Before we get to the interview today I just wanted to do a little promo for Derek. He has a new book that just came out called Anything You Want, 40 Lessons for a New Kind of Entrepreneur. We didn’t get to mention it in the interview but he has been asked by so many people to write a book and finally he told me Seth Godin asked and he went ahead and wrote it. I can’t wait to get my copy and you should pick up yours too. I’ll put a link in the show notes and on the blog. Thanks. Now to the interview.

 

Welcome to the Eventual Millionaire Podcast. I’m Jaime Tardy and today we have Derek Sivers on the show. Derek created CD Baby, an online music store for independent musician which he sold to Disc Makers for $22 million, the majority of which will go to the Independent Musicians Charitable Trust, an organization that he created to fund and support music education for future generations. Recently he started Muckwork, a service to provide musicians with a team of assistants that specialize in doing uncreative dirty work so you can focus on your music. Now I’ve been a big fan of Derek’s since CD Baby helped my husband ship out thousands of CDs when we were in a big pinch and he has an amazing blog at Sivers.org. So welcome, Derek. Thanks so much for coming on.

 

DEREK SIVERS: Thanks Jaime for the flattering intro too.

 

JAIME TARDY: Well, I’m already a huge fan so hopefully I won’t be too crazy. Well first, I’ve listened to a ton of your interviews and one piece that I always seem to be missing is how did you grow up? Where did you grow up and what was it like?

 

DS: Born in Berkeley, California, 1969 and moved around a lot. My dad is a particle physicist and very anti-social and nerdy. My mom was homecoming queen and the joke is that I’m somewhere in between. We traveled around a lot as kids. When I was a kid we moved five or six times by the time I was six because my dad was working at various physics labs so we lived a year in England when I was five and I think it kind of gave me this world view that I’ve been kind of stuck with I think ever since the age of six. I was just very aware that it’s a big world out there and I had had a little taste of it. Moved to Hinsdale, Illinois but was always aware that there is a big world out there I had to get to. That was my growing up.

 

JT: Excellent. And you’re in Singapore now, right?

 

DS: Yes, speaking of.

 

JT: It’s 9:00 a.m. where you are and 9:00 p.m. where I am right now. Excellent. So what made you to decide to travel the world after selling your company?

 

DS: There was this feeling, I think all of us have different reasons why we’re doing what we’re doing. Some people want to be a millionaire because they want stability. some people want to be a millionaire because they want freedom. Some people want revenge, whatever it may be. So, for me, the compass was always freedom. I don’t know why. Maybe just we all have a different outlook on what we want out of our lives. So, for example, when I was 14 years old, actually this kind of is an important thing when you’re talking about growing up and something that shapes who we are and what direction we’re heading.

 

When I was 14 years old I decided I wanted to be a musician for life. Like that’s it, I’m going to be a professional musician but deciding that meant that for example I would never have a job. I would never have a salary. I would never have insurance and even beyond that I imagine that I would probably never have a house, I would never be rich. Then I even went beyond that to imagine well I’ll probably be living that life of a touring musician for life. I probably will never have like a steady family with a dog and a backyard and all that kind of stuff.

 

Like I just kind of set out this life for myself when I was 14 and that’s kind of the life that I feel I’ve been pursuing. So later when somebody asks me, like years later, I mean in fact just a couple years ago, somebody said, “How did it feel that first time you had the courage to quit your job and start your own company?” I was just like I had to stop and laugh. Wow, courage to quit my job. No I never had a job. There was no job to quit. It was funny, it’s almost like that’s a question from somebody coming from a mindset that their outlook on what their life should be is they wanted kind of the steadiness of a job, a steady family, a job and all that and then of course it would take courage to do something that feels scary and mysterious to you to quit your job.

 

Whereas to me, it was like even my circle of friends, I was in a circus for ten years. Literally, I was the ringleader MC of a circus for ten years and so my whole circle of friends, say like 30, 40, 50 people, I didn’t know one single person that had a job. All of us were freelance musicians, jugglers, artists, painters, designers, whatever. I didn’t know anybody that like had a job or a boss or anything like that.

 

So it’s all kind of what you’re shooting for in life. So anyway, for me, I was always looking for the path that would give me the most freedom and I kept making those decisions along the way with my career. Like anytime, we all hit those crossroads, anytime you have a decision, you can go one way or the other and every time I hit some kind of decision I would make the freedom choice that would kind of give me the most flexibility to go anywhere, do anything, any time.

 

By about 2007, I realized that I had really gotten total freedom like I was the owner of my company but I didn’t work there anymore. I wasn’t required for the operations of it so because of that, I could be anywhere on earth and nobody would even know or care. It was like I was just living the laptop life anywhere and because I was the owner of my company but didn’t have to do anything for it, then I didn’t have to do anything and so, yeah, it just kind of gave me that freedom to just up and go anywhere in the world so I did.

 

JT: See and I want to talk about that total freedom in just a minute but what it sounds like is that decision making really comes easy to you. I mean at 14 you were already having your entire life completely planned out for you. How do you make your decisions? I mean it sounds like you sort of go with the flow but how do you actually do that?

 

DS: I think there were some principles. Ever since I was teenager I have been readings books on wisdom and such like say starting with Abraham Maslow’s Pyramid of Self Actualization that really hit me hard when I was a teenager. I looked at that and I was reading about his work about how he studied the healthiest people and what they had in common and you look at that pyramid, do you know the one I’m referring to?

 

JT: Yes, I do.

 

DS: So to me it’s like I look at that and I say well there you go. There’s your recipe for life like your goal is to climb this pyramid of self actualization and shoot for that tip. I think you kind of make decisions along those lines in life like you try to figure out, like say, for example, that you have some mottos along the way like whatever scares you go do it. That’s something I learned also when I was a teenager and whether you use it, even to me like in the little tiny day-to-day ways. I’ve been following that since I was like 17.

 

So even at 18, for example, if there was the girl in class that I was scared to talk to it’s like oh well whatever scares you go do it, here we go. But sometimes in the big picture of life it’s like, Abraham Maslow had a great quote that he said something like, “Life presents us constantly with a choice between safety and risk” and he said, “Make the growth choice a thousand times a day.” Reading something like that when I was 17 and just knowing him and his pyramid of self actualization I kind of went all right.

