Interviews → James Altucher

NOTE: Go to his site, first to read a great summary of this interview.

James:

Hey, Derek. This is James Altucher.

Derek:

Can you hear me?

James:

Oh, my god. You have a radio voice. Your voice sounds great.

Derek:

Well, thank you for calling.

James:

Seriously, are you using like a special equipment or something? Like what’s going on over there?

Derek:

It’s this big Darth Vader mask that I’m speaking through right now. Nah, just a mic. It’s a Blue Yeti mic. Hi!

James:

That’s great. How’re are you doing?

Derek:

Good to finally talk to you.

James:

Yeah.

Derek:

I have spent so many hours with you in my head whether through you books or articles and all that stuff that I’m beaming right now. It’s an honor to finally talk to you.

James:

Well, probably because I steal liberally from what your write. Like you’re reading, kind of regurgitated words. How can I take what Derek said and reword it so it sounds like me? I mean, seriously, your book, Anything You Want, 40 Lessons for a New Kind of Entrepreneur is in my probably top three. I mean, I would give this to anybody starting a business. It’s such a great book.

Derek:

Oh, thank you. Yeah, you and I definitely writing kindreds because I felt the same thing whenever I was reading your stuff. It’s like, “This guy writes just like me!”

James:

Well, I think, I actually think you have a little bit more – there’s almost this kind of like Zen minimalism style to your approach to both writing and entrepreneurship. You take this very complicated concept, like how shall I sell my company? And you boil it down to two pages. It’s just great like this is – people write entire books and give like TED talks on this and you’re like, nah. I just, and do I care enough to sell it? Okay, I’m selling it.

Derek:

Well, I guess I’m just whittling out all those other moments and just sharing the key moment.

So I’ve got to ask you something.

James:

Sure.

Derek:

Did you ever read that Esquire Magazine about radical honesty?

James:

Yes, because A.J. Jacobs, the author that was – has been on my podcast and we’ve spoken about it. And it’s funny. I don’t believe in radical honesty. Do you?

Derek:

I think it’s like nudity. I think it’s to be used in the right situation for the right people.

James:

Exactly. Like I believe in sincerity and transparency but not in vomiting.

Derek:

Right, exactly. So I was thinking that you to me sometimes feel like radical fault-admitting. Yesterday, I realized I didn’t know that you had done another podcast with Ramit and right there at the beginning of the podcast, it’s like you’re so unprofessional, right? Like you’re talking and you kept saying, “Oh, I should have had that before we spoke but I forgot. Oh, well.”

I so admire the way that it seems like you are almost finding ways to admit your faults at every turn, like such a runner that to me it seems like a brilliant way of getting the world – not getting the world – asking the world to love you in a way because it’s like – go ahead.

James:

Well, I -- Yeah, like continue.

Derek:

So showing your weaknesses. It feels like you’re always showing the world your weaknesses and to me the underlying message is, “If you love all of these, you really love me.”

James:

Well, I think also people give themselves permission to admit their mistakes, their flaws. Everyone wants to be on a pedestal or else they think people won’t like them.

Derek:

Right.

James:

And I’m sort of afraid of the pedestal. I think people want the reverse and I want the reverse. I want people to know right off the bat that when they’re dealing with me, bad things can happen. One thing is and this is back to the radical honesty. I don’t say bad things about myself all day long, but I’ll never say bad things about others. So I’ll never put anyone else down or be honest about. It’s not that I’ll be dishonest about it, but I’ll never be transparent about other people’s faults because it’s not business.

Derek:

I like that. Back in the ‘90s, there used to be a great magazine called Musician magazine and they would include, I think like every few months, they will include a sampler CD along with the magazine of: here’s 16 artists you’ve never heard before, one track each.

I used to love to get the CD and just put it on in the background while I was doing other things. One day, there was this one track that jumped out at me because the singer was singing, “Used to be I could go up to Barstow for the night. Find some crossroad trucker to demonstrate his might. These days it seems like nowhere is far enough away – eeeh” and her voice cracked and then she goes, “So I'm leaving Las Vegas today, leaving Las Vegas” and I remember when her voice cracked like that, I stopped what I was doing because I was just listening in the background.

She left that in. That was fucking brilliant and then it made me pick up the CD and who was that? It turns out it was Sheryl Crow. She was an unknown artist at that time.

I so admired that decision to leave in that crack in her voice because it’s like that little fault is what made me like her. There were 15 other artists on that CD that I will never remember, but I remember that one that left in that crack.

So you to me, you’re kind of like that with your writing.

James:

Well, it’s interesting because this relates actually to a lot. It’s funny you pick up on that with Sheryl Crow and let’s even say with my writing because so much what your book is about and it’s interesting it’s what music is about, too. Because people and tell me if you disagree with this. And by the way, I just want to just the bio out of the way. You started CD Baby blah, blah, blah. It was the one of the first websites to sell music. You sold it. It was great. You write books about entrepreneurship. Let me get back to what I was saying, just a second ago, which is: people often buy what they view as authenticity over what might be good music. So for instance, the other 15 singers in that CD might have been good music but what attracted you was authenticity.

Derek:

Yeah.

James:

And you look and I wonder if you agree with this. I take someone like Kurt Cobain. He was authentic say with Nirvana and particularly you look at the songs he covered from like the ‘30s and the ‘20s like these are really authentic musicians from way back. And then maybe he couldn’t come to grips with authenticity as he became like a mega success and this plagued him in some sense. And I wonder if you agree with that? And what is authenticity to you?

Derek:

Oh, big question.

James:

Because your book and your style of entrepreneurship is so different. You’re successful, widely successful but your style of entrepreneurship is so different from what let’s say the typical you know, here’s you’ll be a success type of book. That it really strikes me as your own brand of authenticity and that’s what essentially gave you a happy ending and happy life. Happy ending sounds bad but you know what I mean.

Derek:

Well, okay. Let’s see. Kurt Cobain first. Authenticity. Yeah, you’re right. That’s a good one.

The idea that they couldn’t continue being authentic. I don’t know. That suicide really pissed me off, if we believe the reasons around it: I hate the fame and all that because at any given point, he could cut his hair and apply for a job at a Burger King in Iowa City, and nobody would ever believe he was Kurt Cobain. Do you know what I mean? You can always disappear from fame.

James:

But somehow nobody – you don’t want to. They’re like being – I don’t think that would have been authentic to him, either. Like he was aiming for the fame. It’s almost like he didn’t know what to do when he got there. And I’m not saying what he was saying or the reasons for his suicide were good or bad. I’m just wondering if somehow you know, he lost that drive for authenticity because he was past it.

Derek:

Right. Wow! I hadn’t thought about it like that.

James:

And the same thing happens in like let’s say, rap music. Like take – I don’t know if you listen to rap but like take anybody. The difference between Drake and some up and coming you know, rapper from the Bronx in New York. Like people claimed that even though his music might be good or bad, whatever your opinions are. People say he’s not authentic. So a lot of people don’t buy it for that reason because he doesn’t come out of you know, the hood. And you know, again, people judge music not necessarily on quality of the music often, but on the authenticity of it and…

It strikes me that your approach to entrepreneurship which approach is which techniques you use, you determine more by its authenticity rather than whether it would drive customers.

Derek:

You know, I was listening to the interview you did with Nassim Taleb.

James:

Both one of our favorites. I noticed you have Antifragile as one of your favorite books.

Derek:

Oh, man. I love the way that guy thinks because it so often comes down to these core values. It’s almost like zooming out from the world that in finding some principle that stands above all these other details and then focusing on that principle and then deciding, well, let’s just focus on this principle and extrapolate that and see where that principle goes.

