Infinite Loops

Fresh off releasing one of the most beautiful hardcover books we've ever seen, Paul Millerd returns alongside Infinite Books CEO Jimmy Soni for a deep dive into the broken incentives of traditional publishing, why the industry breeds "cynicism at scale," and how the internet is powering a second Renaissance for creators.
We get into what it means to build a creative life on your own terms, the Taoist approach to growing an audience, how to navigate financial uncertainty while raising a family, and why seemingly boring daily routines fuel extraordinary creative work.
I hope you enjoy this conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, "Hmm, that's interesting!," check out our Substack.
Important Links:
Paul's Website
Paul's X
Paul's Substack
The Pathless Path Premium Hardcover
Good Work
Infinite Books
Jimmy's X
Show Notes:
Make Books Beautiful
Why Paul Turned Down Penguin
Creative Work Should Inspire More Creative Work
Cynicism at Scale in the Publishing Industry
The Long Tail of Book Marketing
Why Paul Launched a Hardcover Pathless Path
Dre, Spielberg & Chappelle: Design Your Own System
Playing Probabilistic Games
How to Live a Pathless Life With a Family
The Creative Perks of a Boring Life
"What If I Do Less?"
Books Are Win-Win
Paul as World Emperor
Books Mentioned:
The Pathless Path: Imagining a New Story for Work and Life; by Paul Millerd
Good Work: Reclaiming Your Inner Ambition; by Paul Millerd
The Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley; by Jimmy Soni
What Works on Wall Street; by Jim O'Shaughnessy
How to Retire Rich; by Jim O'Shaughnessy
Walden (Steel Brothers reimagined edition); by Henry David Thoreau
Why Greatness Cannot Be Planned: The Myth of the Objective; by Kenneth O. Stanley
The Work Is the Win; by Billy Oppenheimer (forthcoming)
Reclaim the Book; by Paul Millerd (essay)
Tiny Experiments: How to Live Freely in a Goal-Obsessed World; by Anne-Laure Le Cunff
The Chronic; by Dr. Dre (album)
Tao Te Ching (Dao De Jing); by Lao Tzu

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