Derek Sivers Interview (Full Episode) | The Tim Ferriss Show (Podcast) | Transcription

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Intro (00:00)

optimal minimal this altitude i can run flat out for a half mile before my hands start shaking when i ask you a personal question now what is it in your front back? what's like the reality i must have a nerdy organism living tissue i will never handle scallop native ferris show this episode is brought to you by wealth front and this is a very unique sponsor wealth front is a massively disruptive in a good way set it and forget it investing service led by technologists from places like apple and world famous investors it has exploded in popularity in the last two years and they now have more than two and a half billion dollars under management in fact some of my very good friends investors in Silicon Valley have millions of their own money in wealth front so the question is why why is it so popular why is it unique because you can get services previously reserved for the ultra wealthy but only pay pennies on the dollar for them and this is because they use smarter software instead of 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right off the bat you never pay commissions or account fees for everything they charge 0.25% per year on assets above the first 15,000 which is managed for free if you use my link forward slash Tim that is less than five dollars a month to invest a $30,000 account for instance now normally when I have a sponsor on the show it's because I use them and recommend them in this case it's a little different I don't use wealthfront yet because I'm not allowed to here's the deal they wanted to sponsor this podcast but because of SEC regulations companies that invest your money are not allowed to use client testimonials so I couldn't be a user and have them on the podcast but I've been so impressed by wealthfront that I've invested a significant amount of my own money at least for me in the team and the company itself so I am an investor and hope to soon use it as a client now back to the recommendation as a Tim Ferris show listener you'll get $15,000 managed for free if you decide to open an 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on for free but if you're that kind of person you should be ashamed because that's disgusting me undies dot com forward slash Tim check it out Derek welcome to the show thank you I am so excited to have you on this has been in the works for for many months and now of course the timing is such and I'm going to read a bio and a short intro for you for folks in a second but we're going to come back to the subject of fasting because I'm eight days into a ten day fast and I was astonished to hear when we were chatting a day or two ago that you have done something very similar if not the same so before we get to that though for everybody listening Derek Sivers one of my favorite humans so excited to have him on the phone and here is a sketch of his background originally a professional musician in circus clown Derek Sivers you should say hi to him at Sivers on the Twitter that is S.I.V. E.R.S. created CD Baby in 1998 became the longest something very similar, if not the same. So before we get to that, though, for everybody listening, Derek Sivers, one of my favorite humans, so excited to have him on the phone. And here is a sketch of his background. Originally a professional musician in Circus Clown, Derek Sivers, you should say hi to him @Civers on the Twitter, that is S-I-V-E-R-S, created "CD Baby in 1998," became the largestseller of independent music online with 100 million in sales for 150,000 musicians. In 2008, Derek sold "CD Baby" for 22 million, giving the proceeds to a charitable trust for music education. He is and has been a frequent speaker on the TED conference circuit with more than five million views of his talks. And since 2011, he has published 24 books, including "Anything You Want," which shot to number one on all of its Amazon categories. It is also one of the few business books, which I think categorically or generally terrible, that I have not only read multiple times, but listen to multiple times, the last of which was in Sweden about a month and a half ago before deciding to take my startup vacation, effectively my retirement from startup investing. So, Derek, thank you for putting out such good work, first before we even jump into it. - Thanks, good to finally, well, officially talk to you. - Really talk off the record, which is kind of funny sometimes because every now and then, people ask me about like, hey, do you know what Tim's investing in? Do you know about this? And I think, every time you and I talk, we just, we talk about women. So here we are having an official conversation, finally. - No, we are. And I should also underscore for people, number one, I'm eight days into fasting. So if I sound like an idiot, I'm gonna blame it on that. But second is that I consider you a reality check for me. And we first met, I wanna say it was that a music and tech or tech and music event in 2007, perhaps. - Yep. - And I was familiar with some of your work. You had read the four hour work week. And the prompt for me to call you often times is, is number one, if I just need a sanity check, where for instance, if people around me seem to be asking the question, how should you best grow your company? And then there's an ABC multiple choice list. I don't necessarily go to you to get a D and an E. I go to you because you will say, well, why do you wanna grow your company in the first place? - Exactly. - That's the wrong question. - And secondly, because you're very good at simplifying and breaking things down, I recall, and I might be getting the location wrong, but I seem to place this in Times Square, sitting on the bleachers, talking about, I think it was SQL and databases. And I was saying that I was extremely uncomfortable, felt out of my depth when talking to engineers, and you're like, oh, it's not that hard. And you sat down and on a piece of paper, sketched out databases and SQL and how it worked. And I just admire the, not only capability, which is not that common, but the willingness to simplify something where I think we live in a world where many people complicate to profit, right? If what you do is simple, then you feel like you're dispensable, if that makes sense. And, but I wanna stop talking and ask you, because I'm not sure I actually ever heard the full story, a recently a professional musician in circus clown. What is the circus clown story?

Derek Sivers: Life Path, Career, And Life Lessons

Derek Sivers, the leader of the circus (08:56)

- Okay, there's actually a good lesson inside the story, is that I was 18 years old and all I wanted in my whole life was to be a professional musician. I mean, ideally a rock star, yeah, but if I was just making my living doing music, that was the goal. So I'm 18 years old, I'm living in Boston, I'm going to Berkeley College of Music, and I'm in this band where the bass player one day in rehearsal says, hey man, my agent just offered me a gig that's like $75 to play at a pig show in Vermont. He rolls his eyes and he's like, I'm not gonna do it, do you want the gig? I'm like, fuck yeah, a paying gig, oh my God, yes. So I took the gig to go up to Burlington, Vermont, and I think it was like a, you know, $58 round trip bus ticket. And I get to this pig show in Vermont, I strap my acoustic guitar on, and then I walk around a pig show playing music, and did that for like three hours, got on the bus home, and the next day, the booking agent called me up and said, "Hey, so yeah, you did a really good job "at the pig show, we got good reports there. "Wondering if you can come play at an art opening "in Western Massachusetts, I'll pay you $75 again." I said, "Yeah, sure, so same thing, "I took the, you know, like a $60 bus out to Western Massachusetts, "got 75 bucks for playing at an art opening." And the agent was there and he was impressed, and so he said, "Hey, look, I've got this circus, "and the previous musician just quit, "so we really need somebody new, "and I really like what you're doing." So there's about three gigs a week, I can pay you 75 bucks a gig. They're usually Friday, Saturday, Sunday. Do you want the gig?" And I said, "Hell yeah, I'm a professional musician now, "this is amazing." So I said yes to everything, which is gonna come up later, you know, with the hell yeah or no thing, that I think it's really smart to switch strategies. But when you're earlier in your career, I think the best strategies, you just say yes to everything, every pilly little gig, you just never know what are the lottery tickets. So this one ended up being a real lottery ticket for me, because as soon as I joined the circus, again, I'm 18, I had no stage experience. And with, after a few gigs, they said, "Hey, so the previous musician used to go out "and open the show with this big theme song "and get everybody up and dancing, could you do that?" And I said, "Yeah, sure." And another gig or two later, they said, "Hey, the previous musician used to close "the show also with that theme song, "could you do that?" I said, "Yeah, sure." And then it was, the previous musician used to go out in between every act and like, you know, get the audience to applaud and thank them and introduce the next act. Do you think you could do that? I said, "Yeah, sure." And I was really bad at it at first, but I got good eventually. I became like the ringleader MC of this whole circus. And I was 18 years old. So if you were to go to the circus, it would have looked like my show. And I did that for 10 years from the age of 18 to 28. I did over a thousand shows. And eventually by the way, you know, got paid more than 75 bucks. Eventually I was getting like 300 bucks a show and it became my full time living. And I even bought a house with the money I made playing with the circus. And then that led to all kinds of other things. So just so many huge opportunities. And 10 years of stage experience came from that one piddly little pig show that I said yes to the little thing. So yeah, the only reason I stopped doing the circus is when CD Baby started taking over my life and I had to start turning down circus gigs. But yeah, that was my life for 10 years. - What did you learn that made you better? What were the lessons learned that made the biggest difference in your performance as this MC? - Good question. It was-- - Were the biggest mistakes that you made early on that you corrected, either one's fine. - All right. Yeah, it's kind of the same answer is that at first I was too self-conscious because I thought it was about me. Like I was going up on stage thinking that the audience was somehow judging me. Derek Siver is like as if I mattered, you know? So I would get self-conscious of what they thought of me. And eventually, and I think it took maybe like 10 or 20 gigs with the-- The circus was run by a husband and wife team. And Tarleton was the name of the wife that she was the one really kind of out on the gigs and leading the circus. The husband was more the booking agent. And she's the one that like single-handedly gave me my confidence that I have today. Like sometimes when people ask me why am I so confident? It's like that's because of Tarleton. That's a longer story we could get into. But anyway, Tarleton is the one that she just kept pushing me from backstage. Like come on, you're up there acting like David Letterman. Like don't do this whole kind of, yeah, I'm so cool. All right, everybody here is the next act. I think I was trying to be cool because I thought that people were judging me, right? And she said, these people came here for a show. Go give them what they came here for. And so one time I decided to go out there and just be over the top ridiculous. I went on stage and I said, ladies and gentlemen, what you're about to see is one of the most amazing things you get, we have an elephant that is going to be coming from backstage and like did this whole thing in the fast talking voice and real like pizzazz to it. And the audience loved it and I came backstage and she said, there you go. That's what people come to the circus for. So now that I've been on stage, you know, thousands of times, that's this really sunk in. You get on stage to give the audience what they came there for. Or even things like this, this interview we're doing, this isn't necessarily for you or me. We could just hang up the phone and talk. We don't need to, we're doing this for the listeners. So we're going to give them something that's useful to them. This isn't about me, it isn't about you, this is about them. So that was the biggest lesson learned. Luckily I learned that early on when I was 18, 19. And yeah. - So I know we could come back to it, but I don't want to forget since I have a low glucose brain, which I think I just made Japanese accidentally. But how did she give you your confidence? Or if you prefer to answer it a different way, because I get this question a lot from fans on Twitter, for instance, you know, how did you get so confident? And there are things I can point to from athletic training with specific wrestling coaches and so on. But if, what did that woman do that help make you more, to help make you more confident, or if you were trying to coach somebody who's going to get up and give their first TED talk, what would you say to them?