James:

Yes.

Derek:

I think that is what I often try to do with life but of course and that comes out with entrepreneurship too is “Wait. Why am I really doing any of these? What is this really about?” Let me just zoom out and focus on this core principle. Now, we’ll extract from that principle. Then of course when you extract from a core principle it comes out being very different than all the usual BS that people do.

James:

Like give me an example. I don’t fully understand.

Derek:

Okay. Let me think.

James:

Well, let’s take your business. You described at one point, you were telling investors you didn’t want to get bigger. You wanted to get smaller. So what was the core principle? What was the extraction from that?

Derek:

Ah okay. Then to me that was the core principle. There was I like being happy and one way I found to be happy is to have less responsibilities for things - to be lighthearted and fun makes me happy. And so the idea of doing an IPO and suddenly being beholden to stockholders and all that, well, that’s not fun. Why would I do that?

It’s like, well, you could make more money that way, but what’s the point of making money? It’s to be happy and if it’d make me unhappy to have so much responsibility, then I’d rather not make more money. I’d rather just focus on the happiness.

Here’s a better example is focusing almost entirely on the customer and what’s best for them then I think, well, are my customers wanting me to do an IPO? When I get a bunch of – what is the – the suggestion box. That classic, the wooden box with a little slot on the top and drop your suggestions in here.

James:

Right. The other one would say, “You must IPO now for my little CD.” I thought that was a great kind of – you can have this metaphor throughout that like it was really interesting. Like your customers don’t really want you to expand. They’d actually want you to be – their ideal dream is for them to your only customer.

Derek:

Right. Exactly. Why would I do this then? I can’t say I’m doing it for their sake. Am I doing it for my sake? No. I’d be happier with less responsibility. I think that’s what I mean about core principles, that kind of zooming out and saying, “Why am I doing any of these?”

James:

Yes. So and let’s get to that. So it seems like I’m going to use one of these catch phrases to describe what you did and the theme that – it’s almost like you participated in what I’ll call the favor economy. So it seems like a lot of your ideas ranging from CD Baby to even what you’re doing now with Now, now, now is you start off with, “I’m going to do a favor for somebody” and then if people respond to that favor and want more, then suddenly you say, “Ah. I can scale this into a business or a platform or something that I want to spend more time on” because you personally like doing favors for people.

So you created a buy now button for yourself, then you did for your CDs. Then you did it for a friend. Then more people started calling to contacting and you realized, “I have a business.”

So this idea of verifying or validating that a business idea is good seems to be – the method seems to be do a favor for someone, see if or do it for yourself first, so you’ll learn how to do it. Do it as a favor for someone else. See if more people ask and while you have a business that cost you no money to create.

Derek:

Yeah.

James:

Does that seem kind of accurate?

Derek:

Yeah, that’s a good description. I love it. That by doing favors for people, it implies that people are asking you to do those favors and to me the key is the asking.

So bluntly put, you shouldn’t start a business unless people are asking you to. You do the things that people are asking you to help them with. Those are the things you do.

Other than that I guess I’m a reluctant businessman. I don’t try to make businesses. I just kind of answer the calls for help when they come in and then see if I can systemize and turn that call for help into something I could help other people with.

James:

Immediately that’s one style like nobody was asking Larry Page. Hey, can you make the 8th failed search engine out there?

Derek:

Right.

James:

Or maybe they were asking, can you make a search engine with slightly better results than AltaVista? I don’t know.

Derek:

Right.

James:

Or maybe he and his mind was asking that. So it helped him so he figured maybe this will help others and he saw it by the usage and so on. But how does someone – let’s say I always use this example. Sitting in my cubicle somewhere. I’m unhappy working for somebody else, how do I know what favors to do for people first? Or what to do for myself and other people say, “Hey, can you do that for me?” Because you say in the book, it took you 12 years of trial and error trying different things before, “Ah, I hit upon doing something for myself that other people ask me to do for them.” So this 12-year period was a long time.

Derek:

Right. Okay. So I’ve been dying to ask you about this: the idea of choose yourself. That when I look back at my life and what was successful and what wasn’t, it seems that whenever I was focused on me, me, me, me, me like all my years making music. It’s me up on singing my thoughts into a microphone, spotlights on me. I’m out there promoting me. It’s all about me. I did that for 15 years and it was hard. It just felt like always an uphill battle. I had some success, but for the most part, it was hard.

On the other hand, as soon as I turned my attention 100% to others, I said, “Okay. Forget me. How can I help you?” That was like the big idea behind CD Baby. When it was just completely putting myself into the service of others and just completely forgetting myself, I ceased to exist. “I am here solely for your service” then boom! That’s where all the successes seems to happen repeatedly in my life.

That’s part of why I have a problem with the idea of say lifestyle design where I hear too many people talk about like, “What kind of life do I want? I want to be in a hammock on a beach and I only want to work from these hours. I want this and I want that, and this is the kind of life that I want. Why isn’t it working out for me?”

I think, well, it’s because you’re focusing entirely on yourself. On the other hand if you just forget all of this self-pleasuring and focus entirely on others, you might find the world rewards you more. Do you know what I mean?

James:

Well, it’s funny because you mentioned earlier you know kind of the core values that you had and one was you wanted to be happy. It seems like there’s a gray area between coming up with you core values as opposed to helping other people achieve their core values.

Derek:

Right. Yeah. It’s kind of you have to serve others within the limits of what you’re able to sustainably do. Right. You can’t do something that makes you absolutely miserable. That’s like the engine that breaks down without oil.

I like the metaphor that happiness is like the oil in the engine. You need it for the engine to continue running. You can’t do something you’re unable to do. But within the realm of what you’re able to sustainably do, if you focus entirely on others that’s where the world seems to reward you the most.

James:

Yeah, that’s really true. So you know, I imagine when you were performing music in 15 years many things were getting in your way. One is venues had to like you, customers had to like your music and distribution. You found distribution companies had to like you. So guy who had just I don’t know graduated high school or college had to say, “Okay, this is the guy we’re going to distribute.” And you depended on whether he had a good day or not that day, whether he was going to like you. And so the whole thing was to choose yourself is I don’t want anybody. I don’t want to have to give – hand over my destiny and my self-esteem to other people who I don’t know. And so when people are coming to you in this kind of favor-based approach, you’re not outsourcing your self-esteem to anybody.

Derek:

Okay.

James:

And so there it’s kind of you created this way. Like instead of relying on, “Oh, can Apple put me on the front page so I sold a lot CDs?” You’ve created CD Baby to sell your CDs. So you eliminated the outsourcing of your music self-esteem to other big large companies.

Derek:

Got it. Okay. That’s a nice way of putting it. I get that.

James:

And then you helped other people do that and part of the thing was that guy that your value is talking you can’t pay for placement. We’re not going to have ads. You can’t pay for any special treatment. You know, let me ask you this. Right now we supposedly have this long tail where everybody could sell you know 50 albums a month no matter how bad you are or where you are in the long tail. But what sense of ... in reality is that Amazon has actually or Apple has created our choices for us. Like oh if you like this you now might like this. And if you’re not in their algorithm, you’re actually further down on the long tail like this kind of democracy of choice has created less choice in a weird way.

Derek:

Yeah, because it’s like, how are you going to find that artist’s number 1.5 million that’s buried in there that Apple is not recommending to you? Yeah.

James:

Right. And so how does that artist now kind of overcome that?

Derek:

Good question. It changes the techniques like say for example, using a....

