Infinite Loops

Derek Sivers, author, entrepreneur, TED speaker, and founder of CD Baby, joins Jim O'Shaughnessy on Infinite Loops to talk about parenting a teenager who is ready to leave home, why he moves countries on purpose and plans to live in Bangalore and Shanghai next, the certainty slider, and how AI can make you less dependent on big tech, not more. It is his first podcast after more than a year of saying no to every request.
Show Notes
Derek Sivers & Jim O'Shaughnessy
Derek Sivers: Author, entrepreneur, and TED speaker, and founder of CD Baby, once the largest seller of independent music online. Derek's website

Derek on X: Where Derek shares his writing. Follow Derek on X

Derek's TED talks: Including "How to Start a Movement," his most popular talk. Watch Derek's talks

Jim O'Shaughnessy: Host of Infinite Loops, founder and CEO of O'Shaughnessy Ventures, and author of the New York Times bestseller What Works on Wall Street. Follow Jim on X

Full transcripts: Transcripts and highlights from every Infinite Loops conversation. OSV newsletter

Derek's Books & Projects
Useful Not True: Derek's book on skepticism and choosing beliefs because they are useful, not because they are true. Useful Not True

How to Live: 27 conflicting answers on how to live, which Derek calls his masterpiece. How to Live

Hell Yeah or No: Simple mental models for deciding what's worth doing. Hell Yeah or No

Anything You Want: Derek's bestselling book of 40 lessons from starting, building, and selling CD Baby. Anything You Want

Tech Independence: Step-by-step instructions and a setup script for running your own server and email instead of depending on big tech. Tech Independence

Books & Ideas Mentioned
Personal Development for Smart People by Steve Pavlina: The book whose idea about seeking surprise sent Derek around the world. Derek's notes

China's World View by David Daokui Li: Derek's pick for understanding the Chinese government's point of view. Derek's notes

Maverick by Ricardo Semler: The book behind Derek's short-lived profit-sharing plan at CD Baby. Maverick

Why Greatness Cannot Be Planned by Kenneth O. Stanley and Joel Lehman: Jim's reference on why new vantage points change where you want to go. Why Greatness Cannot Be Planned

The Beginning of Infinity by David Deutsch: The book Jim calls a definitive look at how he sees the world. The Beginning of Infinity

Nothing & Everything by Val N. Tine: The book on nihilism Derek recommends, with his advice to read only the first half. Derek's notes

Dr. Brent Seales, computer scientist at the University of Kentucky and co-founder of the Vesuvius Challenge, joins guest host Nick Tawil on Infinite Loops to explain how synchrotron X-rays and machine learning are making unopenable ancient scrolls readable, and why the work has now shifted from engineering to reading. This summer in Naples, his team presented results from three sealed Herculaneum scrolls, including the first read end to end.
Show Notes
Brent Seales & Nick Tawil
Dr. Brent Seales: Stanley and Karen Pigman Chair of Heritage Science at the University of Kentucky and co-founder of the Vesuvius Challenge. Brent Seales at the University of Kentucky

Vesuvius Challenge: The open competition Brent co-founded with Nat Friedman and Daniel Gross to read the carbonized Herculaneum scrolls. Vesuvius Challenge

The June 2026 breakthrough: The announcement in Naples of new texts, titles, and authors recovered from the scrolls. The day the Herculaneum scrolls began speaking again

Nick Tawil: Guest host and head of Infinite Films. Connect with Nick

The Scrolls & the Discoveries
The Herculaneum library: Roughly 1,800 scrolls carbonized by Mount Vesuvius in 79 AD, the only library from antiquity that survived. Vesuvius Challenge: the scrolls

Philodemus, On Gods, Book 8: A title and author read from a sealed scroll, establishing that the work ran to at least eight books. CNN on the discovery

The En-Gedi scroll: The burned Torah scroll Brent's team read without opening, containing one of the oldest known copies of the first two chapters of Leviticus in the canonical Masoretic text. Vesuvius Challenge on En-Gedi

