Derek Sivers

Mark Drager

host: Mark Drager

parenting and family dynamics, philanthropy and charitable giving, the nature of happiness

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Transcript:

Mark

Derek, you’re an author, you’re a speaker, you’re an entrepreneur. You’ve built up a business and sold it for $22 million and gave all the money away. And I’m very curious about that. But where want to start is you’ve mentioned in your writing that you like to prepare responses, because if someone throws a question at you or someone throws an idea at you and you’re just immediately reacting, then that’s not the true reaction. That’s not the best thing. And so when you jump onto a podcast or you’re being interviewed, you always like a list of questions in advance, you said. Now I know I did not send you this list. I never send out a list of questions in advance. So I’m curious, are you going to simply give us what you say you do not want to do, which is you’re going to just give us the same old stories that are prepared and all of this stuff? Or am I going to be putting you on the spot? And are we going to have to give you time to think?

Derek Sivers

No. A funny thing about the internet is that you can put something out there in present tense and speak in present tense, and somebody can read it years later thinking that it’s still present tense. But no, I used to want the questions in advance, and it’s still interesting when somebody does that, when somebody emails me questions in advance of a conversation. I do think about them more because I often get a different answer 15 minutes later then the first answer, if you know what I mean. There’s the first answer. And then you think about it a little more and you think, “Well, wait, is that really the case? What’s another way to think about this?” But anyway, no, I’m thoroughly happy to just wing it. I don’t need questions in advance anymore. Thanks for asking.

Mark

Well, I was like, “Hmm.” I like to try and catch people on things. But that’s interesting that obviously. I’ve been told that if you want to truly know who an author is three years ago, read their book because you know, we’re putting out what we’re working on today. And if it’s in real time, if it’s a tweet, guess we don’t call it tweets anymore. If it’s an X, have we landed? Have we landed on what we’re calling this thing yet. Okay. So if it’s an X let’s not do that.

Derek Sivers

No, no let’s never make that a thing. Let’s not make fetch happen. Let’s just keep it as tweets because, you know, maybe he won’t use that term anymore. Maybe the term will become open source now. We can all just call them tweets as a generic term.

Mark

Yeah, yeah, yeah. Like the Band-Aid thing. Like so anyway, so it’s a tweet. You know, it’s an IG story, which I guess they disappear. It’s a reel, it’s it’s a blog post. It’s a book. You know, you’re putting stuff out there. And I did not give you the benefit of the doubt that you would have grown or changed over the years. But that’s on me because all of the stuff that I see you putting out there actually speaks about identity shift. It speaks about growth. It speaks about being able to rewire who we are and learn from our lessons and move past it. And so I was trying to give you a gotcha, and I feel like I was taught a lesson there. And so as--

Derek Sivers

You were trying to give me a gotcha, you were trying to pull the rug out from under me. Oh nice to know your character. Nice to meet you.

Mark

Let’s keep going with this. Right. Your character dictates your future. So for the listeners, what you may not realize is happening is Derek puts out these amazing books. If you haven’t read them, where they’re just these like-- what do I love to listen to them because they’re like 2 to 3 minute chapters, single thought, single idea. That comes from many of the books you’ve written, many of the people you’ve spoken to, many of your life experiences. And what has just happened is I think we’ve probably referenced seven of these types of chapters very quickly. Sorry about that.

Derek Sivers

Sorry about that. Insider jokes.

Mark

But as someone who has lived the last decade plus putting yourself out there, I guess since, what, 2010, 2011, putting yourself out there in terms of your writing, in terms of your books, in terms of speaking. How do you deal with the fact that all of us are judging an old version of you and thinking that we’re still meeting you with where you are at?

Derek Sivers

I’m okay with that. I mean, it’s all me. I’ve actually been putting stuff out there since 1994.

Mark

Hold on. Where were you putting stuff out in 1994? Were you photocopying it and just putting on?

Derek Sivers

No, on the internet. So I was living in New York City, and my roommate was a multi-media major at New York University and told me about this thing called the internet that nobody had heard of, it wasn’t in the common parlance. So it was a pretty obscure thing that took real effort to get onto. I had a Mac computer at the time. And check this out in 1994, the only way to get a Mac computer online was you had to go buy a book called TCP IP Networking for Mac, and in the back of the book, it was like a big 400 page book was a floppy disk glued into the back of the book, like in a plastic sleeve. Then you had to stick in the floppy disk into your Mac to load a TCP IP driver, and that would let you connect to a modem to your Mac and connect to this new thing called the internet. And that’s when I built my first web site in 1994. So I’m an OG man.

Mark

You are. I remember the very first time I went on the internet, I think it was 97, 98, I think it was then I was in grade eight and I was in the library at my school. My friendS said we should go on the internet, and I said, “What do you do on the internet?” And they said, “You just do stuff. You surf.” And the only two things I knew from television commercials was, do you remember there used to be the AOL keywords, right? All the commercials would be like, “Use AOL keyword Oprah.” Right? And I knew Oprah from my mom and I knew NASCAR. So I think we went to NASCAR.com and they had the rankings there or something of the season. And I was like, “Now what do we do?” And he’s like, “You’re doing it.” And I was like, “This is the internet?”

Derek Sivers

Wow, man. In 1994, there were no graphics, it was just text. I remember when graphics came out like later that year or the next year, it was like a new thing that it would take like a full 10 seconds for an image to load. You’d watch it load in pixel at a time. And that was a new thing, like wow graphics on the internet. Who would have thought?

Mark

So you’ve been putting yourself out there for almost 30 years. Next year it’ll be 30 years then.

Derek Sivers

I guess so, yeah, yeah.

Mark

Does that make you feel old anyway?

Derek Sivers

No, I’m really happy being old. I like it, I like the the wisdom of experience. It gives more context to the things that happen today, especially because I’m in a technical world surrounded by other people, getting excited about technical things that have been around for a few months, and I think I’ve seen other things come and go in a few months. Okay, let’s just pick a dumb example that just came up this morning when I was checking email, somebody mentioned Clubhouse and I was like--

Mark

I was pretty aggressively on Clubhouse for about five months.

Derek Sivers

Okay. So I was like, “Oh yeah, I’ve been meaning to check it out. Oh, it’s gone.”

Mark

Well it’s gone. Derek, that is so spring of 2021 like.

Derek Sivers

Right. And so I think when things like that come up and suddenly everybody says, “You have to check out Clubhouse.” I’m like, “I’ll give it a year. If it’s around in a year I’ll check it out.” I think I’m not conservative in my values and lifestyle, but when it comes to tech, I’ve found it very useful to be a slow adopter because then you just get to bypass all the noise that just disappears.

Mark

So this is so interesting to me. So I asked, you know, like, “Hey, it’s been 30 years.” You’re like, “I like being older. I like wisdom.” And, “Hey, does it bother you to put stuff out there and people judge you?” And it’s like, “No, that doesn’t bother me at all.” And so there’s two paths in front of us. I can keep throwing these like, hey, I’m trying to figure out what bothers you and how you overcome it and you can keep giving me what feels like a very loving and and almost like accepting Stoic or Buddhist nature about you or whatever it might be. Or if we can. Have you always been this way? Can we go back to what you used to be like before you were peaceful.

