Packy McCormick is one of the most thoughtful writers in tech and investing.

In this episode of Infinite Loops, we talk about why writing is still the most powerful way to think clearly, how optimism becomes rational when you spend time with people actually building things, and what happens when the internet punishes you for being early and wrong.

Important Links:

Packy McCormick on Optimism: https://www.notboring.co/p/optimism

The Internet Contrarian: https://www.osam.com/pdfs/research/The%20Internet%20Contrarian.pdf

Elliot Herschberg on GitLab Founder and Cancer: https://www.notboring.co/p/the-builder-cancer-problem

Ben Thompson's Aggregation Theory: https://stratechery.com/aggregation-theory/

What happens when you design a company assuming AI should do everything it possibly can?

Jean-Marc Daecius, OSV's Chief of Staff, joins Infinite Loops to explain what it means to be "AI first" — and why he believes he may be the company's last human chief of staff.

The conversation explores how AI can remove meaningless cognitive load, protect deep work, and unlock creative leverage — from reshuffling priorities and filtering email, to reinventing publishing, agriculture, education, and even how we discover books, movies, and ideas.

Important links:

Substack: https://newsletter.osv.llc/

Jean Marc's "The Future of Food": https://newsletter.osv.llc/p/the-future-of-food

The Queens Night Market is one of New York City's most beloved institutions — but it was never supposed to last more than a year.

John Wang, founder of the Queens Night Market, joins Infinite Loops to explain how a side project with a "terrible business model" unexpectedly became one of the most celebrated food markets in the world. From leaving a traditional legal career to imposing a strict price cap in one of the most expensive cities on earth, John shares how the market evolved into a cultural institution representing more than 100 countries through food.

Important links:

Substack: https://newsletter.osv.llc/

Queens Night Market: https://queensnightmarket.com/

Cliff Asness — co-founder, managing principal, and chief investment officer at AQR Capital Management — is one of the most influential quantitative investors of the last 30 years. He's also one of the most candid.

In this conversation, Cliff joins Infinite Loops to talk about why losses hurt more than wins, how bubbles form, why modern investing increasingly resembles gambling, and what the dot-com era can teach us about today's markets.

Important links:

Substack: https://newsletter.osv.llc/

Cliff's Perspectives: https://www.aqr.com/Insights/Perspectives

Cliff's X: https://x.com/CliffordAsness

Tomás Pueyo, the French-Spanish engineer and writer behind the successful "Uncharted Territories" Substack, joins us to dismantle the invisible forces that shape our history and future.

We cover why humans are horrible at understanding exponential change, the geographical advantages of the U.S, why the Luddites might have been right, the "social media politician" of the future, why education is mostly signaling, and how air conditioning and mosquito eradication could change the destiny of nations.

Important Links:

• Tomas's Website
• X / Twitter
• LinkedIn
• Substack: Uncharted Territories
• YouTube Channel

Annie Duke — former professional poker player, decision strategist, and bestselling author — joins us for a deep conversation about why smart people so often make bad decisions.

Annie explains why misinterpretation is more dangerous than misinformation, why data is often true but misleading, and how our brains are wired for certainty in a probabilistic world. From real-world media examples to investing, health decisions, and AI-generated insights, this episode explores how explanations feel satisfying — even when they're wrong.

Important links:

Substack: https://newsletter.osv.llc/

Annie's website: https://www.annieduke.com/

Jimmy Soni, CEO and editor in chief of Infinite Books, is back on Infinite Loops. We discuss what's broken in traditional publishing and how we're fixing it. We also dig into Jimmy's forthcoming book on Kobe Bryant, why the world needs more "problem authors," and why our goal is to make our authors millionaires.

We explore why most industries optimize for prestige instead of outcomes, how digital distribution has reshaped attention, and why authors — and creators more broadly — have more leverage than they realize.

Important Links:

Infinite Books: https://www.infinitebooks.com/

Jimmy's X: https://x.com/jimmyasoni

Substack: https://newsletter.osv.llc/

Books Mentioned:

The Founders by Jimmy Soni

A Mind at Play by Jimmy Soni

The Dao of Kobe by Jimmy Soni (Upcoming)

What Works on Wall Street by Jim O'Shaughnessy

Invest Like the Best by Jim O'Shaughnessy

How to Retire Rich by Jim O'Shaughnessy

The 4-Hour Workweek by Tim Ferriss

The Almanac of Naval Ravikant by Eric Jorgenson (transcribed as "Naval Akan")

Dispatches from Grief (Upcoming)

Mamba Mentality by Kobe Bryant

Slow Horses by Mick Herron

The Boys in the Boat by Daniel James Brown

Happy Holidays! We're taking a short break from new episodes this week so you can focus on finishing that Christmas dinner. We'll be back next Thursday with something new. In the meantime, why not tuck into this conversation with Guy Spier from January 2024, which remains one of my favorites. Enjoy!

_________________

Guy Spier runs the Aquamarine Fund, an "investment partnership closely modeled on the original Buffet Partnerships." He is also a podcast host, YouTube creator, author of The Education of a Value Investor and the host of the annual investment gathering VALUEx. He describes his life's project as "a quest for wealth, wisdom and enlightenment."

Guy joins the show to discuss the differences between Switzerland and the US, how to unlock the British class system, what he learned from Warren Buffett, and MUCH more!

Important Links:

• Guy's Website
• Guy's Twitter
• Guy's YouTube Channel
• 3Blue1Brown (YouTube Channel)
• Numberphile (YouTube Channel)

Show Notes:

• The Differences Between New York, Switzerland & Paris
• Exploring the Dark Underbelly of New York Nightlife
• Psychedelics, Guns & Regulation
• The Advantages of Swiss Democracy
• Don't Short the United States
• The Branding Skill of the Royal Family
• Unlocking the Rules of the Class System
• Life Paths & Premeditation
• Luck, Opportunity & Non-Canonical Science
• Jim's Music Taste
• Mathematical Shenanigans
• Guy as Emperor of the World
• MORE!

Books Mentioned:

• How to Change Your Mind: What the New Science of Psychedelics Teaches Us about Consciousness, Dying, Addiction, Depression, and Transcendence; by Michael Pollan
• The Hypomanic Edge: The Link Between (a Little) Craziness and (a Lot Of) Success in America; by John Gartner
• Write It Down, Make It Happen: Knowing What You Want and Getting It; by Henriette Anne Klauser
• Invest Like The Best; by Jim O'Shaughnessy
• Outside, the Sky is Blue: The story of a family told with searing honesty, humour and love; by Christina Patterson