Interviews → Hack the Entrepreneur

Jon:

We’re back with another episode of Hack The Entrepreneur, and today we had a very very very very special guest. Someone I’ve been waiting a year to talk to this point and I’m really really excited for this. Derek, welcome to the show.

Derek:

Thanks John. I got four verys in there, that was really cool.

Jon:

You did, I was going through the emails and it’s been a year. And I’m so happy that we got to do this. I’m just really excited about it.

Derek:

It’s funny, I don’t mean to be so elusive, but I’ve just found that I have modes where I’m more conversational. And sometimes, like if I’m programming, I’m just in my tech head. And if you try to talk to me when I’m in programming mode, I’m just a drooling idiot, I’m not very verbal. So I think when you asked me before I was just kind of in the middle of some other work and finally just a couple weeks ago lifted my head up and thought “yeah, I’m ready to talk now.”

Jon:

It’s awesome because you should do that and you’re absolutely a man of your word, because you said I’ll get back to you as soon as I’m back in that headspace. And then randomly, like six months later, on my phone, there is Derek, he’s coming on the show! Awesome. Alright Derek, let’s jump straight into this. Can you tell me, Derek, as an entrepreneur, what is the one thing that you do that you feel has been the biggest contributor to your successes so far?

Derek:

I think reading books. I like to take little facts about life, like reading books about psychology, understanding cognitive biases, how our minds work, the fallacies that we make in the way that we think of things and understanding a point like this and then acting on it. Thinking okay, if this is true, what can I do to act on this? I think that leads to a different approach than most.

I think a lot of people just kind of look to the outside world and they look at what somebody rich and famous is doing and they say “I want to do that too”, and they just kind of emulate others, go with the flow. But I think it can be much more interesting to build your life on some core foundation ideas and extrapolate them from there.

I just realized that’s more of my answer on a personal level, but this is Hack The Entrepreneur, so on the business level I think the one thing I do that has been the biggest contributor to my success is probably keeping things entirely, 100% focused on a service mode to individuals. Like: how can I be of service to this person? I never think in terms of crowds or audience. I just think about individuals. Like what can I do for this person that will make them happy to open up their wallet and pay me to do this thing that they need. Which, if you’re really in that mindset, it’s extremely selfless, this has nothing to do with me or what I think I’m offering, it’s all about them. And again, then meaning individuals, so it often means just talking to individuals saying “how can I help? What do you need?” It’s often letting go of the idea of what you think you’re offering, and instead just asking them what they need, and being of service to the world to individuals. And only if multiple individuals have asked for the same thing, then you find a way to turn it into a system, build a business and a system out of it. But before that I just start with individuals and see what they want to pay for.

Jon:

Nice. I love it. So I love your two answers, you have a personal answer and then sort of the business answer. But I don’t think that their distinct necessarily. When you said reading the books, like reading a psychology book and then taking facts about life or something and then seeing how it works, from the outside it seems that that’s what you do with how you’re trying to understand business and entrepreneurship and then service of the one person.

Derek:

Well yeah, business and personal is a very hard to separate. I think of the two as so intertwined. It was actually a problem when I was mentoring at a local business school when I was living in Singapore, I was mentoring for INSEAD, which is like a MBA business school, and people were handing me these 20 page PowerPoint presentations with a kind of pitch deck for their business and say “what do you think?” I’d say “well, I don’t know, who are you? What do you want out of life? What makes you happy? What kind of person are you? What are you seeking out of life?” I mean, these are all intertwined to me. How you shape your business has a lot to do with you and what you want out of life.

So in my case, I wasn’t even trying to start a business. When I started CD Baby I was making my full-time living as a musician and being a professional musician was my dream. I wasn’t trying to start a company, in fact that was an obstacle, that was something that was getting in the way of me and my music. So I didn’t even want to this little hobby to grow. It was something I was doing as a favor to friends. But then it just kept growing, and then friends of friends kept calling and asking me to sell their CD I was like “this thing is taking up hours of my day! This is getting in the way of my music!” And so I didn’t even ones this thing to grow. And that’s why I made some of the business choices I made, which was to make this business very utopian and decidedly non-growth. What do you call that? It was the opposite of growth hacking. I was hacking the growth with an axe to try to chop it down to keep it from growing and yet it grew anyway. That’s when I realized that I started something that the world clearly needed, because I was trying to keep it from growing and yet it continued to grow.

