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