Tribe of Millionaires
host: Jamie Gruber
moving abroad, philosophy of values, selling my company, timeless teachings
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Transcript:
Jamie
Derek, it’s a pleasure. Thanks for being here.
Derek Sivers
Thanks, Jamie, I appreciate. Audience before we hit record, Jamie told me that my podcast long ago with Tim Ferriss was one of the first podcasts he ever heard. And that was a huge honor that to be here.
Jamie
Yeah, well, the pleasure is mine, truly. And yeah, just sharing that quickly. Like, you know, being stuck in a job back and then hearing this guy on this podcast talk about this other life and then in some ways moving abroad, taking steps to get out of a corporate gig and do what I’m doing and everything. A lot of it rooted back to honestly listening to that episode. So it’s been life changing literally. And yeah man, always grateful. Truly grateful to have you here. This is a fanboy moment for me. This is a big moment for me to have you on.
Derek Sivers
Thank you. I like that, that chain keeps going. You know, there are people that I aspire to or whose life decisions made a concrete improvement in my own as well. Some of them, even if they think that they’re no big deal. But this guy, Leo, I don’t know how to pronounce his last name, Babauta. From minimalist Zen Habits. And he was living in Guam and he was a popular blogger writing about minimalism from Guam, and just knowing that he was doing that from Guam is part of what gave me the confidence to move to New Zealand, you know, because it’s like, well, Leo did it. Leo did it from Guam. I can do it from New Zealand. And I just love how random people’s lives can make a real influence on our own.
Jamie
When was that? When did you read that blog? Was that when you were in your business?
Derek Sivers
No, that was probably 2009, 2010. I had just sold CD Baby. It’s funny. You know, somebody recently asked me if I always journal as much as I do and question everything as much as I do. And I said, “Oh yeah, I’ve always been like this. Yeah, ever since--.” And I went, “Huh? Wait, no, I haven’t always been like this.” It’s really since I sold my company, I think there’s something to this idea of the philosopher king that when you’re surrounded by so much work and so many things you have to do, you don’t have time to be philosophical man, you got shit to do. You got to keep your head down and just keep working. And it’s only later when you’ve arrived at whatever that means for you, and you suddenly have more time on your hands, and then you can start to go like, “Huh? So what now? Or what does it mean? Or I could do any one of a hundred different things. Now what do I really want to do? What’s worth doing? Who am I? What matters to me? What are my values?” And it’s no wonder that a lot of philosophers throughout history have been rich. They’re the ones that have the time to sit and think about all this crap.
Jamie
That’s interesting. So let me ask this. Are your teachings I think about hell yeah or no. One of the things I remember, I don’t know if it was from the podcast or from something else you talked about was the story, which maybe we can share at some point of slowing down for the same result. I love that-- I’ve told that story a million times of you riding the bike in San Diego, up and down this beachy strip or whatever. But anyway, these lessons that you teach, these things that you teach, are they applicable to somebody on the other side of an exit or on the other side of some sort of financial windfall, or are they teachable, or are they applicable for the starting 20 to 25, 30 year old, whatever that might be?
Derek Sivers
I try to only share things that feel timeless. Not necessarily universal, but timeless. So say, if I’m talking to musicians about what I’ve learned about marketing your music, because I ran a music distribution company for ten years, I don’t go into the specifics about like, “Hey, go to this website and click that and you’ll get an 11% conversion rate.” No, like that’s too specific. And you know what? There are plenty of other people talking about specific, timely current nuts and bolts. So I’m only interested in the things that feel like timeless principles or the morals or the philosophical different ways of looking at things so that we can think of things differently. Whether you’re listening to Jamie’s podcast in 2023 or you’re listening in 2033 or 2053, I don’t know, through your hologram beamed into your neurons, then I want it to be still applicable to our life, in the same way that we can go back and read books from the 1970s or 1870s, and it can still apply to our life today. So I try to only stick with the timeless.
Jamie
Let me dissect this a little bit. I wrote down a whole bunch of stuff and I wasn’t sure exactly where we’d go. But this is interesting. I love how you know this concept and correct me if I’m wrong essentially is look, “If it ain’t like, fuck yes, like I want to do that, that’s absolutely lighting me up. Then just say no, it’s not-- yeah, that sounds good. But just say no.” But at the same time, a lot of what you have done in your career, a lot of the things that you’ve said yes to like, “Hey, my buddy wants to sell a CD on my website.” Like, that sounds good. Feel like they were incremental yeses. When do you turn off the incremental yes. And turn on the hell yeah.
Derek Sivers
I’m glad you asked because yes, I wrote a catchy blog post called “Hell Yes or No”. And it said, “If you’re overwhelmed with too many opportunities, if you’re spread too thin because you’ve been saying yes to too many things, then consider taking this approach. If you’re feeling anything less than a oh my god fuck yeah, count me in. Anything less than that, just say no. Which means you’re going to say no to 99% of everything. But it will leave some space in your life. So when the occasional rare amazing thing comes along, now you’ll actually have the time. To throw yourself into it and kick ass instead of being spread too thin and trying to half ass too many things.” That’s all I said. But it had a catchy title and people liked it and it spread far. The problem is, a lot of people have said, “Oh, hey, man. Hell yeah or No, I love that man. I use that for everything. That’s my approach to everything. Now, I just got out of college and I’m just saying, hell yeah, no to everything.”
Derek Sivers
And I’m like, “No, no, no, come on, man, it’s a specific tool for a specific situation. If you’re overwhelmed with options, it is definitely not the right thing to do when you’re straight out of college. And you don’t know what your hit is going to be, right.” Opportunities can be like lottery tickets. The more you buy, the better. Especially if they’re free. You never know what’s going to hit. So earlier in your career, it’s a better strategy to say yes to everything. Do it all. Meet everyone. Pursue every opportunity you hear about, run yourself into the ground doing it all. And then when something starts rewarding you when the world says yes, that’s what we want. And people are opening up their wallets to pay you for something and it’s something you enjoy. Then you start to let go of the other stuff and double down on that. And even then, only when you’re overwhelmed with too many things, that’s when you need to basically raise the bar all the way up. That’s what Hell Yeah or No is saying. It’s just raise the bar all the way to the top. But yeah, specific tool for a specific situation. Not for everything.
Jamie
No, that makes perfect sense. I want to get into some of these labels that I mentioned. So these identities, these things that you’ve been and that you are now in a moment. But on that topic, just to kind of close this loop as a 42 year old guy at one point walking away from a big job. People ask me, “How do you do that? Like, I’d love to walk away from my $400,000 a year job, but I can’t see the path out.” And I always say, well, you got to try different things, kind of those little yeses to your point. So what I heard you say is, early in your career, you got to take the little yeses, and I agree. I always say like a 20 year old or 15 year old doesn’t know if they like sushi until they try sushi. You got to say yes to little things and determine what you like and don’t like, but we don’t give ourselves permission to do that at 35 or 40 or 45. It’s like we have to know before we move forward. We have to know that, hey, I spent 17 years in high school, elementary, high school, college. I spent 17 years in a career. The next decision needs to be the 17 year decision, and we don’t give permission to ourselves to make that one year decision or six month decision and then pivot. Go ahead.