But that was a personal choice based on my life and what I wanted out of my life, which was to make music, right? So all of my business decisions were based around that. Whereas if somebody wanted to be the next Richard Branson they would make very different decisions on what they would do with their business and how they would grow it, you know? It wouldn’t be about serving personal individuals one at the time, it would be like “how do I become a billionaire fast?”, you know?

Jon:

Right. And I find it interesting because I try to encourage people to think about what they want out of their business, not what they want their business to become. I think that you were kind of lifestyle design before lifestyle design was a term, meaning that you don’t just start and work as hard as you can in your business to grow it as big as you possibly can and then wake up one day and realize that you don’t have a life. You just have this massive business that you don’t even want to run and you don’t control anymore.

Derek:

Right. Yeah.

Jon:

Because you have to be conscious of it, right? And I love how your book says: it’s not about just getting bigger and bigger, it doesn’t have to be, it’s about what you want. And it should be. Because you’r right, business and life are, or should be, intertwined. And therefore it can really destroy your life.

Derek:

Yeah. We’re talking about two things. One is about your personal happiness and pursuing a lifestyle that makes you happy, and a different thing is pursuing a business and making your business successful. And I think that those are two different pursuits that are often at odds with each other. So let’s think this idea of people saying “I’m trying to find my passion and my calling”, or may be thinking that they are not successful because they’re not following their passion. But I think that passion is overrated bullshit, I think it’s often used as a lame excuse for not doing what’s needed or a sad justification for doing something that people don’t want.

I think the success of your business has almost nothing to do with you and what you want and your personal passions and preferences. Get over yourself. Forget yourself, this isn’t about you. Your business is about them and their needs. Them meaning the people that are going to pay you to do something. Your business is all about them. If you’re just talking in terms of what’s going to make your business successful.

So for example, I did lots of different businesses before CD Baby: I had their recording studio, and a five piece funk band and I was a session musician and a solo coffeehouse artist, I started a record label and I signed a friend to my record label and released his records, I started a booking agency. I was passionate about all of these things, in fact each one of them I felt was my calling. I was even an expert in each of these things. But none of that mattered because none of them were what the world really needed. Granted they weren’t complete failures, I mean I bought a house with the money I made touring, so by some accounts I was successful. But it was always a big struggle, it was so much effort for so little reward.

But then I started this silly little hobby, yet another tiny little side project called CD Baby, and it just took off because it’s what the world needed. I didn’t know that, I mean you don’t know until the world tells you that something you’re doing is what they needed. It was just an ugly little websites with a “buy now” button that I was just doing to help a few friends, but it just exploded. You could even say I actually wasn’t as passionate about CD Baby as I was the other things I was doing. So this idea that you need to follow your passion to be successful is bullshit. You need to be selfless, I think, to be successful and do what other people need you to do. And that, by definition, is quite different from designing your life in a way that makes you happy.

Jon:

I love it. I love it. Was there a point where you sort of consciously realized that you were an entrepreneur? Or is this something now looking back, because I know especially with musicians, the touring aspect and the recording studio, those things are things you’re doing out the passion… Often times they’re at odds with each other, right? With the art and commerce sometimes doesn’t mix. But some of us really learn to master that and get a hold of it, but we are reluctant in that. So were you, looking back, a reluctant entrepreneur and got sort of pushed into it by your actions? Or is it something that you think you’ve always sort of had within you?