A framework for developing confidence (15:41)

And I don't know if the answers are similar. - Completely different answers. So we'll just do the confidence one. I can give TED talk advice later if you want. Is that in my case, you understand, Tarleton was hot. I was 18, she was 33. And even the first time I ever saw her, I told you she was the booking agent's wife. So when I took that bus out to Western Massachusetts the first time, I'm sitting in the Worcester Mass bus station. It's nasty. It's the, you know, the der eggs of the earth with fluids dripping. And it's gross. And I'm sitting there waiting for somebody to pick me up. And then, like, the door opens to the bus station. And it's like that scene in the movie with the backlit woman and, you know, the fan blowing her hair and, "What dream we've heard?" You know, is that moment this gorgeous woman walks in the bus station. I'm like, "Who is that?" And she walks towards me and she says, "Derek?" I was like, "So that was Tarleton." So it's important to know that Tarleton is hot. She still is. And so, you know, I was 18 and I was dating girls in Boston. And, of course, just everybody broke my heart. And this one girl from Texas just dumped me and I was sad. And at that point, Tarleton and I had been traveling together on the circus for a year or so. So she knew me very well. And when I told her about, you know, the girl from Texas that dumped me, she just said, "Derek, like, you don't understand. Like, I've met a lot of guys in my life, a lot of guys." She said, "You are one of the smartest, "was brilliant, like, considerate. Like, you've got a future. "You've got your shit tick out of your life. "If some woman doesn't see that, that's her problem." Okay, so the first, like, 100 times she said this. I just thought she was just being nice, you know? I was like, "Thank you, but I'm still sad." And I think it took about a year where she, like, just kept telling me this and kept telling me this. And after about a year, it kind of sunk in. Like, I just noticed that I had kind of internalized this. Like, "Yeah, sorry, and you can't see me right now, "but I'm just, like, you know, changed my posture." I'm like, "Yeah, I'm pretty fucking awesome. "I'm cool." Like, I really internalized that. So I just carried that with me ever since, you know? Sometimes there's this beautiful Kurt Vonnegut quote that's just a throwaway line in the middle of one of his books that says, "You are whatever you pretend to be." That's such a good line. And I took that to heart that I just thought, you know? I'd also been reading Tony Robbins and stuff by then. Actually, she, oh, God, Tarleton is that same woman. She's the one that told me to read Tony Robbins, "Awaken the Giant Within" when I was 19, and that changed my life. So yeah, she's one of the big three influences of my life. - That's probably the exact same age that I read the exact same book, just as a sign. - That is the good time to read it, those formative years. So, yeah, I think the, you are whatever you pretend to be. I think I just realized somewhere in there that you can just choose to be confident. She helped kind of start it for me, but then I kept it up myself, even when everything's going terribly and I have no reason to be confident, I just decide to be. - It seems like most of my friends who are, what most people would consider successful in various respects can trace their confidence back to either or both end a specific woman and a specific coach or mentor of some type. It always comes down to one or both of those.

How Derek Sivers graduated from the Berklee School of Music in two years (19:26)

- Oh, Tim, I've never told you about Kimo Williams. - It's a great name and I want to learn more. No, I don't know anything about it. - This is so up your alley. I can't believe I've never told you this. Okay, thanks for prodding me. I mean, you prompted me with that because you're right. It was a gorgeous woman, Tarleton, and it was a music teacher, Kimo Williams, that he changed my life a year or two before I met her. Okay, so imagine this. I'm 17 years old now. I'm living in suburban Chicago and I decide to go to Berkeley College of Music 'cause I want to be a famous musician. And just like two or three months before I'm supposed to go, I see an ad in the local Chicago Tribune for music type setting and I'm wondering like how much sheet music I'm gonna have to be writing. So I call up this classified ad in the paper and I say, "Can I ask you some questions "about music type setting?" And he said, "Sure, well, why do you want to know?" And I said, "Because I'm about to go off "to Berkeley College of Music in a couple months." And he said, "Oh, really?" He said, "I used to teach at Berkeley College of Music." I said, "You did? "Do you think you can give me some tips?" He said, "Yeah, here's my address. "Come to my studio at 9 a.m. Thursday morning. "See you then." So, and he lived like way downtown Chicago in an area I've never been to. And I'm gonna do a little foreshadowing of the story. Perfect. Right now, because when I got married years later to the woman I met when I was sitting in Times Square with you, he was one of only three people I invited to the wedding. It was Tarleton from the circus, Kima Williams, my music teacher and my first girlfriend, Camille. Those are my only three guests to my wedding. And Kima Williams told the story to my family. He said, "You know, I tell people all the time. "I get all these kids that want to be famous." And I said, "Yep, show up up at my studio at 9 a.m." And he said, "Nobody ever does. "Nobody has their shit together to show up "when I tell them to." And he said, "So I'd honestly forgotten "that there was this kid that called from a classified ad." That was his way of saying no. Or not, he was like, "No, it's just his hurdle." He was like, "Yeah, all right, kids. "Sure, here's a seven foot hurdle. "Let's hear you do." Exactly. So he said, "So, you know, my doorbell rings "some Thursday morning at 8.59 a.m. "and I opened the door and there's some "long-haired teenager sitting there." And, you know, so now flipping back to first-person point of view is, yeah, Kima Williams is this large black man from Hawaii that was a musician that attended Berkeley School of Music and then stayed there to teach for a while. And so what he taught me in four lessons got me to graduate Berkeley College of Music in half the time it would take. And here was his thing. He said, "The reason I wanted you to study with me "for a bit," he said, "I know you only have "like eight weeks before you go to school." He said, "I think you can graduate Berkeley School of Music "in two years instead of four." He said, "The standard pace is for chumps." I should get a t-shirt made. - I know, this is like totally temporary stuff, right? I can't believe what we hadn't talked about this before that he's the one at the age of like 17, 18 got me into this mentality. He said, "We're the standard paces for chumps." That's, the school has to organize its curricula around the lowest common denominator so that almost nobody is left out. So they have to slow down so that everybody can catch up and he said, "You're smarter than that," or anybody can be smarter than that if they want to be. So you can go as fast as you want and here's how. And so he sat me down to the piano. He said, "Okay, what do you know about music theory?" I said, "Well, I don't know, let's find out." And he just asked me a few of these music questions like, "Okay, how does a major scale go?" "Duh, duh, duh, duh, duh, duh, right?" Okay, show me the tri-tone. Do you know what a tri-tone is? Okay, play me a tri-tone in the C major scale. I'm like, "Uh, uh, uh, okay, BNF." He said, "Okay, now, how can you take that "and what other chord can you make from BNF?" He said, "Okay, that's called the substitute chord. "Now, what is the resolution?" And we realized, and he was just like, "Dum, dum, dum, dum. "This kind of pace." He was doing all this music theory stuff with me. It was so intense. And I was like, "I had all this adrenaline like a video game." I was like, "This is amazing." Okay, keep going. I said, "Okay, do that, do this, do this." And that was like a two-hour lesson that went at that kind of pace. And then he dumped a bunch of homework on me. He said, "Okay, now, go home tonight and take this big book "of jazz standards, find me all the two five substitutions, or two five closures. "Come back next Thursday and we'll do this again." So we did that for like four Thursdays in a row. And sure enough, what he taught me in four two-hour sessions was basically like two years of Berkeley College of Music. He compressed it into four lessons. Wow. So that when I showed up to my first day of Berkeley, I tested out of the first few years. Just thanks to him. And then he even taught me a strategy, just he off-hand mentioned. He said, "You know, I think they might still have a rule in place "where those other required courses that you have to take to graduate." He said, "I think you could pretty much just buy the books for those "and then contact the department head and just take the final exam to get credit." So I did that too. So when I got there, all those required classes like a Bach counterpoint classes, I wasn't so interested in it. So I bought the book, did all the homework, approached the department head, said, "Can I take the final exam for this?" And he said, "Looked at me weird" and said, "Okay." Took the final exam and got credit without ever having to attend the class. And yeah, that's how I graduated Berkeley College of Music in two years. That's incredible. What a gift. I mean, did he ever, aside from just showing up, which is, of course, half the battle, if not more than half the battle, did he ever explain to you why he adopted you in that way? Were you the first person, first student he'd done that for? Or is this something he'd done before? I think he's definitely done it before and since. So as far as I know, last time we spoke, he's still teaching at Columbia College in downtown Chicago in the music department. So I think he's done this for many people since. He's just an amazing guy that is just a great teacher, a very strict teacher. He holds everybody to a really high standard. That kind of, that whole, like, if he said, "Show up at my studio at 9 a.m." If I would have rang the doorbell at 9, 10, he would have said, "Hmm, I guess you're not serious." And he probably would have turned me away, you know? So he does that with his students and yeah. So he's done that for many people before and since, I think. What would he say to you, if you recall, when you did something incorrectly? How did he provide feedback? Hmm. Well, I think for specific things, he just kind of give me that raised eyebrow look like, "Oh, really? You think that?" But you know what? It's kind of the answer to your question is he would question things kind of like you were talking about, you know, calling me when wondering if people are asking the right question. So when I first caught that very first phone call where I said, "I'm going to go to Berkeley College of Music in eight weeks." And he said, "Really? Why do you want to go to Berkeley?" And I said, "Well, because I want to be a famous successful singer, songwriter, performer." He said, "Hmm." He said, "Well, four years and $100,000 in tuition." It's a lot of money to learn to write a verse in a chorus. You know, like that kind of thing. Like, "Oh, really? Is that really the reason you're doing this?" Just constantly questioning. That's so incredibly, especially at that age. I mean, what an incredible molting that he provided. Ever since then, I mean, you and I have often the same approach to life. Like looking for the short cuts are just kind of more like looking at the way that most people do things and saying like, you know, you don't have to do it that way. It's very inefficient. You could just do this. So he just gave me that approach to life. It's great. And on a related note, could you talk about, we've talked about this a bit, but I never tire of it, relaxing for the same result. Because I think this is such a huge observation that it's incredibly important for type A personalities or at least for me because I have a tendency to almost want to burn the candle at both ends to prove to myself that I'm putting forth the maximum effort. I'm not leaving as little as possible to chance. With certain things. But tell everybody about the bike, about the bicycle experience.

Lessons learned from the Santa Monica bike path (28:31)

