An Interview with Derek Sivers, founder of CD Baby

Feb 22, 2017 · 35 min read

Published Jan 22, 2014 by Len Epp

Derek Sivers is a blogger, musician, and founder of CD Baby, one of the first online stores for music by independent musicians. In June 2013 he founded Wood Egg, which is using Leanpub to publish ebook guides to starting a business in 16 different countries in Asia. You can read his blog at and you can find him on Twitter @sivers.

This interview was recorded on January 15, 2014.

The full audio for the interview is here. You can subscribe to this podcast in iTunes or add the following podcast URL directly:

Len Epp: Hi, I’m Len Epp from Leanpub and I’m here with Derek Sivers, blogger, musician, and founder of CD Baby, one of the first, and most popular online stores for music exclusively by independent musicians. Amongst his many activities, including some very popular TED Talks, Derek is the author of Anything You Want, a chronicle of his adventures and lessons learned founding, building, and eventually selling CD Baby. In June, Derek launched his new company, Wood Egg, which is publishing annual ebook guides on how to to start and build companies in 16 different countries in Asia. Along with his team of 22 writers and 17 editors, Derek is using Leanpub to publish and update these guides, which are comprised of thousands of answers to questions posed by over 100 researches to over 300 experts. In this interview we are going to talk about Derek’s professional interests and history, his work at Wood Egg, his experiences using Leanpub, and any suggestions he might have for us at the end.

So thank you, Derek, for being on the Lean Publishing Podcast!

Sivers: Thanks Len, thanks for having me. Hey, I had to say, have you ever heard of this thing how there are an extraordinary amount of dentists that are named Dennis, and there are a lot of lawyers that are named Larry, and how there’s this feeling that our name actually influences our career choices in life? Right, have you heard about this before?

E: I haven’t heard it, but I’ve thought it before.

S: Well, when I first started communicating with you I was like, wow, Len Epp. Lean Pub. It almost looks identical. I think it’s destiny that either Leanpub was named that because of you or that you were working with Leanpub because of your name.

E: It could be, yeah, names are a powerful thing. And definitely I’m glad I didn’t go the used car salesman route because my middle name is actually Lawrence.

S: There you go.

E: So that could be Larry as well. Ok Derek, many of our listeners are familiar with your biography already I’m sure, but we do like to start our interviews by getting people to talk a little bit about themselves. So, I was wondering if you could give me a brief two-minute autobiography of Derek Sivers in your own words?

S: Sure. Born in California, I’m very American despite everything else we may talk about here. When I was a young teenager I picked up guitar and that just changed everything for me. I said I want to be a rock star or at least I want to be a really successful musician. But knowing that one in a million gets to be a successful musician, to me that was a real turning point in my life because I started to focus. Wanting to be a successful musician is like wanting to be an Olympic athlete. You know that you’re going to have to be the best of the best to be that one in a million that actually makes a living doing the thing that everybody wishes they could. It got me really focused and serious as a teenager. I started reading lots of self-improvement books and always trying to learn about the world and learn about business and communication and marketing and all these things. Even just the philosophies of how to overcome adversity and not let things get to you, and healthy attitudes towards making your way in this world. After that I noticed that life became easier and business became easier. Learning to see things from the other person’s point of view really made all the difference in the world for me. When I was 20 years old, I moved to New York City to be a professional musician, and I did it. So, for 13 years I was a full-time musician. I actually made my living playing on people’s records and touring and doing gigs and producing people’s records and even bought a house with the money I made making music. So that’s the life I was living when I was selling my own CD on my band’s website.

Back in 1997 when I was doing this, it was a very different world. There was no PayPal. Amazon was just a bookstore. So if you were a musician with a CD and you wanted to sell your CD online there was literally not a single business anywhere on the Internet that would do it for you. So I had to build my own. So I got a book about cgi-bin Perl programming and it took me three months of effort. But after three months, I had a “buy now” button on my website, and that was huge. In 1997 that was a big deal, so when I told my musician friends in New York City that I had this buy now button everybody went “Dude, could you sell my CD too?” So literally as a favor to friends I started putting my friends’ albums on my band’s website. Like “click here to buy my CD” or “click here to buy my friend’s CD”. And after a while, friends of friends started calling so I had to kind of take those people off of my band’s website and put them on their own website, and that was CD Baby.