Derek:

Well before I answer that I just got to tell you there is a little... I was doing a fun word game with friends recently where I often ask like “was the opposite of this, what’s the opposite of that?” It’s fun to just ask “what’s the opposite of effort?”, because it’s not no effort, the opposite of one is not zero, the opposite of one is -1. So what is the opposite of effort? And somebody came up with the answer: it’s rejuvenation. I said “ah, good answer!” And so I asked “what is the opposite of music?” And there were a bunch of answers that were like silence and noise, and it’s like no, you know some people would call noise music and silence is just like the zero, it’s not the opposite. And so the best answer came from somebody that said “the opposite of music: business.” I like that answer.

Anyway, so that said, I think that to be a musician is to be an entrepreneur. So every now and then, especially if I’m speaking at like a business school or something like that, people will say something like “how did you get the courage to quit your job and strike out on your own to start a business?” And I just looked at them weird, I’m like “no, no no no I never had that.” I knew from the age of 14 that I wanted to be a musician. You get what that means? That means no paycheck, no insurance, no pension, no security, I knew I would never have any of that stuff, because I was going to be a professional musician. That is committing to a lifetime of hustling. The idea of working for someone else never even occurred to me. I only had really just a couple jobs in my life and last time I had the job was 1992, it’s when I quit my last day job. And even the fact that I call it a day job, I mean that’s what musicians call it: a day job. It’s like the thing you’re doing from 9 to 5 just to get some money, because what you really love is the thing you do from 6PM to midnight. I always knew that I would be living this life where every dollar I would make would just be of my own hands, there would be no paycheck.

So that said, I guess I was already in the entrepreneur mindset, CD Baby was like a hobby that I was just doing as a favor to friends. And I really did think of it as just a giving back to the community. You got to also understand that when I started in 1997 people weren’t making any money on the Internet. The Internet was this free useful service where people would go, it was like bulletin boards and newsgroups and things like that, where people would just share advice and tips with each other for free. It felt more like a free useful community. So when I offered to set up something to help my friends so their CDs, it was just a little free service I was doing to give back to the community. And so when that started to take off and I just started getting more and more calls from strangers saying like “hey, my friend said you could sell my CD for me?” And I’d say “oh yeah, your friend of Dave’s, I’ll hook you up.” I was still doing it all as a favor and I realized that I had accidentally start a business, like it or not. So yeah, that’s when I was clearly reluctant to do this thing, it was going to get in the way of me and my music.

That’s why it’s hard for me to relate when people tell me, or when people ask me questions like “I want to start my own business, but I don’t know what to do, what should I do?” And I’m like “well, if nobody’s asking you to do anything then the world doesn’t need you to do anything for them. You don’t do anything unless the world needs you to do it.” You don’t try to push things onto the world, you just answer calls for help. That’s been my approach, I can’t imagine pushing something on the world that the world is not asking for. So usually my advice to those people just go develop your skills, get a job somewhere and just develop your skills until you’ve got so much skill and doing something that you are now an expert in this thing, or you have a certain in or a certain unfair advantage in some way or certain resource that people need, and then you’ll note is that before are asking for your help to do something and now you can go serve them.

Jon:

Yeah, and that’s really an interesting way of putting it, because, like with coding, because you were super into the coding of CD Baby, and you’re still programming.

Derek:

Yeah, I love programming. Yeah. It became a passion, I had never done it and to CD Baby took off. In fact when CD Baby started it was just a static HTML website so there was really no programming involved. And only after it took off and I was doing hours of manual copy and paste labor every day, then finally somebody told me about server-side programming and said “you know, if you build a server-side database you can have all this handled automatically.” I said “oh my God, I need to learn how to do that!” Because I’m spending four hours a day doing ctrl-c, alt-tab, ctrl-v; ctrl-c, alt-tab, ctrl-v, I was like copying and pasting information from one place to another four hours a day and I found out that if I could just learn how to do some programming computer could do that for me automatically, that was the ultimate motivation. But anyways, it wasn’t like a pre-existing passion of mine, it was something I got really into out of necessity.

Jon:

Right. But that’s something somebody could do, right? They could get a job and learn how to code, or learn a specific aspect of the business and get a really really good at it.

Derek:

Yes. I see where you’re going with this now.

