Interviews → Rock and Roll Zen

Mark:

It’s a funny thing. I’m paraphrasing, but are you a fan of Emerson or not?

Derek:

I haven’t read much of his.

Mark:

He was one of my favorite authors, and he had a famous essay called Self-Reliance, but somewhere in there he said.. Something about - in the works of others, they will echo back to you with some sort of alienated majesty, essentially to the effect of, a great idea comes back to you. And you’re going, “Ahh. I had that idea. Why didn’t I do that?”

Derek:

Yeah, I remember when I read Self-Reliance, that phrase got underlined. That hit home.

Mark:

It’s an absolute favorite of mine, and I’ve been called many strange things for my influences because basically, the heaviest influences were him, Rumi, and Jimi Hendrix, I guess you could say, if I were to form a triangle there. But that essay and that particular line resonates so much, maybe for the wrong reasons, because I guess I’ve had a few good ideas too, where it’s like, “Oh, I wish I’d done that.”

Good morning rock stars, and welcome to another episode of “Rock and Roll Zen.” Today, I have a very special guest - someone who is known to many, and yet to some, they’re not quite sure what that name means. But this is a person who, of the many things he’s been called, has even been called “the last music-business folk here” by Esquire Magazine. So whoever would own that moniker is probably someone of interest, and I know that he already is, so I’d like to introduce you to someone who I’ve been following for many, many years - and even been indirectly involved with in business, unbeknownst to him, with a venture that maybe we could say put him on the map. So without further ado, I’d like to introduce everyone to Derek Sivers. How you doing, Derek?

Derek:

Thanks Mark. That’s a hell of an intro. Thank you.

Mark:

I try, man, I try. And you deserve a hell of an intro, and I think, Derek, it’s a funny think. To those who know you, you have this pretty massive online following; you have a loyal following; you’re someone who is well-loved by a whole lot of folks, and yet, I know for a fact that there is some part of the world that does not know who this person is. So let me just do a little set-up here, for those who may not know you as a household name, which I think will help inform this conversation.

Mark:

It goes like this: let me bring you all back to a time when the Internet, like the earth four-billion years ago, was just formulating. Let’s say it’s the late ‘90s, and a lot of businesses are starting to coalesce in this new thing called “cyberspace,” and we’re at the cusp of the dot-com boom, and all sorts of really interesting things and business and ideas are starting to kind of come together. And at that time, I was a musical artist, and I had a band that was called fire ants, and we had a following, I guess, in an odd way. We were one of those people that put our songs up early on the Internet, on this place called “mp3.com,” and all of a sudden, out of the blue, we rose to number-one and got all this crazy notoriety, which was very strange considering we were an unsigned band. We had no budget for PR, we had nothing, and all of a sudden, CNN was calling us, and all of a sudden, Rolling Stone was calling us, and Wired Magazine, and it was a very interesting time.

Well, as an independent artist at that time, we wanted to sell our CDs, and there was no one who wanted to do that at that time. There was no one to sell your music online as an independent artist. There was no one to take on indie artists without, obviously, a major label contract, or major distribution. No one wanted to know you. So that’s my story. Now let’s talk about this guy named Derek Sivers. So, at the same time, Derek Sivers is also a musician, who is having some success in the world. He is touring; he’s got enough success that he buys himself a house in Woodstock. But Derek has this dilemma too, and Derek wants to sell his music online, and evidently comes up against the same kind of situation. Would that be true, Derek?

Derek:

Yeah.

Mark:

OK, so now, what I’m about to say to everyone here might sound absolutely novel. It might even elicit a “whatever, dude” response, because who on Earth would care when I tell you about someone who built a website, put up a shopping cart, and sold their music online? That’s really exciting, right? Probably not. Except - you got to understand it’s 1998. Is that right, Derek? ’97 or ’98?

Derek:

Yeah, exactly. End of ’97, beginning of ’98.

Mark:

OK. So at that time - here’s the amazing part of this. At that time, there were no shopping carts. There was nothing to buy a CD online. This did not exist. There was no iTunes. There was no PayPal. This was an absolute void. This was, if you will, the primordial ooze of the Internet. All these things are still yet to come. So Derek Sivers, who has this idea, “I need to sell my music online; how do I that?” comes up with this idea, “I know. I’m going to - since nobody’s taking on my music, since nobody is taking on my distribution, and maybe I have to figure it out because necessity is the mother of invention,” he decides, “Well, to hell with it. I’m going to build a website. I’m going to figure out how to make a shopping cart, and by God, I’m going to sell my music online.”

Mark:

I could tell the whole story, Derek, but it would be nice if you’d fill in the blanks from here, and just kind of - how it went from there to just the beginning of what was just a necessity - how did you start a business accidentally?

Derek:

I love that you covered the context, because it is hard to understand those times now - that Amazon was just a bookstore and all that stuff. So there was nowhere to sell anything as an independent musician. I really did just put that “Buy Now” button on my website, intending for an audience of only people that were already looking for my website. You know, like, my music was being played on, I think, a couple hundred college radio stations across America at that time, so I just wanted a way for people that were emailing me from New Mexico or Maine to be able to buy a copy, without having to mail me a check and me mailing them a CD. So I really just intended it for an audience of my fans - a way to sell 20 or 100 copies of my CD - but it was right after that that, because I was living in New York City, and all of my friends were musicians, my friends started to say, “Hey man, could you sell my CD through that thing?” And I hadn’t even considered that. It wasn’t meant to be a business.

Derek:

So even then, it was just a favor. My friend Marco was the first one to ask. I was like, “No problem, Marco. I’ll put your CD on my band’s website.” So then my friend, Rachael Sage, said, “Hey, could you sell my CD through that?” And I said, “Yeah, no problem Rachael. For you, anything.” So there was my band’s website with Marco, and Rachael, and pretty soon it was like four or five others, and then friends told friends, and then somebody announced it in his newsletter, and I was like - OK, I got to take these off of my band’s website. This is ridiculous. So yeah, I put it on “CD Baby,” again, just intending it to be a favor to friends, and it would be like a little public service that I was doing to the New York music scene, or to my fellow musicians. But yeah, it just took off like crazy, and I like that we can talk in musical terms in this conversation.

Mark:

Well, we are kindred spirits, in that sense, because I guess we were both doing that dance at the same time, and found ourselves - I guess in similar situations, you could say - for different reasons, but independent artists looking for a way to further connect with the world.

Derek:

Yeah. So I’ve read a lot of interviews with songwriters that often are surprised by the song that became their big number-one hit. They just kind of shrug, like, “I don’t know why that song became a hit. It was no better or worse than any other song I’ve ever written, but for some reason, that song was in the right place at the right time, and now it’s what everybody knows me by.” So I think CD Baby kind of felt like that. Up until that point, I had done a ton of things. I had a record label, and a booking agency, and a recording studio, and a band, and a coffee house act, and I was doing a bunch of stuff, but CD Baby - it hit at the right place at the right time; there were no competitors at all, and kind of like you mentioned: if you were an independent musician wanting to sell your CD online around 1997 through ’99, really, the only way to do it was some guy named Derek in New York who could do it for you. And I just got lucky being in the right place at the right time.

