Derek Sivers - How to Live, Baby

by Music Tech Fest | MTF Podcast

Derek Sivers is best known as the founder of CD Baby and the TED speaker who did that talk about the dancing guy at a festival. In the years since he sold and left his company, he’s become more of a public figure - a prolific author and thinker, currently working on his new book, How to Live.

Derek is a self-described ‘solitary socialite’ - someone who keeps very much to himself physically, but also loves to connect. He discusses his philosophy of life - and why he’s happy to keep changing it. In this interview, he reveals for the first time the true story of the day he decided to walk away from his very successful company - as well as what he did with all those millions of dollars.

Read more of Derek’s thinking at Sivers.org
Follow Derek on Twitter: @sivers


Dubber Hi, I’m Andrew Dubber. I’m the director of Music Tech Fest, and this is the MTF Podcast. Derek Sivers is an author, thinker, and a public speaker. He’s been a professional musician, and he’s played all over the world to audiences of thousands with some of the most incredible artists. He’s a software developer and an early tech entrepreneur who created one of the most well known and most successful online music distribution platforms around, CD Baby. And he’s a good guy.

He’s also something of an enigma. For someone with such a public profile, he’s also one of the most reclusive people I know. And from what I can tell, the coronavirus lockdown has had absolutely zero effect on how he’s living his life. Not going out? Already doing that.

Derek’s spent the past five years with a strict policy of no interviews whatsoever, but since that’s now changed, and he’s gone the other direction, I grabbed him for a long-overdue chat about his career to date and his forthcoming book ‘How To Live’. From his house in Oxford where he lives, plays, reads, and draws with his son, all offline, this is Derek Sivers. Enjoy.

Dubber Derek Sivers, thanks so much for joining us on the MTF Podcast today.

Derek Andrew Dubber, it’s an honour. Last time I saw you in person was July 10th 2007, and, yeah, I consider you an old friend even though we haven’t seen each other since then.

Dubber So why are you talking to me on this podcast? What’s going on all of a sudden? Is this your new thing?

Derek Well, you are in a different category. To me, it’s whenever Andrew Dubber has a question, the answer is yes. If you said “Hey, Derek, will you…?”, I’m just going to automatically say yes, because it’s you.

Dubber Well, that’s very kind, but it’s not just this podcast.

Derek No. So, in general, I said no to all interview requests for… Four years? Five years? Because I didn’t like the position of being up on a virtual podium acting like a know-it-all. I prefer to have the questions, not the answers. If I start acting like I have all the answers to life then it… You are whatever you pretend to be. So if I act like I have all of the answers to life in order to make a good interview, then pretty soon I start thinking I have all the answers in life, and I didn’t like the psyche that got me into. So that’s why I stopped doing interviews for four or five years. Then actually a friend… Mutual friend, you know Ariel Hyatt.

Dubber Yeah, very well.

Derek She’s an old friend of mine that accidentally tricked me into doing an interview. She just called me out of the blue and said “Hey, will you be on my podcast?”, I said “Sure”. She said “Okay, we’re recording”, and I went “Oh, crap”.

Dubber And she’s still doing Music PR?

Derek Yeah, www.cyberpr.com.

Dubber Oh, fantastic.

Derek And so I thought “Okay, well, now… I guess now I’ve done an interview again”. So what I’m doing now is using interviews as writing prompts. So I try not to repeat myself and I use the questions that people ask me in interviews to dive deeper into those subjects, and I end up writing about them more later after we get off the phone. And it’ll probably turn into my next book, all these things that I’ve been talking about the last few months on podcasts.

Dubber And presumably also because you have figured out that you do know the answers, and now you’re prepared to share them.

Derek Now that I’ve uncovered all the secrets of life I might as well let you in on the secrets, yes.

Dubber Well, the title of your new book that you’re working on suggests that that’s the case, right?

Derek Oh, not at all. So the book is called ‘How to Live’, and, you’ll see, it’s a little bit mocking the format of people that think that they’ve got the answer, because each chapter is going to disagree with the previous chapter. And it’s a blast to write. Yeah. You’ll see.

But, no, I don’t think that I have all the answers in life. In fact, I think that… There’s a difference between truth and entertainment, right? So it’s entertaining to have a nice soundbite that can be tweeted, it’s entertaining to have a little pull-quote, but you should never confuse those things with the truth. The truth is always more nuanced, and situational, and “Well, it depends”. It depends who you are, where you are, what’s going on in the rest of your life, etc. But that doesn’t make for a good soundbite. So, no, it’s… Most of what these know-it-alls, including me, put out into the world is really more entertainment than truth.

Dubber Right. Because a Derek Sivers post is not normally a huge, weighty, long thing that goes on for ages and ages. It’s usually this bitesize thing that… It goes “Have you ever noticed…? Here’s the real reason… This is the counterintuitive thing that you should do. And be happy”. And that’s, in a nutshell, how I think of a Derek Sivers post, as following this framework. Are you saying that ‘How to Live’ will go into a lot more complexity? Or is it a series of those that just contradict each other?