Jon:

All I’m saying is because from the outside it might seem like “okay, well yeah you sold the company for $22 million so that easy to say now.” You know what I mean? It’s not actually how that happened. It’s not just that it’s easy for me now because you would still be doing the same thing I think, whether that happened or not.

Derek:

Yeah, so in my case the expertise I had built up that make people ask my help is I had built this little thing to sell my CD in an age before PayPal, when building an online shopping cart was really hard and nobody knew how to do it, so nobody had one, but I had one. So now I have something that everybody needed.

So for everybody listening here, you’ve all got your own version of that. There is some area in your life where you have an unfair advantage, where you’ve got access to more experience in a certain field that most people. For more knowledge of a certain niche of an industry then more people have. And you should focus on those places where you have an unfair advantage, because that’s where you’re probably most valuable.

Let me give another example of this. So when I lived in Singapore, I was really involved with my community and I was trying to help mentor and I kept getting pulled up into the startup scene, which I wasn’t really into but I gave it a shot. Meaning I got involved doing some of those startup competitions where 50 different people come and pitch their business idea and five of them will be winners and get some kind of VC money, right? So 50 people would come in and pitch their business idea. And I swear, like 48 out of the 50 ideas were just generic things that had no specialty and no expertise. It was like hey, we’re going to build an app that is going to show you where your friends are eating today, and everybody’s going to share where they are eating and then you’ll be able to see where everybody is eating. And that’s our idea. And I felt like that so generic. You have no specialty, there is no reason that a bunch of people at Facebook couldn’t just build that tomorrow if they wanted to. You’ve got no special insight there.

But then, I remember this one guy came along I still remember, saying “we’re going to build software for the small aircraft production process.” I said “wait, what?” He said “well, small aircraft manufacturers do not have any custom software to help manage the process of manufacturing small aircraft.” I said “how do you know this?” He said “my dad is in the small aircraft production business. And I would watch over his shoulder over the years and I saw that they’re all using Excel spreadsheets and word documents to manage this complex process of building small aircraft. And since I had a programmer friend and I know a little bit about tech, my friend and I got together and we asked my dad: ’what would you need to help automate this process and to help streamline this?’, and my dad told me and then he introduced me to some of his friends at other companies and we sat down with them. And so we now have built the only software that is available in the world to manage the process of small aircraft production.” I was like “holy shit dude! Fuck yeah! You win! You have developed a niche, this is an expertise that everybody is not doing. You have found your unfair advantage. You have the inside insight into this field.” And yeah, that was the grand winner of the 50 different startup ideas, because he had been niche, an edge. People who ask my advice for “I want to do a startup but I don’t know what I should do”, I say “well, you got to go out into the world and develop some expertise.”

Jon:

And that is like the least sexy startup idea and that’s why it actually makes it so much better. Everybody wants to create a new web app, the new Slack or the new Facebook or whatever it happens to be.

Derek:

In The Social Network movie the line that everybody quotes: “a million dollars isn’t cool, you know what’s cool? A billion dollars!” So actually, I feel the opposite. When people are telling me this big generic idea like we are going to be the next Facebook, I say “you know what? A billion dollars isn’t cool, you know what’s cool? A million dollars!” Don’t focus on being a billionaire. How can you make a thousand people really happy? Even my CD Baby idea, it was taking this completely unserved market, there were a few thousand musicians that were unable to sell their music because nobody anywhere on the Internet would sell it for them. The only online record stores at the time were just front ends to the major-label distribution system. So if you were an individual musician that had pressed up your own album, without a record label, nobody would sell it for you except a guy named Derek in New York. And yeah, I was serving people that have no other solution. And that is so much more satisfying than trying to be everything to everyone or being something generic service with lots of competition and no special niche, you know?

Jon:

Absolutely. Absolutely. All right there, we’re going to move to work if we can. I’m hoping you’re still working these days, but I guess we’ll find out. But first, every blog post right now, every expert talks about the 80/20 rule: do 20% of the work, get 80% of the results. They say do what you’re good at and delegate the rest. At the beginning you told us what you’re good at personally and the one thing that you think in business allowed you to your greatest successes. But could you tell something within business that you are absolutely not good at?

