of living with art and advises leaving empty wall space for a calming environment. Balancing taste and investment, she encourages selecting art that resonates personally, enhancing overall well-being.
27 snips
Nov 27, 2025 • 1h 14min
Adam Moskowitz — The Way of the Cheesemonger (EP.291)
Adam Moskowitz, the King of cheese and host of A Cheese Course, shares his captivating journey from a failed rap career to becoming a leading figure in the artisan cheese world. He discusses how cheese reignited his purpose during recovery, the fascinating dynamics of American artisan cheesemaking, and the emotional connections people have with cheese. Adam emphasizes the importance of cognitive diversity in creativity and delves into the art of storytelling through cheese, all while tasting various delightful cheeses and sharing his innovative ventures.


