Derek Sivers - Living Many Lives: Parenting, Moving Countries & AI (Ep. 329)

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