Yeah, this was kind of profound. Now, granted, I didn't learn this until later, but yeah, I'd been very, very, very type A my whole life. Even before I met Kimu Williams, you know, age of 14, it's just, my friends called me the robot because they would never see me sleep or eat or relax or hang out. I just was like so focused on being the best musician I could be that I would just practice every waking minute. If I'd grudgingly go to a party, you know, I'd bring my guitar with me and I'd be sitting in the corner practicing my scales and arpeggios while everybody was hanging out, getting high, you know. So yeah, I've always been very type A. And so a friend of mine got me into cycling when I was living in LA and I lived right on the beach in Santa Monica where there's this great bike path in the sand that goes for, I think it's 25 miles in the sand. No, hold on. Something like that. The exact number doesn't matter. But what I would do is I would go onto the bike path and I would get like head down and push it as hard as I could. I would go all the way to one end of the bike path and back and then back home and I'd set my little timer when doing this. Huffing and puffing, red face. Red face, huffing and like just pushing it as hard as I can. Every single thrust of the leg just... And of course, you know, that made me quite fun if somebody was in my way on the bike path. I'm sure. That guy's got places to go. So, but I noticed it was always 43 minutes. I mean, you know, if you know Santa Monica, California, you know, the weather is about exactly the same all year round. So unless it was a surprisingly windy day, it was always 43 minutes is what it took me to go as fast as I could for that on that bike path. But I noticed that over time, I was starting to feel less psyched about going out on the bike path because just mentally when I would think of it, it would feel like pain and hard work. It sounds like pain and hard work. Yeah, I mean, it was, but you know, I guess at first that was okay and after a while, I just felt like, "Oh, I don't know, running the bike. Why don't I just hang out?" And so then I said, "You know, that's not cool for me to start to associate negative stuff with going on the bike ride. Why don't I just chill for once? Like, I'm just going to go on the same bike ride, but just, you know, I'm not going to be a complete snail, but I'll go at like half of my normal pace." So, yeah, I got on my bike and it was just pleasant. I just went on the same bike ride, but I was more like standing up and I just noticed that I was looking around more. And I looked out in the ocean, I noticed there was that day there were these dolphins jumping in the ocean and I went down to Marina Del Rey to my turnaround point. And, oh no, actually it was when the breakers at Marina Del Rey, there was a penguin that was flying above me. I was like, "No way." I looked up and was like, "Hey, a penguin!" He's shit in my mouth. I was like, "Yeah, yeah." Was it a penguin or a pelican? Oh sorry, pelican. I was just flying penguin above my head. That would be more than anything. I was like, "What did you take before your ride?" So you had to see a pelican shit in your mouth. What was, that's incredible accuracy. Was that from like, how far away was it? Like 20 feet up. Wow. I don't know if he was accurate or I was. So, I had such a nice time. It was just purely pleasant. There was no red face. There was no huffing and puffing. I was just cycling. It was nice. And when I got back to my usual stopping place, I looked at my watch and it said 45 minutes. And I was like, "No way." How the hell could that have been 45 minutes as compared to my usual 43? It's like, there's no way. But yeah, it was right. 45 minutes. And that was like a profound lesson that I think changed the way I've approached my life ever since. It's because I realized that, I guess, you know, what percentage of that huffing and puffing then we could do the math or whatever. But at 93 points, something present of my huffing and puffing and all that red face and all that stress was only for an extra two minutes. It was basically for nothing. I mean, you know, of course, we're not talking about me competing in something where the huffing and puffing might have been worth it. But for life, I think of all of this optimization and getting the maximum dollar out of everything and the maximum out of every second, the maximum out of every minute. And I think I just take this approach now of going like, or you could just take the lesson, take most of that lesson and apply it and be effective and be happy. You don't need to stress about any of this stuff. And so, honestly, that's been my approach ever since. I do things, but I stop before anything gets stressful. Is there any particular way that you remind yourself of that given a lifetime of hard charging? If I would find, I do find that I sometimes lose track of that type of truth, which I think is a truth in almost every aspect of the endeavors that I partake in at least. Are there any particular ways that you remind yourself of that or keep it present for you? I think it's just noticing the pain. Luckily, I live in a world where there's more psychic pain than physical pain. You have to notice the psychic pain that you're feeling of whether it's doing things you don't want to be doing and feeling the pain and regret of that or the frustration. When you notice this internal, "Rrrr!" That's my cue. I treat that like physical pain. "What am I doing? I need to stop doing that thing that hurts. What is that?" And it usually means that I'm just pushing too hard or doing things that I don't really want to be doing because I was asking the wrong questions and following the wrong path, the wrong outcome. Now, we're winding the clock a little bit. 1998. How did CD Baby come to be?

How CD Baby came to be (34:51)

It was... I was really just selling my own CD on my band's website. I had a band called Hit Me, and I had this CD that was being played on radio stations across the country. It was on 350 college radio stations across America, but the only way to buy it was to mail a checker money order to my address. This is before the average person could get any e-commerce online because there was no PayPal. I guess I could have put it up on eBay or something, right? But that was the only way you could sell your CD online as an independent musician. There was just nobody anywhere that would sell it for you. There were a couple big online record stores at the time. There was a and I think Amazon bought them both. But the only way to get into their system was to go through the major labels, basically to get a major label record deal and then be in the major label distribution system. Then you would appear on This is just a horrible convoluted thing. It should be dead simple. Just put your stuff online, have a Buy Now button and ship it to the person that buys it. It shouldn't need to be that complicated. I did the research and I did the work and I went and got myself a credit card merchant account, which was like $1,000 in setup fees. They actually had to send an inspector out to my location to make sure I was a valid business. I think I even had to incorporate to make them happy. I set up a separate bank account. Did all of this red tape, a lot of paperwork, $1,000 in setup fees. But after three months, I had a credit card merchant account. Then I had to figure out how to make a Buy Now button on my website. That was also hard. It was like, I had to buy a book on CGI bin Pearl scripts and copy the example from the book on how to make a Buy Now button. After three months of hard work, I did it. My band's website had a Buy Now button that was like, wow, look at that. My friends in the New York City music scene, my fellow musicians, said, "Whoa, dude. Do you think you could sell my CD through that thing?" I said, "Do you mean on my band's website?" They said, "Yeah, if you don't mind." I said, "Yeah, sure, why not?" It was like a favor to my friend Marco. Actually, here's a little tidbit of information. Marco, who I just knew as a musician, Marco Atasari. I knew him as a cool musician in New York City. He was technically the guy that gave me the idea for CD Baby. Later, I found out that he's the son of the prime minister of Finland. It was all in the news, and I had no idea. Marco, thank you. He's the one that asked me if I could sell his CD through my band's website. I did, and then I started getting calls like, "Hey, man, my friend Marco said you could sell my CD through your website." I said, "Yeah, no problem. Friend of Marco's is a friend of mine." It grew by request. Which kind of led me to the belief that when people ask me how to grow my business, I've got this business idea. Basically, I'm trying to push it onto the world. How do I push my idea into the world? I have no idea. I have no advice for those people because I've only ever worked on the pull method where people ask me to do things for them. I say, "Yes." CD Baby just happened because all of my musician friends were asking me to sell their CD on my band's website. Eventually, there were so many that I just took them off of my band's site and put them onto their own site, and that was Of your projects that have done well, what percentage have come from scratching your own itch, a la CDbaby?

The co-op business model (38:36)

Are any of the projects that have gained traction, projects that you've thought of sending to a market that didn't include you? Actually, after that first one, I built a thing to sell my own CD, but actually, all of them were scratching other people's itches. I don't want to picture that. For example, shortly after that, I already had a UPC barcode thing. The way it used to work with that, to get a barcode on your album, you had to pay $400 to the Universal Code Council in order to get a six-digit prefix, which then let you assign the next five digits, which meant 100,000 products underneath your barcode product ID or something like that. A lot of musicians in the independent music world wanted to have a UPC barcode for their album that would let them sell it in physical retail stores. A lot of physical retail stores wouldn't let you sell something unless it had a UPC barcode, but they didn't want to all have to pay the $400 to get a company account. But I already had a company account, and so I just let a lot of musicians know, if you ever need a barcode, let me know. I can get one for you. Enough people started taking me up on this that I decided to charge $20 for it, because it would take me some time to assign them an ID and then generate the EPS or TIFF graphic file to be included in their album artwork. Eventually, I automated it. Point is, 100,000 barcodes were assigned at $20 each. That's what I charged for the service. It was like $2 million I made for this $400 setup fee for getting a Universal Code Council account. So you could say that I was scratching my edge, but really that it was more I think of it as the co-op business model. It was responding to demand instead of trying to create demand. Is that? Yes, I've never tried to create demand. I've never done that. I don't know how. I've only basically answered the calls for help. It's usually using this what I call the co-op business model, which is I've already got something. Other people could use it. I'm happy to share it. I'll just charge a little something to help pay for my time and resources so that we can all share this resource that I've already got. So I love this is a great example of spotting something small, perhaps looking at a situation that many, many other people have been presented with and spotting something interesting. In this case, an opportunity. I want to highlight one other example, which is an email that you wrote. I'm going to just read a little bit here. This is from some of your writing.

How one e-mail helped make CD Baby a remarkable company (41:36)

When you make a business, you're making a little world where you control the laws. It doesn't matter how things are done everywhere else in your little world. You can make it like it should be. I know you're better at reading this stuff, but I'm just going to, just because I have it right in front of me. When I first built CD Baby, every order had an automated email that let the customer know when the CD was actually shipped. This is Tim speaking now. Everyone's seen these. They tend to be very plain Jane, very generic, very boring. At first, it was just the normal. This is back to your writing. Your order is shipped today. Please let us know if it doesn't arrive. Thank you for your business. A few months later, I felt it was very incongruent with my mission to help people smile. I knew I could do better, so I took 20 minutes and wrote this goofy little thing. This is the email that would go out to folks. Your CD has been gently taken from our CD Baby shelves with sterilized, contamination-free gloves and placed onto a satin pillow. A team of 50 employees inspected your CD and polished it to make sure it was the best possible condition before mailing. Our packing specialist from Japan lit a candle and a hush fell over the crowd as they put your CD into the finest gold-lined box that money can buy. We all had a wonderful celebration afterwards, and the whole party marched down the street to the post office where the entire town of Portland waved, Bon Voyage, to your package, on its way to you in our private CD Baby jet on this day, Friday, June 6. I hope that you had a wonderful time shopping at CD Baby. We sure did. Your pictures on our wall. It's a customer of the year. We're all exhausted, but can't wait for you to come back to to exclamation points. So, that 20 minutes, what happened after you put that together? Well, people would get it and reply back. Like, whoever replies back to an automated shipping email, right? Whoever replies back to Amazon saying, "Wow, guys, thank you so much." But the fact that this little quirky email had so much personality, for what it let them know, like, "There's real people here." And so, customers will often reply back saying, "You guys are hilarious. That was the weirdest thing ever. That's awesome." But more importantly, people started sharing it. They would forward it to all of their friends. Like, "You guys have to see this." And people who had blogs would post it on their blogs, even just their little blog spot or wordpress or whatever blog. So now, if you take any of those sentences from that email and you put it into quotation marks and search for it on Google, you'll find literally thousands of blogs have pasted my confirmation email onto their blogs. And I think about this when young entrepreneurs ask me, "How can I get traction for my idea? How can I get word of mouth and buzz happening?" I think you can read business books and try to do these very serious, you know, furrowed brow analytical approaches to this. Or sometimes it's just these cute little colorful things that you do that set you apart from the rest that make you remarkable. And that makes people remark on you about you. So, yeah, I think thousands of people heard about CD Baby because of that one little silly email. And I think a comparable might be Zappos, for instance, in their customer service. And what was the anecdote that got spread around? The anecdote was you could call up Zappos for anything. Even if it was unrelated to the product. You could call them up and say, "Yes, I'm looking at the website, but I'd actually really like a pizza delivered to my house." And you figure out how to do it. And on the serious analytical side, you say, "Oh my God, that's such a waste of human and capital resources." And can you imagine if everybody called to order pizza, which of course is never going to happen ever? And they got, I mean, probably millions of dollars of free publicity just by making that okay. And like, how long did that take? What? Not long at all. Plus, you know what, man? I don't mean to sound like New Agee or whatever, but it's the right thing to do for the world, right? It's like, just put aside the numbers for a bit. It's the right thing to do. It's cool. It makes people happier. It makes the people working there happier, which makes them more into the whole feeling of what they're doing. There's so much more to a business than just the money. Yeah. So tell me about, I remember reading about this, but I think we might have talked about it at one point, when people would call CD Baby trying to offer you financing. How did those go?