Derek Yeah, you’re right. It will go into more complexity, and it will also be a series of those that contradict each other. But, yeah, I think I learned the hard way that the more you say, the more people tune out. If you want people to pay attention to what you’re saying you need to be succinct. If they wish I would have said a little bit more then I’ve said just enough.

Dubber Yeah. There’s an academic equivalent to that in conferences, which is that nobody is ever annoyed at you for going under time.

Derek Yes, exactly. Notice, even when I went on stage at the TED Conference… Those talks can be up to 18 minutes. All of my talks were two and a half to three minutes.

Dubber I was wondering if that was a restriction that was placed on you, actually, or whether that was something that you said “No, I don’t want the 18 minutes. Give me three”.

Derek Yes and no, it’s a choice when you submit a talk. You submit a three-minute talk or an 18-minute talk, and so I chose to submit a three-minute talk because, god, I really don’t want to talk for 18 minutes. I like introducing one little idea in three minutes. The average length of an article on my site is 22 sentences. And, yeah, I work hard to craft the idea down to 22 sentences, so that it’s just no extra fluff. Just the minimum necessary to communicate the idea and then send you on your way.

Dubber You’re a hit singles guy. So let’s start with how you and I met. I’d heard of you of course, because 2005, 2006, 2007, you couldn’t really do anything about independent music online, as I was, without hearing about CD Baby. And of course, you were the president of CD Baby.

But then… Obviously people can google the story because you’ve told it elsewhere, but there was a point at which I put out this ebook and I sent it to lots of people, and presumably you included, but you took the step of sending it to everybody who was actually an artist on CD Baby. 2007 I think it was. But, yeah, you got in touch with me and said “I’m sending this to everybody, is that okay?”, and I went “Well, it’s probably going to crash my service. As long as you host it that’s fine, because you’ve got a lot of people on CD Baby”. But was that our first proper encounter, I guess?

Derek Yeah, for you and I, yes. But I always saw CD Baby as a service for the musicians. It wasn’t about distributing the music or whatever, I was just trying to help these musician clients in any way I could. I felt a little bit parental, which is funny because years later I had a real baby and people would say “Oh, didn’t it completely change your life?”, and I would say “No, actually”. It didn’t feel that different from when I had CD Baby.

I think what changed my life was at the age of 29, 28, when I started CD Baby. Something in me clicked, and all I wanted to do was to just serve those musicians and help them in any way I could. So if it was… Like if I read a brilliant ebook, like yours, and I’d like, “Okay, everybody needs to read this”, so I would just send it to everybody. Or if I heard some tip, or advice, or whatever I could do to help my musicians. I just wanted to help them, with no… It wasn’t it some marketing, self-serving way to prop myself up. No, not at all. It was just… I was perfectly satisfied with my life, and I was just trying to help the musicians any way I could.

Dubber Have you always been satisfied with your life?

Derek No. My years as a professional musician were quite hard. It always felt like an uphill battle. It felt like every door was locked and would require some incredibly difficult metaphorical lockpicking to open it. Everything was hard, everything was uphill, but I struggled for years and I did it. And I made a pretty good living making music. Bought a house in Woodstock with the money I made touring.

And that’s when I started CD Baby as a little hobby, just to help out a few friends. And then friends told friends. So I think by the time I realised I had accidentally started this thing, it felt like “You know what, I had my day in the sun. I didn’t get to be a major Rockstar, but I was pretty successful by my own definition. And looking back, yeah, that was a pretty cool thing I got to do for a number of years. And if I can…”

Dubber What were the highlights?

Derek Oh, god, aged 22 playing guitar for Ryuichi Sakamoto to an audience of 10,000 in Tokyo. Well, every night for a few weeks, to audiences of 5,000 to 10,000 around Japan. That was huge. I was 22 years old and I… And not only that but I was in the band with Manu Katché, the drummer for Peter Gabriel and Sting, and then Victor Bailey on bass, from Weather Report. And, oh my god, these legends, I’m in the band with them, oh my god. It was such a thrill, and I was 22.

And then just quitting my job and becoming a full-time musician at the age of 22. Just making a living doing gigs, producing people’s records. Just living in New York City doing the hustle enough to pay my rent. Just that in itself, the fact that I was a full-time musician, was great.

And then learning how to crack the nut of the college university circuit in the US. That was great to get into that scene, and I did some amazing gigs by doing that, and just that wonderful source of self-sufficiency. I didn’t have a booking agent, I was the agent. I didn’t have a label, I was the label. I was just learning how to do all of this myself and, yeah, just this great feeling of self-reliance and self-sufficiency. Then later built my own store to sell my own thing, and that’s what became CD Baby. So, yeah, that was just… All of that was just… It was a highlight just from the personal accomplishment and achievement of doing it.

Dubber Sure. And you were at Berklee, right?

Derek Yeah. So I went to Berklee School of Music from 1987 through 1990, from the age of 17 to 20.

Dubber So where did the programming come from?

Derek Absolute necessity. I started CD Baby as just a barebones little HTML site, the kind of HTML anyone can learn in an afternoon. Just some <h1> <p> tags, whatever, and a simple form that would just send me your information. And I would do it all manually because I’d only get one order a week, right? It didn’t need any automation or programming at first. It wasn’t until nine months later that I started getting four orders a day, and then ten orders a day, and then 30 orders a day, and I was still processing them all manually by hand. And that’s when I said “Oh, man, this is going to kill me if I don’t learn to automate it”.

