Derek Sivers on Developing Confidence, Finding Happiness, and Saying “No” to Millions
“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.
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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):
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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
Anything You Want by Derek Sivers
HELL YEAH! Or No. by Derek Sivers
Learn more about Now Now Now
The Most Successful E-mail I Ever Wrote
Watch Vanilla Sky, the movie that inspired Derek to automate CD Baby
Get Derek Sivers’s book notes
Seeking Wisdom by Peter Bevelin (Derek Sivers’s notes)
The Magic of Thinking Big by David Schwartz (Derek Sivers’s notes)
Stumbling on Happiness by Daniel Gilbert – (Derek Sivers’s notes)
The Omnivore’s Dilemma and Food Rules by Michael Pollan
Learn more about Derek Sivers’s directives project
Check out Weird or Just Different, Derek Sivers 3-minute TED Talk
A Guide to the Good Life by William Irvine (Derek Sivers’s notes)
Radical Acceptance by Tara Brach
A Geek in Japan by Hector Garcia
Au Contraire by Gilles Asselin and Ruth Mastron
Check out Chris Rock’s Top Five
What if You Didn’t Need Money or Attention?
Relax For The Same Result
Saying No To Everything Else
Want more from Derek? Check out his Twitter responses to your questions
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
Kimo Williams
Tony Robbins
Laird Hamilton
Gabby Reece
