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/