Derek Sivers
I totally disagree. I think it’s kind of like market testing. It’s like you never know what idea is going to be a hit with the world. And so you just keep putting them out there, like those people that challenge themselves to come up with 99 business ideas instead of one. Same thing with songwriters. You know, I was in music for a long time, and it was a little tragic when you’d see somebody that had written one song that they believed in this song so much because they wrote it for their mother before she died, and this song means everything to them. And they would go around Hollywood trying to pitch that one damn song. But nobody likes that one song. And on the other hand, you have these songwriters that would just write a song every single day, you know, 300 songs a year. And hey, every now and then one turns out to be a hit. And I think that’s a better strategy. A better success strategy for the world, because you don’t know what’s going to resonate with the world, or even just the zeitgeist of the times. What’s going to stumble into the right place at the right time. So I think at any age it’s wise to just try things to see what works. That’s not something you only do when you’re young.
Jamie
I love that and I completely agree. I mentioned in the beginning author, speaker, all these different things that you are or have been. What are the labels or identities that you most resonate with today.
Derek Sivers
Ah right now really only writer. Anybody listening to this, if you are feeling like you have many adjectives and you’re not sure which label is the right one for you, ask yourself, who are your heroes. This made a big difference for me. I thought of myself as an entrepreneur, a programmer. I don’t know, maybe 1 or 2 other things. But then I realized that my heroes, if I ask myself, who are my heroes. My heroes were all authors. It was the people that were writing these books that were blowing my mind on a weekly or monthly basis. It’s one of the greatest joys of my life, is to read a book that makes me think about life differently, and suddenly I’m like going, “Whoa!” And I’m thinking about my whole past through this new lens, going, “Oh my God, this changes everything.” It’s like I walk out the door, like you know, when you saw the movie The Matrix for the first time and you walk out going, “Whoa, everything’s different.” You know, I love that feeling that a book can do to you. It’s like, these are my heroes, are these authors that change my mind so literally.
Derek Sivers
And ha, that has double meaning. And so I realized, wow, if these are my heroes, that means this is the direction I’m facing and this is who I want to be, because those are my heroes. So therefore I don’t worship entrepreneurs. I don’t worship any programmers. Minorly I do, there are some programmers that it’s like, wow, you know, marvel at their skills. So right now I had to redefine and prioritize and realize that I’m a writer that loves programming as a hobby. And that’s it. I’m not an entrepreneur anymore. I haven’t started a business really since 1998. And that’s why when people ask if I will do an interview to tell my story about how I started and grew and sold CD Baby, I say, “Nope, I will not talk about that anymore. That is so fucking old. I’ve been there, done that. I published a book in 2011 so that I would never have to talk about that subject again. I told my story. It’s in writing there. Please don’t make me tell that it would kill my soul.” So I’m not really an entrepreneur. I’m just a writer. Long answer, short question. Sorry.
Jamie
It’s a great, great answer. Can we play a little game here? Are there three authors that jump to mind that are heroes of yours right now, or 2 or 4, whatever number you want to come up with, that’s your call. But I’d love to hear a why behind each one. If you don’t mind naming a couple and saying why.
Derek Sivers
Sure. Mark Manson, I think is the best writer out there today for the genre. I like.
Jamie
What’s the genre?
Derek Sivers
This kind of pop philosophy. Accessible philosophy. Non-academic philosophy. Applicable philosophy of your life. I love his thinking. And I especially love his writing itself. I think he writes in a way that, in my opinion, like can’t be improved. Whereas I think all of us know the experience of reading a 300 page book. And you just read it going, “This could be an article.” You know, that’s the worst feeling, a 300 page book that really should have been like 30 pages. But they puffed it up to impress the publisher and get it on the shelves. So Mark does the opposite, and I aim to do the opposite, which is every word needs to be there. My books are so damn succinct because my rough drafts can be a thousand pages, but then I’ll edit and edit and edit for like a whole year until I’ve got it down to 100 pages and I’m like, “There we go. Now every word needs to be there.” And that’s a better feeling. Okay, so number one, Mark Manson real quick.
Jamie
Real quick, “The Subtle Art of Not Giving a Fuck” that’s his most notable book right?
Derek Sivers
Yeah. Exactly. That’s his most famous. But everything he’s done since then is great too. He wrote the biography of Will Smith, which came out right before the slap.
Jamie
Incredible book though I love that book.
Derek Sivers
Yeah, yeah. So he he wrote that. And it’s funny because I know his voice well enough. I can tell where it switches from, what Will is saying to what Mark is saying anyway it’s subtle, but Mark Manson, favorite writer. Let me name a couple of others. Seth Godin, we all know. Seth walks the talk. He’s an amazing human being and I really admire his writing. Sharon Kaye, the book is called “Philosophy: A complete introduction”. Dude, that is the most clearly written book I think I have ever read in my life. I’ve read a few different introduction to philosophy books. Her writing is astoundingly clear. She can make a boring subject fascinating and riveting and easy to retain. Clearest writer I’ve ever met, so I emailed. What I always do is when I love an author’s books, I email them to let them know. So every time I finish a book and I think it’s great, I go find their email address and email them and say, “thank you. That was wonderful. That was amazing.” And then put the the book notes on my website. Anybody listening if you haven’t seen it yet, you should. It’s thousands of hours of work, all for free on my site, non-monetized. It’s just my personal website. So if you go to sive.rs/book, you will see the notes from every book I’ve read since 2007 with detailed notes, my takeaways, my review, my recommendation rating on a 1 to 10 scale and I just put it up on my site as kind of a public service. Honestly, it was something I was doing for myself anyway, just to retain what I was reading, and I realized it would take no effort to just take my text files and put them on the website. So there they are.
Jamie
Makes sense. Wow. Okay. With your identity or label as a writer, what kind of conversations is that exposing you to? Or what’s lighting you up when you have conversations now, specifically with that label in mind or with that identity in mind?
Derek Sivers
I love a new point of view. It’s like metaphorically, visually, right. Can you imagine as if life was this very complex crystal of a rock in your hand, and you’re looking at it from this point of view, you’re looking at it from that point of view. You hold it to the left, you hold it up to the light. You go into a dark room and you turn it, and you get to see if it glows in the dark. If you think of that metaphorically with life, every now and then somebody can give you a new angle like, “Hey, check this out. Hold it like this. Look from that angle.” And you go, “Whoa, whoa, whoa. I never saw that little hole that went through the middle or whatever it might be.” Again, sorry I’m being all metaphorical, but I love when somebody does that for life. You asked for three authors, but now I’ll name a particular book where I don’t even know what the author’s name is. But the book itself was brilliant. It’s called, “The Courage To Be Disliked”. And it’s a Japanese author.
Jamie
Fumitake Koga and Ichiro Kishimi.I’m butchering that.
Derek Sivers
There you go. No surprise. I didn’t memorize those names, but the book itself is brilliant. The whole thing is a dialogue between a wise master and a cranky student, like a constantly cranky student. And the whole thing is just a dialogue back and forth between them. But that’s how the Japanese author is choosing to communicate the philosophies of Alfred Adler, I think was his name, who was a contemporary of Sigmund Freud’s back in Vienna. But Freud got super famous and Adler only got a little famous. And so Adler has been mostly forgotten by history. But this Japanese author found Adler’s philosophies and thought that they were life changing. And so he shared them in this weird dialogue way. So it’s a fascinating book because the philosophies in it are fascinating. Like for example, just pick one off the top of my head. Forget about the title by the way, The Courage to Be Disliked is just one of maybe 12 important points in the book. It’s not the point. It’s not the subject of the whole book.