The $1 million prize: The open competition to fully unroll and read one of the remaining sealed scrolls. Current prizes

Films & Coverage Mentioned
The Vesuvius Challenge: The upcoming documentary from Infinite Films and Scott Free, in partnership with Calliope Pictures, narrated by Guy Pearce. Deadline announcement

Secrets of the Dead: The Herculaneum Scrolls: The PBS episode following Brent inside the Villa of the Papyri. Watch on PBS

Cost of Glory: The Roman history podcast Brent and Nick reference while discussing what might still be buried. Cost of Glory

Dead Poets Society: The source of "carpe diem," one of the two ideas Brent would give the world. Dead Poets Society

Ryan Resch, former Assistant General Manager and VP of Basketball Operations for the Phoenix Suns, joins guest host Jimmy Soni on Infinite Loops to explore what happens to competitive advantage when every team has the same data, and why the real edge comes from the questions you ask of it. Ryan traces his path from a cold email to Baylor coach Scott Drew to nearly a decade in the Suns front office and his current work leading data and AI in private equity.
Show Notes
Ryan Resch & Jimmy Soni
Ryan Resch on LinkedIn: Former Suns Assistant GM and VP of Basketball Operations, now leading data and AI at 1949 Capital Partners. Connect with Ryan

Beyond the Dashboard: Ryan's Harvard Business School interview with Boris Groysberg on optical tracking, dashboards, and AI. Read the interview

Shore Capital Partners: The private equity firm founded by Justin Ishbia, where Ryan helped roll out AI tools. Shore Capital Partners

Jimmy Soni on X: Guest host, bestselling author, and editor-in-chief of Infinite Books. Connect with Jimmy

Teams, Leaders & Data Discussed
James Jones: The 2020-21 NBA Executive of the Year, whose Suns rebuild started with raising the floor. Executive of the Year

Scott Drew: The Baylor head coach who answered Ryan's cold email and later had him build lineup data. Scott Drew at Baylor

SportVU: The camera system that brought optical tracking to every NBA arena in 2013-14. SportVU and the NBA

Second Spectrum: The machine learning platform that turned tracking data into tagged plays and dashboards teams across the league use. Second Spectrum and the NBA

Hawk-Eye: Sony's 3D tracking system, used across the NBA since 2023-24. Hawk-Eye and the NBA

Books, Shows & AI Tools Mentioned
Moneyball by Michael Lewis: The 2003 book on the Oakland A's that frames how analytics moved from baseball into basketball. Moneyball

Hyperion by Dan Simmons: The first book in the sci-fi series Ryan is reading, and a window into how earlier writers imagined AI. Hyperion

The Founders by Jimmy Soni: Jimmy's history of PayPal and Silicon Valley, which Ryan handed out at the Suns. The Founders

TBPN and Dwarkesh Podcast: Two of the tech shows Ryan wishes he had more hours for. TBPN | Dwarkesh Podcast

Claude Code and Codex: The coding agents Ryan uses in a workspace built for agents to read. Claude Code | Codex

Brian Chau, founder of Effort News, joins Infinite Loops to explore how AI could fundamentally reshape investigative journalism—not by writing articles, but by searching, analyzing, and connecting millions of legal, financial, and government records that humans could never examine manually.