Mark:

Well, you sure did, but I think - and we’re going to talk about this a little bit, because, of the many things you’ve done, and not too long ago, you wrote a little book, and what I mean is it’s a little book in its size and amount of pages - but it’s a little book with big, beautiful, clean, concise ideas, and it’s called, Anything You Want. And, by the way folks, this will be in the show notes, so I’ll send you a link to this, and to anyone who hasn’t read it out there - if you really wanted a manifesto on how to do whatever it is you want in the world, I could not recommend this book more, because Derek has such an amazing way of just that: brevity, being concise, and really getting big ideas down to a few words, and brevity is such an important thing to get out clarity. So what I want to bring forth about that book, speaking of the beginning of CD Baby, is, you tell a funny story about when you first launched the idea, some guy in the Netherlands writes you and says, “Hey, you got any new releases?” and how, up until that point, you hadn’t even considered that this was a store, and how the whole thing pivoted. Do you want to just talk about that for a second?

Derek:

Sure. I think the lesson for people, in this, is that - especially for entrepreneurs - that whatever idea you have now, that you haven’t launched yet, you have no idea what it’s going to become. So you can just kind of drop this whole know-it-all future-visionary prediction thing, because as soon as you actually launch it in the real world, it’s probably going to morph into something else, if you’re actually listening to what people are wanting. So when I started CD Baby, I really just thought of it as a credit card-processing service. Because remember, there is no PayPal, or Stripe, or Gum Road, or whatever everyone’s using now - there was nowhere that would charge credit cards for you. So I was really just processing credit card payments for my friends, and in fact, the very first round of CD Baby, my friends were actually shipping the CDs themselves. So I really was only processing the credit card and that’s it.

But then, almost right away, my friend Marco, like, spaced out and forgot to mail the CD to the customer, so the customer emailed me back kind of angry. I was like, “Marco!” And he said, “Sorry man, I forgot.” So from that point on, I was like, OK. I better hold onto these things myself, since I’m the responsible party here, charging the credit cards. So even that was a pivot that was like ten days after launching this idea - I guess I’m not just a credit card-processor; I guess I need to actually hold onto my friends’ CDs myself. So that was a change, but even then, I still just saw myself as a credit card-processor that was also shipping the CDs, and some guy in the Netherlands bought my friends CD, and some others, I think, and I mailed them to him, and he came back asking where the new arrivals were, and when I said, “Well, what do you mean by ‘new arrivals’? You mean like which of my friends are you processing credit card orders for?” And he said, “Oh, I’m sorry. I thought you were a store.” And yeah, up until that point, Mark, I seriously hadn’t considered it. I was like, “A store! Interesting…I guess I could be a store, like with new arrivals, and actually, that would be a really cool thing to do for the world, because then I could highlight new albums, and I could divide them into genres, and people might actually come here looking for music.” I hadn’t considered that.

Mark:

That’s so wild. And that’s the thing, and of course we could go on, but I think we’ll end up interspersing this really amazing story of a real success-story of a business throughout the interview, so I’ll kind of leave that just for a second now. So, since I gave you this introduction - since I told my audience a little bit about you and a background - let me start off by letting you tell the world, who is Derek Sivers, and how do you make the world a better place?

Derek:

How does anybody say who they are? How do I make the world a better place? I don’t really think in terms of making the world a better place. I do think in terms of being useful to others - to be of service.

Mark:

That’s a very key theme, so talk about being useful.

Derek:

Well, I think the world often tells you what it wants from you. So it’s your job to just be out there, and be in it, being of service to others. At least that’s mine, and everyone’s got their own, so obviously, some inventors just want to invent their magical widget that everyone’s going to buy, but I can relate more to a service mindset. Being useful. So I’ve been thinking about this a lot lately. There’s a new project that I announced on my most recent blog post, and it’s Sivers.org/2do, and it’s called, “Just Tell Me What to Do.”

Mark:

And I read that, by the way, and to anyone who doesn’t know, Derek’s blog is amazing. So talk about that, because that’s a great idea.

Derek:

So, for the last eight years, I’ve been taking detailed notes on every book I’ve read, and I’ve read two-hundred-and-twenty-something books, and I post all of my detailed notes for free on my website, so it’s at Sibers.org/book, there’s this page that’s just out there for free, with all of my detailed notes from the 220 books, and in fact, I even sort them with my top recommendations at the top. So if you’re wondering where to start, start at the top of the list, obviously, and see what catches your fancy.

I really enjoy reading the whole book, and then underlining my favorite sentences, remembering them, taking notes, and then reviewing my notes, so that I don’t forget what I’ve learned in the past. So just recently, maybe because I had a kid, I started thinking about ways to pass on everything I’ve learned, instead of telling everybody to go read the same 200 books I’ve read. I thought, I should probably be of service to the world and compress that down for people into the most interesting bits I’ve learned from the last 220 books. So it’s a new project I’m starting. I’m not even sure what form it’s going to take, but it seems like a useful thing to do, so just to be very meta, while I was doing that, I came across four categories of things that I think are ways that you can be useful to others. Do you want to hear them?

Mark:

Do tell.

Derek:

OK. So, number-one: get famous.

Mark:

Love it.

Derek:

If you do everything in public and for the public, you’re being useful. It’s really the more people you reach, the more useful you are. The opposite is hiding, which is of no use to anyone. And this hit home for me, because I’m actually really reluctant to this idea, because my natural tendency is to really lay low - to not be so public. I kind of don’t understand how some people, like whether it’s Richard Branson or Tim Ferriss, seem to want to be in the public eye, whereas I really enjoy just laying low and just not dealing with the world.

Mark:

Well, you do have this sort of Buddha aura about you, and as much as you seem to will these grandiose ideas onto the world, seemingly from a cave. You know, you’re so - it’s not so much - you’re not self-deprecating, but you’re - it’s almost like Dylan, “I’m not there.” The idea is there, but Derek Sivers is really nowhere to be found, and yet the ideas are so resonant. So I believe you said, what, three of them? Keep going.

Derek:

OK, yeah. I’ve got three more. Number-two is get rich, and this one also, I have a resistance to, but I’ve, through the years, I’ve realized that I think that money is just neutral proof that you’re adding value to people’s lives. So by getting rich, you’re being useful as a side effect of that pursuit. And then, once you are rich, you can spend the money in ways that are even more useful to other people, therefore, getting rich can be double-useful to the world.

I actually spoke on - Berklee College of Music asked me to come back and speak to the opening key note to the incoming freshmen, and I said a few things - you can see it out there on my site if you want. It’s at sive.rs/berklee, but I think point number six I made to the class was, when you leave here, go out and actually make money. Actually pursue money. Don’t do the typical musician thing of like, “Hey man, money doesn’t matter to me,” because actually, money can be a very neutral indicator that you’re being valuable, and if you’re just kind of sitting there saying money doesn’t matter, then it’s very likely that you’re being useful to nobody. By just going out into the world and seeing who wants to pay you, it’s a way finding out where you are of value to the world. So anyway, how to be useful to others, number two: get rich.