Derek Sivers

No, actually, I’ve always been this way. I found from a happiness researcher. I think it was Sonja Lyubomirsky. If I’m pronouncing that right. University of California, Riverside has been studying happiness for decades and said that they found that happiness is about 50% DNA and 50% under our control. Like half of it is just you’re born with it or you’re not. And I think I got the lucky roll of the dice that I’ve just always been a happy person. And you have four kids. So I’m curious to hear your experience with this. I only have one kid, and he is also the happiest person I know. He’s just always happy, and I think he got the lucky roll of the dice too. Fun random fact we just found out last night at the dentist that he, like me, will also never have wisdom teeth. Apparently that’s a pretty rare thing. And I had it. And I mean, I have that thing that means I’ll never have wisdom teeth. And he has it too. But I’m curious. You’ve got four kids. How different are their natures?

Mark

It’s bananas. It’s I don’t know, it’s--

Derek Sivers

Could you put that into layman’s terms?

Mark

Well, that’s the scientific term. No, my wife and I, we got married quite young and she was 21, I was 22. We had our first daughter at 23, and we had a girl and we were like, “Okay, great.” And my daughter is amazing. Rachel. And and you know, she’s turning 17 and but we’re like, “Okay, this is what a girl is like.” And then we had our second Jonah, a son. And he is a boy, you know, he’s grown up more and he’s now turning 15 and we’ve learned he actually has ADHD and a few other things. But like we were like, “Okay, so this is what a girl is and this is what a boy is. And we totally got this. It makes total sense.” And then we had Silas a few years later, my third, my second son. And we’re like, “Wait a minute.” Like he’s a boy but he’s nothing like Jonah and and he’s very, very different than Rachel. And we’re like, “Huh?” And then we had our youngest daughter, Jordan. And she is totally different still. Just completely different and what I’ve noticed because I like pattern recognition, I like looking into these things. I notice that their personality in the high chair, whoever they are in the high chair at dinner time at the age of like 11, 12, 13, 14 months.

Mark

That personality is them. So Silas didn’t really speak a lot. Very kind of fastidious. Hated having food on his hands, you know. He hated having his hands dirty and now that he’s pre-teen, you know, a bit of a perfectionist. Doesn’t like to make mistakes, likes to look a certain way, keeps his hair a certain way. And I was like, “Wow. That was like right there when he was a tiny little kid.” And Jordan, our youngest, just used to be so joyful. Like belly laughs. She would be sitting in the highchair just like throwing food around. And she’s just like belly laughing. And she loved it. And anything could make her laugh. And she was super lit up and super joyous, joyful. And now she’s nine and she’s in competitive dance and it’s just like, it’s so weird. And I tell parents now, watch, like watch who they are because they’re going to change and they’re going to grow and of course, and become the most amazing people. But there’s something about that core personality that’s like baked right in there at one year old in the highchair.

Derek Sivers

Wow, that is so cool. That’s one of the coolest things I’ve heard in weeks. That is so interesting. Thanks for that.

Mark

You’re welcome. Honestly, I have these thoughts and I don’t know if anyone cares, but it’s so strange how innate who they are is and and how boys are boys. But they’re different. And girls are girls. But they’re different. And everyone is so different. I don’t know how you approach fatherhood in terms of like how much you try to shape who they’re becoming while also giving them the freedom to make their own mistakes, the freedom to be themselves, the freedom to approach their own life. Do you know what I mean?

Derek Sivers

Yeah. My deliberate dynamic with him since he was born basically, is that he’s the leader and I’m the follower. So whenever we’re together, which I put aside about 30 hours a week to give him my full attention. So devices off, work shut down. Just 30 hours a week.

Mark

30 hours?

Derek Sivers

He’s my only kid. You know, that’s it. So 30 hours a week. He and I hang out one on one and he’s the leader. And I just follow him and he decides everything. But maybe a little bit like the, what do you call it? The person that whispers into the king’s ear, like he’s the leader. But every now and then, if I think he’s going astray, I’ll just give a little bit of guidance. But the whole time, letting him practice leading and taking full responsibility for the choices. So he decides what we do every day. And if he doesn’t enjoy his day, he knows it was because of his choice that he should have chosen differently instead of blaming me. So I don’t know. We’ve always done it that way. I just love letting him lead and just see where he takes us.

Mark

And for yourself--. I mean, I have to imagine that’s tremendously rewarding because as you’re watching him learn all of these lessons, you’re reminding yourself of these lessons too, you know?

Derek Sivers

Yeah. So you started young, I started old. He wasn’t born till I was 42. So I’m 53 now and he’s 11.

Mark

Wow. Okay, so for our listeners, you got to keep in mind, as we talk about your story and your company, it’ll kind of age you, of course, to a certain degree. But you do not look in your 50s. And I turned 40 this year, and I feel old already.

Derek Sivers

Well, yeah. Who knows, maybe the having kids at a young age will age you a little faster. I was in a circus until I was 30. So maybe that kept me young, surrounded by jugglers. Anyway, so I don’t actually associate his childhood with my childhood very much. You know, the two are so far apart and under such different situations, and I’m such a different parent than my parents were, that I don’t think about my childhood as much when I’m with him.

Mark

Yeah. It’s interesting. I meant more like often the lesson that I’m trying to teach my kids or the takeaway I realized, like a few hours later. My son will do something and I’ll say, “Well, what did you expect when you did? Blah blah, blah, blah, blah, like natural consequences and yada yada yada.” And then I’ll go away a few days later, a few weeks later, or a few years later and I’ll be frustrated about something in my life. And I’ll go, “Well, what did I expect?” And I find that more so than with my team or my friends or anyone else. And maybe it’s just my wife and my parenting style. Our kids are annoyed by it, but we always try to bring it back to the lesson, right? Like everything is a learning opportunity. And so it’s cool. It’s cool when things go wrong. Okay. It’s cool when we make mistakes. That’s fine. But what can we learn from it and how can we grow and what can we fix. And usually I’m trying to like narrate that and reinforce it for them to try and become that empathetic witness for them that can help take out some of the sting of the things that are terrible and help maybe knock down some of the ego that might be getting in the way or what have you. And then inevitably, I’m just eating my own words because they are just as important for me as they are for them. Yeah.

Derek Sivers

Yeah. Ooh. Good one. I think for me, parenting has been more like meditation practice, because when I’m with him, like I said, I give him my full attention. So I have things I want to be doing. I have projects that are unfinished and I’m just an hour from finishing, but it’s 3:00 and he’s coming home from school. So I go, all right, shut down, save my work. Turn off the computer, hold down the power button for three seconds on my phone. Swipe it to power it completely off. He walks in the door and I just give him my full attention until he’s asleep. And then once he’s asleep, I go back to maybe another half an hour of wrapping up what I was doing, and then I go to sleep myself. But that turning off of the work mind and the surrender to his daily leadership, if we’ll call it that, that’s been more like meditation practice for me.

Mark

That is a really great way to put that. Um huh. Anyway, now I have to imagine if people maybe aren’t as focused on parenting as you are or frankly, it might be a luxury that you have. That you are able to do so.

