You’re reading What They Said, a project by Chris Gallo since 2014.

Derek Sivers

This is a conversation between Bob Baker and Derek Sivers on The Creative Entrepreneur podcast. Derek shares his background from circus ringleader to musician to million-dollar business owner at CD Baby to creating a book publishing company. You can learn a lot from his perspective and his book Anything You Want. Check out an excerpt below and watch or listen to the full conversation here.

Changing Your Operating System

I’m a total Chicago boy. Honestly, I didn’t have any interest in the rest of the world, even just seven years ago.

I was living in LA at the time and I remember my girlfriend wanted to travel, and I was like - why would we go anywhere else? We live in LA. This is like the end of the rainbow. The best place in the world. What are we going to do? Go to a different beach? You know?

But there was somewhere around that time, I was selling CD Baby. I think all of us have a time in our life, where you need to make a major change. Whether it’s a divorce, or a graduation, or a problem with alcohol or whatever. We all hit these different times in our life, where it’s like I need to make a major change now. I can’t just keep doing things the same way I’ve been doing them.

So when I sold CD Baby, it was kind of like that to me. I could just keep go doing this some more, but I feel like I need to make a major change.

For the next few years, it was everything I’m used to doing - I’m going to stop doing. And everything I used to hate doing - I’m going to start doing. I’m just going to say yes where I used to say no. And no where I used to say yes. And just see what happens.

It just sent me all over the world. Sent me off to Iceland and India. And moving to Singapore and getting married. All this crazy stuff.

It’s been a crazy five years, intentionally. Because like I said I kind of wanted to change my operating system.

3 Things that Were Responsible for Your Success

Number one has to be being in a big city. When I look back, it’s surprising how many of the great opportunities were because I was in the big city where everything was happening.

I lived in New York City for 10 years and LA for six years. And in both of those, some huge opportunities came up because I was there. So that’s number one.

While you’re there, meet everyone. And go to everything. Keep in touch with everyone you meet. The people you meet are going to be the ones that lift you up to success.

Sometimes we think success is all of our own doing, but usually the way it happens is metaphorically speaking somebody lifts you up. Somebody pulls you up to the next level of your career.

Go to everything. Keep in touch with everyone. But number one, be in the big city.

Number two - learn to do lots of things. Let’s say musically. That means not just playing guitar. That means playing guitar, and bass, and some keyboards, and able to do some percussion, and able to write well. And play electric and acoustic.

That also means having a home studio. And knowing the very basics of recording, engineering, and producing. The more you know how to do the more you can say yes to every opportunity that may come your way.

Number three is I would just say yes to everything. Like I would just pursue every opportunity. You go through all the little Craigslist classifieds and everybody is looking for something, and you contact all of them and say yes. I’ll do it and I’ll audition.

You take every gig. And you say yes to it. One time, somebody asked “we’re looking for a jazz piano player.” I told them I was jazz piano player, and said “how much does it pay?” 300. Yes, I’m a jazz piano player and I got the gig. And then I learned how to play jazz piano.

That’s the hustler mentality. You’ve got to say yes to everything and pursue everything. And actively go and find every opportunity. Don’t just go and sit at home thinking here’s my path I’m just going to get a record deal and be a rockstar.

You have to do everything around it. And meet everybody.

One Book that Changed Your Life

How to Win Friends and Influence People by Dale Carnegie. It’s got one of the worst, slimiest titles ever. The title is really a shame. Don’t let the title of the book turn you off. I think it really should of been called - How to be Considerate.

Because it really is the best book I’ve ever seen about how to think about things from the other person’s point of view. That’s what the whole book is about.

It’s written back in the 1930s. It’s a classic. And I think that’s really the underlying thing behind all of the best marketing.

It’s thinking things from the other person’s point of view. It’s thinking how to be considerate.

Somebody wants to find some new music - what are they thinking when they’re looking for new music? Are they thinking about your introspective lyrics or your great drum fills? Or are they thinking about having some shockingly unique sound that doesn’t sound like anything they’ve heard before?

It’s learning to think of things from the other person’s point of view. How to Win Friends and Influence People - that book is my top recommendation.


I have to say something that’s not just for me, but for everyone. I think we all have different reasons why we do things.

I was recently driving around New York City and there are all these buildings that say Trump on them. The Trump Tower, the Trump Plaza, the Trump this, the Trump that. And then I even, my wife and I were driving upstate New York, and we were driving an hour outside of New York City - rural, green upstate New York. And then you see something like the Trump something park.

He puts his name on everything. Even out here where they’re aren’t a bunch of Manhattanites to look at it. What’s his deal? Why does he want to put his name on everything?

Then I realized that we all have different reasons why we’re doing what we’re doing.

For him apparently, for Donald Trump, he seems to really want to leave this legacy of putting his name on everything. That matters to him because he could actually make more money if he let other people put their names on things.

If he was an owner, but he got to call the it the Panasonic building or whatever. He could make more money that way. But he actually chooses to make less money, but have his name on it.

And it makes me think about being in the music business or being in Hollywood. The richest people in Hollywood are the ones that you’ve never heard of. They’re the movie producers that live in that mansion on the hill.

But the movie stars are often not the richest. They’re the ones that take the red carpet and the flashing lights and the glamour and all that. They makes less money because they want the glamour. They can make more money if they didn’t want the fame. But no, they want the fame.

So they choose fame. And the guy on the hill that you’ve never heard of chooses money and no fame.

Donald Trump chooses to put his name on things. Some people choose to give - giving it what they love most.

The real point is no matter what drives you - someone is going to tell you that you’re wrong. They’re going to tell you that you shouldn’t be like that.

“You shouldn’t purse fame man, you can make more money this way.” And then say if you’re somebody who is pursuing money, somebody is going to tell you - “oh you’re all about the money man, it’s got to be about the art.”

The point is to just be honest about whatever drives you.

You’ve got to notice this about yourself - what interests you the most. And just go for it and admit it. If you’re interested in fame, and want to be famous, then that’s awesome. It’s a totally worthy pursuit.

And so is being rich or giving or whatever. All of these things - don’t worry, somebody is going to tell you that you’re wrong no matter what is your main drive. And just know that in advance.

What drives you?

I’m driven by experimentation. Two things. And it’s safe to have two things, cause sometimes it’s really the equal. You can’t choose one or the other. It’s the combination.

That project wise, I’m driven by experimentation. That almost everything I’ve ever done started with the sentence - “let’s see what happens if … ” I just want to experiment. I want to try things.

But also lifestyle wise, I’m totally driven by freedom. Meaning I will choose to have less money, less fame, if it means I get more freedom to go bob around the world and live in Singapore and New Zealand.


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