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.

Watch The Tim Ferriss Experiment, the new #1-rated TV show with "the world's best human guinea pig" (Newsweek), Tim Ferriss. It's Mythbusters meets Jackass. Shot and edited by the Emmy-award winning team behind Anthony Bourdain's No Reservations and Parts Unknown. Here's the trailer.

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

  1. I love the idea of microtesting realities in your everyday life and streamlining to what really constitutes who you are and what you want to accomplish. I guess an added comment to supplement the amazing discussion featured in the video is that you have to diversify those who you surround yourself. If you think of it in scientific terms, if you keep microtesting to the same population, you’re only going to get a narrow stream of feedback and it’s going to limit the levels you can achieve, the opportunities you become aware of, and how you essentially begin to integrate and piece together your life. In my “personal mission statement” that I read each day and night, one of my weekly goals (and a daily thing to strive for) is to diversify your experience. This goes very much in line with “lifestyle design” and I really appreciate Tim and his commitment to being a leader in this nontraditional field and streamlining the lifestyle design process even further! It’s an information age, it’s amazing how many ways our generation can take advantage of it with a growing global market to work with.


  2. I had never thought about the concept of cheating quite the way you (Seth) described it here. I have managed to create an amazing muse (under your direction) that I am absolutely crazy about. It’s kind of a Donnie Deutsch (do what you love and the rest will follow) and a Tim Ferriss (what I do for work and what I do for money are two different things) philosophy all rolled into one. The end result after pondering this blog is that I have figured out a way to cheat (find the advantage) through my absolute passion for what I’m doing. The shortcut is the muse AND the passion. Thanks again Tim!


  3. Tim,

    Completely agree with your point on change. Nothing is permanent these days.

    Whilst previous generations may have run businesses or undertaken jobs and careers that spanned 30 years. Those days are long gone.

    Things change so quick and so fast in the modern economy that the faster you embrace change, the more successful you will be in the long run.

    So it means we need to be concerned about testing a new way of working in case it screws up or we dislike it. Any screw up or change has some learning or benefit that comes with it

    So any change is good. And as you say, reversable if it doesn’t work out

    Of course, most of us understand this intellectually – but need posts like this as gentle reminders!

    thanks again


  4. Great conversation, it made the principles in 4HWW much more clearer. I’ve just started reading your blog yesterday and has read for at least 6 hours total. (very addicting and informative, thanks)

    I have a question, with all these crazy experiments how often do you “fail”? (fail as in not reaching the targeted change. e.g. work 4 hours a week and still get everything done but failed)

    I ask because i am now very motivated to challenge my own assumptions and start experimenting with my life.

    Thanks in advance for you answer.

    Ryan T


  5. @Ryan,

    I tend to fail often, but my failures are generally contained to a quick test on Google Adwords, StumbleUpon, or other online avenue. Otherwise, it might “fail” as a pitch to several potential sponsors, buyers, partners, etc.

    I’m not sure of the percentage, as I get better at choosing successes as I learn what I’m good and bad at. Once I understand a market, I tend to focus on developing new products for that market, which also improves my success rate over time.

    Hope that helps!



  6. Hey Tim,

    Myself and a co-worker have both read your book and really want to jump on the serial-entrepreneurship bandwagon. We both have product ideas, me an ebook and him a supplement. However both of us find it really hard to work on ouor products after a long and tedious day at the office.

    I have already made up my mind about quitting and have no idea what the next step will be, while he’s still struggling with his. You bring up a good point on the subject of microtesting as it relates to a career and it inspired me to take a month or two off to see if I can get anything off the ground.

    What insights do you have on the subject of product creation when one is starved for time and when quitting your job at the moment is not a very wise financial decision?


  7. Hi Tim,

    I have heard your name in a couple different circles lately, and wanted to pass along.

    One came in Dan Kennedy’s new book, No BS Ruthless Management of People and Profits, No Holds Barred Kick Butt Take No Prisoners Guide To Really Getting Rich (whew…or something like that!), on page 316. The ironic thing is that he is somewhat bashing the idea behind the 4 – Hour Work Week…then his next chapter is about the Phenomenon…accomplishing more in the next 12 months than the last 12 years. Sounds like the same thing to me…just called a little different.

    The other was for the Early To Rise Profits in Paradise conference…when Howie Jacobson PHD was speaking about Google Adwords, and mentioned your testing and ideas.

    In your response to Ryan T above…you mention some possible businesses you are currently in…and testing.

    Would love to hear some more about those. What they are, testing, markets, successes, failures…you know, the goods!




  8. TIm – had a chance to hear you speak at NSA in NY though I did not get a chance to say hello. Nice job and I have begun to sift through your blogs and appreciate they way you write and think.

    As to Ryan who asked about “failing”. There is only one type of failure and that is giving up. Everything else is simply assimilation of information on what does and does not work. When you look at failure that way you can let go and move on when things don’t go exactly as you planned.

    Life is a continuous movement and as long as you are always moving forward you not failing.