After 10 years of doing that, CD Baby grew into the largest seller of independent music online from 1998 through 2008. It just blew up. It ended up selling music for a quarter-million musicians with millions of customers and 85 employees and a big giant pick, pack, and ship warehouse in Portland, Oregon. It was really much bigger than I ever wanted it to be. I really thought it was just going to remain a hobby, so it really grew against my wishes. So, in 2008, after doing this for 10 years, I sold the company, which is something I thought I would never do. I thought I was just going to do CD Baby for the rest of my life. But, in 2008, the learning, growing experience was to actually move on and force myself to do something new. Probably like most people here reading or listening to this, we’ve all hit a point in your life where you want to make a major change in your life. Whether it’s a divorce, or a death, or a graduation, or getting fired, or something like that. You hit a point in your life when you make, when you want to make a real big change in your life. To me, selling the company was like that. I realized I could go start another company the next day but I wanted to make a real change to my operating system, if you know what I mean. I wanted to change the way I think, and change what I do. That’s when I started lifting my head up to the world and speaking at TED conferences, and visiting different countries, and vowing to spend the rest of my life outside of the US. Trying to expand my mind and see things from different perspectives. So here we are.

E: Ok, great. Thanks very much for that. I know that recently you moved to New Zealand. Can you tell us a little about why you made that decision?

S: Sure. Well, three years ago I moved to Singapore and thought that that was going to be my permanent home. In fact I filled out ten months of paperwork and I applied for a permanent residency and I became a permanent resident of Singapore which I’m really proud of. I love Singapore. I’m really proud of that little country. I really internalized it. I’m really happy to be a permanent resident of Singapore. I love it. But I think we all need to re-evaluate in our lives sometimes why we are where we are or what we’re doing.

Even in the music business, for example, I saw some miserable rock stars. I worked at Warner Brothers for a few years. I was running the tape room when I was 20 years old. It was my first job inside the music industry., and I got to meet a lot of miserable rock stars, because they would come in for a meeting with the VPs or something and then they would kind of come into my tape room to exhale and regroup. So I got to have some interesting conversations with some famous people that were really miserable because they wanted to be a rock star when they were a teenager, and so they followed through on that, and they became a famous rock star. But now they were 30-something with kids, but they were still acting like their 19 year-old dreams. Even though it didn’t really apply to what they really wanted out of life now. You know what I mean? So I think a lot of us are maybe in a job or a situation that we got ourselves into years ago but we but if you re-evaluate what you need in your life now, it’s not always what you want now.

So last year I was in Singapore. Very, very social. Saying yes to every invitation. Every conference. Every university that wanted me to speak to every class and every person who emailed me out of the blue saying “let’s meet for coffee”. I just said “yes, yes, yes, yes, yes” to everything and I was so social that I was getting nothing done. And now everybody knew I was there and so every person that passed through Singapore would send me an email saying “let’s meet”. Even if I said no to four out of five of those I was still swamped in social activities. And I realized that what I really wanted was solitude. That at some point in your life being out there and meeting everyone is what you need, and sometimes at a different point in your life being in here, and meeting no one, is what you need. You need to focus. I just hit that point. And that’s why I symbolically just packed up and went off to New Zealand where I didn’t know anybody and it’s wonderfully under-populated, and nobody passes through New Zealand. Its been wonderful. I’m getting a lot of work done.

E: I’m very interested in when you’re speaking about evaluating and evaluating yourself. It reminded me about something from your book Anything You Want that really struck me which was, I suppose, that negative form of evaluation where you and invoke “the invisible jury”.

S: [Laughter] Yes.

E: I was wondering if you could tell me a little bit about what you mean by that.

S: Ok, the invisible jury. I thought about this first with programming, right. There are a few different ways of approaching programming. Either you can just hack together whatever works. The bare minimum, ugly code, whatever it takes to make the computer do what you want it do. Or you can try to please this invisible jury if you imagine people on GitHub reading your code and you think “Oh no, am I doing my proper object-oriented encapsulation? Am I doing my semi-colons right in a way that I won’t get criticized for on Stack Exchange or whatever it’s called, Stack Overflow?” And sometimes I find when programming that I’m trying to please someone, I don’t know who, this invisible jury that I think is going to tease me if I do something wrong in programming.

And it’s the same thing in business I think. We read books like, whether it’s 4-Hour Workweek, or whatever book that said you start to re-evaluate your business or life or work decisions through the lens of pleasing some invisible person out there that you think is going to be criticizing you if you do it wrong. I think that’s really hard to let go of. It’s kind of tied together with, I don’t know, anxiety or insecurity or who knows what kind of mental issues.

E: It’s just such an interesting idea because, you know, one of the things that I imagine makes it hardest to let it go, is when you realize no one was listening that whole time to your internal defense against that non-existent jury…

S: Yes!

E: …and there was no trial.

S: It’s hard to get over that. To just stop trying to please other people and just let it go and do whatever you personally want. Realizing, actually, sometimes I believe that you need to realize that people are going to tell you you’re wrong no matter what you do. With coding you could have your perfect code that would please whatever Rails guru you look up to or something, and still somebody somewhere else is going to tell you you’re an idiot and doing it wrong. It’s the same thing with life, you know.