Derek Sivers
So, for example, he says all interpersonal trouble comes from people involving themselves in other people’s tasks. And what he means is something is your task if you are the one that is going to ultimately receive the result of the action or inaction from doing that task. And all interpersonal trouble is if somebody involves themselves in your task or you try to get yourself involved in someone else’s tasks, he said. For example, what someone thinks of you, that’s their task, not yours. They’re the ones that receives the ultimate benefit or result of their thoughts and judgment of you, not you. So what people think of you is not your task. Guilt, obligation, all of these things are moot if you look at it through the light of whose task is it. And that, to me, was a mind blower. That’s one of those things that makes you replay your entire life through that lens. Like I said, like holding up the multifaceted crystal at that angle, going, “Oh, wow, look at the way the light’s reflecting off of it now. Interesting.” So yeah, I love when books do that for me.
Jamie
You’ve talked about-- and I really do resonate with this point. My words, but I’ll say them and you can tell me if I’m paraphrasing it correctly, all things in life are inherently meaningless. Meaning that we assign whatever meaning there is to anything, right?
Derek Sivers
Yeah.
Jamie
In this perspective, in that book, is that something around guilt. I can’t remember the other thing you just mentioned, but you’ll say it and I’ll remember, but around guilt, around these different principles where it’s like, it’s not my problem whether you like me or not, it’s kind of yours. Not my problem, but it’s not mine to really meddle in. You know, you make the meaning around that. Is that a furthering or deepening a perspective of yours, or did it change a perspective of yours?
Derek Sivers
Whoa. Good question, Jamie. Both I guess. I guess I have an independent streak that’s a little more than most people. I think I already feel less obligation to others than a lot of people feel. And so that deepened it. But I had never thought about it from that angle, so in that way it introduced a whole new way of thinking to me. You talk about money a lot. I mean, hence the the name of the show. I was thinking about-- let me just paint a hypothetical scenario that your audience can probably relate to. You were damn good at making cookies so good that an international restaurant chain buys your cookie recipe for $10 million. So now you’ve got $10 million, and you call up your friends from back home to talk about it. And your friends like whoa, they’ve never even met a millionaire, let alone a deca millionaire. They can’t even comprehend what this might be like. They’re speechless, right. Your current friends in the city you live in now, when they find out that you’ve just made $10 million, they look at you with a little bit of suspicion. They say, “Oh, you’re going to be one of those rich people now. You’ve sold out, man. You’re going to be one of those rich people now.” And we all know what that means. The $10 million hits your bank account. And so you contact your bank and say, “Hey, does this bump me up to the next to the top level? The premier banking.”
Derek Sivers
And they say, “Oh no, sorry, you need $20 million to be in the premier banking level.” You go, Okay.” You’re blown away with what you’re going to do with $10 million. Oh my God. So you call your accountant in New York City, and after your friends are all just like calling you a rich guy, your accountant says, “Actually, don’t get too comfortable. You know, that’s not a lot of money. You’re not going to be able to live off of that.’ And you go, “Wow, that’s weird. Here I was feeling super rich.” You grew up in a high crime neighborhood, and it’s always been your dream to have a really safe home to live in. So you find a really nice house not too far from where you currently live. That’s in like, a gated community, and you really like the house. So you put an offer on the house, but then the board looks at your financials and says, “I’m sorry, you are newly rich and we have some bad experience with that. So no, your offer is refused. You’re not allowed to live here.” And lastly, you think about where you’re going to live then, and you think about this gorgeous but poor country that you’ve often visited. And you find out that if you were to buy a home there, you could live in luxury in paradise. And not only that, but if you were to donate, say, even a quarter of your savings to the local community, you would lift hundreds of people out of poverty and make a massive difference not only in their lives, but their children’s lives, the education they would get, the health care, whatever.
Derek Sivers
You would be a local hero. You’d be a saint. And so the question is, you have to decide now which reality you want. Like, do you want to feel super rich or medium rich or not yet rich? Like, which of those three feelings works for you? Do you want to reconnect with your roots back in your hometown? Do you want to convince your current friends that you’re not going to be one of those kind of rich people? Or do you want to be surrounded by people that are telling you that you’re not yet rich, or go to a place where you’re hailed as a saint? Which of those works for you? It’s up to you. So the fact that you have $10 million, is the only fact. Everything else is just interpretation and meaning and it’s all subjective. So each of those people along the way will tell you what it means that you have $10 million. It means that you are a jerk now, or it means that you’re unfathomably rich, or it means that you’re a hero, or it means that you’re not allowed in this neighborhood. These are all just projected meanings.
Jamie
You know what’s funny? I always had this sense, this thought and I think I’ve heard you articulate this, that whole exercise or idea that you can assign whatever meaning you decide to assign to something is like liberating. It’s like a white room. And you have a blank canvas and you can paint it. But the way you described it, while it cemented that yes, meaning is in the eye of the beholder or whatever, it also feels like heavy inasmuch as no meaning assign somebody else doesn’t do it for me. It creates so many choices, it creates so many options for me that becomes then so for you, because you’ve had a big exit, I’m sure some of what you just articulated, you’ve lived through to some extent, right?
Derek Sivers
I just fictionalized an oversimplified a situation a bit and added some details but yes. Yeah. And I think I’ve talked to some other friends that have had big windfalls and it’s similar.
Jamie
So for you, you have this super power, this ability not to be impacted by the opinions of others. You kind of live life on your terms. Is that necessary in order to survive or thrive in that example that you just gave? Or are there other skills that could be applied that people may have? Maybe that’s not one of them, you know what I mean? I know that’s kind of a deep question. I don’t even know where you go with that, but where I am with it, is like, how do you resolve and this is for you. You can’t speak for the world, but just for you. How do you resolve the space between, “Hey, I can make life mean whatever I want it to mean.’ And okay, that creates a lot of options for me. And that feels heavy.
Derek Sivers
It stays unresolved. Some people just default into where they are. So a famous friend of mine who is basically a billionaire is plagued by the fact that he’s not a multi-billionaire. He is surrounded by or surrounds himself with multi-billionaires that make him feel poor. And he’s like kicking himself like, “Ah, you know, I got to do more. I got to.” He’s got three super yachts. I can barely afford one, you know, and like, my jaw drops when I’m talking to him, like, “Dude, you hear yourself, right? That’s it’s like mental illness.” And he’s like, “No, man. You’re living off here in New Zealand. You’re in a different world. But you know where I live this is not a lot of money, man. You know, I’m just barely getting in the game.” But then somebody else can take $100,000 and move to a place where that’s it, you’re set for life. And you know, I lived in Singapore, where there’s no minimum wage, and people often hire a domestic worker. Whether you want to call it a nanny or a maid or a housekeeper that often lives with them, it’s often a young woman from Indonesia or Philippines, and they’re often paid, I don’t know, $18,000 a year, $15,000 was it the time when I was living there ten years ago. So I don’t know if that’s changed, but some people would be shocked that it was so low.