 

Again, that’s like a rule of thumb or recipe for what to do and how to make your decisions in life. Make the growth choice a thousand times a day, okay, got it. I guess I kind of just run all of my daily decisions through that kind of filter.

 

JT: You must be really good at this by now, dealing with fear and if you’re always doing something that scares you, how do you deal with that thing that scares you?

 

DS: The second half of the punch line is whatever scares you go do it because then it won’t scare you anymore. With almost anything, once you do it, it’s not as scary as you thought it was. The person you think is so intimidating is not once you actually say hi.

 

JT: Hi, Derek.

 

DS: So the foreign land that seemed so exotic and untouchable and foreign, once you go there and start talking with some people who live there it’s like oh I guess people are the same everywhere. So I guess just by stepping up and doing the thing that scares you, you realize it’s not so bad.

 

JT: Now has that, have you ever had it backfire on you though? I mean it’s not as though everything happens that way, right? I agree completely. I started interviewing millionaires and I was like wow, haha. Now I’m so comfortable with it, it’s not a big deal whatsoever though I was nervous for you, okay? But in general, it’s not always better than you think it is. So where in your life or how do you get past that?

 

DS: Well, okay, then there’s the other kind of philosophies that shaped my decisions in life that when I was 19 I read this book by Tony Robbins called Awaken the Giant Within. That somebody who was a real mentor to me gave me this book and said you should read this and so with a kind of heavy recommendation from somebody I admired, I really gave it my full attention and really dove in and read it not just once but like five times over the next five years and really ingested it.

 

Some of the philosophies that he talks about in there are like there is no such thing as failure so if you try something and it fails, all you really did is you got feedback on okay well that doesn’t work I need to take a slightly different approach. Like you can’t really call it failure until you’re dead. You could safely say somebody could, at your funeral, admit well that didn’t work out. But until that day, anything you do you could just like get feedback on what’s not working and go back and try again.

 

So even, I think those things like you said well what happens when you do something that scares you and it doesn’t work out? Well, either if it’s something that didn’t matter to you anyway, you know you talk to somebody who is really intimidating and then they blow you off then you just go like oh well. You can just shrug it off or if it’s something that really matters to you then you persist. To me it feels like that’s all there is to it.

 

JT: It sounds like none of this actually hits your self esteem or your confidence or anything like that. It’s just another bump in the road as you’re going forward anyways. Is that true for you or do things actually affect your self esteem and confidence?

 

DS: The person that I told you gave me that book when I was 19 is the person that gave me my confidence. I think I wasn’t very confident until then. It was actually my boss at the circus and she just kept telling me for years and years that I was the best this, the greatest that and she’s met thousands of people in her life but nobody like me and all those kinds of things and as a kind of insecure 18 year old, I guess by the time I was 20 or so it sunk in. Ever since then I’ve been one confident mo-fo. Nothing really shakes my confidence too much, no.

 

JT: See, that’s excellent though, the fact that you didn’t before but it is totally attainable for somebody that didn’t have that and of course at 18 it’s a little different than of course where we are now when we’re older. But that’s really cool. So how did you find, or how did you sort of qualify that person as your mentor? Did they say, “I’m going to mentor you” or how did that work for you?

 

DS: Oh no, it was my boss at the circus and when you’re traveling in a circus and it really is, you know, you’re in the truck traveling the country for five days a week, you spend thousands of hours together so it was just more like that, like she was just somebody that I really admired and looked up to and that’s all. It wasn’t any kind of official mentorship.

 

JT: It’s funny because my husband is actually a professional juggler so I know exactly what you’re talking about which is funny. So have you had other key mentors though in where you’ve been going? I mean in business and in life in general or are you just going through life and finding key people that you really want to learn from that aren’t necessarily qualified as mentors?

 

DS: I’ve had both. I did have an actual professional business coach for four or five years. That was great. He was really great at it. It’s funny, now we’re actually just friends, but at the time it was definitely, like I was paying him, I don’t know, whatever, a hundred bucks per hour and we would have a phone call once a week where I would tell him what was going on with my company and whatnot and he’d give me his perspective and advice and that was great.

 

But then there are people you just, I think it’s when you get a real mutual admiration thing. When somebody who you really look up to, it’s really a role model to you, and they like you too and kind of, I don’t know if take you in is the wrong word but give you an open channel. So hey anytime you have a question feel free to ask kind of thing. So I’ve had that with a few people, Seth Godin, for example. There was a great moment where I was a huge fan of his books and at CD Baby we used to get two to three hundred orders a day and we had to process it. It was just kind of like factory style. It would just get turned out.

 

We had 50 people working in the warehouse and every now and then I would just peek in on the day’s orders just to kind of, like I would scan the list of everything that’s going out today or everybody that ordered today just to kind of see like where in the world the orders were going or how big the orders were. Were there any exceptional orders that were over a thousand dollars or something like that. There was some day back in 2003 or ’04, something like that, that I just happened to be scanning through the customer list and it said, “Seth Godin.” I was like no way. I was like maybe there’s another.

 

JT: I know, the Seth Godin.

 

DS: But it said Sethgodin@yahoo.com and it was going to an address in New York. I was like no way! So I sent him an email. I was like Dear Mr. Godin, I’m a huge fan of yours. He wrote back saying, “Dear Mr. Sivers, I’m a huge fan of yours. I love CD Baby, I think it’s brilliant. I think it’s absolutely amazing what you’ve done” and then like his next two or three books he would often use me as an example in his books. So I was like ah we had a real kind of mutual admiration thing and still to this day, even just a few weeks ago I told him something about like what an honor it is that I’m able to kind of talk to him anytime and he said, “You know, you got it all wrong, it’s backwards. It’s an honor of me to be able to talk to you anytime.”

 

Every now and then you have amazing things like that that just happen by chance that aren’t any kind of official mentorships but just friends.

 

JT: Amazingness that happens. Do you have any advice for people that maybe haven’t created a multi-million dollar business to get the attention of Seth Godin or, in general, like someone who has a smaller business that are really looking for mentors or at least just an open channel to talk to someone?