I think about these big life decisions. Big life paths we could take. Some people are pursuing money. And they want to make as much money as possible. And if you follow that path, some people are going to tell you that you’re wrong. They’re going to tell you that you’re being greedy, or that you’re shallow, or whatever. Other people in life are giving up money and instead pursuing the charitable life or something. They’re giving themselves all the time, they’re donating their time, and life, and money to charity or whatever. And you know what, somebody is going to tell you you’re wrong for doing that too. They’re going to tell you you’re stupid. You should try to make as much money as you can now while you’re young. And other people, you know, I’m in the music business, and so I know lots of people that are pursuing fame. Even if it means making no money. They’re getting themselves out there into public situations trying to get famous more than trying to get rich. Somebody is going to tell you you’re wrong for pursuing that. The point is no matter what you choose somebody is going to tell you you’re wrong and you just have to let it go and not worry about that or just accept it in advance. Of course people are going to tell you you’re wrong. There is no path you’re going to follow that’s going to be devoid of criticism. So instead you just have to ignore those other voices and just listen to that quiet voice inside that knows what this is a thing that you really, really want and kind of optimize your life and career to do that, even if it’s an unpopular decision.

E: Speaking of being told you’re wrong in one way or another, that leads very well into my next question. I have a couple of big questions about CD Baby and this one is about — you had a notable incident with Apple and Steve Jobs that you talk about in your book and on your blog. And without necessarily going into the details of what that was here, I would like to ask you what you think the best thing is that Steve Jobs did for the music industry, and what you think the worst thing was.

S: Oh, I’d say there actually is no worst thing, even though that little scuffle I had with him was nasty, and I don’t own any Apple products, maybe because of that.

Actually I think the launch of the iTunes music store in 2004 was massively important for independent musicians. It was one of the best things that ever happened to independent musicians and here’s why. Up until that point indie musicians couldn’t really get their music into most places. Yes, I set up CD Baby because in 1998 there was no place that would sell your music. But within a few years there were lots of competing companies. So if you were an independent musician, you could put your CD out there on a dozen different little CD Baby-type indie shops. And then eventually Amazon started their, I forgot what it’s called, Amazon Associates or something. Amazon Advantage Program I think it was called, where just anybody could put a book or a CD or something into the Amazon system. So technically you could still be on Amazon, but it was very difficult. It wasn’t very optimized. But then CD Baby represented over two million songs or something like that in our digital catalog when the iTunes music store launched. And iTunes called us into their office and asked us to be a distributor. To send all of our catalog into the iTunes music store. And in that moment, that changed everything for musicians, ’cause now every independent musician, no matter how unknown or small, was truly in the level playing field that everybody had been desiring because every album from Madonna to, you know, an unknown plumber from Oslo, Norway now looked exactly the same on iTunes. Everybody had the same treatment, the same placement, the same visual display. Being sold in the same store. There was no difference. And if you went into iTunes search engine and typed, whether it’s salsa music or you typed the name of your favorite song — say you typed in, whatever, “Brown Eyed Girl” by Van Morrison. You decided you wanted to buy that song. You would type it into the iTunes search engine and now there’s Van Morrison’s version and here’s five cover versions by unknown musicians from Finland or Uruguay are listed equally with Van Morrison in a search engine on iTunes. It was brilliant!

And I think it was one of the single best things that ever happened to independent musicians because after Apple did it, then of course the Amazon MP3 store launched a year later, and then the new Napster, and Rhapsody, and Yahoo! Music. All of these companies now, in order to compete with Apple, contacted companies like CD Baby and said “We want everything. We want your whole catalogue.” All four million songs, or whatever it grew to be. They took everything, no questions asked. Every independent musician had equal placement. Now you almost take it for granted. There’s so many companies out there. A new one that I really like is called Personally, actually, that’s where I’m distributing my music through right now. My albums are up through DistroKid. So it’s amazing that just anybody could make some noise into a microphone right now, save it as an MP3, upload it to any number of distributors out there and it will be for sale on iTunes tomorrow. And Amazon. That’s amazing! That’s a world of difference from where we were at ten years ago. Night and day. It’s just amazing the change that one thing made in 2004.

E: And in the contemporary music landscape are there any companies or certain individuals out there who are doing something very special that you think is maybe setting the tone for the next few years?

S: I think that DistroKid, that I mentioned, it’s not a revolution. They’re not doing anything massively different. But, it has the same friendly, no-nonsense, cut the fluff, kind of simplicity that I launched CD Baby with in 1998, and I think made it really charming. I think DistroKid is doing that now for digital distribution. They let go of the concept of an album. If you have an album, you can still create an album, but their system is very optimized for musicians recording a song at a time. As soon as you finish a song, you want to put your song out on to iTunes, Amazon, and the rest. Their system will let you do that very easily. It’s great.