Derek Sivers
But what blew me away is when people told me that, “No, no, no, $18,000, she lives for free here in Singapore. They pay her cost of living. She sends that entire $18,000 back to her village in Indonesia. And she is a hero. Schools are built with her name on it from that.” Just the part of the $18,000 that’s left over after her immediate family’s taken care of. Then it goes to the village where this domestic worker in Singapore is now a hero. She’s the rich woman of the village and I love that reframing. It just reminds us that the Against Malaria Foundation will tell you it takes $2,000 to save someone’s life. That’s about the cost of providing enough mosquito netting so that somebody does not die of malaria costs about $2,000 for somebody to not die that would die without that $2,000. So every time you’re spending $2,000 on your business class flight instead of economy, you think, “Well, someone’s going to die. But I’ll be a little more comfortable for a few hours.” You could think about this in any way that works for you or plagues you, or it’s up to you. It all just becomes personally subjective which of these mindsets works for you. Because it’s different for everyone.
Jamie
So for you others, the concept of others is less about whether or not they approve of what you’re doing, judge you or whatever. The concept of others for you is being service to them.
Derek Sivers
Sometimes that’s one of the instruments in the orchestra that we could play. Sorry for that metaphor. The last page of my last book “How to Live” is the picture of an orchestra seating chart. And it’s no accident that there are 27 instruments in the orchestra, and there were 27 chapters in “How to Live”. And I think of the philosophies that we could live by as instruments in the orchestra, where there is no one right answer, like there is no one right instrument in the orchestra. It’s all about when you want to play them, how you want to combine them. You use time. Sometimes you need the cellos. Sometimes you need them to stop as the flute solos. And then the clarinet joins the flute. There’s no right answer. So living for others is something I value sometimes but not always.
Jamie
Got you. I get that actually. That makes a lot of sense to me. And I think how you do it, the way in which you decide to serve, when you decide to serve, what you decide to serve is all relative. Tthis thought I had recently. Oh. Go ahead.
Derek Sivers
Sorry. Sorry to interrupt you there, but the tricky part is, no matter what you choose, there will always be somebody telling you that you’re wrong. You got to brace yourself in advance. Because even if you choose to be generous, somebody is going to be telling you that you’re wrong for giving it away, or you’re wrong for how you gave it away or whatever. Mr Beast right now is the current example of that, dude is crazy generous. I got to admit, I was dubious at first. I thought it was a trick. I thought he was putting fake money into the suitcases to get clicks. No dude is for real. He is so crazy generous and still gets attacked for everything he does. Somebody’s always there to raise a stink, saying, “What a jerk. How dare you make the Kenyan government look bad by giving the people fresh water instead of working with the--.” You know, there’s always somebody who’s going to attack you no matter what you do. So even if you just choose to keep yourself, you choose to buy your superyacht, whatever it may be. There’s always going to be somebody telling you you’re wrong. So sorry I interrupted you. I just wanted to know. No, not at all.
Jamie
I was going to say, I think that’s a great point. And Mr Beast is a great example of that. The point I was going to make, and this is something that landed with me recently, is we’re in such a connected world, no matter what you try. I know you’re not on social, right. But it’s hard not to be inundated with what’s happening in the world. Just recently, this past week in Santo Domingo, the capital city here in the Dominican Republic, terrible, terrible flooding killed 24 people so far. You know, the body count keeps adding up. In this world versus maybe when we grew up, you hear about everything. So I have to emotionally digest everything. What’s happening in Africa, the typhoon in the Philippines, whatever might have happened in Australia, right. Like the school shooting in the United States, we’re just not equipped, you know, if you believe in God, God is the only thing, person, entity, whatever that’s equipped to emotionally digest all of what’s happening in the world at all times. So to your point about where you decide to be generous, where you decide to be in service to others or what have you, yeah, everybody’s got their thing. We’re all so connected. So we all feel as though through our own echo chamber, our thing is more important than the other thing. And, you know, away we go. I don’t know, that was just a thought that I had.
Derek Sivers
And it doesn’t have to be a final answer. That’s why I like the orchestra music comparison is there’s no final answer for should the cellos play or not. It’s just you know, earlier yes. Currently no. In the future again, maybe yes. So it’s the same thing with our various philosophies of life that we go by. There are some times where for your own peace of mind or mental state. You need to be a little selfish right now. You’ve been giving too much. You’ve been spreading yourself too thin. You’ve been living for others too much. Sorry world got to be selfish right now. Got to take care of my own. Got to work on the production function. Got to take care of the goose to keep laying those golden eggs, whatever it is. And you can’t feel that’s bad. Or, you know, even if somebody attacks you for it, you got to know that this is what you need right now.
Jamie
Yeah. You and I share this desire to kind of see the world. You also, though, went a step further than most in giving up US citizenship, I think in 2011, in order to. So here’s the base question just for the audience, were you running away from something or running towards something by leaving the country and getting rid of citizenship, which is a drastic move?
Derek Sivers
It’s funny. I disagree with the question. You know, we don’t do that. Say you live in a house with a few rooms in it and you decide to sit in the kitchen to read a book instead of the living room. Or, you know, you get up and stretch and you just feel like sitting in the living room for a while. We don’t say, “What are you running away from?” You know, there are many rooms in this house. I feel like sitting in this one now. It’s like we live on this earth that has many parts to it. There are many continents. I feel like being in this one now. I’m not running away. I’m not running towards. It’s just being in this place we’re at, you know. That’s all. That said, I learned a word recently I like, xenophile. Xenophile, which I think means somebody who’s fascinated with what’s foreign or strange. Yeah. That’s me. I don’t know if it’s my amateur anthropologist side. Maybe that’s a future hobby of mine, but I just always seem to be fascinated with whatever seems foreign to me now because of that thing I said where I always love a new perspective. So getting to know new friends in India or in the Middle East. These places that were not part of my worldview before and getting to know people well that grew up there. I hear so many new perspectives that I’d never considered, or I get to know and care about people that have completely different beliefs than I do, and it’s so much more interesting to me than just getting to know more homies, you know. So I think that is also what does keep me driving out into the the unknown for me.
Jamie
I love that. New Zealand is the place you’ve lived I think the longest in one spot?
Derek Sivers
At least soon it’s going to be the longest I’ve ever been anywhere in my whole life, which is crazy. But yeah, that was just an accident of circumstance. My kid’s mom and I were a very short lived relationship. We were only together for a couple of years, but oops had a baby. And he was born in Singapore. But then we moved here when he was a baby, and this is where we were when he broke up. And so here we are still and he’s 11 now. But I love New Zealand. I think it’s my single favorite country. If I had to only be one place for the rest of my life, you know which, that’s what Covid year felt like. No traveling allowed. You got to pick a place. So New Zealand, is that one place on Earth. If could be nowhere else but one place, I would pick New Zealand because it’s home, I love it. I’ve been here 11 years now.
Jamie
I love that. Can you go back though on the getting rid of citizenship. What was the calculus there?
Derek Sivers
That is the story of burning the ships. And that’s really all it was the tale for anyone who hasn’t heard it is a legend of the the Navy captain that lands with three ships on enemy shores prepared for battle, and he has 100 men with him. But there on the shores are like 2000 enemies waiting to kill them. So he turns to one of his men and he says, “Burn the ships.” He said, “We must not retreat. We must push forward. We have to do this.” And so burn the ships became a metaphor for doing something to prevent yourself from retreating, since you know that you will want to retreat. So I did try to leave the US the first time in 2007. I went to London intending to never return to the US. I was going to just keep going out into the world further and further afield. But then, a girl I liked had a crush on me in San Francisco. So I went to San Francisco to be with her, and that was hot for a few months. But then I just felt like, man, I got to quit retreating back to my comfort zone. I got to keep pushing out there. So after I left the US for good. What turned out to be for good in early 2010, I renounced my citizenship to burn the ships to prevent myself from retreating again.
