The Philosophies of Work: A Conversation with Derek Sivers of CD Baby


Derek Sivers is a stud. I thought I’d share the conversation we had at SF MusicTech Summit. Dozens of topics covered include:

- Testing asssumptions vs. cheating
– PR and reaching out to unreachables
– Micro-testing ideas and products: from The 4-Hour Workweek to Trent Reznor
– Personal outsourcing for creatives
– Filling the void and creating meaning outside of the inbox and office

Derek is a programmer who lost his stage fright by doing more than 1,000 gigs as a circus ring leader. He is also the musician who started CD Baby, the world’s largest online music store for independent musicians. Here are some current numbers:

- 242,846 artists sell their music at CD Baby
– 4,574,622 CDs sold online to customers
– $83,590,381 paid directly to the artists

With more than 2 million digitized tracks under management, CD Baby is also the largest provider of independent music for iTunes… and it all started as a hobby.

How does it work now that it’s enormous? From Derek’s blog:

When I was the owner and president of CD Baby, it ran without me, and I hardly spent 4 hours on it in the last 6 months. It’s wonderful.

Here are a few snippets from our conversation…

On “Cheating”:

Seth Godin, one of my favorite marketing authors, wrote this essay once about “cheating”, saying, “HBO is cheating because they’ve got bigger budgets and don’t need commercials. JetBlue is cheating because they don’t have union workers. Aren’t there things you can do in your business where you can cheat?” It doesn’t have to be a bad thing. It’s just finding an advantage… Finding a shortcut.

On 80/20 Elimination and Micro-testing:

There are ways that you can examine and start to pare out the things that don’t work with pervasive group think. [snip] Analyze your time consumption. Try RescueTime [which logs both on- and offline computer use] or MeeTimer. Identify where your time is spent and identify the 20% of activities that are consuming 80% of your time.

Once you have that list ask yourself what would happen if, say in a 48 hour period, you eliminated x or did the opposite of x?

Most people avoid certain actions because they view changes as permanent. If you make a change, can you go back to doing it like you did before? You can always reclaim your current state in most cases. If I quit my job in industry x to test my artistic abilities in a different industry, worst case scenario, can I go back to my previous industry? Yes. Recognize that you can test-drive and micro-test things over brief periods of time. You can usually reclaim the workaholism that you currently experience if you so decide to go back to it.

On PR and Cold Calling:

When I was promoting my own music years ago, I decided I wanted to be in Rolling Stone magazine. So I bought a Rolling Stone and looked in the tiny fine print on page 6 where they publish their contact info. I knew that if I asked Rolling Stone which publicists they like, then I’d know which publicists could get me into Rolling Stone. But before calling the main number, I thought, “Hmm… I want to get through to the editorial department, so I don’t want to sound like a novice. I’ll bet if I sound like the people who do this all the time, they’ll patch me right through.” So I called up and the receptionist said, “Rolling Stone,” and I said in my best weary impatient voice, “Editorial, please,” and she patched me right through. Once on with the guy in editorial, I just politely asked, “I’m not promoting anything today, just calling from a label that’s looking for a new publicist. Wondering – which ones would you recommend?” The guy was quite nice and gave me a few names. I thanked him and now I had my specific road map for how to get in Rolling Stone!

See the entire conversation on video above or read the entire transcript on Derek’s blog.


Odds and Ends: More Interviews, France Ends 35-Hour Workweek, Utah Goes to 4 Days per Week

Here is another of my recent favorite interviews, this with Change Nation.

Forbes: France ends the reign of its world-famous 35-hour workweek

Associated Press: Utah and more states go to 4-day workweek

Posted on: August 8, 2008.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s

Comment Rules: Remember what Fonzie was like? Cool. That’s how we’re gonna be — cool. Critical is fine, but if you’re rude, we’ll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration)

71 comments on “The Philosophies of Work: A Conversation with Derek Sivers of CD Baby

  1. Tim,

    I’m glad you hooked up with Derek. He’s been a mentor of mine for years (CDBaby sold my first band’s CD back in 1999 and I’ve had several releases since then – go to

    More importantly, Derek has always stood for following your passion (whatever that might be) and adhering to sound business ethics.

    Today it seems that Capitalism has created more damage than good. Derek represents a new Post-Capitalist culture that I hope hundreds of others will embrace.

    John Haydon


  2. I really enjoyed this post.

    As one comment mentioned earlier I would like more info on micro testing a product. That is what I’m struggling with.

    Such as how to interpret the results of the testing.

    For example I tested a product on eBay that got a lot of hits but no buys. I interpreted that as meaning there was an interest and demand for the product but somehow I needed to change something for them to make a purchase.

    But am I right in that interpretation? Or am I missing something?


  3. Tim,

    Thank you for your response. What comes to mind for my business on following point #2 would be to contact several of the big name and even some smaller name players in the photography industry, from camera sellers to others in the wedding photography business. Then I could ask them to either sponsor a portion of site development and marketing startup costs in exchange for some free ad space on the site once it launches. Would you suggest calling the marketing departments in these companies to float this ‘non-traditional’ concept? what do you think about this idea–if they do not bite on sponsoring my site development and launch, then to at least provide me with some free banner ads or an article/interview about my site once it goes live, if I then offer to trade them in-kind for a certain # of ads for them on my site?

    Regarding point #1, do you like Romania because of personal experience? Being new to outsourcing, I have never considered one specific region over another to use for this purpose. So if I use elance, are you saying that we should come to an agreement on a standard price for the job (i.e. their market price), then offer, say, 60% for non-launch, or 120+% if it launches, based on the original agreed-upon price?