E: I have one last music industry question for you which is about piracy. This obviously has been a big controversy in the music world ever since things went digital and online. And I would like to know your opinion about it, just in general. I know independent musician friends of mine are often in conflict with each other about whether or not piracy is good for small bands.

S: Yeah, I’d take the side of, piracy is not a problem. I don’t think there are a lot of people out there on PirateBay, or something, searching for the name of a local unknown band. I don’t think it’s a big problem.

I think when you’re not as famous and successful as you want to be, it’s easy to look for anybody to blame. It’s almost a comforting thought to think that if it weren’t for piracy, I would be world famous right now, or I would be rich if it weren’t for piracy. Very often, when I was with CD Baby, people who would email us to complain that iTunes was stealing money from them because they had been on iTunes for three months and hadn’t gotten any money yet. We’d ask them to provide any proof of sales. We’d say “Wow, ok, let’s look into this. Can you show us some sales on iTunes that have happened, that you haven’t gotten paid for?” And they’d say “well, I don’t know any”. Then we’d ask them to buy the album themselves from iTunes. Just to make sure that the system was working. And we’d say “Well, don’t worry, you know if you’re buying it yourself. So you’re going to spend $9.99 but $8.99 is going to come back to you” or something. And sure enough they would buy the album themselves on iTunes and then the iTunes report would come in a few weeks later that that was the one and only sale of that album. So it’s nice to think that we would all be, really, much more successful if it weren’t for piracy. But I think the truth is that piracy may be hurting a few ticket sales of Iron Man 3 or something, but, I don’t think it’s hurting most of us on the independent level.

E: Ok, great. That’s a very clear answer. Thank you.

S: Well, I love the statistics that more people are killed by pigs than sharks each year. That sharks are the newsworthy, noteworthy, media-shocking, headline-grabbing news. But, very quietly, more people are killed by pigs each year. So I kind of feel that way about piracy. That it’s a shocking thing that’s easy to demonize, and talk about how this evil Internet is making piracy rampant. But I think it’s actually the other things that are hurting our careers more than piracy.

E: Oh, and what would one of those other things be?

S: [Laughter] People’s communication skills. People’s production and engineering skills, or ability to go hustle and get themselves some gigs, or their media-friendly presentation. Their photos. Things like that. Just off the top of my head. Any one of those seven things I just named, I think, are likely hurting your career more than piracy. And I’m sure there’s a hundred more.

E: Ok, thanks. Moving on to discuss publishing a little bit. Your first book, Anything You Want was published as something part of something called The Domino Project. Can you explain a little bit about that project and who’s involved in it, and why you were published as a part of it?

S: Yeah. I never wanted to write a book. I know some people have this life-long dream to be a published author and it’s a dream to see their name in lights at Amazon. But I never wanted to do a book. People had been asking me for years to turn my blog posts into a book or write a book and I just said “No, too much work. Don’t feel like it. Not interested.” And then one day Seth Godin called me, or rather sent me an email, saying “I’d like to talk to you. It’s important.” I got on the phone and he said, “I’m starting a new publishing company and I want you to be my first author.” So of course I said: “Oh, yes. Yes sir.”

Originally he thought maybe I would do a music book. Like, a how to make it in the music business kind of book. But as we talked more, he said “No, actually, let’s take a lot of these articles on your blog and turn them into a book, plus add some more. It’ll kind of tell the story of starting, growing, and selling CD Baby, including your philosophies throughout. We’re just going to turn it into a little 88-page manifesto.” That was his big idea. He felt that most books are too long. That most of us have what he called a manifesto inside of us, that would be short, powerful, the kind of book you could read in under an hour. And it would be sold exclusively through Amazon, Kindle and hardcover, using their print-on-demand system, I guess. And that he setup a system with no advance, but, royalties were split 50/50 with the author. Something like that, I forget. The details didn’t matter to me. It was Seth. I said yes. I think I thought it was going to be an ongoing publishing company. Like he had setup this new company that was going to go for years, but he actually just did it for one year.

And in hindsight, I look at other things Seth has done and I realize that’s what he always does. He actually started a record label for a year. That’s how I first met him, when I was at CD Baby. He started a record label and signed a few artists and put them on CD Baby. And he started a publishing company and did that for a year. And he started this and that project. And he tends to do things kind of as a way of testing out his ideas in the real world. But then he delegates it off to somebody else. Or sells it and moves on to the next idea. Which, honestly, I really admire. He keeps his systems very streamlined. He has no employees. When he launches a new project like Domino Project, he got a dozen interns. People that were clamoring to work alongside him. I think he paid them, but it was clear to them that this was just, come in for nine months, help get this company going. You’ll get a lot of great experience and then it’s done and we’re on to the next thing. So yeah, that’s Domino Project. I think it’s — as far I can tell, they’re not doing any new books.