Derek:

Well for me personally is visual design. But I think there is a bigger point here, this isn’t about me, this is about your listeners. So I think sometimes there are more important things than absolute optimization. So at CD Baby, first I really enjoyed programming. I love programming, I think it’s fascinating. And luckily it’s a useful thing to, I mean I think that learning Mandarin is also fascinating but it’s not really useful to anybody else, it just I find it interesting. Hiking and camping is fascinating, but it’s not of use to anybody else. But luckily, programming is useful to others. But it’s something that I could just hire other programmers to do.

And you could say that actually I’m not a great programmer, I’m okay, but there are a ton of people that are better than me. But it’s something that I love doing. So when people were to ask me “why don’t you outsource that, why don’t you hire somebody else to do the programming?” I think well I might as well just quit then, because I would lose all interest. Like, right now my interest in this is the programming, to me that is the most creative and inventive part of what I’m doing. And it’s kind of like you don’t go to the songwriter in a band and say why don’t you just hire somebody else to write the songs for you? You don’t go to the lead singer and say why don’t you hire somebody else to sing for you, so you don’t have to anymore? They say well this is what I love doing! This is what I want to do. So at CD Baby I loved doing all the programming, so I never did hire another programmer, I just did it all myself. There was no team, it was just me.

And same thing with: I ended up enjoying building the computers. So we had 85 employees, which meant we had about 50 PCs in the office and we had a bunch of servers in the business, and I built them all myself. I would go down to like Fry’s Electronics, or whatever your local electronics store, I would buy the beige chassis and buy a hard drive and by a motherboard and buy a CPU and buy some RAM or whatever and stick it altogether and build it myself, and I would install the Linux onto it and that would stay up all night doing this. I just loved it! It made me so happy. And years later I remember telling this to somebody who looked at me with this kind of scowl and he went “yeah, that’s a good use of the CEO’s time.” I said “well yeah, fuck yeah it is! Because that’s what I wanted to do!” I wasn’t trying to please some investors, there were no investors, it was just me. I’m doing this business because I love doing it.

Yes, I could have optimized the business and been more profitable if I would’ve hired a team of programmers and I could maximize the use of the CEO’s time by focusing on sales and building the company. But it wasn’t about that, I was earning enough and I wanted to build PCs because I found it fun, and I enjoy programming. So yeah, this 80/20 thing, it’s optimize what you want to, but don’t forget why you’re doing this. It isn’t just for maximum returns.

Jon:

I fully agree, I fully agree. And I like your songwriter analogy and not outsourcing the songwriting, although the biggest most popular music in the world, that’s all they do.

Derek:

Right!

Jon:

They pay somebody $5000 somewhere to write them a song and they turn it into a machine.

Derek:

Exactly! And actually, thanks for using that example, because that is a good example. Yes, you can get more successful if you hire someone else to do it. Yeah, you could go to the songwriter in a band and say why don’t you hire somebody else to write your songs? The truth is they would probably get more famous if they would hire somebody else to write the songs. And in fact, you could go to the lead singer and say hey, you’re not that good looking, why don’t you play bass and just hire the best looking person you could find to be the front person, and you get more fame is that way. And the truth is yes, you will get more famous if you hire a model to be the singer. But is that why you’re doing this? For maximum money? If you are, that the correct strategy for you. If you’re not, then it’s not.

Jon:

Exactly. It’s the correct strategy for you, but there is no correct strategy. And I love that, I’ve never thought of it as this analogy of the songwriter and to me it give me further insight into you as an artist, and your art is the business at that point.

Derek:

Exactly!

Jon:

But it’s not about optimizing everything, I mean I play drums in two punk rock band still. I do it because I love it, nobody, for the most part, cares to listen to that kind of music in the world, that’s just how it is. I would never care about being on the radio, that’s just not my thing. I just love to play it, I love to do it, I love to bash away really fast on drums. And I’m always going to do it, until I can.