This is just like one little hack, one little quirk, but it worked really well. Some of my best sellers at CD Baby were the ones that did one cover song on their album of a song that had never been covered before. So you can go to iTunes and use their search engine and do a little research for all of your favorite songs. Right? When you find one that only has one version of it, whatever it may be. I can’t even think of an example right now because any example I would give would be one that already has lots of covers.

But say, you think back through the songs you love, you find one, and the only search result is the original recording. Well, boom! That’s a great song to go do a cover version of because now in the future, you do a cover version of it, you get it up on iTunes and anybody searching for that song in the future will only have two versions: the original and yours. And they’ll say, “Well, who is this one?” I found many times that that gets people interested in the whole artist.

So here’s a specific example. Artist named Melissa Rebronja from Toronto did a cover version of – was it called Wonderwall by Oasis. “You're my wonderwall” Wonderwall? Is that what that song was called? So she did a cover version of that and it was the only track number 9 on her full album of other songs that did not sound like that, but her whole album sold really well, because that’s how people found her in the mix that they were searching for Wonderwall, found Oasis and who’s this? Melissa Rebronja. Oh, well. Let’s check out her other track. So there are things like.

You know, the rules change because that would not have been the case 20 years ago. You didn’t walk into a physical record store and say, “Show me every album that has a version of the song Wonderwall on it.”

James:

But that’s a powerful approach. I always think no matter whether you’re a painter, a musician, a writer or even businessman, if you take what’s already proven to resonate throughout the decades or the centuries or even the millennia, if you take that and do something slightly unique with it, you win. So for instance, whether you’re a fan of Justin Bieber and some people are and many people aren’t. If Justin Bieber did a cover John Lennon’s Imagine, bam! That would win.

Derek:

Yeah.

James:

So it’s the same type of approach like if you take what resonates with time, and multiply it somehow or do it, like I do that with my writing. I’ll find obscure stuff wherein like a thousand years ago and take the ideas from it and sort of rewrite it in a modern context and it works. Those are my most popular posts.

Derek:

Hey, so let me ask you question about giving advice. This has been on my mind a lot lately because you know I did Tim Ferriss’ podcast in mid-December, and I got a bunch of people contacting me after that asking my advice on things.

For the last couple of months, I’ve been giving a lot of advice. I find that my advice is so tainted because it’s a reaction against my surroundings, I think. Like sometimes some people ask me a question about what they should do with their career, and I give them my best advice by email. I hit send and sometimes afterwards I wonder like, “Why did I give that advice? Why did I say that?” I think it’s often a reaction to what I feel is not said enough because –

James:

What’s an example?

Derek:

I feel a lot of people are saying this: quit your job, quit your job, quit your job. It almost seems to be the unanimous opinion is that everyone on earth should now quit their job. When people email me and saying, “I think I want to quit my job.” Then I feel it’s almost like my duty to say, “Well, actually maybe you shouldn’t quit your job. Maybe there are reasons to keep your job.” They say, “Well, I can’t believe you’re saying this” but I’m saying it because it feels like everybody else is saying the opposite.

Then I remembered that if I was in a different environment, say if I was working at an HMO. I was working with at a big corporation and nobody was quitting their job and everybody thought that anybody who quits their job is crazy, well then, I’d probably be giving the advice to quit your job because it seems that everyone around me is saying don’t quit your job. I’m giving voice to the lesser-heard advice.

I wonder sometimes how much of your advice, like say, say if suddenly everyone in the world was taking your advice and everyone in the world was choosing themselves and making decisions like that if it became ubiquitous, do you think you might be tempted to advise the opposite?

James:

You that’s... a lot of people always ask me that. Let’s say I say, “Never buy a home because it’s a bad experience.”

Derek:

Good one. Yeah.

James:

Whatever. If everybody in the world follow this advice, nobody will buying homes, the economy will collapse, and so on. So the first thing I always know is it’s never the case that everyone is going to follow your advice.

Derek:

Right.

James:

So that will never happen. So I never think of it that way. The other thing is advice is autobiography.

Derek:

Yeah.

James:

No one wants somebody from a pedestal. They want to know, okay. I had this problem. Here’s how I solved it. So that’s really your advice. Is this all coming from your own – advice is autobiography.

Derek:

Here are the lottery numbers I played. Maybe this will work for you, kid.

James:

Well, and guess who else did that? Buddha always said you could – here’s what I do every morning. You can either try it or not. Like he didn’t say, “Do this.” He just said, this is what I do. I’m not trying to be all Buddhas here. I’m just giving it as a one example of something that’s resonated to the millennia. He just said this is simply what I do every day. You don’t have to do it. You could be a king or a merchant or whatever but this is what I do to become happy. And some people followed it and some people didn’t. So I think qualifying things by saying, “Look, this is what I did.” So for instance take the job thing. I stayed at my job at HBO for 18 months after I started my business on the side. So even if there’s a lot of reasons to quit a job, you have to do it carefully and here’s what I did. So that’s what I usually do.

But it’s interesting though, you bring that up. I know you answered 5,000 emails in a month. Like why did you? Did you feel obligated to answer everybody? Was it stressful to do it?

Derek:

No. I mean, well, it was a lot of work, but I wasn’t complaining. It was fascinating. It’s every writer’s dream to have your finger on the pulse of what people want to know. It was like, “Here’s 5,000…” Actually, in the end it was I think I got over 6,500 emails last time I counted just from that show.

James:

And what was the pulse? Like what do you think? Because I find in those situations there is a common question. And what was that? A theme. What is this right now from what you saw?

Derek:

Oh, boy. I don’t know if I can narrow it down to just one. The first thing that comes to mind is this idea of, I want to quit my job and follow my dream. Or I have this dream that I’m not following. Also this, I don’t know what my passion is. That’s a huge one. I haven’t found my passion yet. I don’t know what my purpose is, what is my calling. I don’t know what my passion is.

I think that’s as dangerous one because I believe that we’ve built up that word ‘passion’ to be so deep. I kind of think like Romeo and Juliet that sometimes those big giant love stories can be really dangerous because they make you think like, “Okay, kids. This is what love looks like. Do you want to know what love is? Love is drinking potion and killing yourself and jumping off of balconies and stabbing others” all in the name of love. If it’s nothing, if it’s less than that, that’s not really love because that’s what love really looks like.

Passion, I think, is this word that gets used like Romeo and Juliet like I had a passion and I am passionate about my calling. I am passionate about malaria in Africa. This is a passion; I’m following my passion. Then some guy in Ohio is just sitting there playing his video games like, “I don’t know. I don’t really have a passion.”

Instead, if you just follow the little things that interest you, like you just notice on a day-to-day basis what you’re drawn towards more, then you just keep doing that more and more and you find that you get kind of driven by it eventually; that things grow slowly. Kind of like good relationships often, grow slowly. It doesn’t have to be this boom! Love at first sight. That it can be this thing that just grows and grows.

If you were thinking like that doesn’t look like passion. That doesn’t look like love. I didn’t freak the fucking out the second that we met so it must not be love. It must not be passion. Then you overlook some of the best things in life.

James:

It sounds like your career if you look at it and slice and dice it in various ways is very much like that in the sense that you had a theme rather than a passion. So your theme was music. You performed, you were an employee at Warner Chappell and then finally after a lot of trial and error, you learned programming. You started selling music online and that turned into CD Baby, which finally in this favor economy way worked out. So it seems like still having a theme like you say noticing different things but then what can you do within that larger core theme or value or whatever, that’s kind of what people should be asking perhaps.

Derek:

Right. Right. I love that you brought that up, the theme. You can have the core theme in your life that often you don’t notice until many years have passed and you notice that a lot of the things that have interested you the most have something in common.