E: Speaking of launching publishing companies, on to Wood Egg. You launched Wood Egg in June, 2013. I was wondering if you could give me a description of what it is and why you founded it?

S: Yeah. So moving to Singapore three years ago I was now living in the middle of South-East Asia and realized that I knew nothing about all of the countries around me. That I could literally see Indonesia out my window but I knew nothing about Indonesia. And I could also see Malaysia out my window, and I knew nothing about Malaysia. And knew nothing about Myanmar. Or Cambodia. Or Vietnam, except something about a war a long time ago, that we see lots of movies about. I didn’t really understand the relationship between Taiwan and China. And I didn’t really understand Mongolia. Some place with Genghis Khan and some yaks I think. I wanted to understand these countries more, now that I was living in the middle of them. So at first I started out just kind of taking trips occasionally. Taking three-day vacations off to Indonesia and walking around and talking to people. But after a while I felt that that was too casual. I wasn’t learning enough, fast enough. I wanted my learning to be more focused.

They say the best way to learn something is to teach it. So I thought, “Yeah, this will help my understanding. I will commit now to starting a new company that for the next five or ten years will publish 16 books about these 16 countries in Asia. Every year. And every year I’ll release the new updated version, improved, rewritten, etc.” And at first I thought I was going to go write these 16 books myself. And that’s actually why I limited it to 16. I thought “Ok, three weeks each in 16 countries. That’s 48 weeks. Take a few weeks off for Christmas and do it again.” That’s how I’m going to spend my next few years. But, that idea only lasted about two minutes because my wife was pregnant at the time. So, then I kind of decided that I was going to be the owner/publisher of this company and I was going to have to turn it into more of a system for learning and research and turning the knowledge into books. So, that’s how it began. Really just out my own self-interest and desire to share what I was learning with others.

E: You’ve got a post at about some of the hurdles you’ve had to overcome along the way in the last, well I guess, not quite a year now. Can you tell us what were one or two of those problems and what kept you going through them?

S: Yeah. So imagine if this was you. Sitting in a hotel room in Indonesia and you decided that you wanted to publish 16 books per year about 16 countries in Asia. But you knew that you couldn’t do it all yourself. So probably then your first impulse would be to hire 16 different writers. Like one per country. Let me hire a guy from India to write the India book. And let me hire a guy from Taiwan to write the Taiwan book. So that’s what I did. And that idea lasted a few months. Actually the people from India and Taiwan did a good job but the guy from Indonesia flaked out and disappeared. And I realized that this was too fragile of a plan. That I can’t have the whole book project collapse because one person changes his mind. So then I had to think a little deeper about everything I had learned about the wisdom of crowds, and wikinomics, and crowdsourcing, and all of those books about combined efforts.

And one of the big points that those books shared that I thought was really insightful is that crowdsourcing works best when people are given simple, specific instructions. I think of Hot or Not as the extreme example. I know it’s been ten years or something since that site. But, if you remember Hot or Not, all you had to do is just, you were just given two pictures and almost like a mouse with cheese you just had to click on the one that you thought was more attractive. Or maybe give it a number or something. And that’s it. That’s all you had to do. So I realized that the problem before, that I was finding a brilliant person in India and saying, “I want you to write this book about India. Please cover these ten subjects. Go.” And it just left, what’s that saying, enough rope to hang yourself with? It was too vague. It was too broad a definition, so that’s why it wasn’t getting done. That’s why authors I was hiring were flaking out. Because it was too broad.

So then I realized the pressure was on me because I wanted to be my target. Or, I already knew that I am the target market for this book. People like me that would consider moving to a new country like Thailand, to live there and start a business there. I know it’s a small niche but there are probably a few hundred or a few thousand of us in the world who consider doing that. And so I wanted a book that addresses that.

So, here’s what I did: I came up with two hundred specific questions that I wanted to know about living and working in these countries. Two hundred questions per country. Two hundred questions to be asked of each of the 16 countries. And then it was much easier because then all I had to do was go onto and and hire business consultants in each of these countries to answer these two hundred questions. And now I had a robust system, in fact, I made it even one level more robust by — again, I realized that if a person dropped out it would collapse. Or if a person gave me a bunch of bad information the book would suck. So instead I hired three researchers in each country to answer all two hundred questions. Now every question had three different answers, and I tried to find a variety of people. You know, one native local person to that country, one ex-pat that had been living in that country for a while, and one third person that would now give a broad perspective to each question. So then I hired a writer to combine those three different research answers into one essay. Now, this was my robust system. Researchers would occasionally drop out. No big deal. Replace them with somebody else. It doesn’t matter that much if they’re brilliant or not because their answer is just one-third, or their research is just one-third of the final answer. And it became this really robust system that has worked really well to make these books no matter who comes and goes.