Derek Sivers

Yeah. Wait. Now hold on. Sorry to pause right there. So a luxury, but also a decision that was years in the making when I was like 13, I heard that John Lennon from the Beatles.

Mark

The other John Lennon.

Derek Sivers

Just, I don’t know, I’m speaking to who knows, you know, generational thing. Somebody 20 years old is listening to this. John Lennon might not be a household name anymore. So that hurts.

Mark

It hurts my soul to hear you say that.

Derek Sivers

I know, but you know what’s funny? I was hanging out with some friends that were in their early 20s, and I said something about one of the most amazing things that ever happened to me is when Peter Gabriel rushed up to me after my Ted talk and said how much he liked it, and they went, I don’t know, I saw this--

Mark

They don’t know Peter Gabriel.

Derek Sivers

I saw this blank look. I said, “Peter Gabriel.” They went, “Ummm.” I went, “Oh, God. Wow. Peter Gabriel was a major household name. Like, not that long ago. But it’s all right.” I guess he hasn’t kept putting out the hits, so, you know. Okay. Anyway, John Lennon had two kids. His first kid was born during the height of Beatlemania, and he wasn’t able to give him any attention. So in 1975, when he and Yoko had Sean Lennon, he just told his agent, “Shut it all down. Say no to everything. I’m going to do nothing for the next five years, but be a full time dad.” And that’s what he did. And I remember as a teenager thinking, that’s pretty cool. Like, I don’t know if I’m ever going to have a kid, but if I have a kid, I’m going to do it like John Lennon. I’m going to just shut down everything when I have a kid. And so that’s what I did. I was a total workaholic from age 16 to 42, and at 42 when my kid was born, I was like, shut it down, move to the middle of nowhere in New Zealand as just a full time dad. It was part of the long plan.

Mark

I used to be a big fan of Garth Brooks, and he had a crazy, wild ride, obviously through the 80s and the 90s. Number one country artist. I don’t have all of his stats memorized, but I think he was the highest earning artist for tours of like, all time or something. There was a time in the mid 90s, I think it was 94 or 95 where he won the Grammy for artist of the year, and he wasn’t touring and he didn’t put out any new music. And he chose to leave the statue and not accept it and this was like in 94 or 95 or something, but swildly successful. But when his daughters were growing up, he decided to stop all of it. He stopped all of it. And for 10, 12, 15 years, whatever it was. And he fathered and he parented. And I remember thinking like, wow, that’s like really cool in the back of my mind subconsciously. And then Covid came for us and for all of us. Covid came and I had to stop working the way I worked.

Mark

I had to stop commuting in. I had to be at home. 70% of our projects were put on hold immediately. And so there was just like less to do. And the last few years I’ve been parenting a lot more, and I’m really proud of it. And I really like how much effort I’m putting in, and I’m really happy to see how much stronger our family unit is. But one, I’m grateful for it because it is a bit of a luxury, but two it does feel like it’s coming at a cost. Right. And I think mother’s are like “Dudes like, yeah, yes, us women have been sacrificing for our kids and our family for a long time. I don’t know why this is news to you.” But it feels like it’s coming at a bit of a cost. And it worries me a bit if I know I’m doing the right thing, but at the same time it’s like, “Oh, there’s all these other things that I should probably be focused on though.” Do you, do you ever feel that way?

Derek Sivers

Yes and no. Like the meditation comparison I made. There are so many other things I want to be doing. But when I’ve put aside that time, like from 3 to 8 p.m. And then all day. I always give him all day Saturday and then say like the first half of Sunday before I switch my attention back to my own work. So to me, it’s about managing. Actually, you know, I had one more minor role model, Mark Fried from BMI. He got me my first job in the music industry when I was 20 years old in New York City. And he later told me when he had kids, I said something like, “Oh, is that is that hard to work?” And he said, “You know, when you have kids, you actually become more productive in a way because you don’t have time to waste time anymore once you have kids. All that wasted time goes away because it’s like you have to either work or be with your kid. And all the time you used to spend just kind of like low quality time. You don’t have time for that anymore.” So he said, “I’m actually more productive now that I have a kid.” So I feel that way that there are lots of things I want to be doing, but I just squeeze them into the other hours when I’m not with him.

Mark

So it’s like the law of constraint. I think that is, isn’t it.

Derek Sivers

Good one.

Mark

So let’s talk about--

Derek Sivers

Anyway sorry. Oh sorry. I don’t know, I feel like I might have accidentally derailed our conversation getting into really long answers about parenting. I don’t know if this is what you actually wanted to talk about.

Mark

This wasn’t. But this is the fun part of the podcast is we can go anywhere we want. But do you want to talk a little bit about the music industry? So what got you in? What did you do? And ultimately, I mean, you may be tired of answering this question, but I am curious about your exit and why you chose to give away all the money.

Derek Sivers

Sure. Well, those are some questions stacked up. When I was 14, I heard heavy metal guitar and it just spoke to my soul, and it was just like everything else dropped. I was actually into computers for four years before that. I got into computers in 1980. I was just actually yesterday reminiscing about the first program I ever wrote was saved on paper punch cards. This was before discs. My dad worked at Argonne National Laboratories. He’s a particle physicist and had big computers at work. And so I wrote my first program. When paper punch cards were the media storage format of the time. So I was into computers from 1980 to 84. But then I heard, I think it was Black Sabbath, and I was like, “Oh, I need that, I want that.” And so I just completely dropped computers and completely just picked up electric guitar and that was my life. And I just knew, like, “Okay, this is what I want to do. I want to be a musician.” So I was completely focused on that goal and and did it. I went to Berklee College of Music in Boston, got a degree in music. I was 20 years old. I moved to New York City, straight to the heart of the music industry, partially thanks to Mark Fried, who I mentioned earlier. He got me my first job at Warner Brothers, and I was in the heart of the music industry, 20 years old, and I was completely focused and completely driven to do it. And so--

Mark

Did that all come easy to you? Music, schooling, the job, the transition, moving to New York. Like when we go through these highlights of your life, it could it could appear that it’s like, “Wow, it all just kind of worked out.”

Derek Sivers

Well, I think when you’re determined, you’ll make anything happen. I think of the metaphor of like, if you say there’s a mountain on the horizon, and if you’re just walking towards that mountain, well, then there could be boulders or fallen trees in your way. You’ll just step right over them. You don’t care. Your eyes are staying on that horizon. You don’t care about the obstacles. Whereas people that are kind of sullen and aimless staring down at the ground, they’ll look at a boulder and go, “Uh, FML. I don’t know what to do now.” But it’s a mindset. If you’re completely determined and driven to get to your goal, then the obstacles just don’t even register. You just step around them. So to me it was easy, but it’s because I was so determined. You know, it’s kind of like a couple of years ago, I lost 15kg. What is that, 30 lbs? And somebody asked me how I did it and I just said, “Well, you just bump it up your values if it’s the most important thing to you, and if it’s really your top priority, you’ll make it happen.” Everybody knows how, you eat less then you exercise, whatever. It’s not the how you’re looking for. It’s just the priority. It’s the importance of it. So me becoming a successful musician. A great musician. Or at least very good was my top priority in life, and so any obstacles the world threw at me just didn’t even register. I just stepped around them.