 

DS: Yeah, definitely just ask. You’d be surprised how effective a simple three sentence email can be. I think a three or four sentence email is so effective and respectful that it’s almost like if you send a real quick pointed three sentence email, who could not answer it? Unless somebody really has their block gates up like they don’t read their own email but I think anybody who reads their own email, I’ve sent other emails off to my favorite authors and they have no idea who I am and I don’t include my website, they’ve never heard of CD Baby or anything like that and I’ve been amazed how well the three-sentence email can get a reply.

 

Just a one sentence qualification like I’m a huge fan of your books and the whatever, this one changed the way I think. Question number two or sentence two, a simple direct question like but I have one question – do you feel that a business should split into multiple parts once it gets over 50 employees or do you feel that that was just in your case only? Any reply appreciated. Thank you. Like something like that.

 

I think if you send somebody a simple direct question, not trying to dump the weight of your life on them or anything but just asking a simple direct question you get a reply and sometimes you can go back and forth like that a few times and maybe then if you’ve just got a URL in your signature and they’re trying to just answer the question well who is this asking, and if they go to your URL and there’s some interesting posts there or you’ve shared your philosophies or your company and what you’re doing is interesting, it may lead to more or it may just be somebody who answers your questions when you ask.

 

I’ve had it both ways. I mean there, well, I get a couple hundred emails a day and I reply to them all. Often I have no idea who I’m emailing. It’s like I’m not replying to them because they are somebody, I’m just replying to them because they emailed. So I do my best to give a helpful answer not based on any qualification of who they are but just because they asked. I’ve been really surprised how reachable people are when you just send a nice simple email. On the other hand, if you send one of those like five page long emails then don’t be surprised if you don’t get a reply because it’s just too hard to reply but send three or four sentences and you’ll be surprised.

 

JT: That’s great advice. That’s great advice. I want to get back to how you were talking about total freedom beforehand because after you sold CD Baby, I read on your blog that you wanted to answer the question what do you do if you don’t have to do anything. I’m wondering if you found the answer to that question.

 

DS: I mean I’m still answering it. The short answer is whatever captivates you. You’ve probably heard of the, there’s a book called Flow and the concept of being in the flow where you’re so engaged with your work, so engaged with something you’re doing whether it’s playing a video game or building a clay pot or anything that you lose all track of time. You’re so into it. Well, I think those are the things in life we should be doing. It’s like I think those are the best moments in life and if you spent a life in that kind of flow and you were laying on your deathbed looking back at your life and you had spent most of your life in that state, I think you’d look back and feel that you’d had a good life and you were ready to die.

 

I think it’s an amazing way to spend your life is to be in that flow as much as possible. So it’s tough that the concept of work, you know, you work because you have to. It’s that word have to that always kind of guided me. Like I always thought that everything I was doing was because I had to and all of a sudden when you just admit to yourself that you don’t have to anymore, it puts you in a really weird place which is like well what do you do if you don’t have to. But then you just end up doing things just because you think they’re interesting.

 

JT: So then I’m wondering between, I understand flow and I think it’s amazing when you can captivate that, you know. How do you sort of balance that? So if you have a business or a job, how do you balance that with productivity. You’ve been sort of on both sides of it. You’ve had a really successful business and then you’ve had free time of all the choice that you’ve ever wanted to do. How do you balance productivity and flow?

 

DS: Well, I think it’s keeping the direction in mind of doing something that’s useful to others. It might even be mildly useful the way that somebody who loves to build clay pots or something, if you just love to build clay pots and you spend all your time building clay pots, if you could just find just enough people who like your clay pots then voila you are being productive because it’s something that other people value whereas playing video games, probably nobody is ever going to pay you to do that.

 

So I think that’s what you’re talking about. I guess what I’m saying is you can shape your career and what it is you call your career based on just doing these things that give you that flow captivation, feeling. Just find a way to do those things and then find a way to make money doing it and then you don’t have to feel like it’s a big separation between work and play where work is something you have to show up and do and slug away and hate it and then you have your flow thing at night. There doesn’t have to be that separation. You can find a way to just, whatever that thing is that captivates you. See if you can just use a little bit of business smarts to find a way to make some money doing it.

 

JT: So talking about the flow and stuff like that, I want to get into talking about Muckwork and sort of the other new ventures that you’re sort of working on. How do you start something new number one and if you don’t know if it’s going to flow or anything like that, how do you start that whole process of creating a new business or a new company?

 

DS: Well, I’m about to find out. I haven’t really started Muckwork yet. I mean I just incorporated it. Well here, let me back up, I haven’t really shared this story on the web yet so what happened is basically had a handshake deal and decided to sell CD Baby on January 18, 2008. That was the big day and it was just coincidentally my sister’s birthday which makes it easy to remember. So that was a big day that I decided to sell CD Baby and it was life changing and oh my God I just, you know, I though I would never sell CD Baby. I thought I was going to do it until I die and this was just a huge change for me and massive life shift.

 

So then it was January 19 that I woke up and went I’ve got a great idea. I’m going to do this business and it’s going to help people and I’m going to do this and I’m going to call it Muckwork and here’s how it’s going to work and like that same day I went and I registered the domain name and I went and I trademarked and I set up this and I started programming the code and I built this and I set up the site and I got about three months into it and I also had to look at myself and say like hold on a second. What am I doing? My whole life I’ve never stopped. I’ve been an absolute workaholic my whole life. I’ve never taken vacations. I’ve never taken time off.

 

If I launch into a new business now, I am going to seriously burnout hard in a few years. I need to stop and take some time off. So that’s why actually Muckwork has been announced for over three years now and I haven’t actually started it yet because after a few months of building it but not launching anything publicly, I purposely just put the brakes on it so I dissolved the corporation. I left got of the person that I had hired to help me with it and I just started, I spent the last three years kind of on sabbatical doing a lot of reading, lot of learning, lot of writing, speaking. Set up my personal site. Moved to New York. Met an amazing girl, got married, traveled the world. Moved to Singapore.

 

JT: Yeah, same old same old stuff. That’s crazy.

