When I started this podcast more than 7 years ago, I listed Derek Sivers as my dream guest (sorry Kelly Slater). Sivers’ gift, I believe, is the willingness to question the premise of all things, delightfully, humorously, and give anyone in his orbit the choice to follow a more original path. An author of philosophy and entrepreneurship, he’s known for his surprising quotable insights, pithy succinct writing style, and commitment to minimalism. (He currently lives in a 4x8 meter house in New Zealand and is building it out slowly, room by room, just to see what he needs.) Formerly a musician, programmer, TED speaker, and circus clown, he sold his first company for $22 million and gave all the money to charity. Sivers' books (Useful, Not True, How to Live, Hell Yeah or No, Your Music and People, Anything You Want) and newest projects are at his website: sive.rs. He loves hearing from strangers and will reply to every email, so if you enjoyed this podcast, shoot him an email and let him know.

If you dig this podcast, will you please leave a short review on Apple Podcasts? It takes less than 60 seconds and makes a difference when I drop to my knees and beg hard-to-get guests on the show. I read them all. You can watch this podcast on my YouTube channel and join my newsletter on Substack. It’s glorious.

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#386 Derek Sivers on Courage, Bold Questions, & the Dangers of Chasing Status