Tim Ferriss

Derek Sivers on Developing Confidence, Finding Happiness, and Saying No to Millions (#125)

The tim Ferriss Show with Derek Sivers

“To me, ‘busy’ implies that the person is out of control of their life.”
— Derek Sivers

Derek Sivers (@sivers) is one of my favorite humans, and I call him often for advice. Think of him as a philosopher-king programmer, master teacher, and merry prankster.

Originally a professional musician and circus clown, Derek created CD Baby in 1998. It became the largest seller of independent music online, with $100 million in sales for 150,000 musicians.

In 2008, Derek sold CD Baby for $22 million, giving the proceeds to a charitable trust for music education. He is a frequent speaker at the TED Conference, with more than 5 million views of his talks. Since 2011, he has published 34 books, including Anything You Want, which I’ve personally read 10+ times.

Enjoy!

Listen to it on Apple Podcasts, on Spotify, or wherever you get your podcasts. You can find the transcript of this episode here. Transcripts of all episodes can be found here.

Derek Sivers on Developing Confidence, Finding Happiness, and Saying No to Millions (#125)

Want to hear another podcast from a tech entrepreneur who built and sold a multi-million dollar company? Listen to my conversation with Bryan Johnson. In this episode, we discuss his path to building a business worth $800 million:

#81: The Rags to Riches Philosopher: Bryan Johnson's Path to $800 Million

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QUESTION(S) OF THE DAY: In this episode, Derek discusses how he deconstructs the ideas from books into useful “do this” style directives. If you were to write a directive based on lessons from this podcast, what would it be?  Please let me know in the comments.

Scroll below for links and show notes…

Enjoy!

Selected Links from the Episode

Show Notes

  • Derek Sivers, the leader of the circus [8:56]
  • A framework for developing confidence [15:41]
  • How Derek Sivers graduated from the Berklee School of Music in two years [19:26]
  • Lessons learned from the Santa Monica bike path [28:31]
  • How CD Baby came to be [34:51]
  • The co-op business model [38:36]
  • How one e-mail helped make CD Baby a remarkable company [41:36]
  • How Derek Sivers responded to those seeking to invest in CD Baby during the dot-com bubble [46:01]
  • On his relationship with money and saying “no” to millions [49:06]
  • The origins of the HELL YEAH! Or No. [57:06]
  • Discussing the Now Now Now project [1:01:21]
  • What inspired the automation of CD Baby [1:03:41]
  • Derek Sivers’s book consumption habits and creating directives [1:12:36]
  • Most gifted books [1:46:36]
  • What purchase of $100 or less has most positively affected your life? [1:49:16]
  • What Derek Sivers listens to when working out [1:51:11]
  • If you could have one billboard anywhere, what would it say and why? [1:52:46]
  • Advice for your thirty-year-old self [1:54:36]

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