Number three: share strong opinions. I find that strong opinions are very useful to other people. In fact, I got this idea from Brian Eno. He said that that’s his main job as a record producer, is to just be the guy in the studio sharing strong opinions. Because those who were undecided, that were ambivalent, can then just adopt your stance. Like if they’re really on the fence, they can go, “Yeah, OK, Brian seems to have a strong opinion about that. We’ll just go with what he thinks.”

Mark:

And he knows how to make records, yeah, go on.

Derek:

Yeah, but on the other hand, sometimes - apparently half the time - he puts out an idea - he’ll be in there with the band, and he’ll put out a bold idea, and everybody will disagree, and they’ll tell him why they disagree. And he said, “OK, great. So you disagree.” So he said, those who disagree can now solidify their stance by arguing against yours. So I find that even if you invent an opinion, for the sole sake of argument, boldly sharing an opinion is very useful to others.

Mark:

I like that. Well, isn’t that the basis of debate, right?

Derek:

Right, it can kind of help under certain perspectives. Although if you take away politics, very often in debates, nobody’s actually changing their minds on anything. Everybody just likes to dig in their heels and refuse to....

Mark:

Right. It’s like a tug-of-war or the opposite. They’re pushing against the force and trying to win one or the other side of the argument. So yeah, good point.

Derek:

So number four - and this is the last one - how to be useful to others, number four, be expensive. I’ve found, through reading all of these books, so many examples bring up things related to this. For example, people that were given a placebo pill, like a painkiller pill that was actually just a placebo, were twice as likely to have their pain disappear when they were told that that pill was expensive, whereas the other half of the group that was told this was a cheap pill, their pain didn’t go away, even though everybody was given the same placebo. So also, you might know from doing shows that people who pay more for tickets are more likely to attend the performance, and in general, people who spend more for any product or service, value it more and get more use out of it. So therefore - ergo - you should be expensive, in whatever you do. It’s not being greedy, it’s actually being useful to the world, because the more expensive you are, the more likely people are to get value out of whatever you do.

Mark:

That’s such a great idea, and you seem to overflow with them, Derek - but anyway, I digress. Just today, I got some message on LinkedIn from some musician, and it said something along the lines of - first of all, the subject is “Hey Mike”, you know, wrong name. And it goes on to say, “Checked you out, love your music, love you production, would love to talk about working,” and so I wrote him back - I said, “Let’s begin with, do you have the right guy? Because you began this with ‘Hey Mike,” so perhaps you’re looking for Mike.” Turns out he wasn’t. But he said, “No, no, no, apologies, apologies. Anyway, I have this music, and I really would love to do a collaborative thing online, I’m oversees, but the truth is I really have no budget, or very little at best, and would love to start something with you, if you’d like that.”

And I have to stop myself, but it’s like, I’m 53, I’ve been doing this for thirty-something years now. And guess what? I know you want to do it for free, and I know to just be bros and just share our love of music, and let me try to make your music better, but guess what? I have a family and a mortgage in New York City, and not a lot of time, and can’t do it. And you realize that, absolutely, be it a Mercedes Benz, be it whomsoever, that thing about - it’s exclusivity that’s the concept of - I’m assuming something, but have you read Robert Cialdini’s Influence book? I would just assume you read that, but maybe you didn’t.

Derek:

Oh, of course.

Mark:

And that’s just one of those things - that concept of exclusion, or to be an exclusive category is absolutely more value that we place on things, but I haven’t really thought about it in the terms that you just laid out, in terms of being useful, and I think that is very innovative thinking. Most people think, “Oh, if I just had the money, I’m in some exclusive club,” but you’re painting it in terms of usefulness, which I think is so cool, but you do that a lot Derek.

Derek:

Thanks, well with this project - I mean, just imagine, I spent - for one, I spent eight years kind of taking notes on all of these books in the first place, but then I just spent the last four months, like full-time, re-reading all 225 book notes, and each one of those is ten pages of notes, so it’s like a little mini-book itself - rereading these and trying to extract the most important points, and then think, how can I turn these into advice for others? Because it’s one thing to talk around the issues. In fact, there are tons of amazing books out there that talk around the issues. They’ll say, “Hey, here’s some information that will help you better understand your mind and the mind of others,” and they’ll tell you a bunch of studies that have been done, and a whole bunch of tests, and the results of the tests, and give you all kinds of interesting insights, but at the end of the book, you’re just kind of left with this feeling of, “Wow, that was really interesting.”

Mark:

Right, but what do I do? What do I do with that?

Derek:

So I was thinking about how we have a reluctance to tell people what to do, because it sounds bossy. You feel like, “Who am I to tell people what to do? I’m nobody’s boss.” But then if you get really humble, you realize, nobody’s going to do what I say anyway, so why not just tell people what to do? Because subtract all the baggage around it, and what you really have is a very efficient way of communicating the philosophy. If you just give a sentencing: “Do this,” well, the philosophy’s actually carried inside of it, a little bit like the dandelion - the little poofs that fly in the wind, and they carry the seeds inside of it. So I was thinking about the Ten Commandments, or something like that. It’s not like there were 75 stone tablets that discussed the pros and cons and the various issues around these subjects, instead, it just said: “Number one: don’t do that. Number two: do this. Number three: stop doing that.” And inside those commandments - I think a better word for them is “directives,” the philosophy is carried inside of it. So I’m trying to figure out how to extract directives from all of this stuff I’ve learned.

Mark:

Well it seems to me that what you’re hitting on here may well be the reason why personal trainers are such big business at the gym, and why life coaches are such big business out there in the world. People need, and I think want to be told what to do, because there’s so much - in this age of information, we’re all drowning in information and in opinions, and data, and metrics, and analytics, and how does someone wade through all that, dig through all that, and actually find “Here’s what you need to do,” and let’s face it. That’s why these people get paid to do what they do, because people really would love to be told. Just give me a road map. Route 80. Get off at 17. Go right.

Derek:

By the way, I did forget to mention - that’s actually how this all started, is because I’m such a fan of these books that often, I’d finish one of these books, and I’m like, “That’s amazing,” and I’d go tell my friends about it, like, “Jeff, dude, you got to read this book. This is so amazing,” and my friend Jeff is a smart guy. In fact, he’s technically a lawyer, he passed the bar, but he’s like a hit Broadway songwriter now. And he’s kind of naturally lazy, and when I tell him about this amazing book I read, he always says like, “Dude, I’m not going to read the damn book. Just tell me what to do.” So that was kind of the inspiration. You’re right, there are a lot of people who aren’t ever going to read the damn book. They just want you to tell them what to do.

Mark:

Right. Just give me the Cliff’s Notes, and say, “Do this, do this, do this,” and that I can handle, and that I might actually implement.