 

DS: The last three years has actually felt like kind of like I went back to school. It has been a self schooling but I mean no less than three to five hours a day are spent in just pure learning whether it’s like reading a book on business or psychology or philosophy or something and underlining and taking notes and then using, I use flashcards. There’s a software called Anki that is flashcard software that I put most of what I learn into the flashcards and I have it quiz me later so I want to retain everything I’m learning and it really is like going to school it’s just that I created my curriculum myself instead of waiting for a university to do it.

 

So I spent the last three years like really intensely just learning and trying to look at life from a different perspective at the same time. So anyway, now that I’m in Singapore and I became an official resident just a few days ago, I’m incorporating Muckwork here and I’ll get back to work on it. But as of now, there is no Muckwork, it’s just an idea that I announced three years too early.

 

JT: I noticed it was still in beta and it had been for awhile. That’s a real interesting story. That’s great. Well I want to get into Muckwork too but what you were just talking about it’s funny, you remind me so much of Leonardo DaVinci and take that as much of a compliment as you can. I’m actually reading a book called How to Think Like Leonardo Da Vinci and he’s so left brain and right brained and just all about learning and I just want to give you a huge compliment and be like, he’s like my hero and you remind me of him so much.

 

DS: Wow, thank you.

 

JT: Well it’s because you have both, you know, the music side and the technical side and all that in between having to do with learning so it’s just an amazing, you’re an amazing person, Derek. Okay, so what I would love to do is talk about Muckwork. What is your plan then going forward starting a new business? I know with CD Baby you said it was sort of like a one hit wonder where you didn’t even really want to do it but people kept asking, you know, will you sell my CD? Will you sell my CD? And Muckwork is sort of starting from an idea, brand new, nobody specifically has told you I want this right now. I know you’ve probably heard it before.

 

DS: Oh they have.

 

JT: Okay.

 

DS: So I don’t have that much to say about Muckwork. First let me just preface this to say that you never know how plans are actually going to work. So when I started CD Baby, it was supposed to just be a credit card processing service that all I was doing is charging credit cards for my friends and then paying them the money. But then, a couple of them spaced out and didn’t send the CDs like they had promised they would so then I said, “Okay, give me the CDs, I’ll send them.”

 

But then as soon as I launched CD Baby, my credit card processing service, I had five friends or I don’t know, maybe it was like 12 friends whose credit cards I was processing and some guy in the Netherlands came in and bought a couple and I shipped them to him and then a week later he came back and said, “What are your new arrivals?” And I said, “What do you mean new arrivals? Like which of my friends am I now processing credit cards for? Why do you care?” And he said, “Oh I thought you were a store.” I went, oh a store, interesting. I never thought of that. Like I guess I could make a store couldn’t I? Maybe that would be a help to my friends, turning this into a store.

 

So just like that, my plan completely changed only two weeks after launching. So I think life is like that. It’s like you can have some plans but once your plans hit the real world, the real world tells you what it wants you to do and it’s often not what you had planned. Anything I could say about Muckwork now might just be moot in a few weeks. But all I can tell you for now is that the reason I decided to do it, well actually, sorry, we should say for the sake of the interview, like what, at least as of now, what’s my plan for Muckwork to be.

 

The idea of Muckwork is that it’s a network of assistants, worldwide network of assistants who are already trained to help musicians with the things they need. Where it’s coming from is for ten years of working with musicians at CD Baby, so often when I’m talking with them about how’s it going, what are the hard things, what do you need help with, everybody says I wish I had a manager or I wish I had an agent and I say well what do you need help with and they say I just need somebody to kind of like all the little stuff, kind of confirming the gigs and booking this and finding a hotel on the road and copywriting our songs and updating our Facebook page and trade marking the band.

 

They’d name all these little things that need to be done that aren’t the music. That’s what we want a manager for. I’d say, “Well, a manager is expensive. They take like 50 percent of all your net worth as their cut. Manager is somebody that’s supposed to be very old and wise and strategic. You’re talking about things that sound like you need an assistant.” They’d say, “Oh well I don’t know how to find an assistant or manage people. I can’t be bothered.”

 

So Muckwork is designed to be the company where it’s the network of assistants so a musician can just say, “Here’s our list of upcoming concert dates, please verify all these. Make sure everything is good, make sure we’ve got hotels and everything like go.” So our assistants will know how to take care of that. Or, “Here’s my newest 40 songs I wrote, I haven’t copyrighted them can you take care of this and we’ll know how to take care of that. So that’s the idea of Muckwork.

 

So why it’s worth doing, you said, like nobody is asking for it. Well, I kind of feel like they are in a way. But even more so, when I decided to sell CD Baby, I put six different projects, I actually had six different ideas of things I thought were very worth doing and I put all six on my website. One of them say, for example, was a documentary about the grassroots music business where we take a video camera into the office of nightclubs and booking agents and publicists and magazines and we show what it’s like to be on the receiving end of your music and we put a documentary together for musicians. So I loved that idea.

 

I thought it was great and then I had like say four or five other ideas like that and also Muckwork. So then when I announced it and I pointed everybody at all six, everything got a pretty lukewarm response. Like my documentary idea I just described, people went, “Sounds good let me know if it happens” but nobody was like foaming at the mouth over it. But Muckwork was the one that everybody was like, “Oh my God, I need this” and every time I would tell somebody about it, it was like a couple days later I’d get an email saying, “Is it ready yet because I need this so bad. I really want this.” I’m like okay I think I’m on to something so let me let go of those other five ideas and I’ll just do Muckwork.

 

Then Song Test was kind of like that too. Don’t need to go into the whole description but if you look at Songtest.com, there’s a description of what it is but that came about with a single little blog post I wrote in 15 minutes saying what if there was an open source song contest where there would be no fee to submit. The whole thing would be self-sitting and not require any employees and that’s why it wouldn’t cost anything and it would be community driven.

