Podcast #006 – Interviewing Derek Sivers Podcast #006 – Interviewing Derek Sivers

Play Practical Personal Development Podcast #6

This week we’re right on track bringing you a super successful speaker that you just can’t miss. Derek Sivers is a dot com mogul, the likes of which you’ve never seen before. He is the CEO and Founder of CD a company that pulled in over $100,000,000 in sales for independent musicians.

Well, he was the CEO, until he sold the company for $22,000,000, most of which he placed into a trust fund which will be used, not for his own spending, but to help musicians. Who needs a lousy 22mil anyway, right?

1. Defining Ourselves For Success

Derek has mastered defining himself, which is a key element for success, but the quality that drives him to success will probably surprise you. After he shares this quality, he gives some solid advice that we can follow so that we too can define ourselves.

Derek describes himself as fiercely driven man, whose theme is centered around rebelling against mediocrity. He’s seen too many stories of high-school music sensations that turn out working dead-end jobs, because they didn’t work hard enough to get it. In a way, the thought of settling scares the shit out of him, so he does everything in his power to reach his goals.

“Look into your past, and see what keeps you up all night … or get you bouncing out of bed first thing in the morning, … or gets you so intensely focused that hours fly by and you don’t even notice.”

2. The Start (and end) of CD Baby

Derek started by making his own CD and then sold a CD for a friend. Soon enough other musicians started begging him to make their CDs, and all of a sudden this hobby spread through word of mouth, and got to $100,000,000 in sales and 85 employees. The reason he sold it? He hates being comfortable, and after 10 years of doing it (actually after the first 5) he was just doing stuff he already knew how to do.

“The key to my success is to try not to grow, and only grow when there is such a demand that the world is saying ‘we really want you to do this thing, please do this, we will pay you money to do this thing'”

You have to blow people’s minds. Derek mentions some concepts from the king of marketing Seth Godin. Seth’s book, Purple Cow, had an interesting theme:

“forget marketing an ordinary product or service, don’t spend a dime marketing something, until the product or service is so remarkable, that people are going around telling their friends about it, not as a favor to you, but as a favor to their friends”

3. MuckWork – The Savior To Musicians

The new challenge for Derek is MuckWork, which is going to be an international-decentralized company, providing virtual assistance for independent musicians. These assistants will do the dirty uncreative work, clearing up more time for the musicians to do what musicians should be doing — making music!

This project answers the artists need for “I know everything I should be doing, but I just don’t have the time to do it myself.” Don’t you see what a monumental moment this is? Derek is helping to match people up with the things they love to do, and sending the stuff they don’t love to do to people who love to do it.

I’m not a musician, but I enjoy marketing, so if a musician would send me a marketing task, and I could send him a request for a beat (or something), that would be a win-win. Of course, MuckWork will be different, in the sense that it’s not a trade-off, or bartering system. Who knows if the Virtual Assistants will even like the tasks, they may very well be doing it for the money, but the work will be done, and the artists will get to play more.

4. Staying Focused In The Internetz World

Derek is a ‘focus junkie’, which is the opposite of an information junkie. One of the ways that Derek does this is by disconnecting from the internet (this is lunacy! lol), and concentrating completely on the work. He stays away from news or blogs, and subscribes to Tim Ferriss‘ ‘informational diet.’

There’s really no point in passively reading about tragedies happening all around the world if you’re not going to take an immediate next action. When you notice what really excites you, block out everything else, and go do that!

5. The Day to Day of Derek Sivers

Living each and every day on his own terms. One moment to the next. This could get dangerous, especially if you spend half a day searching the web on ‘scuba-diving in Iceland’ (you have to hear it on the Podcast to understand).

Having free time is especially difficult when you need to get stuff done. This is where you have to setup your personal priorities. For Derek they are:

  1. Programming
  2. Exercise
  3. Creative Writing
  4. Business Communication
  5. Personal/Social Hangout Time

Derek organizes his whole day in order of priority, with the Most Important Thing (MIT) first. You can hear more about the details of this breakdown on the Podcast.