Derek:

Yeah. Honestly man, I have this book that Seth Godin asked me to write a book and tell my tale. I said “I don’t feel the need to tell my tale.” And he said “well, can you extract the most important lessons from your tale?” And I said “okay, that I can do, that’s useful to others.”

So I have a book out called Anything You Want, it’s on Penguin Portfolio Publishing which means it out everywhere books are sold. And it’s a really short read, it’s like a one hour book. It’s the kind of stuff we’re talking about, it’s like the lessons I learned from starting, growing and then selling my company. It’s kind of the 40 little lessons I think, people could use for their own pursuits.

But yeah, that’s like the common theme that you find behind it: to me how you design your business is your creative expression. It’s like your business, especially if you talk about making a small business, and you’re not just doing it to please investors or something, this is where you get to make your little corner of the universe where everything follows your rules and your laws, right? So the fact that most other businesses do things that way doesn’t matter here. You do things this way. Because you want to. And you think this is the way they should be done. And so I think it’s extremely creative, starting a business, it’s making your own little corner of the universe that follows your rules.

Jon:

Yeah, exactly. I mean, being an entrepreneur to me is creating something out of nothing and putting out into the world. Waiting for feedback. Hopefully some of that feedback includes monetary feedback in a way that allows you to continue to do it and can do anything you want. That’s amazing. And the Internet obviously allows us to do that. And your book, I fully 100% endorse it. If there is one person in this world that I could write like, it would be you. It is. The book, it’s so short that it’s awesome, and I read it on Kindle and I took notes, and the notes are almost as long as the book. So I need to find a way that I could actually take notes from the notes and slowly just boil it down.

Derek:

Actually, you know what? If you like my style of writing, go find Harry Beckwith, he wrote a brilliant little book in the late 90s called Selling the Invisible. And then he followed it up with a few other books on that same vein. And I want to write like Harry Beckwith. And in fact he’s my biggest influence writing-wise. He’s so succinct, he’s got such a friendly direct style. So yeah, if you like the way I write, I think you’ll like Harry Beckwith.

Jon:

I definitely love the way you write. And you’d be my greatest inspiration for business writing at response. That’s the only writing I do, I guess. Alright Derek, this has been a lot of fun, I want to wrap up on one thing, it’s this thing I’m calling the entrepreneurial gap, and I’d love to know how you’re dealing within it right now. So the entrepreneurial gap seems to be this place that will live in as entrepreneurs and dreamers, right? We seem to live in this gap because we’re always looking forward, goals are set into the future, either within new projects we want to start, things we want to achieve and accomplish and it’s always three months, six months, a year, three years, five years, ten years down the road. When I release this book, or when my business does this, or when I accomplish this or stand on this stage, I will be successful. But before we ever get to that point we seem to set five or ten loftier ones into the future. And we just seem to get stuck in this point where we never reach that level of success that what always striving for. I agree it needs to be done, we need to set goals and stuff, and that’s a whole different thing though. But you’ve done a lot of stuff. You’ve come from music, now you get to do what you want based on this business you created, reluctantly if you wish or whatever, and you set yourself up to get to do things and projects that you want. And, as you say, say no to most things. So I would love right now Derek, if you could stop right now, turn around and look at everything you’ve come through, everything you’ve learned, done, accomplished and just give me an honest answer of how you feel about everything up till this point.

Derek:

Sorry, I don’t think I understand the question. So how do I feel about it? How do you mean?

Jon:

Yeah, about your accomplishments, everything you’ve done up till now. Not going forward, not what you want to do but how you’ve done it up till now.

Derek:

Well, I think looking back is not very inspiring. You brought up the idea of goals and I think that one of the biggest lessons I’ve learned is that the future is just something that we imagine, the future isn’t something that actually exists, is just the name that we give to our imagination when we project and try to predict something that we think will happen. We call that the future. But it is really just another name for our imagination.