Show Notes


Brian Chau & Effort News
Effort News — Brian Chau's document-led investigative journalism publication, using AI to search and analyze large datasets while keeping the reporting and final writing human-reviewed. Effort News
About Effort News — More on Brian's approach to AI-assisted investigative reporting and the publication's editorial principles. About Effort News
Effort's Null Results — Investigations where Effort searched the available evidence but found no newsworthy result. Null Results
Brian Chau on X — @brianchau57. Follow Brian on X
Investigations Discussed
The $1.2B Refugee Services Program that Funds Pro-Asylum Religious Groups — Effort's investigation into federal refugee-resettlement grants and the organizations receiving them. Read the investigation
The 19th-Century Family Fortunes Funding Degrowth — Effort's investigation tracing funding for Partners for a New Economy through donor-side disclosures and the Swiss Philanthropy Foundation. Read the investigation
Partners for a New Economy (P4NE) — The philanthropic fund discussed in Brian's explanation of tracing obscured donor funding. P4NE
Swiss Philanthropy Foundation — The organization that hosts P4NE's pooled philanthropic fund. Swiss Philanthropy Foundation on P4NE
How to Go Viral on the New X Algorithm — Effort's analysis of X's open-source recommendation algorithm, which Jim references near the end of the conversation. Read the investigation
Freedom Fuel Network — Brian discusses Effort's then-upcoming investigation into the mysterious network of discounted gas stations in Pennsylvania and New Jersey. Effort has since published its findings, Who Supplies Freedom Fuel?, on its site. Effort News
Books, Essays & Projects Mentioned
Vesuvius Challenge — The project using machine learning, computer vision, and advanced scanning to read carbonized scrolls from Herculaneum without physically opening them. Vesuvius Challenge
The Camp of the Saints — Jean Raspail — The 1973 novel Brian and Jim discuss while talking about how AI-generated writing has changed the way readers perceive older literary styles. The Camp of the Saints
Influence — Robert Cialdini — Cialdini's work on persuasion, referenced during the discussion of why large language models can be effective persuaders. Influence: Science and Practice
What the Tortoise Said to Achilles — Lewis Carroll — Carroll's 1895 dialogue about logic and infinite regress, discussed alongside Agrippa's trilemma. Read the essay
On Liberty — John Stuart Mill — Mill's defense of liberty and free expression, which Brian critiques during the episode's discussion of classical liberalism, consensus, and free speech. Read On Liberty

We're digging out some of our favorite conversations from the archive. This one is from January 2025, with Julian Gough. Enjoy.

Julian Gough sums up his career as follows: "I just sit in my room and write."
Well, I think being an acclaimed children's author, novelist, stage playwright, poet and top-ten Irish musician is a little more impressive than he's letting on…
Oh, and I didn't even mention that he wrote the ending to the computer game Minecraft!
His current project, The Egg and The Rock, puts all of this to shame. This book, which Julian is writing in public on Substack, seeks to do no less than redescribe the universe, arguing that is not some random, dead, purposeless sack of chemicals, but instead a living, evolving organism.
Julian joins me to discuss why the arc of human evolution bends towards man-made black holes, the hidden catastrophe at the heart of materialist science, the strange life of subterranean ice aliens, and MUCH more!
This was such an interesting conversation - I can't wait for you to hear it. 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:
Julian's Website
The Egg and The Rock
Julian's Twitter
Show Notes:
"I just sit in my room and write"
Why write a book in public?
Materialism & science's hidden catastrophe
"The scientific method is in conflict with human nature"
The faulty assumption at the heart of cosmology
Big bangs, supermassive black holes & Darwinian evolution: A ~30 minute masterclass in cosmological natural selection
"I'm predicting very, very large amounts of life in this universe"
The strange life of subterranean ice aliens
Could we spot man-made black holes?
Bringing consciousness into physics
Pulling back the curtain
Julian as World Emperor
MORE!
Books & Articles Mentioned:
The New Inquisition: Irrational Rationalism and the Citadel of Science; by Robert Anton Wilson
Against Method: Outline of an Anarchistic Theory of Knowledge; by Paul Feyerabend
What the Tortoise Said to Achilles; by Lewis Carroll
The Life of the Cosmos; by Lee Smolin
What Is Life? The Physical Aspect of the Living Cell; by Erwin Schrödinger
Isis Unveiled: A Master-Key to the Mysteries of Ancient and Modern Science and Theology; by Helena Petrovna Blavatsky
The Bhagavad Gita
Did the Universe evolve?; by Lee Smolin
The Great Filter - Are We Almost Past It?; by Robin Hanson