Mark

I do want to keep going with your story about in the music industry, but. This is why you’re so fascinating. People love talking to you. You talked about the importance of priorities, right? So you’re climbing for that mountain. You have that goal. Congratulations on losing 30 lbs. That’s huge. I started working out five years ago and I’m about 50 lbs. I had lost 70 lbs, but I gained some back in muscle, hopefully.

Derek Sivers

Wooah 70?

Mark

Yeah.

Derek Sivers

Holy crap.

Mark

For my heaviest to my lightest was 70 lbs. About 25 from from there. But yeah. I know how much we can change. But it’s interesting because you talked about the priorities and we were having that huge conversation about being fathers, and you dedicate 30 hours per week to your son and to one on one time.

Mark

You prioritize him over work, even though it will come at a cost of slowing things down on projects not done as well. And so I’m already starting to pick up these little themes because it seems to me that that you may be really good at dedicating yourself to what you feel is most important and prioritizing that. Is that something that comes naturally to you?

Derek Sivers

Top priority.

Derek Sivers

Yes. My nature. I don’t know if it was this way when I was in the high chair, but maybe. My nature has always been to focus on one thing at a time. I just learned a new word a couple of years ago. Monomaniac, mono one, maniac, you know crazy about. Crazy about one thing. I’ve always had that. When I was five years old, we got a cat and suddenly I was completely into cats for like five years. So much so that, my teacher at school when I was nine years old called my parents in for a little meeting saying, “Derek really talks about nothing but cats. And every time we have a project, he draws cats and we write a story. He writes a story about cats. I just want to make sure you’re aware of this.” And I was totally into cats until 1980, when I got into computers, and I was totally into computers until 1984, when I got into music. Now that’s totally into music until 1997, when I started CD Baby, and then it was all about helping other musicians, and I was totally into that until 2008, when I sold my company. And deliberately forced myself to lift my head up. And I don’t know, one thing you could say I’ve been focused on since then learning. Anyway, so yes it’s--

Mark

Monomaniac I like because I always describe it as this-- like, I get obsessed about things. And I find context switching really hard. You know, I have way too many things on the go at one time because I’ve learned over the last year, especially that I’ve kind of had ADHD my whole life and not realized it. But if I have too many things on the go that are all priorities, that are all really important to me, I get really uncomfortable because frankly, I just kind of want to obsess about something like if we want to talk about gardening, then suddenly it’s like, I’m researching about soils and I just get so into whatever. And I make a crazy amount of progress because it’s so great to just be like, focus on this one thing. The downside is everything else in life becomes a distraction from this one thing that you want and need. And so what a great lesson. But okay, so let’s let’s go back. You’re now in New York. You’re you’re what a superstar right?

Derek Sivers

No. I did okay in music. I recorded an album that I’m proud of in 1995 when I was 25, 26. And it did all right. It got played on a few hundred college radio stations, and it sold a couple thousand copies, and it was when I was building a little website to sell my CD. That’s when I accidentally started CD Baby, because I just built this thing to sell my CD. But then my friends in New York City, my other musician friends said, “Yo, dude, can you sell my CD on that thing too?” And it was just by saying yes to friends that I accidentally started CD Baby, which then grew and became the largest seller of independent music online at the time. And this was from 1998 till 2008 when I sold. CD Baby is still going strong, I hear, but I left in 2008.

Mark

It’s in Portland, Oregon. It’s described as the Anti-label. Do you do you ever Google your old stuff or no?

Derek Sivers

No, no, not at all. I haven’t been to CD Baby in years. I don’t know who works there. I don’t know anything about it, but actually I don’t Google myself either. That’s funny, I know that used to be a thing, but anyway.

Mark

And so you built it up, and we can get through the rise and fall. But let’s get to the question I’m so curious about. So you sell it for $22 million right? Or that’s your share? Your share is 22 million.

Derek Sivers

No I was the sole owner. There were no investors. So it was just me.

Mark

Sole owner built it up from nothing. You sell it for $22 million. Do you come from money? Are you super wealthy? Were you really great at investing? Do you have a secret real estate portfolio somewhere that gave you passive income, where you could just give this money away, like you sold your company for $22 million, but you gave all the proceeds to charity?

Derek Sivers

Yeah. I mean, it was a profitable company. You know, it’s funny in the .com and tech company era, we’re used to this idea of companies not being profitable. Like--

Mark

They don’t make any money, they lose money. You have to have the exit. Because without that, there’s there’s no way for you to earn your money back.

Derek Sivers

Right? So no, this was just a traditional company. No investors. So by the time I sold CD Baby, it was already making like $4 million a year net profit after everything. So I had--

Mark

So you already had you had some money in the bank?

Derek Sivers

Yeah, I had millions and that was already more than I needed. And so when I had this deal to buy my company for $22 million. I had some soul searching questions like, what the hell am I going to do with $22 million?

Mark

Why did you sell, though? Did you want to get out of it? Did you want to change?

Derek Sivers

Oh, yeah. Oh, no. That’s kind of a sad story. People say congratulations, but no, it was a tragedy. The internal culture of the company was-- I think I had mismanaged it. I think I was a terrible manager and the culture turned horrible. It was like a mutiny. Even though I was the sole owner of the company, the employees, the people that I had hired, and a lot of them used to be good friends and slept at my house when they moved to Portland, were staging a mutiny against me and wanted me out because they were like, “Oh, we want to run the company the way we want to run it.” You know? “We need Derek to quit telling us what to do.” Meanwhile, I’m paying them every week, you know. Yeah, it was just awful. And I thought, well, there are a few things I could do here. Actually for about half an hour I shut the whole company down. It was late at night after they had had this big mutiny meeting, wanting to kick me out of my own company, and I just thought, “You know what? This isn’t fun anymore.” So I logged in to the web server and I typed the control apache control halt, and just shut down the website deliberately. And I thought about just replacing it, replacing every page of the website with a page that just said, you know, “Thanks, CD Baby has shut down now. Thank you for your business. We’ll be returning everybody’s CDs and goodbye.” And I while I was writing that text, it was taking too long and it was like after midnight and I thought, I just need to sleep.

Derek Sivers

Maybe I’ll sleep on this and think about this tomorrow. So I typed apache control start. So I booted up the web server again. But that was my emotional disconnect. That felt like, all right, I’m done with this. So then I thought of an idea like, okay maybe I’ll just move the whole company across the country. I’ll just fire everybody. Hire some moving trucks to move all the CDs. Rent a new warehouse, hire a new crew and fix this internal culture from scratch. Because I think it was just really a few rotten apples that spoiled the barrel. You know, that really does happen a few instigators can just turn happy people miserable. It’s funny that this whole like, “we’re upset, we’re angry” came just months after CD Baby was voted the best place to work in the state of Oregon. We’d won one of those big awards and months later people were, you know, revolution. So then I had the fun idea of doing it like Willy Wonka, you know? So if you remember the Willy Wonka and the Chocolate Factory story, he decides it’s time to hand over the chocolate factory to somebody else. So what does he do? He hides five golden tickets into five chocolate bars. So I thought, “Wouldn’t it be fun to do this in real life? I’ve got about 4 million CDs in the warehouse. Created by musicians that desperately want to sell more CDs. How about I hide five golden tickets into five CDs? And I will not tell anybody which CDs they are, and I’ll announce it to the whole world saying, ’Hey everybody! The new owner of CD Baby will be somebody who finds the golden tickets in here.