Jamie
If you had to do it again, would you do the same thing? Has it been hard or has it been, you know, no difference really in your life?
Derek Sivers
It’s been mostly no difference. I don’t recommend it to anyone who wants to go to the US ever again. Basically, you got to make sure if you decide to renounce your US citizenship, you got to do it with the belief system that you might never be allowed to step foot in the country again, because once you don’t have that passport, you no longer have a legal right to even visit the guy at the airport border control might let you in, might not. It’s fully subjective. You might book a two week Thanksgiving trip to see your whole family, and you might arrive at LAX or JFK, whatever. And the guy at the border control might go, “Nope, not feeling it today. Get on the next plane back.” They don’t have to let you in ever again. And I’ll admit that the first time when I first renounced my citizenship, literally two months later, my ex’s dad was like on his deathbed and the mother called saying, “Honey, your father only has 48 hours to live. Hurry home.” And we had a baby, so I just went and quickly applied for the tourist visa to go visit the US, and I was denied, I was refused, they said, “No, you’re not allowed in the US ever again and you may not appeal this decision.”
Derek Sivers
And oh god, that was like the worst week of my life. And she was furious. Furious at me, like, what have you done? You know, we have a baby and I can’t even go see my dad before he dies. And, God, I just had this horrible, horrible, sinking feeling like, “Oh my God, I’ve done something horrible and irreversible. Oh my God, I’ve completely screwed up my life. I’ll never again ever get my favorite burrito from Laughing Planet in Portland. I’ll never again have my favorite taco in L.A. I’ll never again see my parents or friends.” Luckily, in that case, I got it. I did get it appealed. I did get the tourist visa. We did see her dad, but that week was a hard reminder that yeah, it’s why I advise anybody who asks me. I say, I really recommend you don’t renounce your citizenship, sit on the idea for five years and see what you think in five years because you really got to, like, don’t let yourself visit for five years and see how you feel about that. See how you feel about never visiting ever again. And only if you’re totally cool with never stepping foot in the country ever again, then you should renounce.
Jamie
So the five year rule is great. I get that’s for a big, big decision like renouncing citizenship. But you’ve pivoted a lot in a good way, in an amazing way. You’ve done all these different things. We talk about the labels or the identities that you’ve had and the one that you have right now. When I read the book “How to Live”, there’s the sort of like, go do what you want. And then there’s the concept of committing, right, get married, dive in, commit to seeing it all the way through for you again, I don’t think you can only answer for you and then let the audience kind of tease out what they get from it, how it applies to them. But how do you decide when you’ve seen it all the way through versus pivoting too soon? What does that look like? Like there’s the whole three feet from gold or cut your losses like for Derek Sivers. What’s that decision tree look like?
Derek Sivers
Damn, Jamie. Good one.
Jamie
While you’re noodling it again. The reason I ask is, and I want to make sure you and everybody understands this. You have had such significant impact in all of the things that you’ve done in music, in CD Baby, as a speaker, as an author, to me at least, for me at least, you’ve had such significant impact. So it seems to me like you’ve made the right moves for you. Unless there’s some you regret, I don’t know. So I’m just curious how you go through that as just your internal sort of mechanism for making those choices. I don’t know if that helps you at all, but I figured I’d add that context.
Derek Sivers
That was sweet. You know what? I’m going to just candidly share a little moment. You just said, “You’ve had significant impact.” And my first thought was,” No, come on.”
Jamie
I saw your face.
Derek Sivers
And then you listed the things, and I went, “Huh? Yeah. I guess so. Well, that’s kind of cool. I hadn’t thought about it that way.” Let me think. How do I know when I’m done? There’s this feeling of diminishing returns. That’s when I sold CD Baby. Ultimately it felt like early on, yes, I worked hard. And the business was like doubling and doubling and doubling. And I was getting emotional rewards, social rewards, financial rewards, intellectual rewards. And then after about ten years, it’s like, “Wow, I’m working really hard and the rewards are just kind of flatlined.” It feels like I could keep working a ton harder and get maybe 5% more reward. Like therefore I think I’m done. Like that’s what it really came down to. Yeah. There’s probably some kind of visual chart somebody could draw up that. You know, those two lines and then it starts, you know, the amount of effort, the amount of reward.
Jamie
Can we stick with this one for just a moment. Were you right. Looking back on it, because CD Baby was a company that sold CDs from artists. Like today not relevant. So were you right in timing it? Were you right at the point that you were? Was it only 5% greater year over year or after it was acquired? Was it like, “Okay, that could have been $100 million.” Not that that matters to you, but I’m curious if you were right.
Derek Sivers
You nailed it with the latter, that for me, it was right for me personally, for my intrinsic motivations and my personal interests. It was the right time and I was done. Then this kind of whatever company bought it, I looked the other way. Yeah, they bought it for 22 million and ten years later they sold it for, I don’t know, somebody could look it up in the news, search the web, but it sold it for like 140 million, 120 million or something like that ten years later. And. I had maybe about 20 seconds of thinking, “Damn, maybe I should have stayed at the helm for another ten years.” Actually, I don’t even know if the idea lasted 20s. It was like, “Nah, that would have sucked.” I was like, “You know what, I would have paid 90 million to get out when I did.” I made the right choice for me because, oh my God, if I would have just sat there at the helm of CD baby for the last 12 years instead of doing everything else I’ve done in life. Oh yeah, I would definitely choose this. So yeah, for me it was the right choice financially. Yeah, the company was not done, I was done. It’s good to distinguish. Yeah, it’s good to distinguish between those two. And to know yourself well enough to know when you are personally done.
Jamie
Yeah. Take that same question. How do you know when it’s time to walk away for you versus stick through and manage through, say, to relationships or anything else that you want to go into relationships and look, I’m not trying to meddle, but at the same time, following your story, I know that you’ve had many partners. And for you, is that one of those things, have you been three feet from gold and walked away? Or again, apply it to any other thing that jumps into your mind. That’s just the one I thought I’d help with and throw it.
Derek Sivers
You know, fuck it.
Jamie
The most the most raunchy one.
Derek Sivers
On on these podcasts I do. I like to challenge myself, to be honest. So yeah, fuck it. Even though we’re on the Tribe of Millionaires podcast, it’s not like this is the tribe of relationships or whatever. I’ll tell you, 13 months ago I broke up with an amazing, wonderful, loving, devoted woman that I was engaged to. That we were planning on having kids. We bought a house together. We’d been together a couple of years. She basically emotionally adopted my son, and he adopted her. But 13 months ago, I broke up because I could tell that our deeper values were so different that it was like these two--. Imagine two lines on a chart where at the beginning they start near each other, but one is going this way and one is going that way. And they’ve intersected right now, and they’re still right next to each other. But if they just keep going the way they’re going, they’re going to end up in very different places. And it was a very wise decision and I’ve been thankful almost every day, literally every day.