How Derek Sivers responded to those seeking to invest in CD Baby during the dot-com bubble (46:01)

Well, so remember, I started CD Baby at the end of '97, beginning of '98. So it was the first .com boom. And so much money was flying around, and everybody was trying to push money at everyone who had a .com on their domain name or had anything going on. So of course, me with an actual profitable running business that was really the only game in town, by the way, back when I started it, if you were a musician that wanted to sell your music online, there was a guy named Derek in New York that could do it for you, and that was it. There were no other businesses that would do it. Some showed up a year or two later, but at first I had no competition at all. I was it. So yeah, tons of money was shoved my direction. And I entertained the first few calls and they said, "We want to invest in your company." So, "Well, why?" They said, "So you can grow it faster." I said, "But I don't want to grow it faster." They said, "Well, don't you want to scale or get more resources?" They said, "No, I have all the resources I need. I'm good." I was profitable since the first month in business because my startup costs were $495 is what it cost me to start the business and get it running. It took me six days to build the site and get it up and running, and it was profitable in the second month of business when I sold over $400 of CDs that second month in business. I was profitable ever since. And I just didn't need the money. And so, yeah, people kept offering and they would wave these big dreams in my face thinking it was going to distract them or entice me, but it just didn't. And I remember, oh, I doubt you remember was a big deal in 1999 through 2002 or so. They were like the big daddy of independent streaming music online and downloads. And so, they had all, I think, yeah, they had an IPO. They were public. And was interested in buying CD Baby and they asked what my price would be. I said, just not interested in selling. And they said, "Come on, everybody's got their price." I said, "No, I'm not interested. I'm having fun." They said, "Come on, even billions of dollars." And I said, "What are you? Carl Sagan? No, I don't want to sell." There's just nothing in it for me. I'm enjoying what I'm doing. I don't need the money. So, after that point, after the first year or two, I just taught my customer service people. Like, if you get any calls from investors or whatever VC firms or anything, please just tell them, "No, don't even send them my way. We're just not interested." So, that lasted for 10 years. And how did you develop that relationship with money? Is that something from your parents? Is that, and I'm going to ask a very personal question also, and you can feel free to not answer it. Why did your family, why weren't none of your family members at your wedding? Oh, sorry. They were too. Sorry. When I said "Tregus," I meant, "Yeah, exactly." All right. Sorry about that.

On his relationship with money and saying “no” to millions (49:06)

All right. No, no, no. Now that I've checked that, okay? It was in the back of my mind. So, how did you develop this relationship with money where you would say no like that for 10 years? Because that's not what most people would do. Because I had enough. Actually, you know what? It's a bit of a trick reason. Because in the early days, I still considered CD Baby to be a bit of a distraction. Because you remember, I was making my living as a professional musician, which was my original goal and dream. So, I was living my dream. I was touring, playing on people's records, producing people's records. I played about 500 colleges in the Northeast. I was making good money as a professional musician. That's what I really wanted to do. And this little CD Baby thing was just like a favor I was doing for my friends to kind of give back to the community. So, as it grew, well, I didn't want it to grow. Because, yeah, it was taking me away from my music, which was my real love. It's making the music, not selling other people's music. So, there was this moment when I kind of sadly realized I think I've created a business. Oh, well, I might as well make it something awesome. Meaning, I want to make it like a utopian dream come true from a musician's point of view. And I spent a night brainstorming, like, what would a real dream come true from a musician's point of view look like? And I don't know if this will make sense to your listeners, but let's just find out. It was going against everything that was the unfortunate way that the music distribution world worked at the time. So, it's like, number one, I want to be paid every week. Number two, I want to know the full name and address of everybody that buys my music. Number three, you'll never kick me out for not selling enough. Because that was a big problem in the traditional music distribution world, as you were given a window of time. Kind of like physical books are still art. You have to prove yourself in a window of time. They'll put you into the bookstore. If it doesn't sell well, you're yanked out to make room on the shelf for other stuff. And then number four, no paid placement. Because it never felt fair that people could come in and buy up the front page to get unequal footing, right? So, that was like my utopian ideal for how this would work. The reason I'm telling you this is that to set the tone that, like, I wasn't trying to make money. I already had enough money that I had made, you know, gigging and touring and all that stuff. I already had money. So, this was a thing I was doing to give back to the community, to create something that needed to exist kind of artistically, or just almost like a community service kind of thing. So, that was the original DNA of this thing. And, you know, from what we know about DNA, it helps decide what things grow into, right? So, this was the DNA. So, then as it grew, and then it became really profitable. And I was making, I don't know, $100,000 a month doing this thing. And I had all my bills paid off. There was nothing I wanted to buy. So, if somebody from California contacted me saying they wanted to give me lots of money to take a big chunk of my business and help turn it, you know, big, big, big. We think you could do an IPO. I would just sneer, like, "Oh, no, that sounds awful. I don't want that life. I'm enjoying being fully in control here and doing things for the right reasons, doing things for my musician friends to make them happy, make the customers happy, make the musicians happy, like, all's good." What was the business model in the very beginning? It was only two numbers. Actually, there's a cute story. Most of us, you know, when we start charging money for the first time, for our services or our goods, we don't know what to charge, right? So, for Marco, my first friend that asked me to do this, and maybe the next 10 or 15 friends that came after, I was charging nothing. I was just doing this as a free favor. This was my community service. And then once I realized, like, total strangers were sending me their music, I said, "All right, I better charge something, but I don't know what to charge." So, I was living in Woodstock, New York at the time, and there was a cute, tiny little record store in town that sold consignment CDs on the counter of local musicians. So, I walked in there one day, and I said, "Hey, how does it work if I want to sell my CD here?" And she said, "Well, you set the selling price whatever you want. We just keep a flat $4 per CD sold, and then just come by every week, and we'll pay you." So, I went home to my new website that night, and I wrote, "You set your selling price at whatever you want. We just keep a flat $4 per CD sold, and we'll pay you every week." And then I realized that it took about 45 minutes of time for me to set up a new album into the system, because I had to lay the album art on the scanner and Photoshop it and crop it, and then fix the musicians' spelling mistakes in their own bio and all that kind of stuff. And it took about 45 minutes of work per album. So, it shows you what I was valuing my time at those days that I thought, 45 minutes of my time, that's worth about 25 bucks. So, I'll charge a $25 setup fee to sign up for this thing. And then, ooh, at the last minute I thought, "Wait a second. In my mind, 25 and 35, they're in the same brain cell in my head. 25 and 35, those numbers don't feel very different when it comes to cost. You know, like $10 is different, and $50 is different. But $25, $35, that occupies the same space in the mind. So, you know what? I'm going to make it 35. That will let me give anyone a discount any time they ask. Even if somebody's on the phone and upset, I'll say, "You know what? Let me give you a discount." So, I added in that little buffer so I could give people a discount, which they love. So, yeah, $35 setup fee, $4 per CD sold. And then, Tim, for the next 10 years, that was it. That was my entire business model, you know, was generated in five minutes by walking down to the local record store and asking what they do. I love that story and simplicity because I think there is an infatuation of fetishizing of pivoting in the tech startup world that has infected many other types of entrepreneurship, where people think, "Oh, if I'm not pivoting, I'm not doing something correctly. I should change my business model in my entire customer base every two months." Yes. And I don't view that as a virtue. Yes, there are times to change if something isn't working. But if you don't take the time up front to think about that, and then you're constantly chasing the latest sort of fad or whatever appears on the cover of TechCrunch or Ink Magazine or something like that, it's a recipe for failure for most people. Yes. I mean, there's a huge survivorship bias. I'm just going to rant for a second. There's a huge survivorship bias that I think is important to realize if you're hoping to become an entrepreneur or an entrepreneur, if you're only reading the cover stories, you're only getting the happy success stories. And for that reason also, I think it's dangerous to idolize people who bet the farm and just happen to pull it off because those are the people who are going to be written about, much like if you open a barons and you look at all these mutual funds with these spectacular records, well, maybe they just got lucky and all the other ones can't afford to buy ads because they're no longer in existence. And so I think it's very similar. One of the essays that you're best known for is Hell Yeah or No. And this has been extremely important for me to consistently reread or listen to.

The origins of the HELL YEAH! Or No. (57:06)

How did it come about and then what is the gist of that? There was a music conference in Australia that I had told my friend I would go with her to. It wasn't even like the conference themselves were really expecting me. My friend Ariel Hyatt is one of the best publicists I know. She was speaking at that conference and asked if I would come with her as a co-presenter in her mentor session or something. So I had said yes, like six months before. Yeah, sure, Australia. I'm living in New York City. I'm like, yeah, sure. And then once it came close and it was like time to book the ticket, I was like, I don't really want to go to Australia. Right now I'm busy with other stuff. And it was actually my friend Amber Rubarth, who's a brilliant musician. I was on the phone with her and kind of lamenting about this. And she's the one that pointed out. She said, it sounds like, you know, from where you're at, your decision is not between yes and no. You need to figure out whether you're feeling like, fuck yeah or no. And I said, yeah, that's really what it comes down to. Right? The idea is if you're feeling anything less than like, oh, hell yeah, I would love to do that. Oh my God, that would be amazing. If you're feeling anything less than that, then just say no. Because most of us say yes to too much stuff. And then we let these little mediocre things fill our lives. And so the problem is when that occasional big, oh my God, hell yeah, thing comes along. You don't have enough time to give it the attention that you should, because you've said yes to too much other little half-ass kind of stuff. Right? So once I started applying this, my life just opened up because it just meant, I just said, no, no, no, no, no, no, to almost everything. But then when the occasional thing came up, that I was really like, you know what? That would be awesome. Then suddenly I had all the time in the world. And you know, people say this, I'm sure, you know, every time people contact you, every time people contact me, they say, you know, look, I know you must be incredibly busy. And I always think like, no, I'm not. Because I'm in control of my time. I'm on top of it. Busy to me seems to imply like out of control. You know, like, oh my God, I'm so busy. I don't have any time for this shit. To me, that sounds like a person who's got no control of their life. No control and unclear priorities. Yes, exactly. So you asked how it's applying in my life that still just on the little tiny day-to-day level, even personal things. God, even people you meet, even, you know, as I'm dating. You have to do the hell yeah or no approach. People ask you to go to events or God, even, you know, even people asking to do a phone call or anything. I think, you know, am I really excited about that? And, you know, almost every time the answer is no. So I say no to almost everything. And then, yeah, occasionally something will come up. Even a little surprise will be dropped in my lap. Like this thing that happened just two months ago called the now, now, now project, which we don't even really need to talk about. The details don't matter so much. But it was just something that popped up that seemed really interesting and people really wanted. And luckily, because I say no to almost everything, I had the time in my life to make it flourish. So for the last, like, six weeks, all I did full-time, like 12 hours a day, was suddenly work on this brand new thing that showed up because I could, you know. So that's, to me, the lovely result of taking the hell yeah or no approach to life. Where can people learn more and check out the now, now, now project? And also I should note in advance that for folks listening, we will also include links to anything we've mentioned in the show notes, which will be at, all spelled out. But where can people find more about now, now, now?