6. Success, What is It?

Derek and I get into a debate as to what success really means. I’m not going to spoil the surprise and tell you either opinion. I will tell you that Derek does know what the hell he’s talking about! This is where I learn that Derek’s side job is being an advocate, the devil’s advocate that is LOL.

7. Derek’s Crashes and Burns

This is where Derek starts to sound like a page out of a self-help book (which I’m totally into, so don’t hold back!) He actually doesn’t believe in failures, just experiments, and lessons. Derek’s thoughts are that you shouldn’t judge someone until they die, because you’ll never know which way their life will turn.

One of his biggest burns was when the VP of his company stole a bunch of money from him. Derek just moved on, with his ‘ridiculously positive attitude towards failure’. Most people I know would be pretty pissed off to have that much money stolen from them, especially by a person who they invested their trust in. Derek, can I hold 5mil for you? Put it in my Swiss account, you can trust me! LOL

8. Music: The Inspiration

Seeing how Derek has been a pro-musician since age 18, this was the most shocking part of the interview for me. Derek was never a fan of music. His whole life revolves around music, but he doesn’t like it? Actually, that’s not entirely accurate. Derek is a huge fan of the creative process of music, and the necessity to be creative while having a boundary. This makes me want to pick up an instrument!

This is the part of the interview where Derek gives us a music lesson. Haiku, rhyme, beats, etc. I learned a lot! We also learn about the Dao of promotion “sometimes the best promotion you could do is the least.”

I had to pop the question, “Do you have a lot of groupies Derek?” and you’ll have to hear this for yourself.

9. Books That Inspire Derek

Derek points us to a URL on his personal site,, where he lists some of his favorites. Is it a coincidence that he reads a lot and he is successful? Could there be some kind of correlations? Is it true that the size of a successful person’s library should be bigger than his television? Hmmm?

Derek devoured Anthony Robbins‘ stuff since he was 18 years old, and it was internalized by the time he was 23. At 24 he was basically singing along with Anthony. He particularly liked that most things in life are neutral, and it is our thoughts and reactions that are the real creators of what something will mean to us.

10. Final Success Tip From Derek

Whatever Excites You, Go Do It
Whatever Scares You, Go Do It

The theme of his life is, when you love what you’re doing, work is not work, it’s play!

Final Thoughts

Derek is an extraordinary example of a regular guy, like you and I, who has the right philosophy for living life. This Podcast is very interesting and captivating, and Derek’s story really keeps you engaged throughout the whole time. We hope you enjoy!

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Posted by in Podcasts | December 15, 2008 | Digg | | Stumble | Print | 5 comments

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  • Skellie

    About halfway through the interview now – really enjoying it! I have a lot of time for Derek, he’s a great thinker. I recommend his blog to anyone, regardless of what your focus is. Excellent choice!

  • Alex Shalman

    @Skellie, Derek really is the best. Huge personality, really smart guy.

    P.S. I haven’t seen your name in like a year Skellie, how have you been?

  • Pingback: What’s Your HELL YEA!? | Alex

  • Jared |

    I really enjoyed Derek’s suggestions on learning how to say no. We all have the right to say no. One thing I get about Derek, is he seems very humble. Even in his comment about the interview he asked to do, “I’ll do it when I feel like doing it.”

    If you learn to check yourself and your motives, and feel that you’re going to resent the person or thing that you’re committing to, you are doing it for the wrong reasons. Most people feel they are helping others, when their motives are truly still selfish in that their looking for something in return. Whether it be acceptance, being viewed as “helpful” or are expecting that the person now ‘owes them one,’ their motives are insincere.

    “Happiness is when what you think, what you say, and what you do are in harmony.”

    The key to happiness is accepting ourselves for who we are, and that it IS enough. Thus we can so no to others because we’re not always looking for validation outside of ourselves. OR when we do say yes, we’re being truly sincere and it’s out of true kindness with no expectation of anything in return.