Derek:

It comes down to trust, too. If you trust the source - like my friend Jeff trusts me. He knows that I know him; he likes me, he likes the way I think, and he knows that I know him well enough, so that if I say, “Jeff, you need to do this,” he trusts me. I don’t need to provide 300 pages of supporting evidence and anecdotes. He trusts me.

Mark:

It’s your job to be Derek Sivers and somehow extract from that the perfect gems and throw that out there, and it’s like, “Yeah, that’s what I want. Perfect. Good job Derek. Move on. That’s why you do what you do.” I thought that it would be interesting to - Derek, I think you go back far enough to know this reference, but you know, one of my favorite points of influence in my life goes all the way back to Bugs Bunny. And there’s the Bugs Bunny where he meets the monster. Were you a Bugs Bunny fan or not really?

Derek:

Of course.

Mark:

Well just checking. It’s the one where he’s with the monster in the castle, and he’s doing his nails, and he says, “You know, monsters meet such interesting people with such interesting ideas.” But you’re one of those people that you really have such an interesting take, really, on the world, which is why I think people gravitate to you. You’re very much a living version of a contrarian, in many ways. You really have just - even the thought of being famous so that you can be useful. It’s like - what? I mean, I think that when I’ll listen back, it will be like, well yeah, of course, but most people think - to be famous, to ride in a limo and wear white linen, and stuff like that.

It’s sort of a contrary view - or to be rich to be useful. As opposed to to have your mansion, and again, have your big parties and your yachts and things. You’re turning that on its head and saying, no, you can actually use those things to great benefit for others, which I find a bit contrarian, which leads me to something else that came from that book, Anything You Want, and it had to do with the idea for CD Baby, and this concept that we think that, when we’re supposed to have that big idea, that - Monty Python and the Holy Grail, the moment where the clouds part and God speaks to Arthur and gives him his quest for the Grail - that lightning is supposed to strike, and that we’re supposed to just be knocked on our ass about - this is what you’re supposed to do, and yes, of course. But you talk about this thing, and there’s a section that says, “This ain’t no revolution,” and you explain that, rather than being struck by lightning with your brilliant idea, that you were really just a quirky guy who needed a solution, and you followed that idea, and magic happened because, like you said before, maybe you were just in the right place at the right time.

But I’d like to say this: it seems like those people who just go for it in life and succeed, hindsight ends up calling them visionaries and other big, bold words like that, but let’s face it. The world’s littered with zillions more stories of failure. The stories we’ll never hear. I would wonder, though, being that person who was there at that time as an artist, who watched CD Baby unfold, because I was just a part of it - is it possible you’re being a bit too humble? Not accepting at least a little credit for opening the door to the indie artist movement? Because really, to me, what followed, between all the file-sharing that followed, and the fact that now we have these pathways to be independent artists, sell our own music, publicize it to the world - you know, I don’t know. Were you being a little bit too humble?

Derek:

I do take credit, but admitting that I had something to do with that doesn’t mean that it’s something that I set out to do. So I try to tell the story in a way that’s useful to others, so I think - explaining this is important. So, let’s say that a songwriter wrote a song about his cat. Just a personal little tiny song about his cat, and he released it on an album.

But then, let’s say like a political movement - an Arab Spring type thing - thought that that song was a great metaphor for their struggle, and they used it as their anthem, and then millions of people loved it. So does that songwriter now get credit for helping this political movement? It’s yes and no. It’s like, I just really wrote a song for me and my cat. But on the other hand, lots of people seem to be empowered by my song, so yes and no. So, with CD Baby, really I was just helping myself and my friends. But it was at the right place at the right time, so it got huge. The thing that I do proudly take credit for is that I didn’t let it go astray. So I love the fact that I started it in Woodstock, New York, and then even as it grew - actually, Woodstock, New York, even as CD Baby was like booming, the whole mp3 revolution was going on, it was the year 2000 - I was still on a dial-up modem. There were no plans to bring broadband into the little hamlet of Woodstock for another four years. So that’s the main reason I had to leave Woodstock is because I ended up getting two dial-up modems and two accounts, and like pooling them together, just to use the internet. So I thought for one second about moving it to San Francisco, just to be in that big exciting place where everything was happening.

And that idea only lasted a minute, and I was like, “No, I think I’m going to move it to Portland, Oregon,” because this is like an outsider thing, keeping it real for the indies, and I don’t want to be influenced by the stupid Silicon Valley, San Francisco, IPO kind of thing. So I guess I can take credit for not letting it go astray, and instead of diving into that Silicon Valley mess, I kept it focused on being true, and ungreedy, and true to its original DNA, helpful to musicians. So I’m proud of that. But what I mean by DNA is that it was just started to help my friends. So I think that that was its DNA, and kind of like the DNA of a little baby, whether it’s a frog or a person - its original DNA kind of shapes how it’s going to grow. So CD Baby’s DNA of being a public service favor to my friends determined how it was going to grow. So I kept it true to that, instead of doing some weird sell-out thing. I can take credit for that.

Mark:

As well you should. And I think quite honestly - again, there are those who revolutionized the music business or not, but I think that - the thing you just said - and then we’re going to talk about this, because this is something you half to take credit for because obviously, this was your baby, the next thing I’m going to talk about, which is - for those who don’t really know this story out there, it could just be a success story about a guy who starts this online business and sells CDs for independent musicians, and that’s all wonderful, but I’d like to open up something else that obviously was your brainchild, because it was very much something that pervaded the entire CD Baby experience. So again, let me sort of paint a picture from the artist’s perspective, who was a member of CD Baby.

There’s something that I remember to this day, which was, I’d be sitting there online, and we’re trying to do what bands do and build a following, and all this stuff, and then I look in my inbox, and there’s this thing: “CD Baby,” and I forget what the subject was, but it was like, “Break out the champagne,” and however you worded it - maybe you could say this - but it was so great. It was like, “Right now, a scantily-clad young nymph is dancing toward our warehouse shelves to personally take a copy of your CD on a red velvet pillow, and gently place it with feather dusters into a package, so that it can be delivered on the wings of angels to your excited customer.” And I just remember going, “Oh my God,” and I just would have the biggest smile on my face. Now that, was like, who the hell is this company? What is the deal with these guys? Who comes up with this stuff? And it wasn’t until I really read the whole story later, and came to know your story personally that I found out, this was all on purpose.

So your approach to customer service was really, to me, really so innovative, and the people today that might know about a company like Zappos or something, that’s known to go head-over-heels to make the customer experience a great one - can you talk about that? Because this is something that really, to me, sets you apart from so many others. Can you talk about that?