So when people talk about goals that are trying to shape the future, we act like the purpose of a goal is to shape the future. But because the future really doesn’t exist, all that really exists is the present and I don’t mean to sound foofoo about that, but more just being realistic, a goal is good inasmuch as that it improves your present actions. If you have a future goal that leads you to sit around and do lots of daydreaming, but doesn’t make you jump out of your seat and jumped into action, well then that’s not a good goal. A good goal is one that would just in the moments in prove your present actions in a way.

So I actually did a lot of looking back. Let’s say it like when I sold CD Baby, I really felt that feeling that every listener here either already knows or will know at some point in their life, is that feeling that your biggest success is behind you, that you’ve peaked. So CD Baby was such a success that I felt that my gravestone would say “he made CD Baby and that’s about it”. I was 38 years old and I was coming to terms with that feeling of looking back. I think it was something close to depression, I wasn’t actually depressed, but something similar to that where I had no motivation and no inspiration to do anything. I just kind of wanted to get through life and get it over with.

In fact the last couple years at CD Baby were so bad, I had so much pressure and so much kind of negative energy on me from all of my employees that directed all of their frustrations on me, that I just wanted to change my name and legally disappear just to avoid all responsibility. I even seriously looked into it, I read a couple different books on how to get off the grid, legally change your name and disappear without a trace. I really looked into doing it.

I think even having a lot of money can really mess with you in a situation like this, because it can lead to absolute lethargy, because there is no more intrinsic motivation. Everything has to be 100% intrinsic motivation, there is nothing you want to buy, there is nowhere you hasn’t been, if there is something that you want you just go buy it. Is there somewhere you want to go you just hop on a plane the next day. So suddenly everything has to be very intrinsically motivated.

So yeah, I was spending a lot of time looking back at my career and thinking about what I had done, but I think that’s a fairly uninspiring thing to do. It led to just lethargy.

But then I had these two epiphanies that happens just over the course of a few hours. I was sitting on the plane from LA to New York to go to a friend’s wedding, and sitting on that plane I was reading a book, I think it was probably The 48 Laws of Power by Robert Greene and he was talking about some historical examples of power and fame, about how being famous is a source of power that if you can step up to the responsibility of accepting fame that can give you the power to do many more useful things to people. And I thought of power in a positive sense, I think that The 48 Laws of Power often talks about it in a negative way, but if you think of power as the power to help people, you know, using it’s in the positive sense of the word, I realized that disappearing, legally changing my name and disappearing and dropping off the grid is not useful to anybody. Yes, I had a nice bank account that I could just continue to exist and live and have my heyday be behind me. But instead if I step up to the responsibilities of being public and being famous, then the benefits are worth the downsides, it’s worth the hassle. So in that moment I got inspired for the first time in like a year, I decided to step up to those responsibilities.

And almost immediately afterwards, the second if any was having this bigger vision of who I could be. So this is back before TEDx, where TED was just this once a year big giant conference with famous attendees. And to me being a TED speaker felt like winning a Pulitzer Prize or something. I decided that I wanted to do that, but that’s a goal: I want to speak at TED. And in fact I’ve been in the music business so long that what I wanted to do next is I want to be surrounded with, and accepted by, a new community of intellectuals and be known as like a writer/thinker/speaker kind of guy. And John, suddenly this idea was like: this got me inspired! This got me like sitting upright in my seat and inspired in a way that I hadn’t been in a while of looking back. Like suddenly this was changing my actions in the present moment. So I started spending like 46 hours a day just exploring thoughts and finding ways to present them in really short and succinct ways on my blog, editing the hell out of my writing. I spent like six hours to write a four paragraph blog posts, right? But it worked. And I applied to TED and I got accepted to speak, not just once but at three big mainstage TED conferences in a row.

So finally, kind of to answer your question, the sweetest reward came afterwards when my TED talks got really popular, and the most common question from all these new people I was meeting was people would say “so, what did you do before TED?” And I realized that people didn’t know me from CD Baby anymore, that I had successfully done that career pivot that you hear about. To meet was so reassuring to know it can be done. So much more exciting. And I agree with your original question that we often do so many things for the future, but I’d say that looking back is healthy in small doses, but you need to look at the future in order to improve your present actions.