 

So I just posted that on my website in like 15 minutes and that one blog post still to this day has more comments than anything I’ve ever written. There’s something like, I think it’s over 1,100 comments just to that from people going, “Oh my God, yes, we need this! Please do this! I really need this to exist.” I was like whoa, okay, all right so I guess that’s my other thing that’s worth doing. So right now it feels like those are my two things, Muckwork and Song Test, feel worth doing even though you have to humbly admit I have no idea how it will actually turn out. I mean I’ll build it, I’ll do my best and I may launch it and people may go, “Oh no, we don’t want it after all.” You know what I mean? But oh well, it just feels like it’s worth trying, worth doing because people say they want it.

 

JT: Well and you seem to have, I mean you have a huge community of people who are willing to give you their opinions so that’s huge. You sort of did an informal survey of what people would like. That way you didn’t go hey my idea doing this is great. Start doing it and go okay nobody really wanted that.

 

DS: Right, but that’s so crucial. I think even if you don’t have a big crowd, I very often get entrepreneurs emailing me for advice and they often want to be big, big, big, like they have this idea that right now is just like a tiny little seed of an idea, maybe an itty bitty little website or something that they just launched a month ago and they say, “How can I get this to a million people?” And I say, “Don’t get it to a million people, get it to one.” Like find one person that can really use your service and what you’re doing and really make that person happy.

 

Almost think of yourself as personal service. How do you make one person happy with what you’re doing and make them really happy so that they’re so thrilled with it that they will go tell their friends and if they’re not so thrilled that they will go tell all their friends, then keep working on it until that one person is so thrilled that they will go tell all their friends. Then do that with a second person and a third person. Focus on individuals and what they need and get in deep with how you can help them and how you can make your service or product better for them.

 

Then as you improve and improve then they tell all their friends then that’s like organic growth and honestly that’s the kind you want anyway because most businesses collapse when all of a sudden they have too many users. Then their site is down and it looks like hell and it’s kind of like a million people heard of you too early whereas if you don’t mind my telling my CD Baby path was even like a year after I started CD Baby, I still had no employees, it was still just me doing it part time. I still was only getting a few orders a week.

 

I had a couple hundred musicians and a few hundred customers and that was it. But I was, every single day, talking with those musicians on how can I improve this? What else can I help you with? How can I make this better? How could it serve you better? I got to just slowly build and improve and build and improve and so by the second year, then I had two employees and a couple thousand artists and by the third year I have five employees and 50,000 artists or 10,000 or something like that. It grew organically.

 

It didn’t really take off until like the fourth or fifth year and then everybody started hearing of CD Baby and by the time they heard of it, it was like every musician they knew was already using it by the time they heard of it and everybody was saying, “Oh yeah, it’s a great company” and the site was robust and could handle anything and could handle a huge Christmas whomp and could handle different kinds of billing and payments and all that kind of stuff by the time people heard of it the first time. It’s because I had a few years to grow it organically. So I highly recommend always, don’t worry about the crowds, focus on individuals.

 

JT: Excellent advice. That’s great advice. I know so many people that I talk to too are like I want a million dollar business and I’m going okay, do you have a business yet? Do you have customers because that would be good. Excellent. Well it’s funny, I asked a couple of people and I know time is running a little bit short now, but I asked a couple people for questions and one was specifically about focus and I know you said you had six ideas and now you have sort of two that you are working on, how do you deal with focus especially being an entrepreneur with so many ideas?

 

DS: Okay, I have a good philosophy on this that serves me well and I hope your listeners and readers will like. I know a lot of people who want to do so many things at the same time and they say but I can’t choose just one. I can’t get anything done because I can’t choose one. So there’s a parable of the donkey that is exactly equidistant between two buckets of water, one is 30 feet to the left, one is 30 feet to the right. He keeps looking left, looking right, keeps looking at both buckets, can’t decide because they both look equaling appealing and eventually he falls over and dies of thirst.

 

So the reason the donkey was in that situation or the reason the donkey died of thirst is that donkeys can only see the present moment. They can’t future think and say, “Oh well, you know what, I can walk over to that one first and then walk over to the other one next.” Like donkeys can’t think that far ahead. So whenever people are feeling in that situation, it’s because they’re not thinking far enough ahead. They’re living too much in the present moment only and not looking at the long term.

 

Because if you look at the long term, if you think of yourself as 90 years old looking back at your life, and you think of like right now say you’re 25 and you have 10 different things you want to be doing and you think I can’t get anything done, well, you can actually do them all it’s just that you have to be patient and do them sequentially like the donkey with the buckets of water. So you have 10 different ideas. Well throw yourself into one for two years. Actually it’s spelled out, just make like a rough draft of a life plan saying for the next four years I will do this business and then for the next four years I will throw myself into that and for the next five years then I will go be a mountain climber and then for the next four years then I will start a music school.

 

All those different aspirations you have in life, don’t be a donkey. Look long term and realize you can do them sequentially if you’re patient and then you can do one at a time and throw yourself into it totally. So we’ve all experienced this on a micro level. Say, for example, that feeling you have where it’s crunch time. Something is due tomorrow and you absolutely have to do it tonight because it’s due in the morning and so you’re throwing yourself into it completely focused on it and sure you may have like, the thought may enter your head for a second, like you get tired, you rub your eyes and you think I would like to be snorkeling right now or whatever it may be.

 

But you don’t go snorkeling now because you know that you need to focus on the task at hand in order to get it done at all. But if you were to stop and go snorkeling right now, nothing would ever get done. So I think it can be the same thing, with zoom out and make that instead of down to the minute, make that like months or years of your life that you have to realize that you won’t get anything done at all if you don’t focus on one thing. So those other things you want to do like going snorkeling, yes, you will do them, just be patient. You’ll do them whether it’s in a few months or a few years, you’ll do them but you got to focus on this one thing right now.

 

JT: I love that and I am totally going to post on twitter don’t be a donkey says Derek Sivers. That’s excellent. So I know we’re running out of time, I have so many more things I want to ask you.

 

DS: Go ahead I’m good.

 

JT: Oh perfect, okay. So another question that somebody asked was when you’re creating something, because I know you are a musician, you’ve also been a business owner, how do you know when whatever it is you’re creating is good enough to release whether it be a song or something in your business? How do you know?