Derek Sivers

So come one, come all. Come buy some CDs. Maybe you’ll be the new owner of CD Baby.’” I really liked that idea, and I got a little down that path to make it happen. And then a good friend of mine said, “You know, Derek, the company is probably worth like 20 or $30 million. You know, you could also just sell it.” And I went, “Oh, that’s probably smart, isn’t it?” Instead of giving it away to some kid that finds the golden ticket, I was like, “Yeah, that’s probably a better idea. Damn it.” I really wanted to do that golden ticket thing, so I honestly hadn’t thought about selling. That just never entered my mind. So after Ariel Hyatt, that’s my friend who told me that I should consider that option, I said, “Yeah, okay, that’s probably smart.” I’d always had people wanting to buy the company. I always told them no. Like almost every month since I started it in 1997, I’d had people wanting to buy the company, and I ended up just telling customer service, like, don’t even pass those calls to me. Just tell them, no, it’s not for sale. I don’t need to tell them myself. So then after having this thought like, yeah, I should probably sell, like literally a few weeks later, three different companies in one week contacted me asking me to sell the company. And by default reflex, I told them all no. And then that weekend I went, “Oh, right, hold on. This is kind of what my friend said.” So then I called all three--

Mark

I forgot that I am selling the company.

Derek Sivers

And well, I mean, I forgot that I was considering that it, it’s like you have your default answer to things. So I called all three back and I said, actually, I might be interested. And then once I had a couple of offers, then I contacted Amazon saying, “Hey, you know, it feels like it wouldn’t be right for me to not let you know that this was for sale.” So then Amazon came in with a higher bid than everybody else. And I actually chose a company offering less money because I thought that the company would be in better hands. I felt that they understood my clients better than Amazon would. So I chose less money, which was 22 million. So to get back to your question of what to do with it. Then I had to get philosophical, like, “All right, I’ve already paid off all my debts. I have a few million dollars in the bank. I’m fine. What the hell would I do with $22 million?” It’s an interesting question to ask yourself in your diary.

Mark

But isn’t at a deep level-- I know this goes against your philosophy, but isn’t at a deep level more better, like you got a windfall. A few million is great, but 22 million back then especially, I think even today, it’s kind of life changing money you know.

Derek Sivers

Well. Think about it in a physical metaphor. Would you like a wonderful chocolate cupcake? Yes. Isn’t more better? Okay. Have three. Here eat 11 of them. No. In fact, eat 115 of these chocolate cupcakes. You know, soon you’re throwing up and and I say, well yeah, but you like those cupcakes.

Mark

I could use 70lbs.

Derek Sivers

I’m going to send a box of 30 cupcakes to your door every day from now. And in fact, I’m going to pull up a truck. I’m going to just give you 5000 boxes of cupcakes right now. Since you told me you like those cupcakes. There is such a thing as too much. It’s a mental disorder. We call those people hoarders. Those people that think that they need 75 of something when they actually only need one. And they fill their houses and cars with things. They never throw anything out. It’s a mental disorder and it’s not healthy. So no, I don’t think more is always better, especially when you know that there are people that really need the money. There are people that are literally dying because they can’t afford the surgery or the medicine, or dying because they can’t afford protection from the mosquitoes that give them malaria or whatever. And I’m going to just keep this money and buy a Ferrari and just--

Mark

I didn’t say that though. But you could--

Derek Sivers

I know, I know but I’m just thinking.

Mark

You could keep the money, you could invest it. You could take the proceeds and donate those proceeds and then take the tax write off and help with your other-- like, I don’t know, I know you write about utility mode and stuff like that, but like I go into like, why not use it?

Derek Sivers

Well, so that’s what I did. Luckily, my lawyer at the time that I was selling CD Baby had a background in tax law and he said, “Well, congratulations. The deal looks like it’s going to happen. What are you going to do with the money?” And I said, “I’m going to give it away.” And he said, “Are you serious?” And I said, “Yeah, very serious.” He said, “Very, very serious?” I said, “Yeah, completely serious. I’m going to give it all away to charity.” And he’s the one that suggested, he said, “Well, if you’re definitely going to do this. We could structure this deal differently, transfer CD Baby into a charitable trust now. And then the charitable trust will sell CD Baby to the buyer. Not you personally. So that way, instead of them paying you 22 million and you paying 7 million taxes and only giving 15 million to charity, if you transfer the company into a charitable trust, the entire 22 million goes to charity and never touches your hands.” And I was like, “Yeah, that’s what I want. Never touches my hands.” So that’s what we did.

Mark

Now, when you started to make serious money because as you mentioned, the company was throwing off profit and cash, did money change you at all? Did you see yourself changing?

Derek Sivers

I’m such an asshole now.

Mark

No, I don’t mean that.

Derek Sivers

I had a girlfriend that was very skinny. And I’m saying this because she didn’t understand why people were always counting calories and worried about what they ate, because just her DNA was that she was just skinny, you know? So was her grandmother, so was her mother. And she was like, “God, why is everybody so worried about what they eat?” I was like, “Because, you got to understand, most people aren’t like you. Most people have to be careful what they eat. You seem to never gain weight.” So I think having a lot of money feels-- I think about her like that. I’m like, “Why do people care what things cost? So what if the cost of cheese went up? Who cares? Oh, right. Yeah. Most people--.” So I think that’s the only change that I felt in life. Is suddenly everything felt free, if you know what I mean. Like if if something costs $0.05, you think of it as free. But once you have millions of dollars in the bank, something that costs $50 feels free, maybe even 500. Like it just doesn’t even put a dent in your bank account. It helped that I had both a role model and an anti role model, right before I sold my company, a friend of mine sold his company for $30 million like a year before I did. And I got to watch the way he lived and what he did that I liked and didn’t like. So I think I was kind of mentally rehearsing it a little bit like kind of watching him. So when it happened to me, I was a little prepared, so I didn’t go do stupid things.

Mark

What mistakes did he make in your?

Derek Sivers

It’s a trick question because what I thought was the biggest mistake. He whimsically bought a $10 million house in central London. And the reason I never wanted that $22 million to touch my hands. The reason I wanted it to go straight to charity, is because I was afraid that I might do something stupid like that. And that was the main reason I structured the sale, so that the money never touched my hands because I thought, I don’t want to have $20 million to my name, because if it did, I might do something like that and buy a house because it’s only $10 million. I said, “God, I hope that I’d never do that.” Well, the joke’s on me because we’re still friends. And I talked to him a few years later. His $10 million house in London is now worth 30 million. So maybe I learned the wrong lesson from that, I don’t know.

Mark

But I think your lesson is still holds true. Does anyone really need a $10 million house when you can get by on like a 7 or $8 million price, right?