Derek Sivers
I’m thankful that I broke up with her. She was devastated. It was a really hard decision. You know, like I said, we were engaged, we bought a house together. We had this life. We were actually trying to have kids. But then I saw as time went on that we were heading different directions. And I’m old enough now to know how this goes. If we have kids, if we stick to this, it’s going to be really hard. We want such different things out of life. This is going to keep getting harder and harder, and we’re going to keep getting more and more resentful at the compromises we’re making. So yeah, I walked away 13 months ago and I’m so glad I did. So that was another good choice, even though it was a choice in the negative. You know, you can’t look at that from the outside and say, “There’s another way that Derek Sivers crushed it.” You know, but I’m really proud of myself for making that choice.
Jamie
That’s a hard one. I think I disagree with you on that, because what I heard in both stories, and thanks for going into that, the relationship part and also with CD Baby, and I’m sure if you continued to tell stories of when you made the decision to move on, if I boiled it down and again, correct me if I’m misinterpreting this, it comes down to tuning into heart versus head. You mentioned values. So you are looking at what do I value right now and which decision aligns best with that set of values. So at the time that you sold CD Baby, your value was, I don’t know, freedom let’s say. Or you know, the ability wander and go wherever you wanted to go. I don’t know what the values were that were intersecting with this lady that you broke up with 13 months ago. But whatever it was, it didn’t align. The decision to go forward didn’t align with the values that you held. So you have a heart focus versus head focus when it comes to making decisions. Is that a fair assessment?
Derek Sivers
Yeah. And we call it heart but--.
Jamie
That was the question I was going to ask you about. But go ahead.
Derek Sivers
That’s just some weird slang for your deeper, more entrenched values. It’s interesting to look back at your history to see what things about who you are now are kind of part of a current phase versus what have been there the longest.
Jamie
What do you mean by that? I’m sorry. Can you unpack?
Derek Sivers
Yeah, I’ll give a real example that there. There are times when I feel super social when if you look at my blog. In February 2023, I went to Chennai and Bangalore in India and I only had nine days during my kids school holiday where I could go on that trip. So in nine days I sat down and had one on ones with 50 people in nine days, which meant basically somebody at 9, 11, 1, 3, 5, 7 and 9 every single day for seven days. And it was intense and people said, “Oh my God, it sounds exhausting.” I was like, “No, it was exhilarating. It was amazing.” But that’s something that I can do for a short time. And I’ve also had little doses of that where it’s like, I moved to Singapore and I got to know everybody. I moved to New York City and I hosted dinners every single night, and I met a ton of people. But if I look back at my history, those are short lived phases where I’ll do that for a little while. And so I would say that’s not something that’s consistent in me. I would not want to go design a life where that’s something I do every day from now on. Because if I look at my history, that’s something I enjoy doing in short bursts. But I’m 54 now, and if I look back at my history back until I was 17.
Derek Sivers
I have been moving to a new home consistently every 1 to 2 years since I was 17 years old, and I’m old enough now to go, “Yeah, okay. I think that’s pretty solid.” I think there’s just something in me that after 1 or 2 years I feel like, “Yep, that’s enough. I know this place now, next.” And so I can now use that to make future decisions. Like, should I buy a home? It’s like, well, no matter what you’re feeling right now, like, you know, I really think I want to settle down. I’m feeling like putting down roots. Yeah, well, look at your long history. Historically, no matter how you feel in the moment, you find a reason to move every year or two. So I don’t usually speak to myself in second person, but I’d say, “Derek, don’t buy a house. Even if right now you’re feeling like, ’Oh my God, I want to buy this house. This is a house of my dreams. I want to stay here.’ Look at your history. Make a wise decision.” Call it heart if you want, but to me that’s more like these are my entrenched values. This is a deeper identity of what I value. And I can look back and see evidence of it, not just a current emotion that might be gone tomorrow.
Jamie
When you have a kid. I have two. Two boys. Yours is 11 or 12.
Derek Sivers
11.
Jamie
Yeah. When you have a kid. Do you have any sense fear? And this could just be our our own conditioning that, you know, a more, I don’t know, movable nomadic lifestyle. I’m asking this as a parent who’s moved his kids to another country right. I believe in my soul that expands them. I believe in my soul that it’s not destabilizing them. In fact, I think it’s doing the exact opposite. It is expanding them. And that creates more stability. The visual I have on this is like it’s widening their base right. So that creates more stability in their life. What say you on that? Is there a point at which it’s too much? Can you not be too much with a kid traveling? Because your son, I think, has lived in multiple countries at this point, or at least has been to multiple countries. Just curious because I’m the same and I’ve moved a lot. Like the longest it’s been like three/four years in one place. I am 45. So yeah I wonder that sometimes like am I creating a lack of stability for my kids, or is that an echo chamber of a past self?
Derek Sivers
Yeah, I suspect that everybody projects their preferences. Or let’s say, communicates their preferences as if they are moral fact. So when somebody says kids need stability. I hear it as I need stability and I want validation for my current feelings, you know?
Jamie
I like that.
Derek Sivers
And the kids are resilient. But on the other hand, it depends on the kid, of course. But I think in general, listen, I’m about to do it. Here we go. Here it goes. I’m about to do it. I think it’s good for kids to move constantly. It helps them make new friends. It helps them see the world from different perspectives instead of thinking one way is the truth. I see some kids that spent their whole life in one place, and they try to just visit somewhere tame, like France, and they’re just like, “Where’s my peanut butter?” You know, “The milk is all weird here.” And because they think that life should be one way, because they spent too long in one place. So I think living in different places helps entrench you from thinking that things should be one way. You start to see like, ah, there are multiple ways of being and they’re all correct or none of them are wrong. Okay, but you see what I’m doing? I’m just taking my preference, my xenophile, my love for moving every two years. And I’m validating it by declaring it to be a moral truth.
Jamie
When I say-- especially my older one who was eight, you know, most people would say that where you live is unsafe. Meaning in Dominican Republic where you live is unsafe. I don’t know, I get this like, rush, not rush, but like a sense of pride in me when he’s confused by that. Like what? Like that to me means he’s expanded more than the 40 year old that grew up in the same house, you know, and his living still a block away from where he grew up or whatever. I love the fact that they get this, that they get this expansion. Next step though, for me--.
Derek Sivers
Wait, wait. Sorry. This thing we’re talking about right now is actually the subject of my whole book that I’m working on now called “Useful Not True”, which is I think it’s so funny how people declare perspectives to be facts, almost as if to say water is two parts hydrogen and one part oxygen. And Dominican Republic is dangerous. As if these are just facts. And no, but that’s just that’s one perspective. Somebody else could tell you that Dominican Republic is the safest place to grow up. It’s funny, we think of Israel as dangerous and an Israeli friend of mine when he moved to Los Angeles, his mother was terrified. She’s like, “Oh God, you’re moving to Los Angeles. That place is dangerous with the bloods and the creeps and the gangs and the Rodney King and this and that. Oh, honey, I really think you should just stay here in Israel where you’re safe. I’m really worried about you moving to Los Angeles.” And he had to constantly call her to let her know that he’s safe in Los Angeles. And any of these things can have alternate perspectives. And hence the title of the book, Useful Not True, is that I only consider something to be true if it is truly the only right answer. You know, water is two parts hydrogen and one part oxygen. That’s just true. Dominican Republic is dangerous. That’s not true. It doesn’t mean if you say it’s not true, it doesn’t mean it’s false. It just means there is another way of looking at that. Another possibility exists.