So check this out. I’m kind of changing the subject but kind of pivoting on that point. That I was working with this consultant coach dude once.

He wanted to get to what was my core value. I said something about programming. He said, “Well, why do you like that?” I said, “Because of this.” He said, “Well, why is that important to you?” I said, “Because of this.” He said, “Okay. Well, then why is that important to you?”

He kept drilling down. It was like the ‘five whys’ but this version that was trying to get to that why is that important to you, what’s the core value? Why does that matter to you?

He got down to what was supposed to be the final value, but to me it came down to two. That my two most important values were learning and creating. He said, “Okay. Now, of those two which one is more important to you, ultimately?” I said, “Well, no. You can’t reduce it any further.” He’s like, “No. You have to figure out which one of those two is more important to you. Is it ultimately about the learning or ultimately about the creating?”

I thought about it for a bit and I said, “You know what? This is a fault of the English Language” because sometimes, in other languages there are words that take a whole paragraph to say in English but in Portuguese, they may have a word - is it “Saudade” or something like that - that it takes a whole paragraph to explain it in English, but in Portuguese, that’s just one word.

You can’t say that I haven’t figured out my core value because I have. My core value is **learning for the sake of creating for the sake of learning for the sake of creating**. It’s just that we don’t have a single word for that.

To me, that is one core theme is that my whole life I love learning things for the sake of creating things which is for the sake of learning things which then is for the sake of creating things. Like that loop is a thing to me that should be one word. That’s my theme.

James:

So that’s interesting. Let me take that people are saying because a lot of you that love create there’s two reasons maybe someone loves to create because there’s that instant feeling of like, ah. And you mentioned this. How do you grade yourself? You have a section in that in your book. And so some people might grade themselves in two ways when they create. One is that feeling of, “Ah. I know this is good and I feel good about it so now I’m going to release this into the world or not and then I’m going to move on to the next thing I create.” Other people might create because they want other people to like what they created so then a little bit more self interest in that where other people have to like it in order for me to feel validated about what I created. So there could be an additional why there which is why do you love to create?

Derek:

So hypothetically, those examples you just gave, imagine somebody – I think of this as AC/DC. AC/DC has been writing the same song since the ‘70s. Every time a new AC/DC album comes out, you know it is going to sound pretty much exactly like the ones they’ve been putting out since 1975. That is creating, creating, creating, creating. They have written hundreds and hundreds of hundreds of songs, dozens of albums but I wouldn’t say that hardly any of those past the first two were a real learning experience. So that to me is the poster child for creating without learning.

Then learning without creating, to me, are like those people that learn a bunch of stuff but never do anything with it. All right. There are plenty of examples of that.

So what you just said, I like those examples you gave of, you create because it’s something that makes you happy once it’s done like, “Hah, look. I made this great painting that’s just the way I want it be” and you want the feedback from the world.

It’s like creating for the sake of learning something or using your creating as a learning process can be an additional need that doesn’t replace those other ones. It’s, yes. I also want the world’s feedback and all that stuff, all these other reasons we create but to me it also needs to have some element of personal growth and learning in the sake of creating.

James:

You know, it’s funny because I deal with this with my own writing. I see what people liked so much in 2010 and 2011 and sometimes I feel this urge. Okay, I have to write again a post like that.

Derek:

Right. Yes.

James:

And you know, as opposed to finding like another way to reinvent myself or reinvent the writing or do something new. Like how do you – I mean, you’ve clearly reinvented yourself several times like you’ve focused on your being a musician and music, which I’m sure you still do but you did it 100% for a while then you focused on CD Baby 100% for a decade. How do you continue to reinvent yourself and reinvent this, “I’m going to call it passion” but reinvent this passion you have for music and creation?

Derek:

Okay. I’m going to tell you something I think I’ve never talked about publicly. Well, for one, this isn’t the thing yet. We’ll get to that.

I love that we have role models. Public role models to me, some music legends have been great role models in how they shaped their career path and specifically, I’m thinking of Bob Dylan, Miles Davis, and let’s say David Bowie where Bob Dylan, most some of you know maybe. Not all of you know; did this thing where up until I forgot what year it was. Like 1965, he was a very famous folk artist, like the most famous folk artist but folk was kind of more in the purest sense like it was folk as opposed to rock at that time. It’s just the guy with his guitar, all acoustic man, being completely real because it’s acoustic not electric. Then he went on stage at the Newport Folk Festival. He was the headliner and he was as big as can be and the curtains opened and he steps out with a rock band and a Stratocaster in his hand and jaws dropped and somebody in the crowd yells, “Judas” and it was just such blast me, Bob Dylan is going electric.

James:

I didn’t know the story.

Derek:

You don’t know? Man, sorry. Okay. I guess, yeah, as a musician it’s just like these are the tales we grow up with. Everybody knows the story if you’re a musician.

So to me this is like, “Wow, what a bold move he made” is to give up on this thing that he had created because he said he felt that he had painted himself into a corner, that he needed to break expectations to continue to grow creatively, right?

Miles Davis did a very similar thing. Again, he was known as this bebop trumpet player who played with Charlie Parker and so everybody knew him as this bebop trumpet jazz musician and then he started doing albums like what has he got with Kind of Blue which was shocking at first in the fact that it had like almost no chords. The whole thing is just in D. the bridge goes up to E flat and then back to D again. It was like the opposite of everything jazz was about at that time where it was all about this quick jazz changing, changing chords every two beats and for him to go completely against that and then later do things like play with an electric trumpet and all that.

Again, it was blowing off expectations or particularly knowing he was going to anger people but knowing that this was something that was necessary for him to grow creatively. It’s like I’ve been there. I’ve done that. Now it’s time to force myself to change.

Then of course the David Bowie example. He’d be something for a few years and go completely into that persona for a few years and then change persona. It’s just like a creative exercise.

So these to me were – these stories were legend and they shaped the way I think about things that you do something for a while and once you feel that you’ve finished your creative expression of that idea, then it’s almost your duty to force yourself to change.

James:

I agree with that and I want to pose one counter example and so this is a great guy so it’s not a bad counter example, Scott Adams who makes the Dilbert cartoon. He’s been doing Dilbert for 25 years or more and I asked him, “Why are you still doing Dilbert? You’ve clearly achieved financial success. It wasn’t necessarily a dispassion from youth that you had to like draw this cartoon about a guy in a cubicle. You know, you’ve done it. It’s beautiful. You’ve created a whole work, a body of art here.” And the mentioned that he has a whole machine to sustain that like a lot of people depend on this cartoon coming out every day. So what do you if you’re kind of tied to the responsibility of something?

Derek:

Oh, you just say sorry. I wish you best and I would have done it the Bloom County way where it’s like he did a -- Bloom County was huge, I guess, 20 years ago. Just he did it and did it and did until he felt like, “Okay. I’ve done what I’ve wanted to do” or what was it? Calvin and Hobbes, too. Like just, “I hit my point. I’m good with that and sorry. I know that this is going to put some people out of work but I know you’re going to find other jobs and just creatively, I need to make a change now.

James:

And then there’s the other example which is – and I’m trying – and this is where it’s hard to find an example. But there’s the fear when you reinvent that, “Oh, my gosh. It just became a one… I’m going to become a one-hit wonder.”

Derek:

Yes, yeah. Okay. So thank you for prompting me to the thing. I don’t think I’ve ever spoken about publicly is:

When I sold CD Baby in 2008, it was actually a really dark time for me. You can read between the lines in my book and I toned it down because it was one of those things I felt like, “You know, this is just, I’m being a little too personal here. I’m trying to just keep focused on what’s useful to others to read and now I’m getting a little bit into a sob story.” So I had like a couple of chapters that I cut out because they were a little too me, me, me, but it was a really hard time for me.