 

DS: I heard a great quote about this and this is coming from a long time silicon valley investor serial entrepreneur said, “If you’re not embarrassed by your first released you’ve released too late.” I really like that. It’s like saying you know what you will, you just have to put it out there. By putting it out there too soon, then especially when you make it clear to people that it’s a work in progress then they can give you feedback.

 

Instead of you trying to perfect something in hiding and then release it and awe everybody with your perfection, people tend to gauge with perfection. They won’t give you advice on perfection. So releasing something as a rough draft and admitting hey this is kind of rough what do you think, then you’ll get all kinds of great feedback. So yeah, I think release too soon.

 

JT: I think the distinction you just said though is clearly letting them know that it’s a work in progress because I think that’s what people are afraid of when they let something go is they go people are going to judge me on this but if you can clearly let them know that it’s definitely going to be improved on and you’re just getting it out there, that’s really important. Excellent. So two more questions for you.

 

DS: Sure.

 

JT: Specifically we talk a lot on the site about personal finance and I’ve read about you and your personal finance theories and you live a debt free life. Can you tell me your thoughts on personal finance and how you go about working with it?

 

DS: Yeah, I don’t really optimize. Well first let me just say I’ve always been very debt adverse. I don’t like being in debt at all even on the small level. I never bought anything with a credit card unless I had that much money in the bank. The credit card was just a convenience. Like I never went into negative debt on a credit card, even as a teenager because I just hated that feeling. They say that there are two ways to be rich. That one is getting more money and the other one is lowering your expectations, lowering your needs.

 

So if you lower your needs far enough, then you can be rich quite soon. So, that’s what I did when I was 22 is when I quit my last job. So I did actually have a job for a couple of years from the age of 20 to 22 and I had saved up $12,000. So I was 22 years old, that felt rich because I was working in the circus at the same time as I had this other job. It was like two jobs at once and I was working seven days a week and it was awesome but my rent was only $330.00 a month. I had a little place that we split with three guys so my rent was incredibly low. Never even took taxis, never went out to eat. I just ate pasta and peanut butter and jelly and I just focused on my work and I never went out.

 

I didn’t want to, I was really just focused and drive on practicing and improving and building my career. So I had saved up $12,000 and was like whoa. That is like I can live off of that for a couple years. So I did. I quit my job. The last time I had a job was 1992 and I lived off that $12,000 for a couple years and I just kept my costs really low and I was still earning a few hundred dollars a month net profit with the circus. I think with the circus I was earning maybe like $12,000 a year and that was just enough to pay my cost of living. So I felt pretty rich ever since then.

 

I didn’t buy anything. I didn’t want anything. Then there was the level of, I know you talk to millionaires, but to me, like my really feeling rich moment came about once I had like $200,0000. It’s like CD Baby had been running for a few years pretty well and once I had like $200,000 in the bank, then again, I was like wow, it could all disappear and die right now and I would be good. I could live for ten years on that. I would not even need to work. I could just sit and read books and do nothing for ten years just with the money I got right now and what an awesome sense of security that was.

 

But again, it was because I had no, like I kept my cost of living down to nil. I think that’s important. I don’t know, my thoughts on personal finance are just realizing that buying some new shiny thing doesn’t make you happy past a few minutes. Like yeah, to get a new computer or something, like new fancy gadget, new iPhone 7, whatever it may be, yeah for five minutes you’re like oh cool, look. But after a few minutes, it’s like well just another phone. You’ve played with the little apps and the gadgets for a bit but in the meantime you’ve wasted so many hours of your life that you’re going to have to work to pay for that thing now and feel like a slave and all that to buy that thing.

 

Then you see people do it on the bigger with they buy a sports car or they buy a five-bedroom house or a giant thing. It’s like you don’t need that. Then they talk about how they feel trapped and well I have to work, I have to do these things and I have to pay the bills. Well it’s like you didn’t need to get those bills in the first place. You know what I mean? You don’t have to do anything. You could just, there’s that book The Power of Now written by, I forget his name.

 

JT: Eckhart Tolle.

 

DS: Thank you. Where at the opening of the book he describes it like he just hit some point in his life where he just decided to sit on a part bench for a few years and he sat on a park bench for a few years and I don’t know what his cost of living was for doing that, like I imagine take the cost of some bread and peanut butter and jelly or something like that for a few years, and I think your cost of living doesn’t really have to be much more than a couple hundred dollars a month. Anything over that is just your indulging your unfortunate insatiability.

 

So my thought on personal finance is like number one, lower your wants. Just even really deeply internally just make yourself stop wanting all that stuff. Realize that it doesn’t make you happy and then number two, appreciate all the wonderful freedom you have now that you’ve lowered number one and you don’t need all that crap to make you happy.

 

My role models, I told you I was with the circus for 10 years and so not just my circus performers but often even their parents were of this more artistic mindset. For example, my girlfriend of many years, her parents, one did part time photography and one was like a part time seamstress and that’s it. They lived in a house in the woods and it was a nice little house and they raised their daughter and put her through college just with the money that they made just as a part-time photographer and part-time seamstress because they kept their cost of living low. That was such a role model to me.

 

Like you don’t need to do all this kind of rat race stuff that we think you need to do. You can spend your time just doing what you want as long as you can find a way to make a few hundred dollars every now and then doing what you love. That’s enough.

 

JT: That’s awesome. Well it’s funny because you’re describing my epiphany when I was 24 exactly to a tee. Like I was $70,000 in debt and realized hey I don’t have to have my job if I just get rid of this debt and live way below my means. I could actually quit my job like completely even though I made six figures and two-thirds of the income, it didn’t matter because if you lower it enough you could pretty much live on anything. Then it’s a freeing experience. It’s so huge to be like hey I was working that whole time and I really didn’t have to, yeah!

 

DS: Yeah, exactly. When I quit my job that was a big thing. It’s like whoa, why didn’t I realize this sooner? Isn’t that an awesome feeling?

 

JT: Oh yeah. You feel kind of dumb though at first because I was like hey why did I do that? Why wasn’t I smart enough to know that to begin with? But knowing that and being able to move past that it’s just an amazing, amazing, I’m so lucky now where I am. I work part time too. We’re just lucky that I was able to have the epiphany at 24 instead of 64.