Derek:

Yeah, OK. So that email that I wrote - in fact, if you Google the phrase, “packing specialist from Japan,” and put that in quotes, and put that into Google, that sentence from that email that I wrote, and last time I checked, there were like hundreds of reposts of that, that customers who received this shipping confirmation email would say, like, “What the hell? No way!” Hundreds of people posted it on their blog, like, “Hey readers, check out this hilarious confirmation email I got from this store called CD Baby,” and thousands of people heard of CD Baby because of those few hundred customers posting their shipping confirmation email on their blog. But to me, that’s just being considerate. Because here’s what’s inconsiderate: filling someone’s life with yet another stupid, boring, “Your order has been shipped. Your order number is 43625. It should arrive in 3-5 days. Thank you for your business.” That does not do the world any favors. Nobody needs another piece of junk that gives them no smiles. But I love that we’re talking music, here. I love that this is like a music-focused interview.

Mark:

Well, again, to me, not only is it a shared experienced, but let’s face it. People who love music and do it or did it, you have a certain focus and angle of the way you see the world, so I wanted to keep it basically focused. So keep going.

Derek:

I think you’ll get this angle then, that - I often say that your marketing should be an extension of your art. I think musicians’ marketing of their music should not just be some cookie-cutter, like, “Hey, I was really creative in the studio, and now that’s done. How do I market this the same way as everybody else?” I really think that your marketing should be creative too. So if you remember back in 1997 when the “X-Files” was still on the air, there was a friend of mine from high school, who I helped him produce his record, and he called himself “Captain T”, and we recorded an album called “US Aliens” and it was all about conspiracy theories, and Area-51, and alien cover-ups and the Incredible Hulk, and it was intentionally funny, but he would stay in character and play it straight, acting like he was guy that was trying to tell the world, through music, about the aliens and conspiracies. So this is back in the college radio heyday, so we wanted to send his album to college radio stations, but couldn’t afford to hire a real radio promoter. So we decided to do it ourselves, and at first, I almost was about to do things in the normal way, like - OK, I’m just going to send these 500 copies out to 500 radio stations and follow up. Then I caught myself. Like wait a second - this is a very unique, fun album. This whole, like, Area-51 conspiracy theory cover-up thing. Let’s do this in character, right? So what we did, Mark, we bought 500 black envelopes and 500 sheets of brown paper and 500 alien head stickers, and the best part was we got 500 huge stickers from a stationary store that said “Confidential. Do not open for any reason.” And then that’s what we mailed out to 500 radio stations.

Derek:

This is actually considerate, because I put myself into the place of those kids that were working at the college radio station at the time, when - this was before digital delivery, so every day, they would get this big bin of mail with like 50 little padded mailers of 50 CDs a day, and if you were a kid at this station, what would be cooler? Getting another damn manila padded mailer the same as everybody else, or getting this?

So now imagine this kid gets this black envelope that says “Confidential. Do not open for any reason,” with an alien head sticker on it. So he opens it up, and inside was a letter with the CD, and the letter said this: “Dear you name,” and we mail-merged the person’s name in there. It said, “You don’t know me, but I live in the bushes behind your station. I have been here for 12 years, and your station has saved my life many times over. The music that you play has kept me going through my darkest days, and for this I owe you everything. In this spirit, I must tell you that a man named Captain T found me in the gutter yesterday, and he taught me about what’s really going on in the government, and what really happened down there at Area-51. This man has a message that you have to get out to the world, because the people need to know the truth!”

And it was signed, “the man in the bushed looking through your window right now.” And then, we actually took each one of these letters out to the back yard, and literally rubbed it in the dirt, crumpled it into a tiny ball, then flattened it out a little bit, and put it with the CD into the black envelope. It was also just fun doing this. So you talk about this shipping confirmation email I sent. It was fun writing it, and it’s more fun to receive it, so anyway, 375 of those 500 college radio stations played his album, and every now and then, my friend still, to this day, bumps into somebody in New York that will say, “Wait a minute. Are you Captain T?” And they’ll say, “Dude, I remember when I got your album! I wasn’t working in Orono, Maine, at the University college station, and I got your - man, I’ll never forget that.”

So I think this is all - you can call it “savvy,” but I think it’s actually just being considerate to the person on the receiving end of your message - your email, whatever it is your doing. Your website. Anything you’re doing, think of what would be the considerate thing for somebody to receive on the other end. Put yourself in their shoes, and what would make their day better?

Mark:

Well let’s talk about that. Honestly, all of this stuff keeps coming back to the same thing. It to me says that, without really trying to be this way, you just very naturally - you’re thinking of others. You’re thinking, “How can I help others? How to be useful.” So this theme keeps coming back, and so, you look around the Internet, and there’s just so many billions of how-to manuals, and how to create your dream and success stories, and how to build an audience and get more traffic, and how to make great content, and how to be unforgettable, and how to be cool, but let’s face it. It always feels like marketing, and you know that within one or two emails is going to come that blazing buy button, and for just a few hundred dollars more, you could have the real secret behind my secret.

And yet, when I think of all the things out there: The Law of Attraction, The Secret, all these things, it seems to me that you, quite naturally, have figured out something that probably, as far as I can tell, is probably the secret that is the secret of the ages. It’s probably the secret to happiness. It’s probably the secret to all success. It’s that it’s focusing on other people, versus yourself, and do you think that that has anything to do with the secret to your success?

Derek:

Oh yeah. Everything.

Mark:

I do too.

Derek:

I call it “the Tao of business” - that if you can forget yourself, get over yourself, and forget about your own needs, and just be of service to others and be generous, then you get rewarded more than those who are out there being greedy. And I think, even while you were asking this question - there was some word in there that made me remember the old book by Dale Carnegie, called How to Win Friends and Influence People. And I think that’s a really unfortunate title, because it makes it sound like conniving tricks.

That whole sneaky, rubbing your hands together, “Here’s how I’m going to make people like me,” but I really think that that book should have been called, How to be Considerate because I think it’s the best book on the subject of getting into someone else’s mindset, being considerate, and his whole point is like, that’s how you make friends, and that’s how you influence others is basically by being considerate, and thinking of everything from their point of view, which means, to me, I think this is also the best book on marketing ever written. To me, the essence of good marketing is being considerate. It’s not some kind of tracking you’re A-B results and this and this and that. It’s really about, like, how can you be considerate to others, and really, really think of what you’re doing from the other person’s point of view, which we all know, as musicians, is exceptionally hard to do when you spend all of your time in me-me-me-me-me mode.

Like you’re sitting there writing a song, and you’re diving into your own personal thoughts, and your psyche, and “How do I express my feelings?” and then we do this very unnatural thing as musicians, where we get up on stage, and we loudly sing our private feelings into a public address system. It’s very unnatural. It’s very self-focused. “Look at me,” and the spotlight’s on us, and then we do interviews where we talk about ourselves. It’s really hard to click into a different mindset and understand, when somebody goes out on Bleaker Street on a Thursday night at 11:00 PM, and steps into a bar that has live music, what are they really looking for?

Are they looking for your most recent introspection about your cat? To use the previous example. Or are they looking to forget their life, or are the looking to - whatever it may be. It’s hard to get into that mindset of who’s on the receiving end of what you’re doing. And they don’t care about you, and they shouldn’t, and you shouldn’t expect them to care about you at all. This isn’t about your needs at all. It’s all about them.

