22: Success on Your Own Terms with Derek Sivers

“To have something (a finished recording, a business, or millions of dollars) is the means, not the end. To be something (a good singer, a skilled entrepreneur, or just plain happy) is the real point. When you sign up to run a marathon, you don’t want a taxi to take you to the finish line.”

—Derek Sivers, Ask Me Anything

My dad started a band called Mr. Gasoline that he ran for 25 years, and recalls uploading his Mr. Gasoline albums to CD Baby “back when Derek was still sleeping on a couch in the office.” I smiled when I heard that story—Derek’s dedication and humility are two of the traits I most admire about him, and what compelled me to follow his work more closely and start my own /now page

In his recently released book, Anything You Wanthe shares the story and mindset behind the rise of his smashingly successful CD Baby venture, and the tough years leading up to his exit. What first attracted me to Derek was not that he built a $22 million business—but that when he sold the company, he gave all the proceeds to a charitable trust. Who does that? Someone who defines success on their own terms. 

I zoomed through Anything You Want one night before bed, and by the next morning I gave away my copy in a pay-it-forward gesture to an entrepreneur friend. Then I bought six more copies to give to my friend Adam and his design team, who were working on the new Pivotbrand (coming soon!).

I hope you get as much out of the book and our podcast conversation as I did. And if you feel up to it, buy your own copy to pay forward—Derek’s is a story everyone can benefit from hearing!


From his website: Derek is a musicianprogrammerwriter, entrepreneur, and student — fascinated with the usable psychology of self-improvement, business, philosophy, and intercultural relativism. He’s an introvert (INTJ), a minimalist, and a California native now living in New Zealand, Singapore, and Belgium.

Originally a professional musician and circus clown, Derek Sivers created CD Baby in 1998. It became the largest seller of independent music online, with $100M in sales for 150,000 musicians. In 2008, Derek sold CD Baby for $22M, giving the proceeds to a charitable trust for music education. He is a frequent speaker at the TED Conference, with over 5 million views of his talks. Since 2011 he has published 34 books, including “Anything You Want” which shot to #1 on all of its Amazon categories.


  • How he figured out what to do next after selling CD Baby for $22 million

  • Why he pressed pause on the company he started to answer “what’s next”

  • Making deliberate change: what are you saying no to?

  • Derek’s metrics: optimizing for learning, life experience, change.

  • Stop trying to make money; just because you start a business, you don’t have to scale at all costs

  • Question expectations.

  • “The DNA of something matters” – how CD Baby started as a favor to friends, and grew as a business despite Derek’s efforts at keeping it small

  • Why he didn’t go the IPO path, or getting funding from outside sources

  • Why Derek continued doing all the programming himself for CD Baby for years

  • We should all ask: What do you love doing that is also useful to others? What’s the day-to-day experience that you really want?

  • Writing as a tool to reflect on wrapping up a life chapter

  • What inspired him to write Ask Me Anything

  • How different people have different set points for success, happiness, and bank account balances (not everyone wants millions of dollars)

  • Why he decided to give $22 million to a charitable trust immediately upon selling CD Baby

  • Breaking the habit of doing things for money

  • Being scrappy vs. the $3.3 million mistake (on reading contracts)

  • Programming phrase: YAGNI (You Aren’t Gonna Need It) — avoid adding features you think you might need in the future

  • Where confidence comes from: as needing as little as possible to make yourself happy

  • The importance of pessimism and honoring fear; the fatal flaw of overconfidence

  • Mindset: I’m a student, not a guru

  • Ego minimalism: releasing the need to look like an expert


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