Derek Sivers: Systematizing Friendliness (The DOcast)

A talk Derek Sivers from his home in New Zealand.
A talk with Derek Sivers from his home in New Zealand.

In the early dawn of the internet, it wasn’t easy for an independent artist to sell their music online — so Derek, an musician himself, decided to create a system where he could. Then his friends, and friends of friends, wanted to do the same thing — that’s when CD Baby was born. It later became a lean sales machine producing over $100 million dollars in sales and servicing over 200,000 musicians. Derek later sold CD baby, giving proceeds to charity, in 2008 for $22 million — he’s also a best-selling author, musician, programmer, world traveler, and circus ringleader (to get over his fear of public speaking.)

I have the pleasure to speak with Derek, via Skype from his home in New Zealand, to talk about marketing, automation, and how it applies to product-based companies.

Be sure to get a pen and a pad, his story is jam-packed with ideas and tips to grow your business.

Interview with Derek Sivers

Sponsored by: Hanley’s Foods — Louisiana-inspired, natural, fresh foods. Enter “docast” at checkout for $4 off.

  • Focusing on success. (2:40)
  • “For some people, the life of a musician is like party party party. But for me it was like, if I’m going to be a successful musician, that’s like wanting to be an Olympic athlete.”
  • “People later told me that I’m so lucky for the opportunities I had, but I think it’s just because I was that guy that never hung out, never watched TV, never was just chilling. I was always working. Always learning as much as I could.”
  • The start of CD Baby. ( (9:10)
  • “It was 3 months of hard work, but when I was done I had a ‘Buy Now’ button on my website.” (Tweet this)
  • “Here is something that I have, which my friends need, so I’ll just find a way to share it with my friends for a very small fee. That was how the business got created.”
  • The speed of business growth. (11:30)
  • “I went from idea to reality in about 1 week.”
  • “Let the customers show you where automation is needed and what they need.” (Tweet this)
  • When is the time to hire somebody? (15:00)
  • “Most startups fail from trying to grow too fast, too early.” (Tweet this)
  • What do you look for in a new hire? (16:15)
  • “You wanna find somebody who is using you as a stepping stone to their own bigger aspirations.” (Tweet this)
  • SOD – Strategic operating document (21:20)
  • How did you automate CD Baby? (21:50)
  • The E-Myth Revisited by Michael Gerber (book mention)
  • “So much of CD Baby’s success was because of our personal touch, and people loved that we communicated in an oh-so-friendly way.”
  • “Systematizing friendliness. Systematizing a philosophy.” (Tweet this)
  • “If you communicate the philosophy really well, then the specific actions items just flow out of that philosophy.”
  • The only marketing move that Derek ever made took 15 minutes. (28:10)
  • “There is a normal way that everyone does things, and you don’t wanna do that.” (Tweet this)
  • The start of Derek’s new multinational business. (32:00)
  • – Derek’s new book business
  • Business Idea: Asia has no Mexican food. Go start this business. (32:30)
  • “If you put something out there, even if it’s bad, then you’ve already beaten the 95% that never get to that point.”
  • Derek’s fantastic book reviews. (
  • “All marketing, all of business, all communication comes from thinking of things from the other person’s point of view.” (Tweet this)
  • What’s a book, a song, and a quote that you love? (41:40)
    • Book: A Guide to the Good Life by William Irvine
    • Quote: “When you are not practicing, remember, someone somewhere is practicing, and when you meet him he will win”
      – Ed Macauley
    • Music: Derek enjoys listening to music he doesn’t like until he can appreciate  it.

Check out Derek at:
Twitter: @sivers
TED: How to start a movement
Email: derek [at] (Have a question? Drop him a line.)

Play the interview

The DOcast - People doing the unthinkable.The DOcast is a podcast of interviews from amazing entrepreneurs who are doing the unthinkable. With topics on how they got started, where they’re going, and how you can learn from them.
[powerpress] Subscribe at:
iTunes (please support the show by leaving a 5 star review)
Stitcher Radio
The blog (in-which you’ll get more)

DO it big.

Leave a Reply

Your email address will not be published. Required fields are marked *