Julie Fredrickson, Managing Partner of Chaotic Capital, rejoins Jim O'Shaughnessy on Infinite Loops to talk about Montana's Right to Compute Act, why verified human data may become one of the most valuable assets online, what nuclear power and the encryption wars teach about regulating AI, why chatbots keep recommending the same sunscreen, and what 2,089 days of daily public writing taught her about being wrong. It is her second Infinite Loops conversation, three years after Episode 181.

Show Notes

Julie Fredrickson & Jim O'Shaughnessy

• Julie Fredrickson: Managing Partner of Chaotic Capital, an early-stage venture fund, and a former founder in e-commerce and beauty. Chaotic Capital

• Julie on X: Julie's preferred way to be reached. Follow Julie on X

• Julie's daily writing: More than 2,000 consecutive days of public writing, started January 1, 2021. Read Julie's blog

• 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

Julie's Work & Projects

• Montana's Right to Compute Act: The first state law protecting people's right to own and use computers and AI tools, which Julie advocated for. Read the Right to Compute Act

• Valar Atomics: The small modular reactor company founded by Isaiah Taylor, where Julie invested. Valar Atomics

• Julie's first Infinite Loops episode: Episode 181, "Circumstances change. Humanity doesn't. Plan accordingly." Watch Episode 181

Books & Ideas Mentioned

• The Beginning of Infinity by David Deutsch: Jim's reference for why no one in 1900 could have predicted the internet. The Beginning of Infinity

• Carlota Perez: The economist whose work on technology booms and build-outs shapes Julie's view that AI is still in its invention phase. Carlota Perez

• Rainbows End by Vernor Vinge: The novel Julie cites for a future where people earn a living doing small tasks only humans can do. Rainbows End

• Snow Crash by Neal Stephenson: Julie's reference for how ideas spread like a virus through programmers. Snow Crash

• Fall; or, Dodge in Hell by Neal Stephenson: The novel Julie describes, in which Americans mourn victims of a nuclear attack that never happened. Fall; or, Dodge in Hell

• The WEIRDest People in the World by Joseph Henrich: Jim's reference on how long cultures take to adapt to new technology. The WEIRDest People in the World

• Nineteen Eighty-Four by George Orwell: Jim's starting point for cognitive security and invented history. Nineteen Eighty-Four

• From Googlebot to GPTBot: Cloudflare's report on the rise in AI crawler traffic that Julie cites. Cloudflare report

• The Vesuvius Challenge: The project reading the Herculaneum scrolls, subject of a documentary from Infinite Films. Vesuvius Challenge

• Agrippa's trilemma: Jim's reference for why chasing a claim to its source often ends in sand. Agrippa's trilemma

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

Hi everyone, Jim here. We're taking a short pause on new episodes through the end of August. In the meantime, we're digging out some of our favorite conversations from the archive. This one is from August 2023, with Dr. Julie Gurner. Enjoy.

Dr. Julie Gurner is a doctor of psychology and executive performance coach to top percentile executives, primarily in finance and technology. She is also the proprietor of the Ultra Successful newsletter, which delivers a weekly challenge pulled from global business leaders and designed to "help you unleash your power."

Dr. Gurner joins the show to discuss the merits of being unreasonable, why your business should not be your identity, why niceness is overrated, and more!

Important Links:

- Substack - https://drgurner.substack.com - Twitter - https://twitter.com/drgurner?s=21&t=kpNZMw5M-jHHMC0vAkndPg - Website - https://www.drgurner.com/consulting/

Show Notes:

0:00:00 Intro 0:01:24 Main podcast 0:02:20 Dr. Gurner's origin story 0:05:07 How forensic psychology experience can help executive coaching 0:07:11 Leaning into the 1% 0:15:23 Why psychological tests are flawed 0:19:26 The common traits of successful founders 0:29:12 High performance & bottlenecks 0:30:38 Why your business should not be your identity 0:41:01 How Dr. Gurner applies her strategies in her own life 0:44:17 Don't be nice 0:46:48 Be unreasonable 0:51:18 Social validation is not important 0:56:22 How can you improve someone's communication skills 1:01:43 How Dr. Gurner would teach executive coaching 1:03:36 The "no Plan B" mentality 1:06:48 Can high energy be detrimental? 1:10:21 How to unpack charisma 1:15:57 How to turn down work 1:20:01 Dr. Gurner's greatest satisfaction 1:22:31 How has leadership changed in the last 20 years? 1:25:40 Dr. Gurner as Empress of the World 1:31:18 End screen