Jon:

Yeah. And it’s an interesting perspective on my question, you’re making me rethink it. And I agree in ways, like the idea is actually not to look back, the idea is that we live in this gap which is the present moment that I think the most of us, especially people always trying to build new things and do successful things, we fail to live in the day, in the moment, in the now which, as you’re saying, is the only thing that exists. And to me it’s really sad, when that’s the only thing that exists, we never want to exist within it. We’re always trying to exist in the future that doesn’t exist, or past that doesn’t exist. So really it’s just supposed to be a moment where you can reflect and then you feel how you feel about right now basically. And that’s only what you’ve done, that’s not what you’re going to do, because that’s meaningless, what you’re going to do, because we can say we’re going to do anything, but it’s only what you’ve done that is you’ve done up till now.

Derek:

Right. So I think I took a long roundabout way of answering that, but I still think we’re on the same page, my point is that thinking of the future doesn’t matter, it’s not that you’re lost in the future. I don’t think it’s healthy to just sit around daydreaming about the future, or even sitting around talking about what the future is going to be, but your ideas on where you’re going in the future are useful only inasmuch as they change your present actions. So one idea for my future was to disconnect and disappear and just kind of go off in the work on open source software till I die. And another idea for the future was to actually get into this new inspiring reality, and that was the idea that got me to work for many hours a day and change my presence moment and improve my present moment, because I was thinking of a different future. So these things that you think about, even though they don’t exist, are useful if they change your present actions. So it is still living in the present.

Jon:

It is, exactly. And you’ve done an amazing career pivot. And I have to admit that when I first heard about you, I think it was through your blog and I read it and I was into it, and it was several months before I realized that you were the dude from CD Baby. And then I was like “oh my God”, and I’m like a musician, right? From the 90s. So I was like “holy man, CD Baby!” I never even thought of the founder of that, because I wasn’t into business when I was at that point, I was just a dude in a van playing drums across the country. But I knew what CD Baby was, and we’d use it. So you’re not just that person, cause I had even been introduced to you your work after the fact. And I hope you continue to do more of it.

Derek:

I really did think that CD Baby was as good as it as it gets, like that success is as big as I ever have. Even the fact that I got inspired to start putting my ass on the line and start publishing all these blog posts came from a different future vision of what I could be doing. Sorry, still back to the entrepreneurial gap that you’re talking about, that the legacy we leave behind, that the future we’re working towards, all of these things are like just little swirling thoughts in your head, they’re just memories and just imaginations. But all that really matters is how that changes your present moment.

Jon:

Yeah. I love it, I love it. Alright Derek, this has been a lot of fun. We’ve talked about your blog so much. Could you specifically tell the listener where to go find out more about you?

Derek:

No, I won’t tell them where to go, it’s a secret! Don’t go there! No okay, sive.rs is my site. And in fact, anybody that listens to this podcasts, especially if you’ve made it all the way through, you’re my kind of person. So I’m also just going to give you my email address, please feel free to introduce yourself. I mean honestly, I don’t do interviews like this to pitch anything, I mean I think I only make the dollar if somebody buys my book, I don’t really care that much about that. And my site is completely noncommercial. Actually, the main reason I do interviews like this is to meet the kind of cool people that listen to them. You know, some of the coolest people I’ve met over the years are people who just found me through things like this. So yeah, if you’re listening, please send me a little email and say hello and introduce yourself. I answer every single email, so feel free to ask me a question or just introduce yourself.

Jon:

Take him up on that, because he absolutely does respond to them. I’ve been having conversations now for a year, so it’s awesome. And the book Anything You Want: 40 lessons for a new kind of entrepreneur. Absolutely, absolutely recommend this to everyone. It’ll literally take you an hour to read. But then it’ll take an hour to reread your notes. So it’s up two hour read, really. But it’s more than worth it. Alright Derek, thank you so much. Thank you so much for doing this and yeah, just keep doing what you’re doing because it is really awesome and inspiring to watch.

Derek:

You too. Thank John, I appreciate it.