It was basically like CD Baby ended with a mutiny. This company that I started and all these people that I hired just something went kind of fucky in the internal culture. It was like they were making me walk the plank and it was just sad and just made want to hide from the world like forever.

Dude, I was seriously looking into how to legally change my name and change my citizenship and move to some other part of the world and just disappear like I would tell my family and two or three dear friends where I was but otherwise, I just wanted to start anew with a whole new life and have nothing to do with the other one because I just wanted to hide. I hated how much responsibility I had with CD Baby and I just wanted to just sluff off the whole world.

I stayed in that mindset for about a year of really planning on changing my name, dropping off of the grid entirely. I was reading and you can find a couple books out there called How to Disappear. I read them.

James:

I’ve read that book, too. That’s a great – that book actually has beat on Amazon occasionally. Like sometimes it’d come onboard and it’s like pops up and return of best in our list

Derek:

Great title. It was on a plane ride to New York. I was going out to New York for a friend’s wedding and I was reading the book called Forty-eight Laws of Power, I think. It was talking about accepting public fame or recognition as a responsibility. Take on the role of public attention.

I thought about this and I thought, yeah this is kind of the chicken shit to do to run away and hide and change my name and go plug my ears. Shut off the world. I want to disappear. I could probably set up the responsibility. I can man up to what I’ve created and step into the spotlight and do something worthy there.

Okay so here’s the key point. For a year or so, I had felt completely unmotivated. Every day I kind of had no reason to wake up. I had millions of dollars in the bank. I had absolute freedom. I wasn’t even in a relationship at that time. Just on any given point, I could just be anywhere, do anything. I didn’t have to do anything. I didn’t have to be anywhere. It’s like there is such a thing as too much freedom and I had it at that moment for this whole year. There’s this strange lethargic exploratory year with no drive.

Then on that plane ride, I had this idea. I was like I think I want to be a TED speaker. Or not just TED - that’s just a symbol to me - but I want to be like a writer, speaker, thinker kind of guy.

At that time, as you prompted, I felt that I was a one-trick pony. That my gravestone was going to say, “Here lies Derek Sivers. He made CD Baby. Not much since.” That’s how it felt like I had peaked. This was the first idea I had that felt like it went beyond that peak. If could really be a writer, speaker, thinker kind of guy where TED invites me to speak on stage and get into that world instead of just my world of musicians, wow! That’s inspiring.

For the first time I felt inspired to action. Now, I had a worthy goal that made me jump into action. I love that definition of a good goal is one that actually changes your actions in the moment, like right now. Goals are not about the future. Goals are about changing the present moment, changing your present actions.

Suddenly, I was inspired as hell. I started writing six to eight hours a day and working on my thoughts and chiseling them down to make them surprising and cutting and succinct so I could make this point in four paragraphs, short enough that I knew everybody would read it and forward it to their friends and not procrastinate to read it. I put so much work into this and then...

Within nine months I was speaking at the main stage TED in front of Bill Gates and Larry Page and all these intimidating people. I did it three times and then people now know me more from TED and come up to me and say, “So what did you do before TED?” I’m like, “Well, I had this little music store and you probably haven’t heard of it”, but that was my reinvention of 2010.

James:

It’s interesting because again, I think what separates your talks and your book out from anything else is this authenticity about what it’s really like to be an entrepreneur or not – what it’s really like to be an entrepreneur – what it was really like for you to be an entrepreneur and you’ve kind of like you said, whittled it down to what your core value were and how you implemented them and I guess I wonder. I feel so inauthentic at times even though I try to be authentic. And people think of me as authentic but it’s very difficult and it doesn’t seem like it was that difficult for you. Like how does somebody sort of reach inside and figure out their authenticity? Is it this kind of drilling down on the why or what is it?

Derek:

Wait, I’m sorry. But how are you being inauthentic?

James:

I sometimes feel like a people-pleaser. Like I have to – I want to be entertaining. I want this podcast to be entertaining, I want my writing to be entertaining so I’m trying to figure out that balance between pleasing others and doing something artistic and sometimes, I don’t quite know where the line is. But I feel like with your business and with your book, you’re saying things exactly and doing things exactly how you wanted to do them. And I think that’s hard to know. There are so many layers of, “Oh my gosh. When I was 16 years old this girl didn’t like me and I had to wear all these masks to get someone to like me” and 30 years later, I still feel that way.

Derek:

Hmm. Interesting. Well, some of that I think is just being considerate. At any given moment, you could hit record on your mic and you could say, “Hey, everybody. Welcome to the show. Instead of having a guest today, I’m just going to sit here for an hour and a half and just talk about whatever is on my mind today.” You could go there with no script and it would be completely authentic, but it would be completely indulgent and completely boring to others.

So I think it’s actually considerate to shape your message in such a way to edit yourself first, not being fake but just being considerate.

For example, a few times people have asked my advice on giving TED talks and here it is. Here’s my advice in five seconds: just cut out everything that isn’t surprising.

Because people watch TED talks in order to learn something. If they’re not surprised, they’re not learning. If you’re just telling them, “Well this and I this and I grew up here and I got a story.” You haven’t surprised them. You haven’t made their eyebrows go up so they haven’t really learned anything. So instead if you look at whatever message you want to give, whatever story you want to tell, and then just erase every single line of it that isn’t surprising and what you’re left with is a short, succinct surprising thing that somebody can actually learn from.

That’s why my book is only 88 pages. It’s because at every paragraph I’d cut out everything that I felt other people say that’s been heard before, that isn’t surprising and I just focus only on the sentences, the paragraphs that were absolutely surprising. But that’s not necessarily authentic.

James:

Well, I think you did that for your business and your book, as well. So for instance, when advertisers came to you and said, “Hey, you got the traffic. We’d love to advertise” and you said, no, that’s a surprising response. A 100% of other – 99.99% of other businesses would say, “Sure. Let’s flip the switch on advertising.”

Derek:

Well, that to me is like why would you? It’s like letting somebody put a coke machine in a monastery. What’s important to you and I? Really? Is it still just all down to money? You just want money at all costs? Why would you let somebody liter up your thing?

Part of the reason I hardly ever listen to Tim Ferriss’ podcast is because by default my little audio player that’s on my phone it doesn’t have a fast forward button for some reason. I think it’s because it’s the one that’s built right into Firefox or whatever. It doesn’t have fast forward and a couple of times I try to listen to his podcasts like fucking six minutes of ads. Well, Tim why are you doing… I don’t make it past the six minutes. I just can’t sit here and listen to shilling for six minutes and so I don’t.

James:

I like how you put it, though, the coke machine in the monastery. So again, it’s like fueled, like what you do is fueled with authenticity just like a monastery is supposed to be you know, as authentic as possible to believe and you know, being spiritual and so on, whether it is or it isn’t, I don’t know, but that’s the idea. And of course, you’re not going to put a coke machine in a monastery. That wouldn’t be authentic to it. It’s still to me, boils down to authenticity in everything you do. And I think that’s a big theme of your book, even though it’s not explicitly stated. Which brings me to question, why, given that this is you know, sort of advice or lessons for a new kind of entrepreneur which is the subtitle, why did you leave out the chapters that made you cry? Because you’re driving people to the point where you cried.

Derek:

That was very un-Altucher of me. I just think, I looked at it and it felt like this is just me being – and this isn’t useful to anybody else. This was my one weird situation. I don’t think this is universal.