Mark:

And yet as musicians, it always felt like - I don’t think it was even conscious, but let’s face it. Call it what you want, the tortured artist, the starving artist, but there’s that thing about that pathos, of - my God, I have toiled; I have sat here, crafting songs and exposing my deepest feelings. For God’s sake, please give me credit for exposing myself to you and trying to craft that into a wonderful song. Please. And oh by the way, you should feel this too, because I’m actually thinking of you. That, to me, is maybe that falsehood, which leads that lack of - really the word, let’s face it, the concept that you’re really talking about here is empathy, right? Seeing something from the perspective of others, and by the way, Derek, I don’t know if you know this, but by mentioning that book - that perhaps wrongful-titled most famous book on marketing, by Dale Carnegie - if I remember one thing from that book, you did it early in this interview and are still doing it, probably quite unconsciously.

But you said something back to me, and you mentioned my name, Mark. And I remember - the one thing I remembered from that book is always remember the person’s name and call them by their name, and people will remember you. That’s the one thing I remember from that book, because it’s considerate.

Derek:

Yeah. Although it’s funny when you can tell, like the occasional used car salesman takes it a little too far, like, “Hey Mark, so this car, Mark, is what you’re looking for. So Mark, what kind of car are you looking for, Mark? Because, Mark, I think the kind of car you need,” –so I think you don’t want to take that too far.

Mark:

Not to mention in the modern era of marketing, where you insert field here. Where your newsletter is of course personalized. Personalized name here, just to make that really personal newsletter to your list of 20,000 or whatever.

Derek:

You know, I’m glad that I started CD Baby when I was 29 and not 19, because I think this kind of hyper-considerate mindset is something I wasn’t really ready to get into until that point, because I was nothing but a musician from the age of 14 to 29. That was all I lived and breathed.

And I had a decent amount of success with it, kind of like you. Not huge, cover of Rolling Stone success, but good. Bought my house with the money I made touring. So right when CD Baby started, I was feeling at a point in my life where I was feeling very satisfied. Whatever the opposite of needy is. I don’t know what that word would be, but in a mindset where I could wholeheartedly be this generous, and feel like, no I really don’t need anything. I’m good.

Mark:

I think the word is “satiated”.

Derek:

Oh, good one. Satiated. So I do meet a lot of people who are starting businesses coming from this place of real hunger. They’re like, “I want to start a big business. I really want to get famous. I want to be the next Richard Branson. I don’t have an idea yet, but I just have the feeling like I’m just destined for big, big things.” And that’s not really - that might not be the right mindset to be of service to the world. You kind of have to get over yourself first.

Mark:

I totally agree with that. So all this time, we’ve been talking about, really, something that’s really quite an amazing success story, and I think has lead you on a journey thereafter of what would certainly seem to most others to be a pretty great life - not without all the things that come with life, and suffering, and things, and problems, and stuff, but seemingly, a pretty great adventure. It seems, at least to me, and I’m sure many others who follow you, that you seem to be having - and it’s well deserved - so we’ve been talking about success, and all this, building on success, but I think what’s also interesting -

Mark:

--and you know my tagline in this podcast, Rock and Roll Zen is “Awaken your inner rock star,” essentially meaning, of course, how do we get to the person we’re supposed to become? Not necessarily the big idea - it doesn’t really matter the huge thing, but I believe we’re all here to do something important. We’re here to do something that will make, hopefully, the world happy by sharing our unique story, and yet, so many people don’t end up doing. And so, one of the things is - been written about and talked about and podcasted, and books, it’s this thing that, why don’t we do it? It seems to be fear of failure. Fear and failure. These two things. And so, after all these stories of success, I’d like to just see if you would be willing to highlight a little bit of vulnerability in your life, and - got any stories of wonderful failures that hurt? And if so, what did you learn from them, and might they have pointed a way forward for you to learn from that experience?

Derek:

I got asked a similar question at a conference once in New York - some kind of event for musicians, somewhere in Midtown, I forget, and some guy from the back of the room raised his hand and asked a similar question. He said, “What are some of the biggest hurdles that you’ve encountered, setting up CD Baby,” or I think he said, “In your career so far, what are some of the biggest hurdles or mistakes you’ve made?” I thought about it for a long time. And it was more about hurdles. Let’s forget mistakes. It was about hurdles, like what’s been the toughest times, and I thought for a minute onstage, and I was like, “I can’t think of any, so, sorry. Yeah, I don’t know. Can’t think of any.” And what’s interesting is the guy came up to me afterwards, and he said like, “This is really interesting, because I actually know something about you.” He said, “I know that you’ve had a couple really hard times, because I know through - we’ve got some mutual acquaintances who have told me.” And he said, “You really, in this moment, can’t even remember them, can you?” And I said, “No.” And he said, “That’s interesting. I actually did get my answer by the fact that you couldn’t think of anything.” He said, “You really just don’t focus on the negatives. You just step aside them like they’re a pebble in the road.”

Derek:

I said, “Yeah, I guess so.” I remember, well, two things: it’s funny. These are both Tony Robbins related stories. I read Tony Robbins’ book, Awaken the Giant Within when I was 19, and it made a huge impact on me, and I read it again and again over the next few years, and really internalized it, so I think it’s just become just the way I live my life. I probably don’t even realize which things in my life are kind of credited to the book, since I read it at such a formative age.

But the two things that I do remember is: he had a story about when he was learning Karate, specifically how to break boards with his hand, you know, that classic - chop through the boards. And he said what the teacher taught him, he said, “He forget about the boards. Don’t worry about the boards. See this point just below the boards there?” He said, “Just focus all of your life energy on that point right below the board.” He said, “Now just put your hand there. And he said that that ended up being a great metaphor for life for him. He said, “Of course there are things in the way, but whatever.

Don’t even think about them. Don’t even worry about them. Just step around them, get through them, whatever. Just focus on the point past them.” And I think I do that so inherently now that when you ask me what were my biggest failures, I can’t even remember.

And then somebody pointed out, “Dude, a whole chapter of your book is called, ‘My Biggest Mistake.’” I’m like, “Oh, right. That one. OK, I forgot, yeah.” I just don’t even think about them. There was another kind of habit that I picked up from Tony Robbins, is he said, “Whenever something goes really wrong in your life, you need to ask yourself, ‘What’s great about this?’” And the first time you hear that might sound really hokey. Like sappy California self-help, big-teeth dude.

Mark:

With big hands.

Derek:

So I remember at first, when things would go really wrong, like a couple days later, I’d still be mad, I’d still be angry, and it’s like, “OK, I guess let me try that Tony Robbins trick of what’s great about this,” and of course the first answer is always, “Nothing. Nothing’s great about this. This just sucks.” And then you think a little more, and you think, “OK, actually, there is this upside to what happened.”