Books Mentioned:

- The Art of War; by Sun Tzu

Hi everyone, Jim here. We're taking a short pause on new episodes through the end of August. In the meantime, we're digging out some of our favorite conversations from the archive. This one is from November 2022, so a few of our references (and jobs!) are out of date, but the ideas have only gotten better. Enjoy this conversation with Lulu Cheng Meservey.

Lulu Cheng Meservey is the Chief Communications Officer and Executive Vice President of Corporate Affairs at Activision Blizzard. She joins Infinite Loops to provide us with a masterclass in communications for startups. A must-listen for current and aspiring founders. Important Links:

• Lulu's Twitter • Lulu's Substack • Episode summary from Podcasts Recapped Show Notes: • Why people write hit pieces • The insurgency framework • How to access your audience's neural real estate • How to develop a spontaneous elevator pitch • Tips for becoming better at reading the room • Speak directly and take the hits • Defining business objectives • Learning from other industries • Personalising your message • Overcoming resistance to the unknown, what Christianity can teach us about comms • Escaping corporate jargon • How comms resembles rugby • Taking ownership of comms • Moving to a new model of comms • "Don't let things happen to you. Go and happen to things." Books Mentioned: • The Network State: How To Start a New Country; by Balaji S. Srinivasan • The Hero with a Thousand Faces; by Joseph Campbell

Hi everyone, Jim here. We're taking a short pause on new episodes through the end of August. In the meantime, we're digging out some of our favorite conversations from the archive. This one is from February 2023, so a few of the references have aged since (mine included), but the ideas have only gotten better. Enjoy this one with the wonderfully heretical Jesse Michels.

Jesse Michels is an investor at Thiel Capital and the creator and host of 'American Alchemy', a Youtube channel dedicated to highlighting the most heretical thinkers and ideas of our time.

He joins the show to discuss the transmission theory of consciousness, whether mushrooms are aliens, the reawakening of the Boomers and MUCH more!

Important Links:

- American Alchemy - https://www.youtube.com/@JesseMichels/about - Jesse's Twitter - https://twitter.com/alchemyamerican

Books Mentioned:

- The Half-Life of Facts: Why Everything We Know Has an Expiration Date; by Samuel Arbesman - The User Illusion: Cutting Consciousness Down to Size; by Tor Norretranders - Gödel, Escher, Bach: an Eternal Golden Braid; by Douglas Hofstadter - The Beginning of Infinity: Explanations That Transform the World; by David Deutsch - The Immortality Key : The Secret History of the Religion with No Name; by Brian C. Muraresku - The New Inquisition: Irrational Rationalism and the Citadel of Science; by Robert Anton Wilson - How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression and Transcendence; by Michael Pollan - Chaos: Charles Manson, the CIA, and the Secret History of the Sixties; by Tom O'Neill - Weird Scenes Inside the Canyon: Laurel Canyon, Covert Ops & the Dark Heart of the Hippie Dream; by David McGowan - Prometheus Rising; by Robert Anton Wilson - Quantum Psychology: How Brain Software Programs You & Your World; by Robert Anton Wilson - The Cosmic Trigger trilogy; by Robert Anton Wilson - Communion: A True Story; by Whitley Strieber

Nat Eliason joins guest host Jimmy Soni to discuss Founders School, a new high school for entrepreneurs that guarantees students will generate $1 million in gross profit by graduation or get their tuition refunded. We explore how AI is changing what teenagers can build, why traditional entrepreneurship education falls short, and what happens when we take young people seriously. Important Links: Learn more about Founders School: https://founders.school/ Read more from Nat here: https://www.nateliason.com/

Philip Howard joins Infinite Loops to explain how America's legal and regulatory system became too complicated to function effectively—and how we can rebuild it around judgment, accountability, and human agency.

We discuss why government has become unmanageable, how thousand-page rulebooks discourage individual judgment, why infrastructure projects can take decades to approve, and how public institutions end up costing more while delivering less.