So just out of sheer necessity I had to learn programming. So I went and got a $25 book on PHP and SQL programming, and I just made myself go through the examples and learn just what I had to learn to solve today’s problem. I think that’s just the best way to learn. I never could have done well in a university course on Computer Programming 101. I never would have majored in Computer Science. It was really just a means to an end to solve my problem of the day. I think it’s the best way to learn.

Dubber Learning is a word that I associate with you, because all the things that you do have been about, or the result of, learning something. And did you learn how to learn fairly early on? Or how you best learn early on?

Derek No. Actually, I think everything up until a few years ago, since I’ve seen you last… Everything up until the age of 40, even, was only learning as a necessary means to an end. Like that programming story, right? I had to learn marketing in general, the basic, holistic, global view of marketing, as an absolute necessity in order to make a living, to pay my rent doing music, instead of depending on a day job. I had to learn basic HTML in the first place to put up my own website to help promote my music. I couldn’t afford to pay somebody else to make a site for me, and things like WordPress didn’t exist yet. I had to learn database stuff in order to have a mailing list of the 500 universities that were hiring musicians to play on campus, and so I had to learn about mail merge, and databases, and related tables, and all that kind of stuff in order to reach 500 universities at a go. And, yeah, so just all of these things were just absolute necessity, means to an end that I had to learn only what was necessary to do what I needed to do.

It wasn’t until much later, after I sold CD Baby and then I was retired and had a blank slate for the first time in my life, I didn’t even know what I wanted to do next, that’s when I started getting interested in learning in general. That’s when I started watching TED Talks about whatever, and reading books about anything, and learning weird, obscure things that wouldn’t have interested me two years before that when I was just too busy with everything on my plate. So, yeah, the general interest in learning came much later. Everything before that was just necessity.

Dubber Right. Because there was a time you were churning through books and summarising them, and then putting those summaries online, and then… At an astonishing rate.

Derek I think it only seems like that if you zoom out. If you look at www.sivers.org/book, that’s the URL where I keep all of my book notes, there are now something like 300 books there, but that’s everything I’ve read since 2007. So I’m not actually a voracious reader, it’s just that… It just adds up over time. So it looks like a lot when you see them all like that, but, no, I’m not actually a… There are a lot of those people who read a book every week or even a book every day. I’ve never been like that.

Dubber So take me from the beginning of CD Baby when you’re teaching yourself code, to the end of CD Baby when you’re sitting on a train listening to a recording of a staff meeting.

Derek You alone know that final day. Sure. So, yeah, just imagine a simple little hobby. I just made my own band’s website to sell my CD. My friends in New York said… Actually, it was Marko Ahtisaari, who is a musician from Finland that was living in New York City at the time, he was the one that said “Hey, man, you know that thing you built to sell your CD? Could you sell my CD on your band’s website?”, and I went “Oh, huh, I guess.” That was never part of the plan, it was really just… I built all of it just for me. And then once Marko wanted to do it, well then a few of my other friends said “Oh, hey, man, could you do it for me, what you did for Marko?”, I said “All right, sure”. So pretty soon it was on my band’s website. I had ten other musicians on my band’s website. That’s when I finally took them off my site, got www.cdbaby.com, and put it there.

Dubber Why ‘baby’, out of curiosity? I know why CD, because, you know, the time that it was, but why ‘baby’?

Derek My girlfriend suggested it and the domain name was available. It was literally… She was walking through the room. I was like “What should I call this new site?”, she was like “CD Baby”. I went [typing sounds] “Hey, it’s available, thanks”, she was like “No problem”. Years later when we broke up she made me pay her $300, or something like that.

Dubber I think you got a bargain, to be honest with you.

Derek Yeah, it was a good name. So, honestly man, the next six or seven years were almost a blur because it was one of those classic success stories, that I can appreciate because everything was so difficult up until that point, but it felt like I had written a hit single. Suddenly every door just opened to me. Suddenly everybody wanted to take my call, and suddenly everybody was pouring my direction, and I was getting swamped with people sending me their music. And the next seven years are just… CD Baby was doubling in size every single year, I never did a damn thing to market or promote it, it just steamrolled, or… What do you call it? Snowballed, yeah, it snowballed. And all I did for the next seven to ten years was just managing the growth and trying to keep it under control somehow.

And that’s it, it was just a constant state of… I was working seven days a week from 7 AM to midnight, seven days a week. I did nothing else but this one thing to obsession for ten years. I didn’t hang out, I didn’t relax, I didn’t vacation, I didn’t do anything but work on CD Baby for… Maniacally for ten years. Until the last time I saw you, July 10th 2007.

On my way up on the train from London to Birmingham, I listened to a recording that was on the server at CD Baby that was a regular Monday weekly meeting, which I had missed that week. And so we’d always record it for whoever wasn’t there. So I pulled it off the server, I put it on my phone, and I listened to it on my headphones on the way up to see you that day. And the recording of that meeting was devastating, because it was basically a mutiny. And I’m not being overdramatic. It was like… I had tried to do a profit-sharing with all the employees, but then it went awry. And so I had to stop it because it was like they were just distributing all of the profits to themselves, and so I had to yank the programme, which made them really mad because basically everybody’s salaries doubled for a few months and then stopped. So they were really mad about that.

