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.


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 (stream below or right-click here  to download):

#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…


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]

People Mentioned

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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

  1. Thanks for introducing this wonderful human being into my life. Since I started listening to your podcasts almost every quest contributes something positive to my life!

    Derek has such an easy way of speaking, you can tell he a being real about everything he is saying.

    I needed this!!!

  2. My takeaway from this podcast was: Instead of writing book summaries, start writing a web of combined knowledge that can be turned into directives. We don’t think in books, we think in ideas and looking up an idea based on a book is not a great reference system. Writing summaries would just lead to leaving tonnes of files on a hard drives.

  3. Hi, Tim.

    I have been reading the 4 hour workweek in order to develop an app and also listening your podcasts, this one with Derek is my favorite so far. The “hell yeah or no” mindset its changing my life in a very positive way.
    Sadly, as you recommended on the book, I didn’t found your personal email so I will ask you trough this blog.
    My question is: What was your dream job when you were a kid and do you feel like you left any passions behind in order to be who you are today?
    I have deep interests in many things and sometimes I think it is an unreasonable number of things. I question myself if I would be able to accomplish them in just one lifetime.
    Have you ever experienced the same feeling? If so How did you managed it?

    Thank you


  4. Enjoyed this episode too. Went to view the list of books on his website to keep as a reference. At first was doubtful of credibility of the list since everything initially was a 9 out of 10. Turns out they’re sorted in descending order. He made a comment on an interview (article) somewhere about having thought of someone he hadn’t seen in years, and when he’d gotten off the plane (or into the airport)… he ran into them. I think that was the gist of it… can’t find the post now.

    Says a lot about you and the session since he’d given Tool of Titans a 4/10… and nice rapport between the two of you regardless.

  5. did anyone ever find the name of the book written by the Italian on his travels in America….? Enrico…who?