Discussing the Now Now Now project (01:01:21)

It's, if you go to now, now,, you'll find more about that. It was just in short, I noticed that everybody has an about page on their site and people have a contact page on their site. But usually whenever I'm looking at somebody's personal site, even yours, a big thing I often wonder is, like, I wonder what he's up to right now, like working on kind of stuff. And Twitter and Facebook don't answer that. You know, you can see somebody's stream of stuff, but it just kind of says like, "Okay, here's what I had for dinner last night. You know, here's something in the news I'm mad about or here's a cute thing I'm sharing." But it doesn't really tell me like, "How are you?" You know, like, if you and I haven't talked for a year, like, "What's up? How you doing? What you working on?" So to me, the whole idea of a now page on your site is just a general, like, "Here's what's up with me now." So I just had one of those on my site. I had a now page and then a guy named Gregory Brown liked it. He put one on his site and all I did was just retweet him when he told me. And I said, "Cool, I wish everybody had a now page." And like, within a few hours, there were eight more people who had a now page and then within a month, 550 people had a now page on their website. So I just put together now, now, It's just like kind of a cute collection of people who have a now page on their website. Anyway, but you know what I mean? The point is the details don't matter, but like, I'm so glad I had the time to do that. And it was only because I say no to almost everything that I was able to just throw myself into this project and build this new thing on a women catch the momentum. So I am reading a section of this blog post that I wrote about you and your, the best email you ever wrote with the Japanese boxing specialist and so on. And one of the paragraphs that I put here for those people interested, it's just the most successful email I ever wrote, but it's everywhere online. And it reads, "Strangers still at its largest. Derek spent roughly four hours on CD Baby every six months. He had systematized everything to run without him." And feel free to correct that if it needs to be corrected. But what, assuming that's roughly true, what were some of the most important decisions or realizations that made that possible?

What inspired the automation of CD Baby (01:03:41)

Hmm. I love the timing for when I read "Four Hour Workweek" because it was actually just after I had done this like complete delegation of everything. That it was feeling the pain from everything having to go through me. It was my business, right? 100%, no investors, no nothing. It was me. And so I hired people to help me. It was all me, me, me. So four years into it, it was growing. It was really taking off. I had 20 employees, but still almost everything went through me. And it made my day kind of miserable because I'm a real introverted focused kind of person. I love to just sit down for 12 hours and do one thing without distraction. You're an INTJ, Myers-Briggs. Yep. Are you? I'm 100% INTJ. Yeah. So I hated going to the office and being distracted every five minutes with my employees asking me questions. So that's what I just felt such pain about this. Like, "I hate this!" That I really literally meant I booked a flight to Kauai, I believe. And I was going to move to Kauai and not give my employees my phone number. And literally move. I don't mean like take a vacation. I mean like I am now going to be running or I'm going to be the owner of CD Baby on a little island in Hawaii. And you guys just figure out your own damn problems. Because I was just having so much psychic pain about this. But then luckily with lovely coincidence that night that I booked the flight to Hawaii, I watched the movie Vanilla Sky. And in Vanilla Sky, Tom Cruise is like the owner of this big publishing company. But he gets all caught up with these crazy women and gets too overwhelmed with his life and focusing on his own happiness. And all that. And pretty soon his company has just wrestled away from him. And I thought, "Oh, I don't want that to happen. Like I don't want to just plug my ears, close my eyes, run away, and have my company taken away from me. I need to give this, I need to deal with my problems instead of running from them." So I canceled the trip to Hawaii and went into work the next day and decided to fix this thing. So then next time somebody asked me a question, I gathered everybody around. I said, "Okay, everybody, Tracy just asked me, you know, Derek, what do we do when a guy on the phone says he wants a refund?" I said, "Okay, everybody stop working, everybody gather around. Okay, Tracy asks what we do if somebody wants a refund. Here's not only what we do, but here's why. Here's my philosophy. Whenever anybody wants a refund, well, we should always give it to them. And I would just explain not just the what to do, but the why. It was constantly communicating the philosophy to get to the core of it. And I think you mentioned this back in four hour work week. There's almost nothing that really has to be you. Like you can almost get kind of AI and figure out how your brain works, how your decision making process works and just teach it to other people so that other people can do it. And yeah, that's what I did for every single thing that ever came my way. I would gather everybody around, explain the philosophy behind it, why we do things this way, why I'm about to say, what I'm about to say. And now here's what I think we should do. Do you understand why? Now please write it down. But it was also important that I taught it to multiple people, not just one, and had them write it down. And then the cool thing is I wasn't doing the hiring anymore. The company I had taught other people how to do the hiring. So soon my employees were doing the hiring and then they were teaching new people how to do this thing from the book. And yeah, so by let's see. So that really started four years into the company. It was six months of difficult work to really make myself unnecessary. But then my girlfriend at the time decided to go to film school in LA. So decided to follow her down there. So I moved down to LA to be with her, which was a nice symbolic way to let the company know. Like you're on your own. I'm still the owner. And in fact, so there's one little caveat to the thing where you said that I was working on CD Baby for four hours a year or whatever you said. Yeah, four hours or six months. Is that that's how much time I spent doing this stuff I didn't want to be doing, right? The monotony, the bureaucracy stuff that I had reduced down to almost nothing, like a few minutes a week. But what I was doing from seven a.m. to midnight every single day was programming like the future of CD Baby. And that's just the stuff that I loved doing. So it was just it was about making my life the way I wanted it to be working on the stuff that I wanted to be working on and not doing the stuff I didn't. Which I'm glad you brought that up because I want to clarify something that is a common misconception related understandably to the title of the four hour work we can do. And there's I it is the it's like the single largest blessing and curse that is going to follow me for the rest of my life. But it's a catchy title. Yes, I tested it on Google AdWords. Yes, I had a great conversion rate. That's why it's that instead of something stupid like lifestyle hustling or the chameleon bla bla bla. I had a bunch of terrible titles that one performed best. But the objective is not to be idle. The objective is to control this non renewable resource called time so that you can allocate it to the things you most want to be doing. So I don't have in other words a trouble with heart. I don't have a problem with hard work as long as it is applied to the right things that are determined with some degree of self awareness and forethought or planning. So that's that's sort of PSA not for you Derek. No, I read the book, but for every like deck who stands up at a public Q&A and goes, well, I just want to ask, do you work for hours a week? And this one will like turn into one of the fantastic four and punch him in the neck from 300 feet away. But for everyone who is who's maybe inclined to stand up and ask that question, there's the answer. Read the book. And I bumped into somebody recently. You mentioned this book with the, I guess, frequently asked questions. And he was like, you should just make. Because I told him, I was like, you know, I try to be really patient. I try to spend a lot of time answering people's questions when they have them. But it's so clear that most people asking questions have not read the fucking book and they'll be like, can I eat bananas on the slow carb diet? You know, can I quinoa after chocolate custard on the slow carb diet? And I'm just like, fuck, if you have to ask, the answer is no. And you clearly didn't read it. And he's like, you should just make, you should just have t-shirts that say, what was it? R-T-F-M? Yeah, read the fucking manual. But alas, I'll cut that, that scream a little short. The book itself, I want to get to dig into some specifics with this manual, this rule book. When you had multiple people write it down, how did you then put together a resource that could be shared with new hires and so on? Actually, I think we put it on a, um, on a wiki inside, but honestly, most of it was just word of mouth kind of legend inside. Like, there were a few internal stories, kind of like the Zappos pizza story you just told. The one I always heard was Nordstrom's that there's some legend about Guy buys a shirt from Sears. It gets like burnt up in a fire and he goes to Nordstrom's to return it and they give him his money back. Like, they have like such a liberal return policy that they'll even let you return burnt stuff from another store. And so a legend like that will travel down. And it carries the philosophy inside of it. So it's almost like a little story like that can replace 20 pages of an employee handbook. Totally agree. Yeah. It's an aphorism or it's a school. Yeah. Exactly. Fable. Fable. So there were quite a few of those inside CD-baby, especially for the early people, would see the decisions that I had made and the people that I had given all their money back in case anything went wrong. You're just talking to me in the conversations and getting my philosophies and the early employees at CD-baby really got it and then they would spread it to the new people. On the, so if we flip from book writing to book reading, you have a page on your site,

Derek Sivers: Personal Perspectives And Habits

Derek Sivers’s book consumption habits and creating directives (01:12:36)