And so as the years went by - and this is like, very slowly this happened - it became closer and closer. So originally, it would take me two days later before I asked that question, and then it was two hours later, and eventually two minutes later, and eventually, just two seconds after something goes wrong, I find myself just instinctively jumping to that question, “What’s great about this?” And because of that, I think things don’t really even stick in my head as failures. As soon as something goes wrong, I’m immediately saying, “OK, well what can I learn from that?”

There’s the Thomas Edison metaphor of - he tried 10,000 different filaments to get the lightbulb, and the first 9,000 didn’t work. So what? They weren’t’ failures. So I guess I just think along those lines. I always think very, very long-term, so whenever anything goes wrong, it just feels like, “Oh, OK, well now I know what not to do.” Kind of like - dude, I hadn’t thought about this before - bad relationships.

Derek:

A lot of my friends are single and dating and kind of telling me all of their dating stories, and we’ve recently noticed, or realized, that most of us don’t know what we want until we experience a bunch of bad relationships so we know what we don’t want. And if you ask most people what they want out of a relationship, they’ll just tell you all the things they don’t want, and that actually helps shape what they do want.

So it’s kind of the same thing with failures. Like whatever you’re career, a whole bunch of bad things happen, and with each one, you say, “OK, I know not to do that again. Now I know that that doesn’t work for me,” or, “Oh, people tended to hate that,” so you just build your expertise by all these things that go wrong. So yeah, sorry to sound like such a California - ...

Mark:

No, man, you don’t. And as a matter of fact, of course, you know how this goes on the Internet. Here we are doing an interview, and it’s September of 2015, but God knows, whenever someone, let’s say, hears this interview, whenever it is, let’s just say that at the time of this interview, what you just said about “What’s great about this,” I believe, is kind of relevant to this moment because - and I’m a follower of yours - you just wrote a blog post, and it was about how you love being wrong, and if I remember correctly, I believe you uttered that very phrase in the context of that blog about - you said, “What’s great about this?”

So, I’d like you to just talk about that for a second, because if memory serves me about that blog post, you mention how, in the moments you asked that question, your initial response was, “Nothing is great. This sucks,” and how friends came around. Could you talk about that? How maybe, if you don’t get the initial answer of what’s great about this, what were the conditions, even to make you write that post, that ultimately came around, where you came back and found, “This is what’s great about this.” So if you could talk about that - because I think that’s such a great way of viewing things.

Derek:

Thanks. Well it’s just - I realized, at that time, because that was a real low point for me - I noticed that I was ringing up a lot of my friends. Even some friends I hadn’t talked to in a year. And just being vulnerable and admitting, like, “Hey man, how’s it going?” and I’ll say, “Not good. I’m actually doing really bad right now,” and they’ll say, “Whoa, dude, what’s wrong?” And I realized that I was in more of a learning mindset. That when I’m just feeling top of my game, I mean, yes, I’m constantly reading books and reading in some ways, but for the most part, I feel like, “Yeah, I’m Mr. Cool. I know what’s going on, I’m doing well. I don’t need your lessons.”

But man, when you’re down, you are so open to advice, and I just found that it’s like, “Wow. I’m actually learning more than ever. I’m changing my mind more than ever because I’m feeling so broken-down right now.” So it’s like, “So even this is pretty fucking awesome. I’m feeling so down so it’s putting me into this learning mindset in a way that I haven’t felt in a long time.” So yeah, it’s like my cup was empty.

Mark:

And I guess that makes you humble, doesn’t it?

Derek:

Yeah.

Mark:

And humility, of course, is where we get to learn a lot of great lessons. So -

Derek:

Sorry to interrupt, but you mentioned a minute ago, a thing we still haven’t touched on yet - you talked about the fear of failure. And I think this is something that doesn’t get discussed enough.

One of the wisest books that’s out there today is a pretty new book called Thinking Fast and Slow, by Daniel Kahneman. So I highly recommend anybody interested in this to - either go to Amazon and find Thinking Fast and Slow or go to my book notes at sive.rs/book and find “Thinking Fast and Slow.” I think it should be right near the top of my list. A lot of these books on behavior psychology or behavioral economics that are out there right now, such as The Paradox of Choice, Predictably Irrational, Stumbling on Happiness - a lot of them are kind of students of the work of Daniel Kahneman. He won a Nobel Prize for his work in behavioral economics.

He’s getting quite old, and so he says at the beginning of this book, like, “This will be the last book I ever write. This is the culmination of my life’s work.” So the big point - I’m just adding a lot of weight to the tiny quote from him I’m about to quote - is that somebody recently asked him, what does he feel is the single biggest or most common human mistake. And he said, “Over-confidence.” Really when it comes down to it, he said, “I think most humans are over-confident.”

So if you talk about fear, or how do we get over our fear of failure or our fear of being public, or our fear of launching something, I think I might channel him a bit and say, like, “Don’t get over it.” Be thankful that you’re feeling fear, because there are a lot of people with broken spines that weren’t scared to jump off that cliff that should have been. And so, pay attention to those fears, and instead, address them. Honor them, and be thankful for them, and say, “OK, these are legitimate fears. This thing might fail.” And one of the lessons of stoicism, which sounds like such a stupid, boring, ancient, robe-wearing philosophy, but it’s actually - I highly recommend this book called, A Guide to the Good Life. It’s about stoicism in the modern age, and I think it’s a bad name for a great approach in life, which is: addressing the worst-case scenario, always. Not ignoring it, not doing the kind of, “Hey man, positive thinking! Everything’s going to be great,” but instead, looking at those fears, and saying, “OK, so what happens if this fails? What’s the worst that could happen?”

And let’s even say, OK, I put out this product into the world that I think everyone is going to love, and they don’t. Then what’s the worst that can happen? And if you address those fears in advance and do something about them, you end up being more robust. In fact, your plan improves if you look for and acknowledge all the things that could go wrong and address them.

So, Charlie Munger is the mostly-quiet partner of Warren Buffet, the famous investor, one of the world’s richest people, and all that. So Charlie Munger is pretty much his equal partner but prefers to lay low, and I don’t think he’s even written a book himself, but a couple people have compiled his speeches into a book, and his kind of most famous quote, or the one that he likes the best, and he likes to say the most - it’s kind of a joke.

He says, “All I want to know is where I’m going to die. Then I just won’t go there.” And he means it in kind of like a cute, cocktail party kind of funny quip, but actually, it carries in it the gist of his approach to investing, or business in general, which is - let’s look at all of the things that could go wrong, and let’s look at all of the - what do they call those? Biases - those mental biases - cognitive biases that we have - we have cognitive biases, like loss-aversion and things like that, that cause our mind to think irrational and make logical mistakes.

So he says, “I really want to focus on all of these cognitive biases, and all the ways that a business could go wrong, and all the mistakes it could make - I want to focus on those, and just make a point of avoiding those. And if I avoid all of those, I think we’ll do pretty well.”