E: And the books, you intend them to be updated annually?

S: Yeah, so, in fact, the ones that you see on the website right now are actually the second year’s books. Last year in June I released 16 books that were not very good, and luckily I knew that from the beginning. I think when I first had this idea, the reason I said that I was going to commit five or ten years to doing this is I think any of us who think about launching something, or I’m sure you have plenty of listeners who would like to write a book and have not yet and are scared of the criticism of putting a book out there into the world that might not be genius — I think it really helps instead to commit a few years to doing constant improvements. Because then you admit the first one you put out there is just not going to be that good. And you admit that up front, but you commit then to the following year, making it better, and the following year making it much, much better. So, yeah, my motto was that I know the first year’s books would be not-good. Second year’s books should be quite good. The third year’s books should be very good. And maybe by the fourth or the fifth year I’ll be able to call them great, or even amazing. If you just keep committing to massive improvements every year.

E: And at that point there will also be a record of how things have changed over the last few years as well. And actually there’s, I mean, you’ve covered 16 countries. It’s an amazing project. There’s one country I’d like to ask you about specifically, which is Myanmar, or Burma. Can you tell us what you’ve learned about the situation for entrepreneurs there, and how it’s changed in the last couple of years, and where you see things going in the next few years?

S: Sure. Actually, I don’t have that much to say about Myanmar. It’s so really tough. Up until just two years ago I think, they were completely closed to foreign investment. You really couldn’t go to Myanmar and do business. It wasn’t allowed. And just two years ago they started to open some doors but it’s still incredibly difficult. There’s even mixed information about how to incorporate a business. Some people say that you can just fill out the official forms and set up your business. And other people say that you have to prove that you have a million dollars in capital and then you have to know someone, or bribe someone, to get your company even started. It’s all a big chaotic mess but in a, hey — rule number one of investing is risk equals reward. So the few that are in there doing it right now and learning the ropes are probably going to be the ones that are rewarded the greatest in the future. You think of the people that came to the US in the late 1700s and setup the first, whatever, boot manufacturers or something. It was probably incredibly difficult to start a company in this untapped land, but those who got in early and stuck it out through the difficulties are the ones who profited the most.

E: Speaking of being there at the beginning of a big change: you’re the founder of CD Baby, and now you’re getting into publishing, and I’d like to ask you how you think the book publishing industry in 2014 compares to the record industry in 1998?

S: There aren’t many similarities but the biggest, and most important one, is that there are now no gatekeepers. In a very similar position, in 1998 things had changed radically just in four years. Because say in, like, 1994, if you wanted to put your music out into the world so that people could buy it, you couldn’t. [Laughter] You couldn’t. You would have to go know someone who knew someone to kiss some ass at a cocktail party to get a meeting with a lawyer who could introduce you to a record executive who, in between puffs on his cigar, might think that your music is good enough to sign you to a deal. And only then, and after a year, and after this and that, and debt that will never be recouped, could your music get out into the world. That was the only way in 1994, say, to put your music out there. Except obviously you could sell your CDs and cassette tapes off of the stage in person. But that was it. The only way to get into record stores was through the major labels.

So in 1998, that all changed. Now you had companies like CD Baby that would sell just anybody, anywhere, internationally. So, I think 2014, as compared to just a few years ago, now anybody who wants to put a book out into the world can do it. There’s no gatekeepers. Think about what a huge difference that is from just five or ten years ago or something. You couldn’t. If you had a book in you, the only way to get it out to the world was to know somebody that knew somebody that tried to get an appointment with a publisher, and in between puffs on his cigar, if he liked your book, you know, maybe it would be released to the world a year later. Now just anybody can put it out there. So, that’s huge. I think it’s not appreciated as much afterwards, what a massive difference that is. We take it for granted now.

E: Yeah, that’s very interesting. It reminds me again of the, if I remember, one of the main issues that happened in your incident with Steve Jobs was that he said “You know people can just put their music on there.” And then you say in your book that he obviously changed his mind about easily letting independent musicians onto iTunes. I find, I don’t know if you’ve encountered this as well, but often in the publishing world there’s a sense of elevated status. That people are, even to the detriment to their own interests, protective of the power that, say, I guess in the music world, that big labels have, to make you a real musician, and that big publishing companies have to make you a “real” author.

S: Yeah. And culturally, speaking of Asia, that’s still more true in parts of the world where in the US, for example, or in America in general, there’s this champion of the underdog that’s almost cool to be indie and not sign your life away to a corporation. But in Asia, the biggest one is still considered the coolest one. It’s actually, you don’t want to tout your credentials as a small underdog indie as much in Asia. Instead it’s almost better to appear bigger than you are, and you can see a culture difference.