I'll link to it in the show notes. I think it's book. Correct me if you are all wrong. You have notes on more than 200 books. You appear to be a voracious reader. How do you select the books you read and how do you read them? Okay. I select, really I let usually large numbers of people decide, meaning like lots and lots of five-star reviews on Amazon. Occasionally somebody that I really respect and that knows me will tell me you need to read this book and even if it's had no reviews on Amazon, I'll just trust them. But for the most part, I tend to go for things that I've seen, lots of rave reviews, then I browse through the description on Amazon, then I look at the review, actually read the reviews people have said and it really sounds like something, okay, this sounds worth my time because I don't read fast and I don't try to read fast. I like to sit and ponder as I'm reading. So when I'm committing to a book, yeah, that's 20 or 30 hours often. So I don't take it lightly. So yeah, I tend to go with lots of Amazon reviews, but then I also give up quickly. So if like chapter three, if by chapter three I'm not really into it, I'll just ditch it and you don't even see those on my side. So I've ditched almost as many as you see there and I just don't write them up. I just delete them on the Kindle and move on. But here's the interesting thing is, okay, there's a couple of interesting things. So years ago, actually it was around 2007 when I first read four hour work week. I was living in London, even though CDV was still up and running back in Portland, Oregon, just because I wanted to experience the world. I was living in London at the time. And actually, you know what's funny? I don't know if I ever told you this cute story. It was my friend Ariel Hyatt, who I mentioned earlier, that told me about you and the four hour work week, but she told me a little fable about you. - Uh oh, uh oh. - So I can't remember if I ever confirmed this with you. - We'll find out. - She said. - We'll find out right now. I think at the time she was going to some kind of mastermind seminar by one of those, like, how to be a millionaire kind of guys. And apparently, you know, like five or six of those, how to be a millionaire kind of guys, held some big mastermind thing in Hawaii or something. And you were supposed to be there. And you didn't show, and I think like Robert Kiyosaki and people like that were there. And you were supposed to be there, but you didn't show up until the third day where you showed up like covered in mud because you had just on a whim decided to try sleeping in a tree or something like that. The legend goes. And she told me about the four hour work week, but basically like in this context of this guy, Tim, that doesn't give a fuck about convention. And it totally sounds like you're kind of guy that is doing things the way that you do it, because you don't give a fuck about convention either, and you should read his book. So that was like, yeah, I think it wasn't even available in England at the time. I had to go, I think the first time I got four hour work week was some like illegal PDF download of it off of BitTorrent. That's how it happens a lot. So that story, I believe is true. So I remember this particular event in Hawaii around the time that the book came out, or maybe a year afterwards, within the year following publication. And I remember going to Hawaii and realizing that I wanted to explore Hawaii as opposed to sitting in the conference room. So I rented a car and ended up finding a bed and breakfast where this house was built in the trees. But it wasn't available, or it wasn't on the market. And the caretaker ended up being this very attractive woman. And I said, well, is there anything that I can do to be able to sleep in this tree house? Because I'm really obsessed with this idea, and it looks like Jurassic Park here with these prehistoric looking plants. I'll even, and she had some like, ditch that needed to be dug or something. And so I did that. And did all this manual labor, then I ended up being able to stay in the tree house. And I think that it was on the Hana, I want to say the Hana highway if I'm getting that right. Just spectacular. I think it was in Maui. And so I did show up to the event late, like a tank top and these absurdly now even to be embarrassing, like European short shirts. I don't know why. And yeah, that's a true story. That's true. It's so confirmed. Yeah, it's so funny. I forget what tangent we were on. Oh, we were talking about how you read books. Ah, okay. So right around that time, I had been reading books foraciously for years. And people often ask about like mentorship. And did you have any mentors? And I say, well, no, books are my mentors. Like books guide almost everything I do. Like the stuff I've learned from books totally guides my life. So I realized though that I would love a book while reading it. And maybe it would still echo with me for a few weeks after, but you know, two years later, I couldn't even remember if I had read it or not. And I thought that's really a shame. Like I remember at the time that book meant a lot to me. Why is it now two years later? I've forgotten everything. I said, no, no, no, that's not good. So what I started doing in 2007 is every book I read, I would keep a pen in hand and I would underline my favorite sentences, circle my favorite paragraphs, right notes in the margins. And then after I was done reading the book, I would put aside like two hours to open up a blank text file and type out everything into a plain text file. So that I could knowing that plain text files are about the most permanent long last date format. There can be they will work on everything. You can read them on phones or new devices we haven't even thought of yet. We'll always be able to read plain text files. So I started doing this for every book I read and then I would review my notes later. So every time I'm, say just eating breakfast or something for ten minutes, I'll pull up one of the notes from a previous book I read and just kind of re-review it. Sometimes kind of stop, take a sentence that means a lot to me right now, open up my diary and write about that for a while. Like really internalize. Basically, I wanted to memorize every lesson I had learned in every one of these books. So that's what I started doing. I even started putting them into the space repetition systems and that didn't really work out too well because I wasn't sure how to formulate that knowledge into a Q&A flashcard kind of format. You're using a super memo or something like that. Exactly. So. Unkey side note for people means wrote memorization in Japanese. Really? A and K.I. Sorry to interrupt. So it wasn't until say 2010 that I realized that I just had all of these lovely book notes hidden on my hard drive just for my eyes only. And I thought, you know, why don't I just put them on my website? If the publishers tell me to take them down, I will. But maybe it's used to people. So, yes, What you're seeing is all of my detailed book notes I've taken since 2007. If you were to, and this may be a very difficult question to answer, but to suggest five to start with. Or so. I mean, I'm just throwing out a random number. But if you were to suggest some books to start with at And by the way, this is not a setup for my own book. This is just... Oh, no, no, no. God, wouldn't that be cheesy? First, the four hour quick. Second, see rule number one. Yeah, no. So, I've actually already answered the question for you because once I posted them on my site, I realized I should give them like a one to ten rating because I knew this is the next question people are going to ask is, well, which ones would you recommend? So, I give every book a one to ten rating and it's when you go to, it's already sorted for you with my top recommendations up top. And I think it's... You know what? I hadn't told you this either. Back in 2008 or nine, you and I were sitting down the hill from your house, that local coffee shop. And we were talking about the Charlie Munger book. That big thick black one, I forget what it's called. Oh, Seeking Wisdom. Seeking Wisdom. From Munger to Darwin or maybe the other way around. By Peter Bevelin. That's it, yes. So... That's a fascinating book. Well, I'm glad you have turned you on, too. Oh, yes, I appreciate it. So, after turning you on to that book, I remember we were talking about the books that changed our life. And you told me, I think, was it the magic of thinking big? Yeah, that's right. David Schwartz, I have it face out on my shelf in my living room so that I can see it. Okay. So, when you told me that the magic of thinking big made such a big difference to you, I think like the next week, I picked it up and I read it. And it did nothing for me. Yeah. I was still thinking. Yeah, and asked to catch you at the right time. Exactly. And so that's why... And it's also one of those books, just sorry, I'm getting defensive, but it's one of those books that I read in around 2000, maybe a year or two after college, when I was in a... Shitty, 100 plus hour a week job where I'm sleeping under my desk and sitting in the fire exit, because that's the only place they can fit me. But yeah, it has to find you at the right time. Exactly. And so there have been people that I tell about how Tony Robbins awakened the giant within totally changed my life, and I give it to friends and they go like, "Eh, did nothing for me." So you're right, it does matter when you read a book. Even I noticed on a specific subject, I read and loved stumbling on happiness. Loved that book. And so I read like two or three more books on the subject of the study of happiness. And by the time I got to the third one, I forget what it's called right now, maybe Happiness Project or something like that. Whatever the third one I read was, I remember flipping through the book quickly, like, "Yeah, yeah, yeah, yeah, I know, I know, I got it." And so I gave it a really bad rating on my website, and somebody emailed me later going, "Hey, that book changed my life. I can't believe you gave it a two out of ten rating." And I looked again at my notes and I thought, "You know what's actually probably a really good book?" I just read it at the wrong time because I had just read two other books on that subject. Exactly, just in a different order it might have been a ten. Exactly, if I would have read that one before stumbling on happiness, which I gave a ten to, then I would have given that one a ten and stumbling on happiness might have been like, "Yeah, yeah, yeah, I know this story." Stumbling on happiness is a great book. I think that it's for those people who are familiar with the term that I use in the four hour work, the deferred life plan. So in other words, sort of saving and working in order to retire at some point in the future, maybe ten, twenty years down the road, thirty, perhaps, to redeem all of that toil for some reward, like sailing around the world in a sailboat. Stumbling, I always forget, is this something on or upon happiness? Stumbling on happiness. Stumbling on happiness by Daniel Gilbert, is that right? Yeah. So, what is a great reality check for that type of, I think, extremely risky, prone to failure, deferred life planning? Yeah, so I've got to tell you, so we haven't really talked about this yet, but this is so up your alley, or your listener's alley, or for the people who were into books. We'll appreciate this. So a lot of my friends, actually I don't think any of my friends are as into reading as I am. Okay, a couple are, but most aren't. And so whenever I tell them about some amazing book I've read, the gist I get from my friends is like, well, just tell me what to do. So like, give me the next card, yeah. Yeah, like they don't want to read the book. And so my friend Jeff is a smart guy. I mean, he's a lawyer, he's smart, but he just looks at me with these tired eyes and he just says like, I'm not going to read the book, dude. Like, just, you can stop pushing it on me. It's just never going to happen. He said, just tell me what to do. He said, I trust you. I like you. You know me. So tell me what to do. And I realized that if you trust the source, you don't need the arguments that so much of a book is arguing its point. But often you don't need the argument. If you trust the source, you can just get the point. So after reading, you know, taking detailed notes on 220 books on my site, I realized that distilling wisdom into directives is so valuable, but it's so rarely done. In fact, the only time I can think of that was done was Michael Pollan with his three books in a row about food, each one getting shorter and shorter. I think the first one was, was it like omnivores dilemma? Omnivores dilemma, yeah. Which was big. So I know that you're the kind of guy that would... It's a great book, but also, I mean, there are like 70 pages on corn production in the US, and most people just drop out. Even I was like, God, my eyes are glazing over here, but I know there's some good stuff coming, so I'll slog through it. But yes, a very great book, but a very big book. And then he did one a year later that basically took the best of the stuff from omnivores dilemma and made it into a shorter kind of more pop market, two to three hundred page book, I believe. I forget the name of that one. And I have an offensive food. That sounds right. Yes, thank you. So even that one, I remember somebody telling me I should read it and me looking at it going like, I don't know if I really want to read 300 pages about food. But then a year later, he put out a teeny, tiny little book called Food Rules. I think that's what it's called. And it's like, you basically can read the whole thing while just standing in the bookstore. It's... He took the energy and the effort to compress everything he's learned into very succinct directives. And that's what it's going to... Sentences that tell you what to do. Do this, do that, or don't do that. If your grandmother wouldn't recognize it as food, don't eat it. And his tagline for that book, the popular phrase was, eat food, mostly plants, not too much. Right. And I so admired that. I got inspired by the effort it takes to distill the blah, blah, blah, blah, blah down into the specific sentences for the people that just aren't going to read that 900 page book. Right. Like probably all of that same information is in the 900 page book, but we just have to realistically admit that most people will never read the 900 page book. So as I'm reading these 300 page books, 220 of them, very often there will be some like brilliant, amazing, important point on like page 290. And I feel a little sad that almost nobody's going to read that. Like I wish that these little tiny points were extracted like without all of the surrounding argument. So especially, okay, I'll admit this is also sparked by the idea of when I had a kid and I thought like I might not be alive when he's my age or even when he's 19. I might die before he gets older. How could I compress everything I've learned that I think he should know into a real succinct format that he will... definitely read. And then of course then I thought, and you know, other people will read too. So I got onto this idea of the do this project, which is instead of talking around a subject, just giving directives saying do this, do that, don't do this, don't do that. Which is kind of funny because it feels very presumptuous, right? Like who am I to tell others what to do? But then I think, well, who am I not to, right? It's useful. So get over myself. Kind of like you asked about like, you know, me on stage when I was 18, what was the biggest lesson learned. Like this isn't about me. People aren't here about me. They're here for their own gain. Even that, oh, you asked about my advice to TED speakers. That's my main advice to TED speakers. It's like people aren't here to see you in your life story. People come to TED or watch TED videos to learn something. So just speak only about what is surprising and skip everything else. Well, anyway, if people could talk, if people could start with one of your talks, I know I'm interrupting for a second, but which talk would you suggest as a starter? My favorite one is the one, I think on the TED site, it is called Weird or Just Different. I call it the Japanese addressing system. And I actually know what that means. Yeah. It can be so confusing. Until somebody explains it to you and then you realize like, oh, it's just a different way of thinking. And here, I'll just give you a little teaser. The talk is only three minutes long. So you go to and search for Derek Sivers and it's called Weird or Just Different. But the little teaser is it blew my mind when I found out that in Japan, the reason the streets don't have names is because they think of the streets as the empty, unnamed spaces, because the blocks are the things that have names. The blocks are the piece of land with houses on them. That's what's important. Whereas in America, and most of the world, if you say, what is the name of that block, people will look at you weird, like, well, this is Oak Street, this is Third Avenue. What do you mean? And they say, well, what is that block called? You see, that doesn't have a name. We don't name our blocks. We name our streets. The blocks are just the unnamed spaces in between named streets. So in Japan, it's the opposite. The streets are the empty, unnamed spaces in between named blocks. So I realized that how many things in life actually work just as well, the complete opposite way we're used to thinking of them. Both ways are correct. So anyway, that's the idea. But we were talking about directives. Yes. And the advice you give Ted Speakers is just how I took us off track. Yeah, all right. So go ahead. No, no, no, I was going to ask, and I'm not trying to cut the short. I'm just so I don't forget to ask, where can people find the directives? Only in this podcast. No, it's true. I haven't done anything with it publicly. At first, I thought I was going to make this into a big keynote speech. I was doing at a conference, the World Domination Summit Conference in Portland. I spent four months of full-time work from like 7 a.m. to midnight for four, you know, seven days a week for four months in a row, just rereading all 220 book notes, extracting or trying to turn all of this advice or this knowledge, this wisdom, trying to turn it into directives. Because a lot of it almost never is in the directive format already. People talk around a subject. They talk about findings and research. But it takes some real effort to kind of like the old philosophers. You've read the Stoicism book, "The Guide to the Good Life?" Yes, I have. I have that up on my living room wall as well. So in that book, he says, right in the intro, he said, "If you ask a modern person who calls himself a philosopher, "What should I do with my life?" He said, "Sit down and get comfortable "because they will tell you, well, it depends what you mean by what. "And it depends what you mean by do. And really, it depends what you mean by life. "Or really, maybe it depends on what you mean by my life." He said, "People are talking around the issues so much these days." But he said, "Back in 600 BC, if you would have asked one of these philosophers, "What should I do with my life?" They would sit down and tell you exactly what to do with your life. Do this, don't do that, pursue this, don't pursue that." So I was really inspired by that intro too. So the idea was, "Now, how can I go back through all of these amazing books I've read "and compress all of this wisdom into specific directives?" So it took me four months of work to come up with the following 18 sentences. Do you want to hear them? I do want to hear them. I'm super excited about this. So this was going to be a 35-minute long keynote speech, and it turned out to be a horrible 35-minute long talk, but it's entertaining for about three minutes. So here's the three-minute version. Okay, first I had fun categorizing them. So this is the category called "How to be useful to others." Ready? I'm ready. Number one, get famous. Do everything in public and for the public. The more people you reach, the more useful you are. The opposite is hiding, which is of no use to anyone. "How to be useful to others?" Number two, get rich. Money is neutral proof that you're adding value to people's lives. So by getting rich, you're being useful as a side effect. Once rich, spend the money in ways that are even more useful to others. Then getting rich is double useful. "How to be useful to others?" "Share strong opinions." "Strong opinions are very useful to others." Those who were undecided or ambivalent can just adopt your stance, but those who disagree can solidify their stance by arguing against yours. So even if you invent an opinion for the sole sake of argument, boldly sharing a strong opinion is very useful to others. "How to be useful to others?" "Be expensive." People given a placebo pill were twice as likely to have their pain disappear when told that that pill was expensive. People who paid more for tickets were more likely to attend the performance. So people who spend more for a product or service value it more and get more use out of it. So be expensive. That's it. Okay, this is good stuff. So that's how to be useful to others. That's just one category. I've got a few more if you want to hear them later. Yeah, well, what is your favorite of the remaining categories? Maybe we could do one more. Okay, good. If you imagine that I've got a few more that are done in that format, I've got this is very stoicism. I've got a whole category called "How to Thrive in an Unknowable Future." It's like prepare for the worst expect disaster. Own as little as possible. Choose opportunity not loyalty. Let's do that one. I mean, you know I'm a sucker for stoicism. Alright. Let's talk about that one. Okay, so "How to Thrive in an Unknowable Future. Prepare for the worst. Since you have no idea what the future may bring, be open to the best and the worst. But the best case scenario doesn't need your preparation or your attention. Some mentally and financially just prepare for the worst case instead. And like insurance, don't obsess on it. Just prepare and then carry on appreciating the good times. "How to Thrive in an Unknowable Future. Expect disaster." If you ever watched a VH1 behind the music, you know that like every single success story had that moment where the narrator would come in and say, "And then things took a turn for the worst." So fully expect that disaster to come to you at any time. You have to completely assume that it is going to happen and make your plans accordingly. Not just money, but health and family and freedom. You have to expect it to all disappear. Besides, you appreciate things more when you know this may be your last time seeing them. "How to Thrive in an Unknowable Future. Own as little as possible. Depend on even less. The less you own, the less you're affected by disaster." "How to Thrive in an Unknowable Future is choose opportunity, not loyalty. Have no loyalty to location, corporation, or your last public statements. Be an absolute opportunist doing whatever is best for the future in the current situation, unbound by the past. Have loyalty for only your most important human relationships." "How to Thrive in an Unknowable Future. Choose the plan with the most options. The best plan is the one that lets you change your plans. For example, renting a house is actually buying the option to move at any time without losing money in a changing market. And lastly, "How to Thrive in an Unknowable Future. Avoid planning. For maximum options, don't plan at all. Since you have no idea how the situation or your mood may change in the future, wait until the last moment to make each decision." "Which of these have you most concretely implemented in your own life from this category?" "Oh God, I really internalized this category. It's the whole way I see the world. If you look inside my head, you'd think I was a little nuts and just that I'm always expecting everything to disappear. Even as I'm like, I step outside, I'm living in New Zealand now and I step outside. It's just gorgeous surrounded by nature's blue skies. I just inhale and I think, "Yup, this is all going to disappear. This is all going to go to shit. Pollution is going to wreck this all." But I don't think that in an awful doom and gloom way you can tell I'm not E-or. But it's just part of my appreciation for everything now and every person I know. Even just my health, even just God, when I stand up in the morning and I wake up full of energy, I think, "Yup, in another couple of decades, that's not going to happen anymore. I really appreciate this." So, yeah, it's more of just a deep mindset. I give a short five minute talk on practical pessimism. I think it was just stoicism as a productivity system. I talked about this because I think it's so important that not to be brainwashed into looking at everything with rose-colored glasses because it is not always a constructive exercise. In fact, it can very much be the opposite. And the primary reasons that I'm fasting right now, I'm in eight days into a target of ten. I'm getting a little woozy today, but all things mostly manageable. And I'm also, this is what I haven't mentioned to you, also unshaven, also wearing the same clothing, pants, jacket, et cetera, all week long. And the reason for that is actually, and you just said it reminded me a lot of Marcus Aurelius' meditations, which were the Emperor of Rome's wartime journal, never intended for publication. But it would always start with, like, today you're going to meet rude, ungrateful, arrogant people. And this is how you're going to contend with it. And it seems very depressing until you realize that he was setting a creating a mindset that could deal with those worst-case scenarios if they presented themselves. And similarly, to Seneca, who's very controversial stoic, but nonetheless, my favorite to read. And I have a huge, like, 30 hours of audio coming out related to Seneca shortly. But one of my favorite passages from Seneca is one that reads, and I'm going to massacre this, but it's paraphrased. Set aside some time, each month, where you subsist on the scantest affair, the cheapest of dress, et cetera, et cetera, et cetera, asking yourself all the while, is this the condition I so feared? And so not only are you mentally preparing yourself by visualizing the worst-case scenario, you're actually practicing your rehearsing poverty or lack of variation, or in my case, no food. I've done this before with, say, rice and beans for five days. And you're like, okay, it cost me $2 a day or less to eat, and I feel fucking fine. And in fact, not having the paradox of choice, having to go to the Thai restaurant and pick from 150 items that all have the same six fucking ingredients. That's been really relaxing. And so on and so forth. So that's maybe a slight digression, but I've always appreciated that about how you have designed your life on the books. So I want to give -- I'm sorry, go ahead. >> Wait, actually, before we close out this subject, I have to just give you the one little punchline ending to these directives, because there were some that didn't fit into this, do this format, do that. And I didn't want to start making lists of what not to do, because I liked the idea that every single sentence should be actionable, right? And so don't do this, don't do that. Didn't feel actionable enough to me. So I had fun kind of like, you know, our mutual hero, Charlie Munger, had a speech once that I think he gave at USC. But I think he gave at USC about like how to be a failure. And it was like -- so I made a category that was called "How to Stop Being Rich and Happy." So this is like after you're rich and happy. How to stop being rich and happy. And I thought you'd appreciate this first one. Prioritize lifestyle design. You've made it, so it's all about you now. Make your dreams come true. Shape your surroundings to please your every desire. Make your immediate gratification the most important thing. How to stop being rich and happy. Chase that comparison moment. You have the old thing. You want the new thing. Yes, do it. Be happy for a week. Ignore the fact that happiness comes only from the moment of comparison between the old and new. Once you've had your new thing for a week and it becomes your new normal, then just go see happiness from another new thing. Yeah, you get the idea. No, I do. And I agree with the first point. I mean, people might think that I wouldn't, but been doing a lot of reading and practice with meditation and so on. But if you read, say, Tara Brock, which is a fantastic book called "Radical Acceptance," which I highly recommend to people who are Taipei in particular. But most suffering, actually Tony Robbins would say this too. I attended my first live event a few weeks ago, which was very fascinating. And a lot of fun. But that most suffering comes from a focus on me on the self. And as soon as you receive a piece of advice, maybe five years ago from someone, they said, if you're having trouble making yourself happy, just make someone else happy. And it sounds so cliched, but it's actually really pragmatic. And it makes me think of this, something simple that I've been doing that Gabrielle Reis, Gabby Reis, who was on this podcast with Laird Hamilton, both very famous athletes and they're married. And she said, go first. And all she meant by that was during your day, be first. Like, be the first to look at someone and smile. Be the first to look to walk up to. When you walk up to the barista, ask them how they're doing. Be the first to initiate that. And it's such a simple way to put a smile on people's faces, not always, but a good portion of the time. And that can change your own state. Two things on books, just because you're sharing your methods, I'll share a couple that I've enjoyed. One is on Amazon, I will look at the four star most four. If it has a sufficient critical mass of say five stars to be worth looking into, if that's how I'm filtering, then I will look at the most helpful critical reviews that are four and three star. In addition to that, I will go to, I think it's just and I will read the public highlights. So I'll take maybe five minutes to look at the most critical three and four star reviews, because the five star and the one star and two star tend to be worthless in a way. Yeah, because they're so one-sided. So look at the three and four star most helpful critical reviews, and then I will look at the Kindle highlights. And that is in effect seeing the movie trailer. It's like, if you don't like the highlights from the movie trailer, you're definitely not going to like the full feature film, especially when it takes 30 hours instead of one and a half. And the reason I started using a Kindle was specifically so that I could export my notes as text files. Yeah. And the, so that's one of the ways that I filter books these days. But the question that I always ask that I'd like to ask you, and I think we might have to do it around too sometime, because we're probably going to have to hop off maybe ten minutes or so. But what, there's so many questions I want to ask you. What is the book you've given most as a gift?

