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Full of liberating and challenging opinions, Derek Sivers joins us for a discussion on passion, fearlessness, integrity, and the importance of their roles in entrepreneurship and life. If you think you have read all about those topics before, I urge you to read them again here, for the first time. Enjoy!


Allentrepreneur : It`s a pleasure to have you with us Derek! One of the things few people know about CD Baby was perhaps your reluctance to start it. You mentioned a few times in prior interviews that the company you are now most famous for started as an accident.  You did it as a favor to friends. However if CD Baby had never come to pass, you would still be doing what you do best: music. And this is where I want to start this discussion. Can you tell us about the importance of nurturing a passion or the potential perils of not having one?

Derek: It’s dangerous to think in terms of “passion” and “purpose” because they sound like such huge overwhelming things.  If you think love needs to look like “Romeo and Juliet”, you’ll overlook a great relationship that grows slowly.

If you think you haven’t found your passion yet, you’re probably expecting it to be overwhelming.

Instead, just notice what excites you and what scares you on a small moment-to-moment level.

If you find yourself diving into book about Photoshop and playing around with the program for hours, go for it!  Dive in deeper.  Maybe that’s your new calling.

If you think for one moment about something like putting on a huge conference or being a Hollywood screenwriter and you find the idea terrifies you, there’s a good chance that would be a worthy endeavor for you.

You grow by doing what excites you and what scares you.

For me, CD Baby was just a curiosity: that little hobby that kept me up until 2am every night, programming and experimenting.  It just grew from there.

Allentrepreneur : I have followed your blog for some time and as posts went by, I realized that one of the reasons the advice you give seems to resonate so well is because it is rooted firmly in realism and doesn’t take itself too seriously. My question then is how much importance do you give dreaming, and when or how do you reconcile doing and imagining?

Derek: I love that “dreaming” has two different meanings. Dreaming at night is surreal and absurd.  You’re talking to your friend Tracy but now she’s a cat, and knew that Tuesdays the sky opens up so you can fly when holding oranges.

Dreaming as imagining can be that creative.  It’s great to try ridiculous options.  What if I move to Brazil to start a surf shop?  What if I franchise my new company worldwide before it even starts?  What if instead of paying money, people paid compliments?

Then, only when you hit upon something that makes you say, “Hell yeah! That’d be awesome!”, should you commit your real-world time and money to the actual doing.

Allentrepreneur: I would like to point out the circumstance during which CD Baby was brought to life: you saw a gap in the existing way of doing things, and decided to fill it yourself. There’s a crucial business lesson here. Wait until there’s a demand. What other piece of business advice has helped you most along the way?

Derek: Know that when you create a business, you’re creating a little universe with its own rules.  You can make it your own utopia.

Just because other companies put Terms of Service agreements and Privacy Policies on their website doesn’t mean you have to.  Just because other companies have titles, meetings, or mission statements doesn’t mean you have to.  You could declare your official return policy to be “tell us a funny story and we’ll give you a full refund.”

Start sentences with, “In a perfect world…” – and aim to make that happen.

Allentrepreneur : There is something else about the way you handled business that hasn’t been mentioned often but I saw as undeniable to your success: fearlessness. I’m not talking about that Utopian quality present only in Spartan warriors, but rather the fact that whether or not CD Baby took off was not essential to you because you were already a full-time musician. You were already earning a living doing what you love. Am I wrong in assuming this played a crucial role in your daily management of the company? Is there yet another lesson in there for the rest of us?

Derek: You’re right. It shaped the core DNA of the company. CD Baby was my Utopian experiment. I wasn’t depending on it for income, so it was really just designed as a “musician’s dream come true” service, with profitability as a side-effect.

Everyone who worked there (at least for the first six years) really understood that this was the mindset and mission, so all decisions should be made with this in mind.

A customer asked for some Big Red chewing gum in with their CDs?  Hop down to the store and pick some up.  They’ll be thrilled.  (See for a great example of this.)

The culture of a company is created by consistent actions, not a mission statement.  By detaching yourself from the profitable outcome a bit, you can make much better day-to-day decisions based only on what would be a dream-come-true for your customers.  Then you just have to trust that it will pay off, too.

Allentrepreneur : One of the most famous advice you give is: Whatever scares you most, go do it. I would be interested in hearing a particular moment of your life when things were particularly scary for you and the essential steps you took to convince yourself that what you were doing was something worth doing.

Derek: It’s more about lots of small moments, and there aren’t convincing steps – just immediate action.

A musician scared to call a big venue to ask how to get booked there.  Seeing one of your heroes in public and being scared to say hello.

These are the little moments that usually make all the difference.  By doing that stuff that most are scared to do, you set yourself up for rare rewards.

Again, like the “passion/purpose” topic, don’t think that destinies are only created by massively important do-or-die moments like in the movies.  It’s your integrity that shapes the thousand small things.

Allentrepreneur : You gave a speech on perfection at Indie Buzz Bootcamp in 2008 where you pointed out that some of the least successful people are the ones treating everything with a do-or-die attitude (where I sadly recognized part of myself), while the most successful are those who are just trying something. I found that extremely liberating. Would you care to elaborate a bit more on this issue?

Derek: Life is unpredictable.  You never know how things will turn out.  You could spend a year working on the most brilliant idea ever, only to find the public hates it.  Or you could do something on a Sunday afternoon that may change the world.

So I think about quantity: trying lots and lots of little things.  Not knowing which will get a great response, you need to force yourself to not get too stuck on any one idea, and go for quantity instead.

One way to do this is to start sentences with, “Let’s see what happens if…”

It’ll be more fun.  It’ll detach you from the outcome.  And it’ll get you to be more creative than if you think of everything as heavy and important.

Those are great qualities that’ll set you apart in a world where everyone is doing the opposite.

Allentrepreneur : In your interview with Alex Shalman you talk about pushing against the tide, about rebelling. Isolating yourself when everyone was going out while living in NYC; harnessing ambition while slackers surrounded you in Oregon, etc. What would you say is the most valuable thing this mindset gave you? Has this attitude always been with you or was it something learned along the way?

Derek: I’ve always been that way, but I guess the common theme was me working while others weren’t.  By seeing myself as unusual, I didn’t mind everyone teasing me for not hanging out, partying, relaxing, or vacationing.  I just stayed focused on practicing and creating, which of course pays off very well.

Allentrepreneur : There’s a quote I came up with that I’ve been putting to the test everyday: Life is interesting, as long as you’re interested. What do you think? Remember you heard it here first!

Derek: I love it.  You could swap in many different words in place of “life”.

Accounting is interesting, as long as you’re interested.

Meditation is interesting, as long as you’re interested.

Anyone is interesting, as long as you’re interested.

Allentrepreneur : And finally, I won’t ask you about the future of music, but I will ask you this: Is there any hope of ever seeing you in Montreal during the Montreal Jazz Festival?

Derek: Nope!  I don’t like live music.  🙂


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