Mark:

That’s a great way to look at it. I guess the devil’s advocate to that conversation is that someone with that much success, it would seem, would have that much more ammunition to be so methodical about seeing an end game, and going, “OK, there’s the battle field - there’s a bunker over there. Chances are, based on these statistics, that we’re going to get killed if we go over that hill. So let’s just not go over that hill.” Right? I’m strange that way, too. It was music and military, but I read The Rise and Fall of the Third Reich in sixth grade, and my teachers thought that, while that was really impressive, it was a little bit strange. But there’s something about - I always see the world in terms of military terms, too, the battle field of things.

But back to the fear of failure, and that thought of - when you’re that person who has chosen to let your fears overcome you, or overwhelm you, to the point where they immobilize you, what would Derek Sivers - not even Charlie Munger, but what would Derek Sivers say about - because let’s face it. That’s more the average story than not, about people who ultimately chose to not take the risk, to not - pick your cliché. Walk that fire coals that Tony Robbins would have people do. The people that stop - you got any advice for people? You have it built into your DNA now how to dance around whatever we call obstacles or things, and just keep moving forward, but what might be a trigger - something you could say that might say, “You know, yeah I know you’re feeling scared, but…” What might be that “but” that might help people to just keep going?

Derek:

You just made me realize something that I hadn’t realized before, about that Charlie Munger quote, is that is a late-career strategy. This is an important point. You’ll hear people like me and everyone else out there, giving advice, and you have to understand that a certain strategy is not to be applied always. You need different strategies for different situations. So to give an example, one of my most popular blog posts is called, “Hell yeah or no,” and it says in short, like, “If you’re feeling overwhelmed, and if you have a tendency to say yes to too many things, and you’re feeling overwhelmed, do this. Instead, if you find yourself trying to decide between yes and no, don’t do that anymore.

“Only decide if you’re feeling ‘Hell yeah’ about this. Like ‘Oh my God, that would be amazing, that would be the coolest thing ever.’ Then say yes. But if you’re feeling anything less than ‘Hell yeah,’ then just say no. Because that will get you to say no to almost anything, and then the very few things that you say yes to, now you have more room in your life to let those few amazing things fill up your life. If instead, if you say yes to too many things, then you don’t even have time for those occasional ‘Hell yeah’ things that come along, because you’ve filled your life with a bunch of mediocre ‘yes’ things.”

So that’s a strategy that I’ve shared widely with the world.

Mark:

And that I’ve read, and that is a wonderful post.

Derek:

Thanks. So every now and then - actually, it helped me when one day somebody said, “Yes, but I’m at the beginning of my career, and I don’t have a lot of opportunities.” And I said, “Ah, then you should not be following this strategy. If you’re at the beginning of your career, do not apply the ‘Hell yeah or no strategy’. No. At the beginning of your career, you need to say yes to everything. Just answer every classified ad, say yes to everyone, say yes to every gig.”

As a musician, whether someone’s asking you to play jazz piano or put on makeup and dance around as a children’s musician, or be a heavy-metal bass-player, just find a way to say yes to everything, because you never know which of these tiny things are going to turn into major opportunities. So the proper strategy, at the beginning of your career, is to say yes to everything. And then later, when you’re overwhelmed in opportunities, and it’s more than you can handle, you need to switch strategies.

And there’s a brilliant book about switching strategies called What Got You Here Won’t Get You There. I think the author’s name is Marshall Goldsmith. And I love that this book is written for a very small audience of already-successful business people, and what it’s saying is, the techniques and strategies that got you to where you are now are not the ones that are going to take you to the next level. And it calls out business owners on a bunch of stupid things that they tend to do, that might have made sense when they first were starting out, but now are holding them back.

Man, when I read this book, it felt like he was hiding in my office watching all of the things I had done wrong, because it just catalogued like dozens and dozens of things that I had personally screwed up at CD Baby and done, and were some of the worst things that I had done, he named them all in his book. I was like, wow, I’m such a cliché. So yeah, I think it’s really important to not just listen to everybody’s advice, but to understand when that advice is best applied. So, yeah, what you just made me realize is that Charlie Munger’s approach of - “All I want to know is where I’m going to die, then I won’t go there,” that is the correct approach for somebody that is already successful and managing a billion-dollar investment fund, and if he just avoids mistakes, then it’s naturally going to grow quite well. But that is not the approach of a 19-year-old wanting to go make their mark in their world, is to just avoid mistakes - you’re right.

Mark:

Well, and likewise - touché, because you just made me think of something, which reminds me that - so when you go out there into the world of the blogosphere, and you’re looking to reinvent yourself, let’s say, or you’re looking to find your passion, live your purpose, and all the other versions, or even here. Or awaken that inner rock star. We’re all talking, oftentimes, about the same thing: how do you ultimately live the life you were meant to live? So you go out there, and you find somebody you like - and this is just from my own personal experience, where it’s like - and then you just decide that’s it, walk out the door of whatever it is, place you don’t like, and just start anew, and this is how I did it, and this is how I built, and I never looked back.

And oftentimes, you read that person, and find out a bit more about them, and it’s like, oh that’s right, because you’re like 26 or 28 right now, you’re single, you’re living in Ohio, and sure. Why not? Just pivot and go for it. But how does that relate to someone in their thirties or forties or fifties who’s looking at a changing world, who’s thinking about “How do I reinvent myself and be relevant in this world, and have a mortgage and a family, and maybe I can’t just walk out the door. Maybe there’s different advice for me.” And so, yeah. Thank you. That really reminded me that there is advice for certain people at certain times. It’s a target audience, and it’s a target for certain times and where you are in your career. So that’s great.

What do you want the world to know right now about what you’re working on, and how can we learn more about it?

Derek:

I think the main reason I do interviews like this is it always sparks some interesting ideas. It’s like a great conversation that sparks some interesting ideas that I hadn’t thought of before. But the other reason I do it is I find that the coolest people I’ve met over the years are the ones that came to me because they listened to and liked a whole interview like this, whether it’s read my book and liked it, or very often, read or listened to an interview like this and liked it.

Therefore, the other reason I do these things is I really like hearing from people that liked it. People who like this are my kind of people. So what I’d actually like to share is my email address. Because I put aside a little time every day to sit and answer everybody’s question. I answer every single email that comes in, and I kind of enjoy the challenge. I get kind of tossed some curveballs and some things. And anybody that made it this far through the interview, please send me an email. I really enjoy hearing from people.

Mark:

Well Derek, I cannot thank you enough for this interview, because as always, you have fascinating point of view of how you see the world, and you’re just a fascinating guy, and I’m not the kind of guy who kind of blows smoke, but you’re just one of those people that I’m really happy to say that I know in the world, because you really embody what I think is great about people.

So I really want to thank you for this, and to the people listening to this interview, go to the show notes. I’m going to outline all of these links, and if you came into this not knowing Derek Sivers, all I can say is, really check out his blog posts - I’ll send you to those places. Check out his blog, check out the books, because he’s really just an amazing resource for just cool information, cool ideas like some of the things you’ve heard here, and just one of those people that you should know. So, Derek, I just want to say thanks again, man. It’s always great to talk to you.

Derek:

Thanks, Mark, it was a really fun conversation, so, anytime. Thanks a lot.