Most gifted books (01:46:36)

Geek in Japan. In Japan. Geek in Japan by Hector Garcia, because I'm fascinated with understanding the mindset of a place, right? Like, I would love to really understand the philosophy of Brazil, India, China, Finland, France, Japan, Thailand. Like, to me, each place seems to have its own cultural norms in how it approaches time or long term versus short term thinking, or what's precious and should be protected, or human interactions, relationships, dealing with obstacles, conformity versus rebellion, or just how it approaches people who are unfortunate. So we think of philosophies like existentialism, stoicism, nihilism, but I'd love to study Brazilism, Japanism, I really do think of each country's culture as kind of like a working, modern applied philosophy. So Geek in Japan is written by the Spanish guy who's been living in Japan for ten years. And while most of the book is kind of like, "Hey, check out this, look at that," it has a section in the middle that I think explains the Japanese mindset better than anything I'd heard before. And I'd spent months in Japan over the last 20 years. I've gone there five or six times and I used to play guitar for a Japanese pop star and toured the country, but somehow Geek in Japan made me understand Japan more. So I give that to everyone who's going to Japan. But actually, an even better book I've found since than on describing the mindset of a country is called "Ocontre, Figuring Out the French." It's so deep. It explains the mindset so well. I wish there was a book like this about every country. I highly recommend it. So you listeners out there, if you know of any other books like this that like explain the mindset of a country, please email me to let me know. There is a book and I'm going to rely on the readers as well. What is your email, Just Eric? If you want to leave it out. Yeah, And in the comments, guys, all the show notes and everything, links to these books will be at But there is a book out there. I want to say Enrico, something is the author. And I'm pretty sure it was an Italian. It effectively writes geek in America. But from the standpoint of Italian traveling through the US, including the heartland. So that's one. Cool. What's $100 or less purchase has most positively impacted your life in the last six months or recently?