And so on July 10th they held this meeting that was basically just “Fuck this guy. We need to get him kicked out of the company. We need to run this company the way we want. Let’s get him… We’ve got to… Let’s get him removed somehow. How do we get him removed from the company?”. And these are dear friends that slept at my house, that I… And all of that stuff, that these were my employees, these were my buddies, and they were… We’d hung out, and these people are trying to get me kicked out of my company, which is impossible because I was the sole owner. I think they missed that point. And, god, it was just devastating and I never again went back.

That’s when I actually decided to quit CD Baby. It was that day, the day that I saw you last, and I was just feeling done. It felt like somebody that’s been working on a novel, or a mural, or one of those big, long, ongoing art projects, and you finally add the final sentence or the final brush stroke to your painting and I just felt like “Yeah, that’s all I have to say. I have no future vision for this thing, I’ve done everything I wanted to do with it. I’m feeling done with it”. And, yeah, it was as I was feeling that that three different companies in one week offered to buy it, and I said no to all of them as I always did. I had always had these offers to buy the company, and I’d always just said no by default. But, yeah, after three companies asked in one week I just spent some reflective time that weekend and thought “You know, maybe I should say yes now”, and so I did. And that’s that.

Dubber And the company that you said yes to gave you a big pile of money. And to me what’s interesting is what you then did with that big pile of money.

Derek Well, this was supposed to be a secret. I was never going to tell, but then in some interview a year later somebody asked me a really direct question about like “So what are you doing with that big pile of money? Just drinking daiquiris on the beach?”, and I said “No, I gave it all to charity. I didn’t need the money”. And he’s like “What? What, are you serious? Are you joking?”, like “No, I’m serious. I didn’t need the money, I gave it all to a charitable trust I set up”. And he’s like “Well you have to tell me more about this”, and I was like [exasperated noises].

So, yeah, I had to do some soul-searching because the company that bought CD Baby offered $22 million, which was way more than I needed, way more than I wanted. In fact, I thought I’d have to be a raging idiot to spend $22 million in my lifetime. What kind of fool does that? I don’t want Ferraris, or gold-plated beds, or whatever people do.

God, I saw this disgusting thing. Have you seen Drake, the Canadian musician? There’s this whole thing that’s going around the media now about “Drake is giving tours of his mansion and his bed alone cost $500,000”, for a bed, and the rest of his house is just as ostentatious. It’s just ridiculous, and I feel bad for the guy. Man, that’s almost… That’s like a mental disorder to think that you need a $500,000 bed.

So, anyway, I just… I did some soul-searching, and I just knew I didn’t want $22,000,000. So instead, I just structured it in such a way, with the help of a tax attorney, where I first set up a charitable trust where all the money’s going to go to benefit music education. I transferred the ownership of the company into the trust months before the sale so that when the purchasing company bought it they bought it from the charitable trust, and the entire $22,000,000 went straight into the trust and never touched my hands. So that it just all goes to charity and I didn’t even have the option of changing my mind or deciding to spend it on something stupid. It’s just… I just wanted to keep it out of my hands.

Dubber Was there at least a moment where you thought “Yeah but I could… Just that one guitar or that house”?

Derek No, because CD Baby was already very profitable for the years before I sold it. It wasn’t like your classic Silicon Valley start-up that hangs out in debt for years until it sells, it was profitable from day one.

Dubber You owned it, right? It was just yours?

Derek Yeah, I owned it 100%. I had no investors, and it had been profitable since the second month I began. Every single month was profitable. So by the time I sold the company it was making $4,000,000 a year, right? So I had already paid off all debts, my house was paid in cash, I had a few million dollars in the bank that was just sitting in the bank, right? I didn’t need this $22,000,000, and I still don’t. So, yeah, I still don’t regret it. Every now and then I stop and think “Well, what if I did have that $22,000,000 now? What would I do with it?”, and every time I sit in my diary trying to think about that, the answer is just “Nothing”. I just don’t need it, so no regrets.

Dubber Wow. Let’s talk about TED Talks for a bit, because you mentioned that you started exploring TED Talks and then you started giving them. How did that happen?

Derek That was a very deliberate career strategy choice. It’s 2008, I sold CD Baby, and I was lost. For about a year and a half I didn’t know what to do next. I was just a blank slate. I felt like “I’ve peaked, my best work is behind me. I’m only 38 but I’m going to go to… My gravestone in 50 years will say ‘He made CD Baby and nothing since’”. I really thought that that was my new reality, my best is behind me. And I stayed in that state, kind of adrift, for a year and a half.