Jamie
What’s the useful part in that title?
Derek Sivers
Useful to me means whatever helps you do what you need to do and be who you want to be or feel at peace. And it’s a good way to judge ideas, statements. Judge them by not whether they’re true or not, because basically almost nothing is absolutely, inarguably true, but instead judge them by whether it’s useful or not. So watching the news and hearing that in Detroit, a pregnant woman was stabbed like, that’s not useful. I’m not going to do anything about that. But for you, hearing that there was a flood in Dominican Republic is useful to you. It’s not useful to me here in New Zealand. I’m not going to be doing anything about that flood in Dominican Republic. You might be. So that’s useful for you. Not useful for me. Yeah, it’s a good way to judge philosophies, judge statements that people make. Just run them through the filter of not asking, is that true or not? Because let go of that. Because once you declare something to be true, that closes it. It’s like, no further questions. That’s just true. Once you declare something to be not necessarily true, it opens it and you can start to-- just saying not necessarily true invites other perspectives. It encourages you to say, “Well, what’s another way of looking at this?” And I think that’s one of the most powerful tools in our mind to do that. So that’s why it’s basically a self-help kind of book saying that we should be doing that more often. That’s why it’s good to declare as little as possible to be true.
Jamie
I think about a statement you might make say, if you’re going to quit your job, “It’s scary to quit my job.” I think it’s a useful statement in some ways. Tell me if you think I’m wrong. Meaning like okay, so then, but is it true? Well, no, I’m not going to declare it to be true because that opens my mind. But useful in as much saying, “Okay, well then to make it not scary, what are the steps I need to take?” The side hustle, I need to build the business. I need to buy the real estate portfolio I need to go after or moving overseas is difficult. It’s like, okay, that’s useful because it means I’m not going to declare it to be true. But it is a useful statement for me to then say, “Well, what do I need to do?” I need to buy the one way ticket like you did from Portland to London. I need to then find the car. I need to find the place we’re going to live. You know. What school are my kids going to go to? Are we going to home school? Like all of these decisions can be made by making a useful statement. This is my take. You tell me if like, nope, you got the book premise completely wrong and I’ll take it. But it’s a useful statement to say it’s it’s difficult, but if I declare it to be true, then I just shut down the opportunity or the possibility of it but saying it’s not true opens me up to saying, okay, well, if it’s difficult but not true, then I can take steps to resolve it.
Derek Sivers
Yeah.
Jamie
Is that your intention?
Derek Sivers
Yeah. And is it useful for you. So for some people, hearing that something is hard is not useful. It actually makes them shut down and run away from it. For somebody else hearing that something is hard makes them excited and want to step up to that challenge. So it’s all about, again, not declaring it to be absolutely right or wrong in any way. You just say, is this useful for me for now, for where I’m at? I’m not saying for anybody else, but is this a useful for me? So for you saying we’re thinking of moving to DR and it’s going to be hard, it’s like, yeah, this is going to be great. Like it is going to be hard, but this is great. I want a challenge. I’m in the mood for a challenge. So yeah, for you for now it’s useful. By the way, as I was putting together the book, I noticed that all of these things come into the category of future predictions. Somebody says, “Oh man, if that jerk gets elected, this country’s going to hell.” It’s like, well, the future doesn’t exist by definition. The definition of the future is something that hasn’t happened yet. So the future doesn’t exist. It’s the term that we call our imagination and our predictions. So when you say this country is going to go to hell if that guy gets elected, what you’re really saying is, I don’t like this guy. I disagree with his policies. I’m scared that bad things might happen if he gets elected. Now, those are true statements. Speaking in present tense about your subjective, personal feelings on this. Those can be true statements saying this world is or this country’s going to go to hell if that guy gets elected. Under no definition is that true.
Jamie
I like that. That makes sense.
Derek Sivers
So same same thing with, “Moving to DR is going to be hard.” That’s a future prediction. That’s a guess. And maybe what somebody’s saying is, “I’m feeling overwhelmed by all of the unknown things that I’ve never done before and have no experience doing.” Now you’re speaking the truth. Now you’re communicating more accurately and maybe getting a hold on your own feelings and thoughts more accurately. Whereas, especially if we’re talking with friends. And you say, “Moving across the world. That’s going to be hard.” And your friend goes, “Yeah, man, you’re right.” It’s like, now we’ve got a social reciprocity. Now somebody validated our feelings. So now it can feel even more true is when your friend says, “Yeah, man.” So you got to watch out for that.
Jamie
I love that, honestly. Like just listening to you. It’s funny, I’m sitting here, I’m like, I’ve got this next question, but I just paused and really listened to you. And the deep introspection you go through is really, really cool. And I don’t know where this question came from, but it just kind of going back to you talked about the mentors you had, Seth Godin, Mark Manson, I think, and I forget the lady’s name that wrote the--.
Derek Sivers
Sharon Kaye
Jamie
Thank you. When you’re coming up with these books, like I think you had a different title for How to Live, if I’m not mistaken, and maybe Seth Godin changed that title. Is that--.
Derek Sivers
No, that was my first book, “Anything You Want”. Yeah, I wanted to call it The Music of Business. And he said, “No, no, we’re just we’re going to call it Anything You Want. All right. You’re the publisher.
Jamie
Make it simple. But as you’re writing these books, as you’re putting these things in the world, as you’re now defining yourself as a writer, how much do you then interact? Because, I mean, you’ve got great connections. I heard you on Tim Ferriss, one of the first biggest podcasts out there, still one of the biggest podcasts out there. So you have a great network. How much do you leverage that network? Kind of getting into the tribe element here. But like, how much do you leverage that network? These mentors, Seth Godin, Mark Manson, like, do you know them? You said you email them, but do you leverage them? Do you talk to them? Do you seek guidance from them? How do you leverage this network?
Derek Sivers
I don’t. In that way I’m actually very unambitious.
Jamie
Why, what’s the reason? Do you feel like you’re bothering?
Derek Sivers
No, no, no, we’re just friends. Like Tim and I are friends. We just spent a whole week together here in New Zealand, and we just talked about love, life and sex and gossip. Very un-pc wonderful things that we can’t say in public. It was hilarious to be able to say them together in private. Same with Mark Manson, we shoot the shit about love and life and money and fame and Seth Godin and I are--. Yeah, he’s more of like the classic mentor to me. Like, we haven’t spent a week together or anything. But no, I don’t call on them for-- I do occasionally call on them for, say, perspectives, “Okay. How would you think about this situation?” And it’s kind of cool to hear somebody I admire that also knows me really well as a friend, kind of give me their perspective, but I don’t want much more out of life. I don’t want much more external stuff out of life. I don’t want more money. I don’t want more fame. I don’t want more whatever you call it clicks or platform recognition or any of that crap. I do like meeting interesting people. That’s why I do these podcasts. For example, I’m not here to sell books. I’m here to meet interesting people. So, audience, I actually told Jamie this right before we hit record. He said, “Is there anything you want me to plug or mention?” I said, “No, I’m not here to promote anything.”