Derek Sivers

Actually, I’m working on this right now here in New Zealand. I bought a dumb little piece of land off grid. There was like an auction. I just put in a low offer, a ridiculously low offer, and I was the only one that bid. So I won a little piece of land here in New Zealand. And I was thinking about what to do with it, and I could put the home of my dreams on it. And I have spent so many hours thinking about what that would be, or how I should approach this, until I very slowly realized that the home of my dreams was, or what I was calling the home of my dreams was trying to live up to some ideal of what I felt I should be wanting. Because honestly, I spend all of my time in a tiny little room like I guess three by four meters and I just work basically every waking hour that I’m not with my kid. And when I’m with my kid, we go out. We don’t hang out in the house. So really, my dream home is tiny. And just last night, I think I was making a decision to buy a little prefab well made, well insulated, ready to go tiny home. And that’s what I will put in my piece of land and become my home.

Mark

That’s brilliant. I’m a car guy. I don’t own a lot of cars. Because, frankly, I don’t go anywhere anymore. Like I used to drive a lot, right? I used to drive 35, 36, 37,000km a year.

Derek Sivers

Which, let’s just say if you drive a lot, then having a good quality car makes a massive, massive difference in the quality of your life. Like they say, excuse.

Mark

That used to be my excuse with my wife.

Derek Sivers

But it’s not even an excuse. That’s smart because they say that the things that are closest to you physically are the things that you should splurge the most on quality, have the best quality shoes, have the best quality mattress. These are the things that you spend most of your waking life in or sleeping life, most of your life in your your shoes, your mattress. Things like that should be high quality. So yes, if you’re driving that much. It’s thoroughly rational to splurge on the best comfort for your car. Sorry.

Mark

No, this is actually helping me because I’m realizing as I’m talking to you now, that’s a past version of me. So last night I’m out for a walk and I see this truck, and I’ve got a truck. It’s a good truck. You know, it’s a 2016 and it’s it’s okay. But I used to drive so much that I would replace my vehicle every 2 or 3 years. And it would always be like an expression of me. And I’d get to pick it would be something different. And it was fun and it was exciting. And now I’ve had this truck 7 or 8 years and it’s super functional because all I do is go to the grocery store or to the gym or to like Home Depot, like, that’s pretty much my life. But I’m walking by this truck and I’m like, “Man, that’s a good looking truck.” And it’s like, should I? I’m like, “Oh, maybe next one. But do I need to spend $100,000 on a new truck when there’s nothing wrong with my old one? But not only that, this new truck isn’t really functional for my family of six, so I think I should probably also like-- I really kind of want a Jeep though too, because they’re convertibles and they’re standard.”

Mark

And I was like, “Well, if I could get a new truck and a Jeep. But those are both like they’re kind of bigger things. And it’s like, you know, I want a little sports car for my wife and I to go out on date nights with.” And here’s the other thing about me I own a motorcycle and I have dirt bikes with me and the kids. And I don’t go anywhere right. I caught myself going, like I could figure out a way in my life to buy all these things, to pay for the insurance, to somehow store them, you know, in my garage, or build some new garage or driveway or something like build something to store all these things just so they could depreciate in value and not actually add anything to my life. And I was like, but I really want them. And then I hit this thought. I texted it to myself, just because you want it doesn’t mean you get it, doesn’t mean you need to work for it. Because I’m an entrepreneur, so I’m always like, okay, if I want it, let’s work, let’s get it. But I’m like, I don’t have to have these three vehicles and I don’t have to work towards them, and I don’t have to do any of this stuff.

Derek Sivers

Right. And in fact, now you’re going to be a maintenance man for these three vehicles. Now, it’s like you’ve go to steward these things and, and take care of them and house them and--

Mark

Well, ideally I’m also going to hire a personal assistant to help manage all this stuff because we keep adding my wife and we keep adding, adding to our lives.

Derek Sivers

And now you’ve got to employ somebody to take care of the stuff you bought. Like, what are you doing? God, this is so-- I never talk about this, but this question is on my mind so much. It’s a messed up thing to have the ability to buy anything. And then have to be philosophical about what’s worth doing. That was my second book. Hell yeah or No.

Mark

That’s how I make-- and what a great book. Let me just say, if I can please. What a great book. And this isn’t a real problem to me. And yet it’s something that I have to constantly wrestle with. It doesn’t feel like a justifiable problem when there are so many more important problems to have.

Derek Sivers

See, that kind of thing that you’re talking about right now is kind of the root of philosophy for me. That thinking about these cars for you. Like, what’s the real point? Do I need them to get somewhere? No, I have something. On the other hand, would they bring me so much joy that even though I don’t need them? That that’s what’s life is about. But then you’ve got to, like, really balance for yourself. Like, how much happier would it make me to have the nice shoes, even though my existing shoes work? Or the nice Jeep when my existing vehicle works? Because you might still make the decision, say, like if you love bicycles and you ride bicycles a lot and there’s like a a new Trek bicycle that the people in the ebikes say is the best e-bike on the market. And at least here in New Zealand, it’s $17,000. And I remember looking at that going like, if I really cared about bikes, that’d be interesting. But I don’t care that much. I have like an old steel bike. That’s fine that I hardly use. So even though I could do it, why would--? And then you’ve got to ask yourself, what’s more important? Because if you buy a thing, you’re going to put some hours into it.

Derek Sivers

But is the hours spent on that thing perhaps better spent with your kids and not having the thing and just letting it be something you go, “Yeah, now I know that there’s a really nice Jeep out there. I can just be happy to know that exists. Maybe I can rent it for one night, find somebody who’s renting it, and I can spend a night driving that Jeep.” And then you get into questions of identity. Like, is it that I just think of myself as the person that has that Jeep? And if that’s so, is it for telling other people that I have that Jeep? Do I want other people to know that this is who I am? Or is it truly just for me? Like, would you still buy that Jeep if nobody but you knew you had that Jeep? And if so, then what’s that about? Why do you think that your identity is based on a thing? Which is my favorite comeback? When the Instagram hashtag “Look at me. I bought a car.” I’ve always thought, well, any idiot can buy a car. Just go with your credit card. You say there. Now, I’ve bought the car. That takes no skill at all. What takes skill?

Mark

But it is an achievement for those .who have worked towards it

Derek Sivers

Maybe paying it off would be. I think there are a lot of people who put the car on their credit card just to--

Mark

See, here’s the thing, I buy all my cars for cash, which is actually apparently terrible. I’ve been taught that you should never pay cash for depreciating asset, but I don’t know. We buy everything for cash, so if you have the money, we buy it. If we don’t, we don’t.

Derek Sivers

Okay, see, that’s an example of two different very wise people. I’ve read authors on money. Oh, boy. What’s his name? The philosophy of money. I’d recognize his name if you said it. But also the one I just read, William Jay Bernstein.

Mark

Morgan Housel “The Psychology of Money”.

Derek Sivers

Yes. Thank you, Morgan.

Mark

If anyone wants to know of all the books Derek’s read, go to his website because he has a whole list of books there.

Derek Sivers

Sive.rs/book singular. You will see my list of the last 400 books I’ve read since 2007, with detailed notes on every one.

Mark

Even older actually, because The Art of Profitability, which was like, “You’ve read that, that’s in such a great book.” I think you referenced it to 2005.