And I was enjoying watching TED Talks back then. I don’t anymore, but I did back then just for random inspiration. I found them intriguing and interesting. And it was while sitting on a plane just reading some little book that I suddenly had this bolt of inspiration inspired by one random sentence, it doesn’t even matter what, but I was like “Oh my god, I know what I want to do. I want to be a writer, speaker, thinker kind of guy. I want TED to invite me to speak on stage. I want to be one of those people like Seth Godin or Malcolm Gladwell, or something, that when I write people want to hear my thoughts”. Because until then I wasn’t. I was just the guy that ran CD Baby. People wanted to know me because I ran CD Baby and they thought maybe I could help their career as a musician, but nobody was particularly interested in my thoughts on anything. And so suddenly this goal made me shoot up in my seat, like nothing had up until that point, and made me take action. I started furiously writing a plan for how I was going to do this. “How am I going to be better known as a writer, speaker, thinker kind of guy?”.

And as soon as the plane landed I started putting that plan into very deliberate action, started working towards it. I started writing for five hours every single day, posting an article every two days or so, sharing them everywhere I could. Started looking to what it would take to get invited to the TED Conference. This is before TEDx. TED was just a once or twice a year big mainstage thing, and it was a big deal. So I was like “Okay, how can I crack that nut? How can I get into that?”, and, yeah, I set out this very deliberate plan to do that, and made it happen.

Dubber And what’s the trick? How do you become a Tim Ferriss, or a Tony Robbins, or a Seth Godin?

Derek Oh, wow. Well, those are three very different… So Tim’s trick was to… He always optimises his actions, or he used to, for being remarkable, and noteworthy, and click-worthy, spread-worthy. So even things that he had done years before ‘The 4-Hour Work Week’ came out, like getting some kind of Tango Award from Argentina or losing a whole bunch of weight in nine minutes, or whatever, he would write those articles, and share his work, and share the “How You Can Lose 100 Pounds in 15 Minutes”. He would write those articles in advance, but then didn’t release them until his book was ready for sale. So he was a crazy self-promoter that way, but waited until his book was for sale and then just did a bunch of random remarkable things to just become this random remarkable guy online.

Tony Robbins did his thing through in-person coaching, helping people almost like a drive-through shrink, helping people get over phobias in ten minutes and stuff like that, and just became remarkable and noteworthy for getting onto major media doing that very direct self-helpy thing.

Seth Godin has this remarkable persistence of writing an article every single day. For the last 30 years or something he’s posted an article every day and shared it everywhere. He used to write for Fast Company Magazine and other magazines, and posting his stuff out there, and constantly writing books, and just sharing his thoughts by writing.

So it’s like these different plans. And so, of course, yeah, you make your own mix that suits you. But for me, I guess I was following more the Seth Godin model where I wasn’t trying to be a shocking self-help kind of guy or even super interesting like Tim Ferriss, I was just trying to do the Seth Godin idea where I was just finding an interesting angle about things that people hadn’t written about and sharing it just through writing. Yeah.

Dubber So you’re one of them now.

Derek In a way, and in my own way. I’d like to be. It’s interesting noticing how our role models change, how our heroes change, right? So for 15 years of my life all my heroes were musicians, but even then it was interesting to note I didn’t want to be Bono, I wanted to be Brian Eno. I didn’t admire the people that had to get on stage every night, and put on the monkey suit, and sing the same 15 songs every night for two years. I wanted to be more like Brian Eno, where every day was a fountain of new invention and creativity in the studio. Yeah, that’s who I wanted to be. So it’s interesting paying attention to who you admire, who you’d like to be.

So then after starting CD Baby, when I made that switch, then for quite a while my role models became people like Richard Branson. “How did he do that? How did he make all these little offshoots of Virgin this, Virgin that”. And my own version was I made CD Baby, then Host Baby, and Promo Baby, and Studio Baby, and Tour Baby, and I enjoyed that branding of a word while providing different services to musicians. I didn’t want to be a billionaire, I was just thinking how could I be this serial entrepreneur, providing a lot to a lot of people.

And then after I left CD Baby it took me a while to realise, actually it took me years to realise, that now my heroes were these authors. These authors of my favourite books. And by authors I mean non-fiction authors writing things, like Daniel Kahneman, or Tyler Cowen, or… These people that would write these interesting books that would blow my mind, that’s who I wanted to be now. So that’s still the case, my heroes now are still authors, and it took me years to realise “I think I’m more of an author now”.

Dubber Do you have any programming heroes?

Derek Yeah, but a lot of them I don’t know their names. I’m in awe of these open-source contributors. Just one off the top of my head, his name is Jeremy Evans, who writes in Ruby making this SQL interface. Like an object-relational manager in the Ruby programming language to connect to the SQL databases. And he’s just an amazing programmer that does everything open-source, and just everything he contributes to the world, and it’s out there for free on GitHub. You can download it, you can improve it. And there are a lot of people like that that are just… Not nameless, but just not famous. Just so humbly out there writing the software that powers all of our websites and computers, and often just doing it for free in their spare time while they’re employed by… Well, they’re, yeah, profitably employed by some big company, and in their spare time they just contribute their work to the world for free. Those are my programming heroes, yeah.

Dubber Interesting. It’s interesting to me… I get author, but public figure is something that I find surprising about being an ambition of yours. Because I think of you very much as a… Not an introvert as such, but introspective I guess, and somebody who can work in a solitary fashion for a long period of time on something big.