This was a really weird thing that happened where because of the unique situation I had where I had a bunch. I had 85 people all between the ages of 20 and 26 basically and it just created this weird little perfect storm of this anti-pattern of culture. I didn’t think that there was a universal lesson in there so much. I hadn’t extracted a universal lesson from that other than a rotten apple really does spoil the barrel. That when I looked back at what made the culture so bad there. In the end, it was like this beautiful culture for eight years. It was a great place to work and then just something changed and it turned awful. When I look back, it really was just a couple of rotten apples like just a couple of people that spoiled the barrel.

James:

It’s not because I call that a – so I had a similar situation in a business I started and I call that the virus. And as soon as you see the virus appear, you have to immediately eliminate it because otherwise, it spreads in the stair wells, it spreads in the lunches or the coffees. And then everybody has the virus and you can’t kill yourself. You’re too late. You did summarize in the chapter title which is, delegate but don’t abdicate.

Derek:

Right. Well, I found a very nice diplomatic way. I hinted at that. I didn’t dive into it. I didn’t dive into the ‘woe is me’ thing too much.

But you know what’s kind of sweet, by the way? A few years after the book came out, one of the guys that worked for me in customer service named Dan, he’s now a guitar teacher in Idaho and he’s actually opened up his own music shop where he’s got a couple of people working for him. I hadn’t heard from him in years or I hadn’t heard from anybody. I sold the company in 2008 and it was – sorry I’m sticking my middle finger in the air right now. It’s like, “Fuck you guys. I’m never speaking to you again.” They never spoke to me again. I’ve never spoke to them again. There was bad blood at the end.

Here I get this email from Dan, years later, saying, “Hey, I don’t know if you remember me. I used to work for you at CD Baby. Now I’m this guitar teacher and I have a people working for me. Suddenly, I realized how hard it is to be a boss and be a manager. It’s really hard and they try to blame me for all of their problems in life. It made me realize we really did that to you, didn’t we? I’m so sorry. I don’t know what came over to us. I don’t know why all of a sudden we just decided you were the bad guy. There was a weird kind of mob mentality that happened that time that I didn’t even notice it at that time. But now that I’ve got employees myself. I just want to say I’m sorry. I don’t know why we treated you like that.”

I was like, [sigh…]

James:

That’s great that you got that email because I think a greater than 1% response from your ex-employees is you know, 1000% more than anyone else gets.

Derek:

Yeah, that was really nice of him.

James:

That’s great that he recognized that. You know, you said another thing very interesting and I’ve been dealing with this a little bit. When people are either your customers or your employees they feel very strongly that they know you and that you kind of should do or conform to some behavior that they expect and you have this chapter about excluding people and it’s a very healthy reminder that you can’t – you know, there’s that saying, “You know, if you try to please everyone, you end pleasing nobody.”

Derek:

Yeah.

James:

If you try to please everybody all the time, you end up pleasing nobody all of the time or none of the time. Or, I don’t know. Some quote like that.

So I think it’s a very healthy reminder in building a business that you’re not going to be a monopoly of the world and of every constituency of your business. You can’t do that. Even if your job is to please the people you want to please, you just can’t do it. There’s going to be this vocal minority that hates you and your key, your job then is to exclude them from what you do.

Derek:

Yeah. I think you’ve talked about this before. This idea that on your blog you might get 99 nice comments and then you get one negative one and it’s human nature to look at that one and go, “Hey. What the hell? Why isn’t every single person happy?” You focus so much on the one person that’s not happy with what you do but yeah.

Again, music is a good role model; music that tries to please everybody is what? It’s the elevator music and the way that you make great music is by doing something that somebody’s going to hate. You take a chance. You push it to some new extreme. You say something in a way that some people might find offensive but a few will find extremely refreshing and honest and real.

James:

So and I bet that one of the questions that you got in among these 6500 questions that you got in past month or so is, I’m afraid to take the chance of being myself, being authentic, saying what I really feel because of maybe a boss won’t like me or my colleagues won’t like me or a future employer won’t like me or future customers won’t like me.” That’s a big fear for people.

Derek:

I meant to tell you this when we first said hello. This is the last interview I’m going to do for a long time. In fact, my book called Anything You Want, it was re-released in August and so I did a whole ton of interviews from August to December and then I did Tim Ferriss’ in December and I said, “That’s it. No more. That was exhausting. I am done.” I told my assistant, that’s it. No more interviews. She said, “Do you want me to say no to everybody?” I said, “Yeah, everybody.”

I said, “Wait. Except James Altucher. If I hear from him, absolutely. I want to do that one” A week later, you emailed. I was like, “Ahh!”

James:

That’s excellent. The timing was right.

Derek:

That’s destiny.” So this is for real this time. This is my last interview for a long time.

So here’s a very embarrassing story. This is one of those classic, Altucher kind of things like, “I shouldn’t be saying this, but I’m about to.”

James:

These are the only stories.

Derek:

Yeah. There was this girl I knew once that was an aspiring entrepreneur, very ambitious but not yet so successful. She was a good friend of mine but also really looked up to me. She just noticed that nothing bothers me. Like I never get mad, I never get too upset. And she’s like, “How can I be as carefree as you? Nothing bothers you. How do you do that? How do you just let everything roll off your back?”

I thought about it for a bit and said, “Well, first you get a million dollars.”

James:

That helps.

Derek:

She just thought that was the funniest thing. That was the real answer and we’re not supposed to say that. Again, maybe I’m giving this contrarian advice because I feel that I’m surrounded by people that say that money doesn’t matter. Or is it okay?

Maybe if I was working on Wall Street I might be saying money doesn’t matter. In my world, I’m surrounded by people that say that money doesn’t matter and so I feel my contrarian need to say, “Actually, it really helps.”

I feel it’s like a big reason I feel so comfortable and not needing to please others. It’s this feeling of like, yeah. There’s a reason they call it “F.U. money”. I don’t need anybody. I don’t need anything from anyone. I don’t know. That’s a big part of it.

I highly recommend if you were somebody that was thinking of perhaps getting rich and not sure whether you should or not. I highly recommend it.

James:

Well, and the thing is this really is like a guide book. Again, I’m going to get back to the beginning, which is, and it took you 12 years of testing different ideas, doing things for yourself, figuring out the right favor you could do for yourself that other people would then ask for that then scaled into a business and that’s how – that really is the way to make a million dollars is if you do a million favors and you do it in a way that’s scalable, then bam! You have it.

Derek:

Right and then you’re right. Exactly. There are different methods. I think that Ramit same thing and all that kind of I will teach you to be rich and all the things that are out there teaching you how to make a lot of money, most of them are correct, if you actually follow through.

My friend Ian Rogers read this fitness book that LL Cool J put out years ago. It was like the LL Cool J Guide to Fitness and Ian Rogers actually went through the whole book and actually followed it to the letter and did absolutely everything he said to do and ate exactly what he was supposed to eat.

Then years later, he met LL Cool J and he said, “I actually did your book.” LL was like, “I’ve never met somebody that actually did my book before. Lots of people read it. They do it half ass, they do a little bit of it. They tell me, “Oh, good book, man. I really want to do that someday.” He said, “You really did it? You really did everything in it?” He said, “To the letter.” He said, “Man. No wonder you’re good in shape.”

James:

And so it worked.

Derek:

I think that about a lot of those programs that are out there that say if you do this, you will make a lot of money. I’ll bet that most of them work if you actually do it. Instead of just think that you should and mean to get around to it someday.

Sorry. That was a tangent. Something else we were talking about. I forget.