Derek Sivers

Oh, okay cool. So 2007 is I remember where I was when I started taking notes. So that’s when I started taking notes in 2007 anyway. But both Morgan Housel and William Jay Bernstein, both brilliant authors on the subject of money and investing. Separately in their respective books, said that even though it may make rational sense to take on debt. That they just choose to pay things off, that they emotionally like the way it feels better to know that their debts are paid off. So they say, even though I could earn more money by getting a mortgage than investing the money myself, I would rather just have my debts paid off. And ultimately it comes down to how you feel. So I feel the same way. Pay it off. Pay cash.

Mark

When my wife and I bought our first place a little semi-detached. We closed in August of 2008 on our first house. And that was right before the recession. And we we made sure to try and get something much lower than the banks told us we could afford. We had a really small mortgage, which was very helpful because when the recession happened, my company was making no money for like a year and a half. But that $300 mortgage payment or whatever it was, which is again, very small. We had to scrape to get by. But a few years later, you know, the company turned around and we started making better money. And so I think we were like 29 or 30 and we paid off our mortgage. And it felt so good. Like it felt so good to be like, “I have no debt.” I always like to preface this with I realize how privileged we are that that I worked and then went to school and used the money I earned to pay for my school.

Mark

So I graduated with zero debt. And then I worked and worked and worked and worked and worked and worked and worked. And we paid off that debt. And then my wife’s like, “Let’s buy a new place.” So nine years now, we’ve been in this place. And I’m glad we got in when we did because the market’s gone crazy. But I’m also in the situation where I was like, I think we could pay down our mortgage more aggressively if we wanted to. But it doesn’t make any sense. Like what you’re saying. Like there’s two different things here. Like, it just doesn’t make any sense for me to do that rather than take whatever money we could pay it down with and just invest or do all these other things. But it feels so good to not have to make the mortgage payment and to know that you own your place and to know you are debt free and all of that stuff. It just feels so good.

Derek Sivers

Yeah. And to me, everything comes down to that feeling anyway, right? Like everything we do, the reason you’re doing this podcast, the reason you buy a truck.

Mark

I thought you were going to say a Jeep.

Derek Sivers

Yeah, I was trying to switch it up. So it all just comes down to how you feel anyway. And then what’s weird about that is that you can manipulate how you feel just by thinking of things philosophically and choosing a different angle, like choosing that, say, with your business. It makes you happier to be generous. Than it does to be profitable. That can completely flip the way you run your business. Actually, since we’re talking about homes, want to hear an uncommon preference of mine. I really like moving every year or two. I really enjoy it.

Mark

That is-- I mean, I understand maybe you like change or whatnot, but moving is the worst. I mean, unless you’re a minimalist.

Derek Sivers

I don’t have any stuff. So for me, moving takes an afternoon. I mean, there’s no stuff here, so, yeah, moving takes an afternoon. I really like moving to a new house. I mean, I really would prefer to move countries every year or two, but for now, since my kids in school and his mom works at the government here and she can’t move. I really like moving houses. And I’m really glad of all the different--. Like I don’t value stability. Stability to me is way down my value list. In fact, I think it’s maybe in the negative. I do not value stability. Stability, to me feels like something’s gone wrong in my life. I’d like constant change, learning, growing new experiences, all that kind of stuff. Anyway but once you know that you have this value system, once you realize this in yourself, like, okay, I like moving every year or two, it helps shape so many other decisions because now any time I think about what was it. Just last night I read about this thing, I needed to steam my jacket and I was like, “Okay, do I need a portable handheld steamer?” And somebody said, “Well, ideally you should invest in a steam closet where you could hang your clothes and and close the door, seal it tight and it steams them overnight.”

Derek Sivers

So I thought about that for a mere two seconds before I realized that would make it harder to move every year. That would be a big thing. I couldn’t move that to Dubai. I couldn’t move that to Brazil. It would be stuck here. Whereas if I get the portable steamer, I can bring it with me to Dubai, in Brazil and Finland and wherever else I move. Therefore, I will be getting the portable one. So once you know that you have a certain preference, you can shape all the decisions along the way. My sister, on the other hand, she’s only two years younger than me. Her top value in life is stability. She loves having this house and luckily her husband agrees. They have three kids, two dogs. They’ve been in the same house for 30 years. It makes them deeply happy. Good for her. So her house is filled with stuff because they know that they’re going to stay there forever. Like this is this. This is the house we’re going to die in. That makes them very happy. So you have to know your own values. Don’t try to adopt other people’s values just because they are glorified and famous. You have to know for yourself what your values are and then shape your own life decisions accordingly.

Mark

There’s a chapter in Hell Yeah or No where where you talk about like if you know that you want to be wealthy. Then first, like admit to yourself you want to be wealthy and then start doing the steps that’s required to become wealthy. And I think you mentioned that in reference to like, hey, you spent time in Hollywood and the people who have the most fame, i.e. attention, don’t have the most money and the richest people in Hollywood, you would have no idea who they are. Because if you want fame, then you have to just work so hard constantly to get the spotlight and get the attention. Whereas if you want money, it’s something else. And I think the more freeing thing though, in the whole lesson is like, just be comfortable. Like it’s okay to want what you want and not to judge yourself perhaps for that.

Derek Sivers

Right? Because no matter what your preference, somebody’s going to tell you that you’re wrong, somebody’s going to attack you for it and say, “You jerk, you idiot, that’s wrong. You shouldn’t want that. You should want what I want. Let me tell you my values.Those should be your values.”

Mark

You shouldn’t want to move all the time. You should want to live in a place for 30 years and collect a bunch of junk like I have.

Derek Sivers

But I mean, any values. I mean, even if whenever I say that I’ve given some money to charity because even after selling my company, even now when I sell my books, I give that money to charity too. So I’ve given over half $1 million to the Against Malaria Foundation from selling my books and there are people that come out and say, “You idiot, that’s stupid. It’s irrational. You should spend that money on...” And they tell me what I should be doing with it. And on the other hand, when I set up that charitable trust, it pays me out my living expense. And there are some people that tell me I’m wrong for having that. They’re like, “You jerk, you’re keeping that money. Why didn’t you just--.” So no matter what you choose, you’re going to get attacked. People are going to tell you you’re wrong and stupid. And so you just have to have a secure sense of who you are and what your preferences are and just understand that you’re going to be attacked no matter what.

Mark

Now, the reason I love this book list on your website is one. I mean, I got a little thrill each time I would scroll and be like, “Oh, I’ve read that book. Oh, I love that book too. Oh, I’ve read that book.” Because, you know, it just makes me feel like, you and I are both cool people who’ve read all these books. My life has changed quite a bit since I’ve started following this new rule I gave myself, which is if someone I respect has written a book or read a book and liked it, then I don’t question it. I just buy it and read it. So Ryan Holiday, in at the end of one of his audio books, is talking to Tim Ferriss because Tim produced the audio versions of Ryan Holiday’s books, and they’re both kind of just quickly rhyming off. They’re like, “Oh, like Small Giants. Oh, I like this book. Oh, I like that book.” And I’m like, just taking notes. And I’m like, “Oh, I got to read these.” And then I do, and they’re just mind blowing how much effort authors put into giving you all of the things that they’ve learned, and that you could buy it for like 15 or 12 or $30. And all I have to do is just listen to it or read it, and it’s all there. Blows my mind. Where I’m going with this is I’m curious. And you don’t have the list in front of you, and that’s fine. What are the books that you believe have shaped you the most?