Derek Oh, yeah, I’m a total introvert. You know what’s amazing? Partially because I was living in New Zealand with my kid, but in the last seven years I think the number of days I’ve spent in the company of another adult is probably something under 20 days in seven years. I live a very, very, very solitary life. If you go to https://sivers.org/soso it’s an article I wrote about being a ‘solitary socialite’, where I’ll sit in solitude in nature in New Zealand but email 500 people in a day, or talk for nine hours on the phone to 12 different people, but all from my remote location. That’s my kind of interaction. Instead of meeting up in person with three people for two hours each, I’d rather talk to hundreds by email or many by phone. Yeah, I’m a total introvert.

But about the same time that I realised what I wanted to do next after CD Baby, that story I told ten minutes ago, it went hand in hand with realising that I like being a little bit famous. I don’t want to be super famous. I don’t want to be as famous as Tim Ferriss, or Tony Robbins, or maybe not even Seth Godin, but I really like the little tiny bit of fame I have now because it opens doors where… Whenever I read a book I love, I always email the author and tell them that I loved it. And almost every time they email me back and are open to talking with me and meeting with me because I have some kind of public profile myself. That’s amazing, it’s so cool.

And then because I have a bit of a profile I hear from 20 to 40 strangers every day send me an email and introduce themselves. And often it’s some guy who’s… I don’t know, whatever, building log cabins in Finland, or somebody who’s an investor in Uruguay, and I just find such an amazing sense of both connection and security knowing all these people from around the world. It’s such a nice feeling that if I ever get on a plane to go to Uruguay someday, I’ve got a list of 55 people I know in Uruguay, just because they’ve emailed me and introduced themselves. That’s an amazing feeling.

So I like that my profile is just high enough that I meet a lot of cool people, but it’s not like I ever, ever get recognised on the street or anything like that. That happens once every two years. Somebody goes “Hey, you’re the guy that did that TED Talk, right?”. Yeah, that’s a really nice level of fame. I not only like it, but I would recommend it. I think it’s wonderful. I think everybody should try to get a little bit famous in their field. My dad’s a particle physicist, and in his field of particle physics he’s kind of well known and famous in his little circles. Nobody but another particle physicist would ever recognise him, but those 150 people in the world would.

Dubber Interesting that you bring up your dad being a scientist, which I get where the brain comes from I guess. So your programming mind or your analytical mind. Tell me about your mum.

Derek Oh, I don’t know, there’s nothing to say. I don’t know.

Dubber Is that where the creative side comes from?

Derek No, no, no. I’m very thankful that my parents were basically just laissez faire, just left me alone and I just raised myself. So, no, they weren’t actually a big influence in… And even the programming, you say “Oh, I see where the brain comes from”, but I think programming isn’t actually that difficult. Yes, if I was programming some kind of deep artificial intelligence robotics thing for Google that would be a different thing, but most programming is just moving text around. Somebody types their name into a form, you save it in a database and you split it by the space character to grab the first word of it, and you save that in a separate field. It’s not really Brainiac kind of stuff, it’s not that hard.

Dubber Depends on where your sitting, I guess. If you’re someone like me who doesn’t do a whole lot of programming then it’s amazing what you can find impressive.

Derek Well, it… Do you remember how the mixing board in a recording studio used to look overwhelming?

Dubber Yes.

Derek You know when you see one of those 32 channel boards and you walk in and you go “Woah, you must be like an airline pilot able to run this thing”. But as you get to know it a little bit you just look at one channel you go “Oh, okay, so there… Oh, that’s just the treble, mid, and bass frequency. Oh, okay, there’s the slider for the volume, there’s mute and solo”, and it’s like “Oh, all right, now you’ve just got 32 of those”. It’s actually not that complicated, it just takes you a minute to wrap your head around it, but then… Yeah. All in all, I’d actually say that learning something like Cubase, or Ableton Live, or doing the things people do with all of their Native Instruments synths and all that, that’s way more complicated and a much steeper learning curve than learning SQL, and Ruby, and JavaScript. By comparison it’s way more complicated. So, no, I don’t… Programming isn’t as impressive as it seems from the outside.

Dubber You know what? That sounds like that would make a really good Derek Sivers post about things not being as complicated as they appear. It’s got this nice little counterintuitive thing to it, and this generalisable thing about the world that you can take away. That seems like a really nice Siversism, if that’s a word.

Derek I feel this… I do have a thing out there that says “What’s obvious to you is amazing to others”, and I got that from me being amazed with Seth Godin but then other people being amazed with me. And I’m just not at all amazed with myself. Everything I put out into the world I know exactly where that idea came from.

And then that makes me think about music. That for years most of the music I made was a very deliberate exercise in taking like this Beatles melody, mixing it with this James Brown beat, mixed with this pop song I heard on the radio last week and I liked the structure or the arrangement of it. And I would just very deliberately take these ingredients, stir them in a pot, put it into my studio, make a thing in a day or two, and put it out, and I knew exactly where those influences came from. And then somebody else would hear it and go “Woah, dude. Where did you come up with that?”, and I’d think “Well, it’s easy. It’s not obvious but…”, but to somebody else it would seem amazing from the outside because they didn’t know exactly where I got it from.

