Show Notes
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
More from Infinite Loops
Spencer Greenberg, mathematician, founder of Clearer Thinking, and co-author of The 12 Levers, joins Jim O'Shaughnessy on Infinite Loops to talk about which self-help techniques hold up to evidence, why memory works like autocomplete, how exposure therapy cured his lifelong social anxiety, why the law of attraction can backfire, how to design hiring interviews that predict performance, and what his team found replicating new studies from top psychology journals. Show Notes Spencer Greenberg & Jim O'Shaughnessy Spencer Greenberg: Mathematician and entrepreneur, founder of ClearerThinking.org and Spark Wave, and host of the Clearer Thinking podcast. Clearer Thinking
Pre-order No One's Coming to Save You today: https://infinitebooks.com/products/no-ones-coming-to-save-you David Rhoiney was five when his father walked out, forcing David to become the "man of the house." Compton, Oakland, Long Beach: no matter where they turned, fear and hunger waited. Long nights in the homeless shelter. Drive-by shootings. Strangers in overalls dragging his mother away. As his world collapsed, David lost hope. No one was coming to save him. But he could save himself. When basketball threw him a lifeline, David grabbed it. So began an unlikely journey, one that carried him from living in a Volkswagen Jetta onto the courts of Division I, through the halls of the Naval Academy, into the corridors of national intelligence, and under the watchtowers of Guantánamo Bay. At last, scalpel in hand, David reached the operating room, where he could become the man his family needed. Ed William, a former lawyer, spent several days interviewing David and spoke to dozens of people from his life. The result is Ed's first book, No One's Coming to Save You: The Escape of David Rhoiney, out from Infinite Books on 8 December and now available for pre-order: https://infinitebooks.com/products/no-ones-coming-to-save-you "A powerful and deeply moving account of a boy forced to grow up too soon and the man he fought to become." —Rob Henderson, bestselling author of Troubled Ed joins Jim to discuss: The time David was forced to fight a schoolyard bully in front of his family.
Emma Camp, senior newsletter editor at The Wall Street Journal's Free Expression, joins Jim O'Shaughnessy on Infinite Loops to talk about why Gen Z is dating less and spending more time alone, how therapy culture and helicopter parenting can turn growing pains into permanent labels, why the fix for the housing shortage is more housing, and why she invites everyone she's met to every party. She also previews her forthcoming essay collection on Gen Z and risk aversion. Show Notes Emma Camp & Jim O'Shaughnessy Emma Camp: Senior newsletter editor at Free Expression, The Wall Street Journal's opinion newsletter, and former Reason magazine editor. Read Free Expression
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
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