 

DS: It’s funny, I still follow this. When I decided to sell CD Baby for $22 million, like when that was the agreed upon price, it was like whoa $22 million dollars, what the hell do you even do with that and the funny thing is I did a poll among my friends like what would you do if all is said, like something you were doing, like you were just told that you were about to be given $22 million what would you do? It was so interesting hearing different peoples reactions.

 

So one friend would say something like well I would buy a big house for my parents and a big house for my brother and a big house for me and I would get a Ferrari and I would get something, something and if there’s anything left over … So I had a few friends that would say variations on that. Some that wanted to do such charitable things like they say I’d instantly open a school for the needy in Africa and I would throw myself into humanitarian. I would use all my money to save lives. Like okay.

 

I actually I asked my lawyer who has been this music industry lawyer for a long time and his reply was funny. He goes, honestly, Derek, it’s not that much money. I mean yeah it will carry you for a few years but it’s not like real fuck you money, you know. But it’s funny like he is coming from that point of view where he has a multi-million dollar house and five cars and to him, that wouldn’t sustain him that long.

 

Anyway, but my best friend, Meredith, had a really interesting thought. She said, “Well, I would put it all into the bank or put it all into like a safe, very conservative investment kind of thing where I wasn’t ever going to lose it and it was just going to grow at a few percent and I would never, ever, ever touch it for my whole life. I would only live off the interest.” I’d say, okay, what is the interest on $22 million well then that’s my cost of living and she said, “I would just adjust my cost of living accordingly so that I would only live off the interest.” It was really sweet. It was kind of like right on, I hadn’t told anybody that that was my thought too but she said that and she put it so bluntly and directly.

 

It was like that’s kind of what I was thinking too and so that’s what I did with this charitable trust that you can read on my site where I really did give it all away. I put it into this charitable trust and it’s irrevocable. I could never, ever, ever get it back no matter what but it does pay me out 5 percent per year and that’s enough. So I adjusted my needs accordingly so I’m just living on that interest and will never touch the principle and it will all just go to charity when I die. Hopefully by the time I die in fact it will be, I hope it will be $200 million by the time I die, that it could just compound and grow for my whole life so that by the time I die it will be a lot more.

 

The thought being that while I’m alive I can do helpful things for the world with my actions but when I’m dead I can’t. So when I’m dead the money will have to be helpful in my behalf.

 

JT: I love that. I love that and it’s funny because my site is Eventual Millionaire and it’s not about, of course, the million. It’s about the person you’ll become and what you’ve done in order to get there. But that’s awesome because everybody assumes when you become a millionaire you’re like oh everything changes, everything is different and, you know, you put it away and you’re getting 5 percent a year and that’s it and that’s an amazing thing that you chose to do. Excellent.

 

DS: It made me happier. I know another friend of mine kind of was in the same position as me a few years before me. Sold his company for about the same amount of money and he took the lump sum and like he went and bought himself a $10 million house and it was kind of sad that even when he was telling me about it, when he said something like I realize that was only $10 million we could afford it and I never want to hear myself say only $10 million. Know what I mean?

 

JT: Oh yeah.

 

DS: I don’t even want to be in that mindset. I think there can be a thing of having too much money so that you’re doing really wasteful things and not doing that math like we described. The iPhone, will it really make me that happy? No it won’t. It’s like still using that math. Like even though you can afford it, yes, but still acting as if you can’t. In a way, trying to think like how happy will this really make me?

 

That same friend, when he flies around the world, he flies on Virgin Airlines upper class which, I don’t know if you know, like it’s beyond business class. It’s even beyond first class. They have like an upstairs cabin where it’s I think it’s something like $10,000 to fly from LA to London or something like that and he takes it just because he can and he’s like it’s more comfortable, you get to recline. I’m like yeah but you’re trapped on the same plane with everybody else. You’re getting there at the same time as everybody else. It’s only ten hours of your life and you’re going to spend $10,000 to be a little more comfortable.

 

It’s like it’s so sad when you think of all the other things that that $10,000 could do. Hell, that could hire you a part-time assistant for a year if you had some ideas that you wanted to turn into reality and you need some more help doing them. Or it could sorry to do the usual charitable route but hell, look at what they’re doing with malaria nets and think of how many lives you could save, like people who will not die because you give that $10,000 to them instead of to Virgin upper class.

 

So part of me I deal with locking away, putting all the money into the charitable trust was like I don’t want to be able to touch it. Like I don’t want access to it because I don’t want it to change my perspective on what’s worth doing or buying.

 

JT: It’s so funny because after interviewing so many millionaires, they all have this same mindset, you know what I mean. Even the ones that do buy the Lamborghinis, it’s only after they’ve made so many millions that it doesn’t matter and that was the thing they wanted since they were a little kid and that’s why they got it. But it’s never about the money and it’s always about keeping the value of a dollar still the value of a dollar and that’s huge.

 

DS: Interesting.

 

JT: Yeah, it’s great to hear to everybody who’s not a millionaire that they can do the same thing and once they get to that point, it’s going to be the same not angels don’t fall from the sky, you know what I mean. These huge things don’t happen just because you hit millionaire status. I don’t know yet but I hopefully will find out, you know.

 

DS: On that note thought, let me, I’ll tell you the flip side for the fun of it.

 

JT: Okay.

 

DS: I realize that this is the perfect audience for this joke, true story but, there was a girl in Portland who was like 22 and really looked up to me. She was one of those people that would kind of like ask me questions all the time. She said she wanted to be like me. I was kind of like a role model, how can I live like you and I was telling her like yet another thing had gone wrong in my life. I had a relationship break up and she said, “God, how do you do it? How do you keep your sunny disposition? How do you stay so positive” and she said something like nothing really gets you down. How do you do that? I was like huh, let me think about the real answer for a minute.

 

I was like hmm. I was like well, first you get a million dollars and she just thought that was like the funniest thing. She laughed for like ten minutes straight because you know what, it was really bluntly shockingly honest that I’ll admit, a lot of my security and relaxed happiness comes from feeling rich. But like I said, I mean I’ve had that ever since I was mid 20s. It doesn’t actually take a million dollars but that feeling of security like I don’t need anything from anyone.