Derek Sivers

Ooh. Number one by far without question. Tony Robbins Awaken the Giant Within.

Mark

Really?

Derek Sivers

Because it matters when you read something. So yeah, Tim and I talked about this, that he read The Magic of Thinking Big as his first self-help book when he was a teenager, and it changed his life. And then by the time he read Awaken the Giant Within, he was like, “Uh, no, no, no. Not great.” And so I had the reverse. So I read Awaken the Giant Within as like my first major self-help book, and it blew my mind. And then when I met Tim in 2007 and he was telling me like, “Oh, man, The Magic of Thinking Big, that’s the one that changed my life.” I was like, “Ooh, I can’t wait to read this one that changed Tim’s life.” And I read The Magic of Thinking Big. I was like, huh? Same old shit. But it matters which one you read first. So yeah, to me, Awaken the Giant Within is a flawed, messy book, now full of very outdated references to O.J. Simpson and Michael Jackson and Enron and whatnot. He wrote it very much to be timely in 1989 or 90. But man, I read that book when I was 19 and again when I was 21 and again when I was 23, and it shaped the way I see the world so much.

Derek Sivers

That I didn’t even realize how much it’s shaped the way I see the world. Kind of like people don’t realize how much their religion shapes them, right? Like if you talk to somebody in India that was brought up Hindu, that all their friends were Hindu and just everybody’s Hindu. And if they’re talking to somebody who just grew up Christian and everybody around them is Christian. They don’t even realize, like to them it’s just like, well, duh, this is the way the world is. I mean, you come back again and you know it’s the karma. And that’s why, you know, the woman in poverty is the way she is because she did something in her past life. Obviously, that’s just how life works. But then you compare it to somebody else with a different worldview and they don’t realize it’s their books that have shaped their view. Like, none of these things are real. None of these things are absolutely, positively, undeniably, objectively true. It’s just the filter. The perspective that their religion has given them. So that’s what Tony Robbins Awaken the Giant Within did to me. It was like my religion without realizing it, because I ingested it at such a formative age that the whole way I see the world is shaped by that philosophy.

Mark

Thank you. What a great story. And as you were describing that, I was thinking, you know, this is just a few years ago now. And I’ve read some self-help stuff earlier, but Marie Forleo’s Everything Is Figureoutable. Which I think came out in 2018 or 19, but I remember downloading it. I remember she was on Tom Bilyeu’s show Impact Theory. I heard it, I liked it. I downloaded it and it gave me permission to make mistakes as a recovering perfectionist. And then I was lucky enough last year I think I was at my Let’s Book launch helping behind the scenes with some stuff. And Marie was one of the speakers there and I kind of pulled her aside and said, “Listen, I hope you don’t think this is unprofessional, but I just wanted to say, like, how impactful your book was for me and how, you know, this story and this story and this all shaped it and everything. I don’t know if I’m breaking the rules because I’m not asking you to sign it or anything, but just thank you.” And she gave me a hug.

Mark

And she’s like, “No, tell any author you meet. Like, if you ever meet anyone who’s written anything, tell them if their book has helped, because they never get tired of that.” I know that there’s a book for a different time. You know, I have I have certain books where I’m like, I need like, the Subtle Art of Not Giving a F*ck. I started it and it just wasn’t for me. It bounced off me. I was like, “This is too cliche. There’s too many swear words like, I get it already. Like how many times can we say fuck? Like I get it.” And it just didn’t do anything in about a year and a half later or whatever, I was like, “Oh, let me circle around on this thing. And I was like, this is the greatest book ever written.” So I know that there was timing, but I’ve never really considered how the books that introduce you to something, I guess like music, right? You’ll remember that Black Sabbath was that song or that artist that got you into it. Whereas if you heard something else, it would have been that.

Derek Sivers

Great comparison. Yeah, that Black Sabbath song does nothing for me now.

Mark

And that’s okay. Because you’re allowed to change what you like, right?

Derek Sivers

Yeah, yeah.

Mark

Oh very cool. Thank you so much for your time and for jumping on the podcast with me. I do have one final question for you before you go. At the end of the day, what does it all come down to?

Derek Sivers

I was thinking how fun it would be to completely change the tone and say, at the end of the day, you know, really all comes down to you buying my book everyone.

Mark

Yeah, money.

Derek Sivers

At the end of the day, buy my book.

Mark

But we know that’s going towards, you know, mosquito nests or anti-malaria medication. So you could do the like, “For every book that we sell, we help one more person in need. Let’s get some books sold, people. Let’s go.”

Derek Sivers

But, you know, that’s a messed up motivation. That’s a fascinating subject of what was it? Daniel Pink had the book called Drive that dove into people’s motivation, that if somebody’s doing something, like if they’re volunteering at an organization and doing something nice and charitable and generous, and then you offer to pay them. It completely changes the incentives, and then people start to complain more about their work because they’re internally representing it as something they’re doing for the money. Whereas if you give them no money at all, they internally represent it as something they’re doing to be good. So I actually hate when people say, like, buy this book because it gives money to charity or donate to my walk across Illinois because it’s going to raise money for breast cancer or whatever. I just think, well, no, no, no, no. Like if you want to give money to cancer research, then give the money. And if you want to buy this book because it benefits you, then get the book. And it’s so messed up when people braid those things together. Sorry. Your real question was at the end of the day, what does it come down to? Is that the question?

Mark

It was. Yeah.

Derek Sivers

Let me think. I think everybody has their own answer. I think at the end of the day, if I can think of something universal for everyone.

Mark

No, no. It could just be for you, even.

Derek Sivers

I know, but I do these podcasts for the listener. I don’t really need to talk about myself.

Mark

I do these podcasts for me. I’m just joking.

Derek Sivers

I think anybody listening to this, the what it comes down to at the end of the day is, to try to shut out the noise of the world, to think of it as input, but detach from it a bit. And spend some time with yourself, whether it’s in a journal or just sitting there thinking or talking to a friend about what really matters most to you. To me, the most interesting bit of this conversation, besides the high chair personality thing, which was fascinating, was this thing about the Jeeps and the trucks and this desire to have more or have that and how philosophical that gets. To question why you even want something. Why you’re even on social media. Why you put yourself out there. Why do you go to work? Why are you doing this? Why do you want to get married? Why do you want kids? We do so many things just by default, or because other people have told us we should value this. And I think we can feel a such discomfort in our gut. Or such as like molasses, kind of drain of energy, that everything feels hard. And I think it’s because we’re living a life that isn’t really our life. We’re trying to live someone else’s life. We’re trying to walk other people’s talk. Whoo, I like that. I’ve never said that before, I like that. And you just feel the friction of that of like your natural nature might be this way, but you’re trying to make yourself go this way because people tell you that that’s what you should be valuing. So at the end of the day, to answer your question, what it all comes down to, I think, is knowing yourself well enough to walk your own path. To go with your nature, and then you’ll just find that everything flows easier. Because you’re doing what suits you. I’m glad you asked that. I was not expecting to go there. Thank you.

Mark

That’s the final word we leave on.

Derek Sivers

Thank you.