James:

No, but I think that’s true and I think for you it was the being authentic to what you’re interested in, being authentic to being happy but also kind of sticking to this core idea. You mentioned it throughout the book which is that your customers are always going to come first before any expansion, before any standard ideas of how to make a business bigger, before raising money, before an IPO. You stuck to this authentic value that was important to you which is that you wanted to sell music and you wanted it and it’s like conflict-free as possible way for other musicians to sell music. And I think that was what scalable as oppose to, “Yeah. Let’s get advertising, let’s sign up with Universal or whoever” and you do these things that would cut corners for you.

Derek:

Well, I guess, it often helps to say or to start a sentence with, “In a perfect world… How would it look?” I think that’s where a lot of those things came from.

Well, in a perfect world, how would this work? Of course, there would be no advertising.

In a perfect world, there would be no paid placements. So anybody had just as much of a shot to be on the front page as anybody else. So you would not be allowed to buy up the front page.

In a perfect world, I get paid every week.

In a perfect world, I’d know the full name and address of everybody who buys my music. In a perfect world…

Even though I am saying all of this stuff and acting like I’m taking credit for it, you got to admit that I could have just been some guy with all of these philosophies and some store that didn’t go well.

A huge reason I’m successful it was just the damn luck of right place at the right time. It was late 1997, beginning of 1998 and there were no other online music stores at that time. So my little rinky-dink thing that was ugly and amateurish-looking just was – I was the guy on the surfboard when the huge wave came in. I just rode the wave. It was amazing timing. I couldn’t have done it a year before or a year later.

James:

Well, and so now, coming towards the end of your book here, how do grade yourself now?

Derek:

To me it’s how much I create. Yeah it’s the thing that I said earlier about learning for the sake of creating for the sake of learning for the sake of creating. Ultimately, the measurable thing is how much I’m creating, maybe because I won’t let myself just keep creating without learning something. To me, I need to measure my output for my own personal measure of success. I can’t imagine just learning things without using what I’m learning to create.

James:

So what are you working on now? When’s the next book?

Derek:

I don’t know.

James:

You got to do another book. I loved that one so much. You’re like the Zen master of like entrepreneurship writing. But maybe there are other things, you could be the Zen master of.

Derek:

Well, you know, it’s funny. Did you read Smart Cuts by Shane Snow?

James:

I’ve read. Shane’s been on the podcast – the second I read it by the way, was like 6:00 in the morning. I wrote Shane and said, “You got a call in to the podcast today.”

Derek:

Oh, good. That book punched me in the gut. I’d loved that book.

Hey, wait. You know what else I’ve meaning to ask you forever? In was it Power of No or Choose Yourself!? In one of your books, you said something like, “Pick a subject that you would read a hundred books on that subject.”

James:

Yeah. So I say, “Go into the bookstore, which section will you read the entire section of? And then that’s what your – that can help you find out what you’re interested in.”

Derek:

So have you actually read a hundred books on a single subject?

James:

Oh, yeah.

Derek:

Really?

James:

I’ve read like a thousand books on a single subject.

Derek:

Come on, no exaggeration? Really a thousand books?

James:

Yeah. Like for instance I love games. So I’ll read – I’ve read at least a thousand books on chess, for instance.

Derek:

Really?

James:

Yeah.

Derek:

A thousand? You’re not exaggerating? You’re not going to look back. Okay. Well, it’s actually 180 but it felt like a thousand? It was really a thousand?

James:

No, no, no. Ever since I was 18; I’m 48 now. I read you know, a hundred books a year on chess, maybe more.

Derek:

Wow! All right.

James:

So, that’s an example. Now I can’t if -- we would do that professionally but perhaps there are other ways to act professionally. You can program a chess computer or you can write books yourself or you could organize tournaments or whatever. I don’t know. I read probably several hundred books on poker, as well.

Derek:

All right. Well, I will just leave my jaw over there on the ground and I’ll try to keep talking.

James:

I’m sure you’ve read or gone through a hundred books on music.

Derek:

No, no.

James:

What about like even like books of – I forgot the word. Excuse me and it’s the most common word in the world. You know, where they have the notes, pages where they have notes.

Derek:

Oh, sheet music. Well, okay.

Every book I’ve read since 2007 is up on my website, if your listeners...

This was something I was doing for myself privately and then realized there’s no reason to keep this private on my hard drive. I should share this with the world. Every time I read a book I read it with – if it’s a paper book I read it with a pen in my hand underlining the sentences I like. Then I would open up a raw text file afterwards and I would type in every sentence I liked from that book so that I could just freely give the book away or just not worry the book ever again and know that I had saved in a nice searchable format just plain text file all the best bits I love from that book because I really wanted to get them into my soul. I wanted to memorize what I had learned and now the Kindle makes that even easier so I put them up on my site at sive.rs/book

James:

I highly recommend that page, by the way. I’ve read most of the books on that page. You definitely have a passion for entrepreneurship and high-concept thinking like Antifragile and so on.

Derek:

Yeah.

James:

So I think it’s a great list of books.

Derek:

Okay. So Shane Snow. I’m curious to hear your thoughts on this. One of his points that punched me in the gut in the middle of that book – it was a great book all around but there was one point that was a little toss-away sentence that he said something like, “The business you’re in might not be the business you think you’re in. You need to look at what people are really responding to.”

He used the example I think of Flickr, I think it was. That it started out as something else but then they noticed that everybody was using their engine to share photos and they realized, I think we’re actually in a different business than we thought we were in.

So when I read that sentence I had to stop and put the book down and think for a while. That I’ve been calling myself a programmer for the longest time like when people say, “What do you do?” I say, “I’m a programmer.” It’s actually part of my way of just shutting down the conversation so I don’t have to get into the ‘what do I do’ kind of thing. If you say programmer, most people just go, “Oh”. If they can actually talk programming well then I do actually want to talk to them.

When I think about that, nobody is responding to my programming. Nobody cares about the stuff, even with CD Baby. Yes, I did all the programming all myself for CD Baby but it was just some barely functional e-commerce store. It was actually all of the words around it. It was all of my talking that I was doing in my newsletters and blogposts and speaking at conferences. Those were the reasons that people really signed up to CD Baby was because of all the talking I was doing around it.

I was like, “Wow, actually what people really respond to is my writing. So wow! What if I’m actually a writer? I never thought about that before.”

I always just considered that writing was just some little thing I did on the side to share what I’d learned but I’m really a programmer, but I think I might need to flip that. I think maybe I’m really a writer and programming is something I enjoy tinkering with, the way that somebody enjoys tinkering with their car -- the old Corvette in the driveway idea, right.

Then my thinking was flipped around this twice because I don’t earn any money writing. Maybe I could if I really tried, but my only income comes from investing. Well, does that mean I’m really an investor that likes writing? I don’t know.

I’m curious what your thoughts on how do you define – do you define yourself based on what gets the biggest response or where your money is coming from or just what you like doing the most?

James:

I totally define it on what I like doing the most with the idea that I also have to think of what feeds me and my family. But writing is what I love.

Like you asked what’s – hundred or a thousand books that I read. I certainly read a thousand good novels or collections of short stories in order to improve my writing. This is the thing I think about all day long and care about the most. I used to go on. I was like you. I had something like you had CD Baby. I used to go on and I made financial websites. I used to go on CNBC and talk about stocks and finance but I realized almost everybody on these shows is just talking BS and here I am going through constantly anxiety about money and all these things despite being a so-called you know, expert like everyone else on CNBC about money. So I just wanted to write the truth.

And this is where I was authentic and I wanted to write it well through stories. That’s how I got the greatest satisfaction for myself. Like you said that before. It helps to be doing things that have made you money and make you money and investing certainly helps that but I never think about my investments. That’s where I’ve delegated and I’ve abdicated. I hate thinking about it.