 

I’m good, I’m happy, I’m self-sufficient. I have the ability to take care of myself. I can do things with my own two hands that can make enough money to make me happy or I don’t need to. I don’t need to take shit from anyone. Like that’s an incredibly powerful feeling and again, I think a lot of it comes from reducing your cost of living so that you can just have a part-time job and support yourself just like that. But there’s a huge deep sense of happiness that comes from feeling that secure and a lot of that comes from having enough money that you can walk away from things you don’t want to do or don’t have to do anything you don’t want to do.

 

JT: That’s excellent. You explained the reason why I’m so happy, right, apparently.

 

DS: Yep.

 

JT: That’s awesome. Well, it’s funny just thinking about, you know, I worked at a corporate job, made great money and was totally not happy very often. But now, I don’t even make six figures anymore and I’m sort of like yeah, yeah but things are good. I make my own choices, I’m well set. But it is that security of going well I don’t have to worry about that. That’s huge. Excellent. Thank you for putting it into words for me.

 

So for the last question then that I have, this is the same question I ask to everyone, what is one action that everyone can take this week to move them forward towards their goal of a million?

 

DS: Action? You only want one.

 

JT: You’re Derek Sivers, you can give me more if you want.

 

DS: You can’t help but say it’s like, you know that I’m going to say that reducing your cost of living and realizing that you don’t need all that crap that people say you need. To me, that’s just a starting point. Let’s just almost use it as an assumption but I’d say that the biggest one is looking at the what I call the starving artist problem. If I’m feeling hot, like if I’m in a room right now and it feels like the temperature is hot, like it’s too hot in here, that feels like an objective fact. It doesn’t just feel like my opinion. It feels like no it is hot not I am hot and the rest of you are cold. It just feels like it’s hot in here, right? That’s how we all feel.

 

So a lot of people are doing something that they feel is valuable. They say, whether it’s a songwriter saying this song could be a number one hit or somebody creating a business that they feel should have a million customers. It feels like objective fact to them. Like this is a hit song. This is a great business. It doesn’t feel like it’s just merely their opinion. It feels like fact. But the problem is that money is a social thing. Like the little green pieces of paper only have value because we’ve all socially agreed that they do.

 

So value isn’t objective like that. It is subjective on the opinions of others, not you. So what you’re doing only has value if other people agree that it has value. This whole thing of I want to be a school teacher and I want to be a millionaire because I’m a great school teacher, not that that happens that often, but unfortunately it’s a shame perhaps, but the world has determined that a school teacher really only makes barely minimum wage and somebody working a desk job at a bank gets extremely rich even though one adds a lot of value to the world and the other one just seems to suck value out of the world but oh well, that’s kind of what our current society, that’s what it has valued and put numbers on.

 

So never forget that what you’re doing has to be valuable to others, not just to you. If it’s valuable to you and not valuable to others, well that’s the starving artist problem. That’s where you are doing something that you think is brilliant and nobody else does and then you just complain that you’re not making any money and nobody values art anymore. Well, it’s true, they don’t value your art.

 

So with all of your listeners and readers that have plans on how to make a million dollars, just make sure that you’re not in isolation, that you’re not just sitting there by yourself thinking you’ve got a plan to make a million dollars. Instead, focus on individuals, get out into the real world and find what people are willing to open their wallets and pay you to do right now and once you’ve found something that people are willing to, that a single person or two or three, is willing to pay you to do for them right now and are happy to pay you, then find a way to do more of that. Then eventually find a way to systematize it so it’s a system that does the work not just your two hands. If I can all wrap up all those things and call them one action then that’s my answer.

 

JT: That’s perfect. What everybody can do for that one action is just set aside some time to ask those questions because those are huge questions and a lot of the times we’re so busy we don’t ask those questions or at least we’ll ask ourselves and then think of something else and not answer it, right? Our mind gets to busy. Excellent. So set aside some time everybody that’s listening. Even write it on your calendar if you can’t do it right now because you are in the car or something like that but really try and pay attention and ask yourself those questions and get definitive answers because that’s huge. Otherwise you’re a starving artist.

 

Excellent. Well thank you so much for coming on Derek. I’ll be linking to all the other interviews because I listen to all the other ones with you in there also amazing. So in the show notes I’ll have that and I’ll also have that great Ted talk video that you had which we didn’t have a chance to talk about but everybody should check it out, of course, if they haven’t already because I know it has been around quite a bit.

 

So excellent. Is there any way, you know, tell us where we can find you, where we can find more information and what’s going on?

 

DS: Oh yeah, if you just go to Sivers.org to my site, Sivers.org. I keep everything there. It’s my home page so everything I’m doing there and actually my biggest advice is click the little email list button and just give me your email address there. I don’t ever give or sell it, I just use it to let you know when things are worth knowing about or going on and lastly, actually, the thing I want to say if somebody has listened this far is to just send me an email and say hi. Or ask me a question that’s on your mind. I find it funny when people preface their emails saying, “I know you must be incredibly busy but” and I always shock them by going no, I’m not busy.

 

I think busy is what happens when you’re at the mercy of someone else’s schedule but it’s like I told you, it’s like no I don’t have to do anything for anyone so I don’t do anything I don’t want to do and I’m happy to answer peoples questions so I got time, it’s cool.

 

JT: And I just want to thank you because that, you said that at the end of a different interview that I listened to and that’s the whole reason why I emailed you and that’s the whole reason why you’re on the show right now.

 

DS: Awesome.

 

JT: Oh yeah, inviting that was awesome. Completely awesome. So thank you.

 

DS: See how worth it that was and we got to have this great conversation. I mean worth it for me I was saying. See I love the fact, like the people who actually take the time to email me and say hi, I like almost all of them. I have met some amazing people through just being open to meeting strangers. So yeah, email and say hi. I would love that.

 

JT: Perfect. It will be a cycle so someone else will have you on their, interview you, so that way, because they heard of you from my show. So excellent. Well I hope you have an amazing day over in Singapore and take care, Derek. Thanks so much.

 

DS: Thanks, Jaime.

 

Just to know, you can download the top ten tips from these millionaire interviews on the blog.

 

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