Dubber Is writing easy?

Derek It’s not hard like lifting 150 kilograms is hard, but it takes time to keep thinking past the obvious, to keep pushing, to… In my songwriting days I would often write 25 verses in order to find two good ones. And I would sit for the longest time… There would be one line. I’d have six syllables to express a certain thing I wanted to express, because the melody already had six notes there I only had… I could only make these six syllables. And in fact, the word emphasis, the emphasis of the syllables, had to be just such because the melody was already there in place. And I would spend hours trying to think of “What words can I fit into six syllables to say what I’m trying to say here, because the next line’s already in place? I want to communicate this”.

So the writing I’m doing now is not any different than the songwriting I did for those years. So I do put a lot of labour into it, but it’s not hard. It doesn’t hurt my brain, it’s just time-consuming. I put in the time to… And then I put in the time to edit it too. So now I’m not matching it to a specific melody, but I’ll often say what I want to say in 20 paragraphs of thoughts, and then I edit it down to the minimum number of sentences I can possibly make it in order to get that idea across because I’ve just found that it spreads easier that way. It’s easier for people to pay attention when you’re only asking them to read a one-minute thing. I don’t expect a lot of people to sit down for 20 minutes and read a 20-minute thing, but a one-minute thing, people will read that. So I try to keep my things under one minute.

Dubber And you mentioned minimalism, I guess, in that. And it’s been something that you’ve talked about in the past, this idea of, almost in a Marie Kondo fashion, living in a minimalist style. Is that something that you still ascribe to?

Derek Yeah. I don’t like having anything I don’t need. It creeps me out when I go to people’s houses that have clutter and stuff around, and their kitchens are full… You open their fridge and it’s just full of food, I’m like [grossed out noises]. Creeps me out to just have more than I need, just makes me… It’s viscerally icky to me. So, yeah, my house looks uninhabited. Right now my kitchen literally… My fridge has two eggs in it right now. There’s two eggs and there’s a little jar of ketchup. That’s all that’s in my fridge, and that makes me happy.

Dubber Right. That would make me alarmed. But I like cooking, so, yeah.

Derek Yeah, exactly. My sister’s like that. My sister’s house is very, very, very full, and that makes her feel cosy, and homey, and comfortable. With her three kids and all of their friends, and the two dogs, and the house full of stuff, and hundreds of books on bookshelves, and just decades of accumulated stuff. That makes her feel cosy and homey.

Dubber Surrounding yourself with your life, I guess.

Derek Yeah, and to me that freaks me out. No, so even my desktop on my computer is… It’s just literally nothing, there’s not a single pixel on it. There’s just… Yeah, I’m just like that in every aspect of life. And my writing I just try to… Absolute minimum necessary makes me happy.

Dubber And, not to put too fine a point on it, now you’re writing a book called ‘How to Live’.

Derek Yeah.

Dubber And that’s how to live?

Derek Oh, god, no. No, no, no. I don’t prescribe this, no. I don’t ever tell people that they should be like me. In fact, I like it better when they’re not. I would be terrible in the debate club because I don’t want people to think like me. I don’t want to convince you to my way of thinking. No, the ‘How to Live’ book is just a blast. It’s an homage to one of the most creative, wonderful books I’ve ever read, which is called ‘Sum’ by David Eagleman. Its subtitle is ‘Forty Tales from the Afterlives’, and it is this amazing format of answering the same question in 40 different ways.

And you know, what it reminds me of is a Roland poster. You know Roland, the company that makes synths and stuff. Back when I was at Berklee School of Music I had a poster on my wall that was just an advertisement from Roland for one of their new effects pedals, or rackmount units, or something like that, but it said… The headline was something like “Make each note do what it had never dreamed of”. And they had, whether it was one artist or 40 different artists, just do an eighth note, which is the circle, and the stem, and the little flag on it. But it was done 40 times in 40 different styles, so one looked like it was shiny platinum, the next one was this twisted charcoal, the next one looked like it was dripping water. And I loved that poster, and I would keep it on my wall as inspiration whenever I was recording. That anytime that I would just record myself doing a guitar part or something, I’d think “Okay, well, that’s one way to do it. What’s another way to do it? What’s another way to twist this sound? How can I make the drums sound like a cow? Or how can I take a recording of a cow and make it sound like a drum?”. I just loved to think of “What else could I do? What other creative angle on this have I not tried?”. And so I’m still doing that to this day in different ways.

So, yeah, my book ‘How to Live’, that I’m still writing right now and should be done soon, is that but applied to life philosophy. It’s answering the same question in 27 different ways. “How should you live your life? Chapter three has a strong opinion. Chapter four has an equally strong opinion that completely contradicts chapter three”. It’s the same as that Roland poster, it’s the same as… The same thing. It’s the same as the book ‘Sum’ by David Eagleman. It’s just, I love this format of making yourself answer the same question in many different ways.

Dubber I like that. I was… Somebody tried to convince me once that music could be essentially reduced to rhythm, harmony, and melody, and that’s all that music was, and all of music was rhythm, and it was harmony, and it was melody, and it was nothing else. And that just did not make sense to me because I think of music in textures, I think of music in space, and all these different dimensions of it. So I really like that idea of “Here are 40 different ways, at least, of thinking about how to live your life”. And you seem to be somebody who changes their mind about not just how to live your life, but where.