E: That’s very interesting.

Now, moving to just a couple of questions on Leanpub. You chose Leanpub to make your books. I know that you’re also selling them on Amazon. Can I ask you what led you to choose Leanpub for your publishing company?

S: Markdown. I love that Leanpub uses Markdown as the book format. That was just amazing. I think even, I don’t know if you consider CreateSpace to be competition, but I looked into CreateSpace once and they talked about “upload your Microsoft Word file.” I was like [blows raspberry]. Gone. Forget that. These books are generated by my database full of essays written in plain text. I’m not going to put things into a stupid — I don’t even own a copy of Microsoft Word. I don’t want to, you know. So, I love how Leanpub is this, kind of, Linux nerd-friendly, programmer-friendly system for those of us that like to use a format like Markdown. I think it’s just brilliant. And then the fact that you, that the same system system that helps me make the books also sells them at a wonderful, friendly, author-friendly price, is just ideal. I’m a huge fan and I’ve been sending everybody your way. Everybody that asks. You know “Hey, I’ve been thinking about writing a book. What should I do?” I tell everybody to go to Leanpub.

E: Oh, ok. Well that’s great. Yeah it’s interesting what you say about Microsoft Word. Yeah, I mean, it makes me cry when I open it now. And I spent, I mean, I’ve got a Ph.D. in English and I spent all those years writing in Microsoft Word. And it was absurd when I look back on it now. So it’s great to hear that, because one of the big bets for Leanpub was that Markdown is the way to go for the future. And so it’s really great to hear that people like you agree.

S: Absolutely.

E: Can you tell me a little about how you found about us? Were you just surfing the web, or did someone mention us to you?

S: I think, well I’m a Ruby programmer, and a lot of Ruby programmers put their books on Leanpub. I think JavaScript, a couple of the Node.js books that I bought in the past were through Leanpub, and JavaScript Allongé or something like that. And Hands-on Node.js I think. I had already bought a handful of books from you, just because I’m a fan of — I’m really a book learner, so a lot of what I know from programming is learned from books more than videos or courses or whatever. So I had already bought some books from Leanpub, and was already a fan, so I knew I was going to use you guys once it was time.

E: OK. Actually, one thing I’m sure that our listeners who are either publishers or self-published authors would be interested to know is how you’ve gone about promoting the Wood Egg books.

S: Actually, I don’t have anything interesting to share there. Because Wood Egg wasn’t started as much of a business as it was a personal curiosity project, that I only finished this year’s books 12 days ago. And up until 12 days ago, everybody would ask me “Hey, what’s your marketing plan? What are you going to do to sell these?” And, I would just shrug. I just wanted to get them finished. Get them done. I was 100% focused on just getting them made. I was spending all my days just editing, and improving, and writing. Just as of 11 days ago now they exist in the world, and it’s such a huge relief. But, don’t have any business, marketing, brilliant ideas to share. Sorry.

E: [Laughter] Ok, nope, that’s fine. It’s actually, there’s a lot of important things I think for Leanpub authors in that answer. Including, think about the writing first, maybe, before you get ahead of yourself and start worrying about a lot of the marketing.

S: Well, it’s funny because, if you don’t mind, let’s look at the flip-side. There are some people making a ton of money doing helpful ebooks in the world. I forget, it was the top story on Hacker News today, it was somebody who made $350,000 on an ebook about creating iPhone apps or something. And there lots of stories out there that are worth paying attention to, but I think the difference is you can choose upfront whether you are making a book for the marketplace, or whether you’re making a book out of a sense of, like, personal, this is just something I feel like doing, whether it makes me a dime or not. So if, on the other hand, you feel like making maximum profits from the book, the best time to think about it is actually before you start writing. If that’s your intention, to make a lot of money and sell a ton of books, then you should be thinking, before you write a single word, what does the marketplace want? And the 4-Hour Workweek book gives some brilliant examples of that about — I think he wanted to call that book Drug Dealing for Fun and Profit because he was running a vitamin supplement company at the time and he was going to share some lessons learned from running his vitamin supplement company — and felt very passionately about that title. He loved that title. Drug Dealing for Fun and Profit. But apparently he contacted Walmart and found out that they would not sell a book with that title.

E: Right.