Derek Sivers
I said, “I am here to meet people.” So the kind of person who listens to this podcast all the way to the end. And I really admire Jamie’s great questions today. Yeah. If you’re interested in this kind of stuff, you should email me. You should go to my website, sive.rs. And you should email me because I answer every email myself. And it’s like a part of my day that I actually really enjoy. It’s manageable. I put aside the time to do it. I actually really enjoy it. I get a thrill out of meeting people. Whether it’s, you know, “I’m a surf instructor in Costa Rica.” And, “I’m a guitar builder in France.” And, “I’m a digital nomad living in Cyprus.” And I love meeting these people that email me out of the blue because they heard me on a podcast. So this is my great reward. I don’t want money. I don’t want fame. I do like meeting interesting people. So, that’s why. No, there’s nothing I would ask Seth Godin or Tim Ferriss or Mark Manson. Notice we use the full name when we’re talking about the famous person, the famous public figure. There’s nothing, I have no asks for them because we’re just friends.
Jamie
Yeah. Have you satisfied the How to Live principle of being a famous pioneer in any way? You mentioned about fame, you’re not seeking it.
Derek Sivers
Ooh. I guess a little bit. So you read it. Yeah. That’s a chapter that I think was was fun and I think was worthy. I was mostly inspired by AJ Jacobs and Tim Ferriss with that. But I do think it’s a worthy thing to do. To go out and do the daring thing. Even to sit and do it very publicly, to set an example for others. So maybe in a way I think I do. What seems like social signaling might be, but I think I more often am trying to be useful to others. Like when I told the story about how I gave the $22 million from selling my company, how I gave it all to charity. I wasn’t going to be public about that. But then people kept asking me about it and I thought, “You know, I could try to be humble, low key. But actually sharing this story might reach somebody else whose company is structured in such a way that they could do this.” Because it was kind of-- if you read the story, it’s at sive.rs/trust. And I give some of the details of how I actually transfer the ownership of my company into a charitable remainder unitrust first before it was sold, so that when that $22 million purchase happened, none of it touched my hands. The entire $22 million went to the charitable trust and never came to me because the company was already profitable.
Derek Sivers
At that point, it was already making like 4 million a year net profit, and I was the sole owner. I had no investors. It was just me. All debts had been paid off. House, car, whatever house that I lived in for only two years. And I didn’t need the money. And so I just realized it would make me happier if this entire $22 million went into the charitable trust. And it was a unique. No, not unique. It was an unpopular or not widely known thing that I only knew about because my lawyer just happened to have a background in U.S tax law, and so he knew about this structure and knew that we could structure it in such a way so that the entire $22 million went to charity, whereas if the $22 million would have come to my hands, $7 million would have gone to the IRS, leaving only $15 million for charity. So if I wanted the entire $22 million to charity, I had to transfer my company into a trust first before the deal was irreversible. That was the condition. There was still a chance that the company purchasing company could have backed out, but because the company was owned by a charitable trust, then when the purchase happened, all 100% of every dollar of that 22 million got to go to charity. So that felt better for me.
Jamie
I could take you another three hours, but I won’t. I want to ask this, though. Will you do something for me?
Derek Sivers
Yeah, well, let’s find out.
Jamie
This is almost like if you’ve watched Seinfeld for a long time and you’ve seen him do a bit from afar and you have a chance to hear him do the bit live. You want to hear it?
Derek Sivers
Okay, I get it.
Jamie
I told you at the jump one of the most compelling stories blog posts it was in. I believe it was in “Hell Yeah or No” was about the concept of speeding up. I’m sorry of slowing down for the same result. Can you tell that story?
Derek Sivers
Gladly. I haven’t in a while. Why not? You know what’s funny. I was a full time musician for 15 years of my life, played over a thousand shows, and so much of getting up and doing shows is singing a song that you’ve sung a thousand times before, and you get up and you give it your best and you actually kind of enjoy it because each time it’s a new telling. So anyway. Yeah, I’ll sing that song. Totally true story. I was living in Santa Monica, California, on the beach in suburb of Los Angeles, and I was just four blocks away. I lived on fourth Street, and right after fourth Street was the sand, and there was a bike path that winds for something like 15 miles in the sand. And so for exercise, because I was just sedentary every day for exercise, I’d get on my bike, I’d go on that bike path and I would like, push it as hard as I could, like, you know, head down, leaning just red faced. And I’d get the little, the watch, the timer, the heart rate meter, and I’d push it as hard as I could. And every day after the initial say, like first week. Every day this 15 mile loop would take exactly 45 minutes. If it was a super windy day, it might be 46 minutes, but like never below 44 minutes, it was always right there almost exactly at the 45 minute mark.
Derek Sivers
But after doing it for a few months, I noticed that I was like kind of over it. That like the idea of going out and like the burning muscles and the bright red face and the feeling exhausted for two hours afterwards, like I was doing it less. So I thought, “Okay, you know what? I need to chill a bit. I’m going to go at half speed today.” Like, it’s actually going to feel weird how slow. Almost like if you’ve ever tried to walk down the street slowly, it almost hurts to walk that slow. So it was like that on my bike. I just went on the same bike path, but I was like just chilling. I was looking out at the ocean and there were dolphins that day. And true story in Marina del Rey, there’s a breakwater point that has a bunch of pelicans on it always. And I went right near the breakwater point and suddenly all the pelicans, like got up and went over me. I was like, “Whoa.” And as I was looking up a pelican shit in my mouth.
Derek Sivers
I was like, “Holy shit. It just shit in my mouth.” I was like, “Whoa, I can actually taste that.” Like digested oyster shells. I was like, “Oh, that’s a unique experience.” And so I was just chilling and I did the same path as usual. And when I got back, I looked at my watch and it said 48 minutes. And I went, “Wait, what 40? What?” I was like, “No, that should have been like 90 minutes.” I was going like half speed, but no, sure enough. I was only giving it half of my usual effort, but it took me 48 minutes instead of my usual 45. Only three extra minutes. So then, like, I went home and that just sat with me for the longest time. Like, “Damn. So the months of face red burning muscles exhausted was only to squeeze out an extra three minutes. What the fuck have I been doing? And then what the fuck am I doing in my life that seems hard. Where if I just gave it, like, half the effort, I’d get 95% of the results.” Yeah, that stuck with me a lot. There are so many things. I do in life where I see people really sweating things that they could probably do with without sweating and get almost the same result.
Jamie
That story pops into my head. No bullshit every time I make a decision between work and kid.
Derek Sivers
Oh, wow.
Jamie
Deciding on the kid instead of the work. You know, like, what am I really going to be able to accomplish in this next hour and a half that’s going to be life changing. Truly. Like I might get 2%, 2% more whatever out of that. But the ROI on that time spent with either of my kids in that time, you know the answer to that one. So yeah, man, this is one of the coolest interviews I’ve done. We’ve been blessed to have some great names and everything, but for me to have you on, it’s sort of a full circle moment for me. So I appreciate you being open to it. Thanks for answering the email. I can’t believe that you-- I mean there’s bigger shows as you’ve been. I can’t imagine your inbox and this is how you manage it. You get so many emails.
Derek Sivers
No I got a good system. I’ve written some shortcuts, you know, sentences that I say the most often I’ve assigned to single keys. So I’m able to type basically crazy fast because, you know, I reuse my most common sentences in a single keystroke. But yeah, I read every single email and I read and reply to every single email that comes in, and I really do enjoy it. So yeah, anybody listening to this, go send me an email, introduce yourself, say hello, ask me anything.
Jamie
I love it. Thank you so much Derek. I appreciate you being here, man.
Derek Sivers
Thanks, Jamie.