Derek Oh, god, I change my mind about everything all the time. It upsets people around me that get annoyed at how often I change my mind, but I don’t mind. Ideally, I would change my mind about something every single day. I love it when a belief that I held yesterday is upended today and reversed. I actively try to do that. I’ll just almost catalogue through my beliefs and think “Well, which one can I change my mind about today?”.

Dubber Does that make writing, putting down what your thoughts are in a concrete form, a problem for you later?

Derek Well, no, because I never am trying to find the right answer. That’s the way I don’t think of what I’m doing as philosophy, so much. I think of it as pop philosophy, in a way, but I’m not trying to be a Schopenhauer type that’s saying “This is the answer to life, this is what life is. We’re trying to get to the truth of things”, no. I’m playing, I’m experimenting, I’m thinking “Well, how else can we look at it?”. I’m still doing that Roland poster. “How else… What else can I do to that note that hasn’t been done before?”. So, no, when I’m writing down my thoughts it’s just an exploration. It’s really interesting that the word ‘essay’…

Dubber To try.

Derek Yes, it’s the French word ‘essayer’, to try. And Michel Montaigne coined it as a term for his writing, that he would write his ‘essays’, which meant ‘to try’. To try to figure out what he thinks about something today.

Dubber Yeah, an attempt. That’s really nice. So, on that note, what happens next?

Derek Oh, god, I don’t know. I feel that I’m at the end of this ten or 12-year arc that I’ve been on. I’m feeling ready to do something very new, but at the same time I’m feeling ready to take myself more seriously as an author. And by more seriously I don’t mean a lack of fun and laughing, I mean more like I didn’t really think of myself as an author until just a year or two ago when I realised “Oh, wow, this isn’t a little side hobby, this is my main thing that I love the most”. And so I’m planning on doing much more of that and using books as my medium more, instead of just random scattered blog posts. So, yeah, I guess that’s what’s next.

If anybody listening here wants to go to www.sivers.org and introduce yourselves… Especially, actually, besides just the fact that it’s you, and like I said I would say yes to anything you asked, I’m really missing music and musicians. I would really love it if a lot of musicians were to send me their music for me to listen to, and just feel more connected to that scene again.

And I’m saying this somewhat selfishly, because I feel that 12 years ago when I sold CD Baby I accidentally got miscategorised as an entrepreneur. People thought that because I had a big exit now that I was an entrepreneur “that could tell us something about how to make lots of money”, but that never felt like me. And I think I accidentally got sucked into that world for a while, but then I would meet entrepreneurs and I always just felt like “Man, I have nothing in common with you people”. They were talking about how to raise your financing, and your angel round of Series A, blah blah blah. It was never about the money for me. I had never had any interest in making money, and most entrepreneurs seem to be focused mostly on that.

But then I would meet musicians and I’d go “[Relieved exhale] Finally we can talk about creativity, and writing, and making things, and searching for a different angle, and communicating your vague thoughts, or putting your vague thoughts into a concrete form, and putting your ass on the line, and putting your creations out into the world. These are my people, this is my stuff”. So I still find that I have way more in common with musicians than I do entrepreneurs. So, yeah, I really hope to meet the next generation of musicians.

Dubber Right. On that, finally, what I guess would be more appropriate as an icebreaker, but we didn’t need one of those. It’s one of those flight versus invisibility questions. Let’s say you could only choose to hear, from today forward, only music that you have heard before today or only music that you hadn’t heard before today. Which way are you going?

Derek Oh, absolutely the latter. I love my Debussy, and I love… Well, whatever, I could name music I love. But, god, no. I would absolutely choose new music. My favourite, favourite moment in music is when people combine instruments or sounds in a way that I’ve never heard before. That’s in general what I love about Debussy or Ravel, as compared to say a Mozart, is the orchestration, the innovative arrangements. And so I love it… I love being surprised by arrangements. I’m not really into lyrics, and so I’m not really into rock bands that are the same old guitar, bass, drums, but hey, you’ve got some new lyrics over it. Who cares? I don’t. Somebody cares, I don’t care. But, man, when people combine new instruments in a new way that I’ve never heard, that’s… I just love that, I love that surprise. So, yeah, I would choose the music that I haven’t heard and continue to be surprised.

Dubber Fantastic. Derek, thanks so much for your time today.

Derek Thanks Andrew, it’s so nice to talk to you.

Dubber That’s Derek Sivers, and that’s the MTF Podcast. You can find Derek and everything he thinks, even if it contradicts everything else he thinks, at www.sivers.org. I’m Dubber, you can find me online @Dubber. Music Tech Fest is, of course, @MusicTechFest, everywhere you socially mediate. The MTF Podcast is out every Friday, so click the subscribe button wherever you get your podcasts so you can just get the next one automatically. And you can share, like, rate, and review, because it helps other people come across it who might find this sort of thing interesting. I’ll catch you next time. In the meantime have a great week, and we’ll talk soon. Cheers.

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