S: So he, you know, begrudgingly said “OK, I guess I need a new title.” And he started Google AdWords campaigns with a handful of title ideas, and then even with his subtitle ideas. I forget what the subtitle is. Something like “How to join the new rich and live a free life” or something. Each one of those things was tested in Google Ads to see what phrases people would click the most. And choosing that ended up helping him — seeing which phrases people clicked the most ended up shaping his whole project, in deciding what kind of book to write based on what people were clicking on the most. So Leanpub is actually a great way to do that kind of thing, I think, where you can, first start running some ads or surveys, or whatever it may be, to find out what kind of book people want. Or what will be the biggest seller. And then you can start writing it, and that as-you-go process, chapter by chapter. Getting feedback on people saying “Yes! You need to talk about this some more.” And voilà, your chapter three is now different than what you had already expected because of what feedback people gave you in chapter one and two. So I think you could write a much more successful book if you think about the marketplace from day zero.

E: Hmm, yeah. That’s very interesting. One of the features we do have that is intended to accommodate that, is that you can easily create a landing page for a book with different titles and people can sign up and say “I’ll buy this if and when you release it.” So people could do tests of different books they might want to write. Even different titles. But it reminds me, Peter Armstrong, Leanpub’s co-founder, has this great line about how “A big success for Leanpub can be when an author stops writing a book.” And that’s because, as you were describing earlier, often, people can, well I think we were talking about this, but people can feel like the thing needs to be complete and done, done. And you work pm it for years. Toiling, toiling away. And then you release it and, you know, crickets can happen sometimes. So one of the things about Leanpub is, set up a landing page. Test the idea. If you get some responses, then work on that project. Get to the end of three chapters. Get going. Start publishing that and seeing if there’s interest out there for what you’re working on. If that’s a necessary, an essential criterion for evaluating your own success — getting a lot of readers.

S: Exactly, yeah. And I think most people probably would like to sell as many books as possible. But for those of us that are actually just doing this more as a personal project, like, this is something I feel like writing for my own sake. Even technical books. I know a lot of people — I think there’s a guy, Steve Klabnik or something, that’s currently writing about Rust a lot. And he’s writing about the programming language Rust on his blog as a way of learning Rust. So to him, he might end up — somebody like that might write a book about Rust as a way of learning about Rust, and whether it actually sells a lot or not is a secondary concern. First and foremost it’s your own self-education or personal project. As long as you know which way you’d like it go, you can optimize your workflow based on which one.

E: Speaking of self-education, that actually leads right into the last question I wanted to ask you. Not just self-education, but dedication and training. You have a great post about learning to sing over the course of 15 years, I think, on your blog. And you talk about the years of practice and hard work it took you to get to the point where you could sing well enough that people assumed you’d been born with a great voice. Have you taken a similar approach to writing?

S: Writing. Programming. Everything. Even my cultural understanding in living outside the US and traveling. I think once you understand that you’re not going to be great at anything at first, it really helps to instead make that long-term commitment. There’s a book called Mastery by George Leonard, and I’m sure there’s some other books like this, that use the martial arts metaphor, that if you go into a karate dojo, studio, and say “I want to be a black belt this year,” they’ll just laugh because that’s not — you don’t get to be a master like that. First you need to do this simple move 150,000 times before you’ll really be good at it.

It’s all about the ongoing dedication. So the problem is if you’re impatient. You just want to be great and fast. In anything. I want to be a great writer. I want to be a great programmer. I want my business be big, big, big! If you’re impatient, which sometimes we think that impatience is a virtue: “Hey, I’m not going to stand for the speed limit that everybody else sets for themselves. I’m going to, what is it called, growth hacking. I’m going to hack master. I’m going to hack marketing. I’m going to hack this. I’m going to speed this process.” The problem is, if you are expecting everything to go so fast, then you might end up being a miserable dabbler. And that’s where you do a couple years of this, and then you get frustrated. You throw that away and go do a couple years of something else. You spend a couple years trying to be a good writer, but you’re not a great writer after nine months, so you lose interest and now you try to go get your pilot’s license or something, I don’t know. So that is the opposite path of mastery, that you will never be great at anything if you have that impatience — that instead you need to understand that to be great at anything, it’s going to take a long time.

Maybe having that impatience upfront can be healthy if it makes you focus harder, try harder, practice more. But then you still have to understand that it’s still going to take years. Maybe if you’re impatient you’ll be much, much better in ten years than somebody who is just kind of lackadaisical and committed for ten years, but you still have to understand that it’s going to take years regardless. So, yeah, sorry, to answer your question, it took me 15 years of trying to be a good singer, and I think it’s going to take me 15 years to be a good author and 20 years to be a good programmer. I just assume that these things are going to take a long time, but work as hard as I can in the meantime.

E: Well, “Focus harder, try harder, and practice more” sounds like a great slogan, not just for martial arts, but for anything!

Thanks very much Derek for being on the Lean Publishing Podcast, and for using Leanpub as a platform for Wood Egg.

S: Yeah. I love it! Thanks Len!

E: Thank you.

Originally published at

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