  9. Tim,

    A quick few notes:

    1. Bistro Corner- Rad Place, Good Burgers for $5, you can’t beat it.

    2. Cafe Luxembourg Great Desserts, pricey but D@mn good.

    3. Just got the book The 22 Immutable…… Awesome read and simple reading. It really gets the meat of the matter.

    Do you make a conscious habit of having interviews with different people?

    Thanks for the advices ……..

    Jose Castro-Frenzel


  10. Tim,

    I really look forward to every post of yours. Each one is a treat. Each post is well thought out, planned and executed. Obviously this post wasn’t from an interview you did a few days ago. You put some thought into this, and weren’t insistent on it coming out right away, but on it being another great post. I am, and will continue to be a 4 Hour advocate, and am still striving on my own path to achieve this. Thank you and I look forward to the next post.


  11. Tim:

    Thank you once again for sharing a video of you speaking at a conference. I avidly read the blog but find that the videos help realign my thinking or get me to continually look at my to-do list/responsibilities to see what else I can outsource, micro-test, etc.

    A very simple example is I have always used online banking but realized I’ve never set it up for automatic payments. Something very simple and only took 10-15 minutes to do. While watching this video I thought of it because it was time to login and submit some payments. Now all of my payments are set up for automatic bill pay.

    Keep up the great work!

    Are you still considering a meet-up in NYC soon?

    -Justin Levy


  12. Great post Tim!

    YOUR BOOK ROCKED MY WORLD, and I have been thinking differently ever since! Now I am excited to learn of Derek’s success and read his blog as well. Thanks for sharing this video. Your posts are always chock-full of useful information. Really glad you didn’t go with Broadband & White Sand for the title!

    Can I buy you a beer and pick your brain?

    I’ve got a great idea for you, and I’ll put the $125 Google AdWords testing money where my mouth is. My lengthy email was forwarded to you on 7/23, as I was told it would “Make Your Day” but I would love to elaborate in 3 sentences if you are interested!

    Be well,


  13. Hi, Tim

    thanks for all the great inspiration. Do you have any ideas on how to best micro-test products that take longer to develop and produce than 4 weeks?
    I am in traditional book publishing and somehow it is not really fair to micro-test a book idea and then tell people: “By the way – you have to wait another 6 – 12 months until we wrote, designed and published the book.”

    Greetings from Berlin
    PS: It is more than possible to even run a traditional business such as a publishing house on a 4 (or more honest 4 – 8 hr) work week – and have enought free time to do interessting things like sitting on Bin Ladens toilet (serious – no joke!).


  14. Sorry if my letter below is not appropriate here- was not sure where to post it. Feel free to delete.

    Dear Tim Ferris,

    Hello from Hokkaido, Japan. I am a Russian-born New Zealander living in
    Japan since 1997 where I incorporated my company in 2003.

    I have almost finished reading your book. It is amazing, absolutely life
    changing (my company’s business hours are 3 hrs per day, but after reading
    your book I feel like reducing those!).

    Japanese society where often people work long hours without getting many things
    done need your book like fresh air.

    Of course I bought a few copies of the Japanese version to give to friends
    as gifts. And found out how bad the Japanese translation was. It omits too
    many things which is a real shame. Your book deserves better than that.
    The Japanese translator or the publisher were either lazy, or underestimated
    the mentality of Japanese people, or idiots, or something else.

    I want to promote your book in Japan and beyond. PR is simply my hobby, and
    my customers need to read your book to make their life easier. If I were
    you, I would get someone to translate it properly into Japanese, so it would
    get the attention in Japan it really deserves.

    I would rather promote a book that was translated properly. Quotes from
    famous people make your book extra intelligent, and they are not in the
    Japanese version (I have looked for some, but was unable to check the whole

    I am not a translator, so I am not offering any services to you. I am not a
    publisher either. I am just someone who wants to use your book as a bible
    for time and life wasters. You wrote a high quality book, and it should be
    high quality here in Japan too.

    If you have any questions or need any advice (no charge), feel free to
    contact me. I might be slow at replying, but I will help if I can.

    Lastly, if you haven’t done a Russian translation yet, I would suggest to do
    one. I visited Russia last week, and I know a lot of people there would
    benefit from your book.

    Thank you for writing your book and I look forward to buying your next one.

    Natalia Roschina
    For ALL Co., Ltd.
    Author, “Yubari he no tegami” (published by Nikkei BP, featured in FORBES
    Japan May 2008 & Nikkei Woman September 2008).

    2-1 Kiyota 4-jo 2-chome, Kiyota-ku, Sapporo, Hokkaido, Japan 004-0844


  15. Hey Tim

    18-year-old college student here, and I would just like to say that I bought your book and found it to be very interesting and insightful. I am very interested in starting my own journey toward a 4 hour work week, but I am a little cloudy as how to go about this. Your book had some very helpful information, but it’s a little difficult for me to take it all in and spit out a business plan. Any helpful start-up advice to get me and other curious students on the right track would be greatly appreciated.
    Thanks in advance.

    Liz W.