  4. Hi Tim,

    I read and watched the entire interview on Derek’s website….

    On Testing the Market, you mention using Wordster and Sitespect… I had a good Google around and Wordster seem to be a game of words? Can you clarify how you would use this for the purposes of testing?

    I am confused… (“…he is confused!”)




  5. Great interview, haven’t read your book, but plan to when I can get some free time.

    You mentioned a lot of people hate you. An answer to why people may hate you is cognitive dissonance, people build a mental model of the world and when things don’t fit their model they make them fit. Anyone who contradicts their world view pisses them off. Basically if you’re right it means that the assumptions they built their lives upon are false, which makes them fools who wasted their life. In other words they can’t handle the truth, and would rather live a lie than face reality.


  6. Incredible. You’ve done all this cool stuff and you’re only how old? While I just turned 40, busting my butt 40 hours a week at a stupid job just to survive another day and I fight and scrape for a few hours time to live my life’s calling, my music, the only thing that keeps me half sane. I’d love to duplicate your success, but I guess I’m not that smart… well, good for you. I’d like to be rich and free too, but I guess I might have to wait until the next lifetime for that. Cheers.


  7. It’s cool that the guy did 1,000 gigs as a circus ring master. It’s not so hot that was the only way he could tame his nerves. I say that because it’s not necessary to go to that effort and extreme to get comfortable in front of an audience. There are easier ways to accomplish this feat…. And for someone who wants to make life less work and more pleasure, those secrets might be worth investigating.


  8. Wow nice video. After watching that I think that one thing (maybe the main thing) that is probably what made you so successful is that you strategize everything.


  9. Tim,

    Thank you for making this conversation available. Good stuff and a handful of insights and takeaways.

    The one point you made that really resonated for me was about who we choose to emulate. My question for you, however, is how far do you take that? No one has it all together, do they?

    For me, I’ve come across many “successful” people who are raking in money but they spend it as fast as they make it. I tend to take a close look at the diets and bodies of these financial successes and very rarely are they taking care of themselves. There seems to be something fundamentally unhappy and insecure abou this type of person. It’s a big concern for me, so much so that while I don’t disagree with their accomplishments, I come to a point where it’s hard to accept their perspective because of glaring weaknesses.

    You seem like a guy who has his proverbial sh$% together and I’ve absolutely learned a great deal from your perspective. So, if you can, give me an example of someone you completely and genuinely emulate. Additionally, give me an example of someone who really isn’t someone you’d want to be like, but have emulated an apect of their being anyway.

    Thanks and keep it up. You’re making a difference.


  10. On Philosophy other than ‘work’

    Hi Tim. Having read much of your work in the book, and while now slogging through blogs, vids and the like…I have to ask. What was your religious background growing up (if any) and what are your philosophies (outside of business) at this point in your life?

    Why do I ask? Well, partly to test a theory about the organization of your book and systems, and partly to denote the mores of the NR. This line of enquiry seemed conspicuous by its abscence in your book. We are given logos w/o philos (other than the effecient/effective).

    PS I do understand that marketing is always easier without mentioning sex, politics, or religion at all. ;~) Will you satisfy my curiosity regardless?

    Best Regards,


  11. One thing to keep in mind about product microtesting of actual products is that you have to have to have something to show the prospective customer.

    Texas Instruments did similar “product testing” . They would offer a $50K or so “award” to the most promising products. They’d then develop that product and do test marketing. One of those products was Speak & Spell.


  12. Hi Tim

    Natalia here again from Japan. I complained to your Japanese publisher today about the slack translation and selling of the book in Japan. I suggested they retranslate it using another translator who has guts to translate the intelligent quotes you included, etc, and republish it. I also wrote the same on the Japanese Amazon review today.

    I hope they will take some action. It embarasses me being here in Japan when some Japanese publishers want to take advantage of foreign best sellers without doing proper work themselves.

    If you have any requests or comments to me personally in regard to your book in Japan, please email them to me direct, as I have no time to read comments on this blog. I write here as I don’t know your email address. Oh, one more thing. I use your book as a textbook in Japan now, and advise everyone who comes to my speeches to buy it.

    I surely promote it more than my own book!

    Natalia Roschina
    For ALL Co., Ltd.
    Hokkaido, Japan


  13. I’m from Australia and am wondering if anyone has found an equivalent to or that provides Australian / New Zealand companies that manufacture and drop ship. The only company I’ve found charges really high prices for poor products and is really in the retail game not wholesale – no lifestyle for me in that!! All advice would be appreciated.


  14. Hi Tim,

    I got your book through Derek’s site as I am a cd baby artist and a website owner selling dual sim solutions.
    It was great to see you both together.
    I am almost through your book but there’s so many interesting things on the we about your philosophy too preventing me from starting, but hey..I can have my VA in India start for me;-)



  15. Hi, Tim
    I was recently granted a patent on the “ABLITERATOR”, an amazing complete abdominal workout machine guaranteed to work your entire core faster than any other machine. The amazing part is that you are standing during your entire workout. This is not a gimmick, this machine is virtually indestructible and will be given a lifetime guarantee on all parts.
    If you are ever in the Southern California area, please give me a call, I think you would have a blast working out on this machine. Any ideas on where to go to market it would also be appreciated. Guthy Renker was almost ready to go with it, but they had bad luck with their last ab-machine.
    Yours in health and happiness,
    Dr. Todd