Derek:

Interesting. I didn’t know that about you. I thought it was still kind of a side passion of yours because you still talk about it a lot.

James:

I talk about it because I know a lot about it. And so I feel like bad when other people make mistakes that way and I could say from experience, oh look. Here’s when I tried to raise money from so you know, that’s a story but it’s a story where I made a potential mistake and you know, I used it to help other people not make mistakes through storytelling.

Derek:

I can relate. The entrepreneur thing or even let’s just say talking about CD Baby. I personally wish I never had to talk about it ever again.

I mean, part of the reason I put out that book was to close the chapter on that phase of my life and say, okay. Here’s all the lessons I learned from that. I’m done.

It's kind of funny when years later people invite me to speak at a conference and I’ll say yes and I’ll think that I get to just get up there and talk about whatever I want and then after I’ve said yes and they’ve put me on the program they say, “Really, we want you to talk about how you built and grew and sold CD Baby.” Really? That is what the crowd wants. Okay, I’ll do it one more time.

James:

But entrepreneurship is so – people want the XYZ technique but the reality is, and I think you kind of refer to this in your book in a lot of ways. It’s very personal and very psychological how to build a business like it’s difficult and people don’t realize it’s not about where you put the Facebook ad. It’s about where you change yourself in order to deal with all this psychological problems that come up.

Derek:

You know, I thought you were going to make that into a Hollywood line there. It’s not about where you put the Facebook ad. It’s about where you put your heart.

James:

Maybe I almost said that.

Derek:

I love that as a songwriter. I think actually -- but I’ve spent 15 years of my life as a songwriter. I still think it shapes the way that I think about words. You think of the symmetry of words and things having a pattern.

James:

Well, you said it earlier. You were telling me a story and you started off with: there was a girl I once knew and that’s totally in the beginning of like a song.

Derek:

Kevin Kelly once gave a talk where he said we should focus on making a living not on making something huge. I emailed him afterwards: “Kevin, Kevin. You missed the line. It’s about making a living not making a killing.” And he goes, “Oh, thank you. That’s awesome. I want to use that.” He said, “Can I use it?”

James:

Oh my gosh. That’s great.

Derek:

I said, “Of course!” I’m always looking for those little symmetry of words. It’s the songwriter in me still.

James:

Well, I want to close with this because this a line that I’ve inadvertently stolen from you and I only this by accident because people keep retweeting me saying it but it’s actually just want to give you full credit for it, which is the quote, “If it’s not a hell, yeah, then it’s a no.”

Derek:

Yeah.

James:

I see it all the time. I’m tweeted as saying it but it’s totally you. And I don’t know how I got to say it but it’s your saying.

Derek:

I’ll give full credit. My songwriter friend Amber Rubarth came up with that one day when I was wrestling with the decision on whether to go off to this conference in Australia.

I was living in Union Square in New York City and I had agreed or told a friend that I’d go with her to a conference in Australia. Once it actually came close, I was like, I don’t know. I was describing my decision-making process to her and she said, “It sounds like you’re not trying to decide between yes and no. To you it really comes down to either fuck yeah or no.”

I said, “Yes, that’s it. it’s either fuck yeah or no.”

There’s my full credit: Amber Rubarth came up with that. So I wrote it up on my blog as fuck yeah or no and then at the last minute I decided to make it more PG 13 and I changed the fuck to a hell so yeah. Hell yeah or no.

You know what’s nice man? One of the nice things about sharing your philosophies publicly and writing things on your blog all the time is that your friends echo your own philosophies back at you. I’m not getting just yesterday. I was trying to make a pretty big decision in life and I called a friend to ask her thoughts and she said, “Well”. She listened to me and said, “Well, this smart guy I knew once said something called hell yeah or no. I think you need to be taking that advice right now.” I said, “You’re right.”

James:

What was the big decision? Can you tell us?

Derek:

Just a little. I have as of this minute a business in Belgium that I started in Belgium because it made a legal resident of Belgium which then in five years leads to citizenship and I was doing it but then for the last two years I’ve had this Wood Egg business running in Belgium but I hate it. The business just doesn’t need to be alive anymore. It’s nothing the public needs. I don’t believe in forcing something on people and I believe in shutting it down if people don’t want it and yet I was keeping it active just to keep the Belgium government happy and I was asking a friend’s advice. She said, “Yeah. You’re giving me a bunch of reasons why you could and should keep it active, but I can tell you’re not feeling hell yeah but in just the fact that this thing is sitting in your life taking up any mental space. You’re violating your ‘fuck yeah or no’ rule. I said, “Oh, yeah.” That was the decision moment. Once she said that I said that’s it. That’s really what it comes down to, isn’t it? I’m not psyched about this thing so why should I do it? So yeah, I’m in the process of shutting it down right now which means I’ll no longer be a Belgium resident which is a little sad. I love Belgium. Oh, well.

James:

But you know what? I think it reminds me actually of a Warren Buffett quote which is, his 5-25 Rule. So list the 25 things you most want to do in life. Now, separate out the first 5 from the last 20. The last 20 are still things you really want to do in life but they’re below the top 5. And then his point is, never, ever, look at that bottom 20 again.

Derek:

Yes.

James:

Because even though you really want to do them, you don’t want to do them as much as that top 5 and they will always distract from the top 5.

Derek:

I saw Ray Dalio in an interview say something similar. I doubt he came up with that. I think it’s conventionalm but it says:

“You can have pretty much anything you want in this life. You just can’t have everything you want. You need to prioritize.”

I love that. That’s powerful.

James:

That is good. And so, Derek, I really want to hang out. You got to look me up next time you’re in New York City.

Derek:

Yeah. Look me up when you’re in New Zealand.

James:

Which is never going to happen. That’s not my, “hell, yeah”.

Derek:

No, honestly, I will be in New York in a couple of months. I’ll let you know. I miss it. We always go back.

James:

Excellent. I have three pianos in my apartment so you’re more than welcome to hang out and play one of them or all of them.

Derek:

Okay. So the last thing I’m going to leave you with and like I said this is my last interview for a long, long time. So for one last time, I’m going to do something that people think I’m a little crazy for doing is I’m going to give your listeners my email address.

I do this because for years at conferences, I used to, when I was running CD Baby I would go to all these music conferences and I’d bring a big stack of a few hundred business cards and any person that asked, I would give them my business card. So I would know how many I gave away. I would often give away a hundred, two hundred business cards at conferences to musicians that wanted something from me. Then I would notice that nobody would email me. I get like one follow-up from the entire conference and most people don’t follow up. It’s amazing. The people that do and I get these emails are people who go like, “I don’t know. I’m sure you’re busy. I hate to be bothering you.” They’re so apologetic, how dare they bother me. The thing is I wasn’t coming on your show to pitch my book. I don’t care about whether I’m going to make another $8 if I sell a hundred books. I really just do it for the people I meet.

I mean, honestly, I’ve been wanting to talk to you forever because you’re just of my favorite thinkers. So this was an honor to finally chat with you. Instead of just making this a personal call the main reason we’re doing this public is for the people I meet. So yeah. If you have any questions for me or just want to say hi and introduce yourself, send me an email.

James:

Well, I encourage people to write you because your book so much fits into the category of what I call a “choose yourself book, career, vision, and so on.” That’s why I wanted to talk to you. So I hope people email you.

Derek:

Thank you and I’ll let you know when I’m in New York.

James:

Excellent, Derek. Thanks, so much.

Derek:

See you.

James:

Talk to you soon. Bye.

Derek:

Okay, bye.