What purchase of $100 or less has most positively affected your life? (01:49:16)

Well, I'm such a minimalist that I always avoid letting any new possession into my life, right? But I took my three-year-old kid to a cafe one morning that had a huge box of toys, like little figurines and cars and dolls and monsters. He was just in the zone for like two or three hours, completely engrossed in all these toys. So I was like, yeah, okay, I can't push my minimalism on him. He needs toys. So that night I went on to eBay and I found someone selling a huge box of old used toys just like that, figurines and cars and stuff, 20 bucks. Endless hours of entertainment since. Best $20 I've spent in a long time. Yeah, that's awesome. Do you have a favorite documentary or movie? No, I really don't watch hardly anything. I don't, I mean, relatively to the norm, right? I mean, I watch movies, but more kind of for the artistry, the cinematography, and I listen to music, of course, but like, I don't watch TED Talks or documentaries or TV shows. I also, I don't even read blogs or articles and I don't listen to podcasts. In fact, I listened to my very first podcast two weeks ago. That was the one with you and Tony Robbins. That was like the first time I've ever listened to a podcast because I just have this lovely optimized life where I just wake up and I write, write, write, write, write, write all day long. I have no commute. I'm never really driving anywhere. So I don't have any downtime like that. And if I'm outside, I want to hear the birds and the trees, you know, and if I'm working out, I'll either. Crank up the hip hop or sometimes just enjoy the total silence except for the hardcore sound of the clanking metal plates, you know, so I really just prefer books as my medium of learning and input of information intake.

What Derek Sivers listens to when working out (01:51:11)

What do you listen to? What are you listening to now or recently for working out with music? I've started realizing that I don't know my American history of hip hop, that I've always been loosely aware of it, but I recently saw the Chris Rock movie Top 5 and the running punchline in that movie is like, he goes around like, what are your top five? And people kind of name their top five hip hop artists are the ones that they feel are the most important. And there were some in there, I realized like, I know who these people are. Of course, we've all heard of KRS1 and rock him, but it's like, wait, I don't think I actually know their music well. So I've started giving myself an education in the history of hip hop. And so lately, I've been listening to nothing but hip hop going back to the very beginning, the wild style movie and the kind of early stuff and giving myself the chronological history of hip hop. It's been fun. Any favorites so far? I would say Eric, being Rocky, I'm our way up at the top for me. Yes, especially once I understood the context when you hear the before and after, like right now you can take. Rock him, for example, I mean, you can take him for granted the way that now if you listen to Jimi Hendrix, you can take what he was doing for granted because people have expanded on that. But if you think of like, what people were doing with guitars before Jimi Hendrix and after, it was just mind blowing. And so I think Rock him is like that for hip hop, that it's listen to what was going on before him. And then he came along with just such a whole new approach that changed everybody since. If you could have one billboard anywhere with anything on it, what would it say?

If you could have one billboard anywhere, what would it say and why? (01:52:46)

Well, my real answer if I was taking that literally is that I would remove all the billboards in the world and ensure that they were never replaced. You know, like, have you ever driven through India? You know, it's so sad. Well, I haven't driven. On my way to the Calcutta ER where I spent a week, I was not briefly looking at the windows. You know, even in these small towns in Kerala, like, there's almost no space that is left without advertising. So I really admire those places. Like, I think Vermont and Sao Paulo, Brazil, that ban billboards. But I know that that wasn't really what you were asking. So my better answer is, I think I would make a billboard that would say it won't make you happy. And I would place it outside any big shopping mall or car dealer. So ideally, actually, I think, you know what would be a fun project is to buy and train thousands of parrots to say, "It won't make you happy. It won't make you happy." And then you let them loose in the shopping malls and super stores around the world. That's my life mission. Anybody with me? Let's do it. Yeah, it won't make you happy. Very stoic. Very stoic. Which does not mean you can't have joy in your life. But it's, I think stumbling on happiness is a great one for people to peruse. Do you have notes on stumbling on happiness? Yeah, that's on there. Alright, great. So we will link to that. Okay, last, effectively last question. I'll give one or two more. And then I think we might have to sometime soon talk about around two. People are interested. So if you'd like to hear more with Derek, please let me know at T Ferris on the Twitter T-F-E-R-R-I-S-S. And you can loop in @Sippers as well.

Advice For The Younger Self

Advice for your thirty-year-old self (01:54:36)

What advice would you give your 30-year-old self? And place us, if you would, for where you were at 30 and what you were doing. Hmm. At 30. Well, let's see. I had just started CD Baby at 30. But I think the biggest advice I would give to my younger self, or more like knowledge learned like, "Hey, younger self, you should know this now." Is that women like sex? You didn't know that until I was 40. I think I didn't get that. I think through, you know, like teenage movies or whatever. We're kind of taught the opposite that's like, you know, men always want sex and women don't. I don't know why the media portrays it like that. But later I found out that's not true. I think the more interesting answer is that my advice to my 30-year-old self would be, "Don't be a donkey." And as soon as I mean. Well, I mean a lot of 30-year-olds that are trying to pursue many different directions at once, but not making progress in any, right? Or they get frustrated that the world wants them to pick one thing because they want to do them all. And I get a lot of this frustration, like, "But I want to do this and that and this and that. Why do I have to choose? I don't know what to choose." But the problem is if you're thinking short-term, then you're acting as if you don't do them all this week that they won't happen. But I think the solution is to think long-term, to realize that you can do one of these things for a few years and then do another one for a few years and then another. So what I mean about "Don't be a donkey" is you've probably heard the fable about, I think it's Beridin's donkey, who it's a fable about a donkey that is standing halfway in between a pile of hay and a bucket of water. And he just keeps looking left to the hay or right to the water, trying to decide hay or water. Hay or water. He's unable to decide, so he eventually falls over and dies of both hunger and thirst. So the point is that a donkey can't think of the future. If he did, he'd clearly realize that he could just go first drink the water and then go eat the hay. So my advice to my 30-year-old self is "Don't be a donkey." That you can do everything you want to do. You just need foresight and patience. Right, so say for somebody listening, if you're 30 years old now and say you have like five different things you want to pursue, then you can do each one of those for ten years and you'll have them all done by the time you're 80. You're probably going to live to be 80. So it's ridiculous to, I mean it sounds ridiculous to plan to the age of 80 when you're 30, right? But it's a fact that it's probably coming, so you might as well take advantage of it. It's like use the future. That way you can fully focus on one direction at a time without feeling conflicted or distracted, because you know that you'll get to the others in the future. And I think you'd also, just to build on that, I agree. I think most people, and this is not something I've thought up on my own, but underestimate, they overestimate what they can achieve in a day or a week, so they have 20 items on their to-do list, but they underestimate what they could achieve in a year or even two years. And the way that, for instance, if you look at a lot of what I've done, much of which ended up being a result of accidental discoveries, but you had the book career, but then you had the angel investing start around 2007, 2008, and I treated that as a two-year self-imposed MBA. And it was like, okay, I want to try this and really focus on it for two years, and I'm not going to expect to have any financial return, but just as an MBA, I'm going to sink this amount of cost into it, which was identical to Stanford graduate school business at the time, and assume that the network and relationships, and lessons I would learn would be worth that two years. And just viewing them as two-year experiments, which I did with the TV also, which did not turn out as ideal as I would have liked, although I'm very proud of the Stanford experiment, podcasts, same thing. It wasn't a three-year commitment, but it was also not a one-day or one-week commitment. I was like, okay, I'm going to do this for at least six episodes, maybe it takes me six months, and then I'll correct course at that point. But yeah, you do, I think, a lot of 30-year-olds feel pressured or younger or older for that matter to pursue many, many things in parallel when, if you were just to tweak that slightly and make them serial, the results would be much better. Yeah, that's a really hard lesson to learn. We can even say it right now, but it's really tough. I even find that now. Yeah, it's a constant challenge. The five-minute journal, I find very helpful. I've mentioned this before to people, but so I won't be leaving the point, but people can check that out if they want to, or the Pomodoro technique also really helpful. Yeah. Okay, we are going to wrap this first conversation up for our dear public, but do you have any asks or requests of my audience before we close up? Really? I mean, honestly, the main reason I do interviews like this, like public ones instead of you and I just, you know, sitting on the phone and shitting the shit, is that I really like the people that I meet through them, like the kind of people that would listen two hours into this conversation are my kind of people. So I usually just tell people, just email me, I read them. I kind of enjoy putting aside a little time each day to read emails, and I answer every single one because I said, "Hell yeah, I know to the rest of my life, so I've got time to do it." So yeah, that's it. Just feel free to email me if you have any questions or anything. We're just to say hi. Awesome. And for those people who do not want to wait for round two, Derek, you're hilarious. I put out a tweet recently, which was, "What should I ask? What would you like me to ask at Sivers?" I'm going to be interviewing him soon, and I couldn't ask any of them because you went online and basically answered all of them on Twitter. So if you search @tferris2rstu as an @sivers, you will see, or you could just look at my tweet and the various responses and then Derek's responses to almost all of them. You can get an encore performance. I just had the feeling we probably weren't going to get to all of those questions. So better to answer them with a tiny punchline. Oh yeah, yeah, I know. This is hilarious. No, fantastic. Well, Derek, as always, so much fun to jam. We need to spend more time in person soon. And thanks so much for taking the time. Of course. Thanks. All right, and everybody listening, thank you all for listening, redundancy of department redundancy. And the show notes, as always, you can find for all episodes at for this episode specifically at Hey guys, this is Tim again, just a few more things before you take off. Number one, this is "Fibolut Friday". Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun before the weekend? And "Fibolut Friday" is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the eso-tear. As I do, it could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short. It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out. Just go to That's I'll spell it out and just drop in your email. And you'll get the very next one. And if you sign up, I hope you enjoy it. This episode is brought to you by me, Undies. If I'm not going commando, I'm in me undies. I have been testing these underwear for three to four months now. Pretty much every day. And in fact, threw out a bunch of my underwear this morning. And on the road in the house, they are extremely comfortable. They look good, feel good. They are made of micro modal. Two times softer than cotton, as scientifically tested using the call-but-to method sounds very fancy. Of course. And I get a lot of compliments from the ladies for these. You don't get diaper butt. You don't get the tired elastic band. They look great. And they have underwear for both men and women. Check out And you can see everything I've been wearing. They're ridiculous. They sublime. Everything in between. Including my favorite, which is called out. And I would be remiss if I didn't mention their lounge pants. This is a new thing. And I've been wearing their lounge pants when I record podcasts. I've been wearing them out and about when I'm walking the dog. Meeting people for coffee. And they are extremely comfortable. They're made from the same material as the underwear. But some of them, like the blue ones, I have, have pockets so you can walk about without seeming like you're off of your meds and completely crazy. So that is awesome. And if you're not happy with the first pair you try on, I assume that first of the underwear, they'll refund you completely And you can keep the pair you tried on for free. But if you're that kind of person, you should be ashamed. Because that's disgusting. Check it out. This episode is brought to you by Wealthfront. And this is a very unique sponsor. Wealthfront is a massively disruptive, in a good way. Set it and forget it investing service. Led by technologists from places like Apple and world famous investors. It has exploded in popularity in the last two years and they now have more than two and a half billion dollars under management. In fact, some of my very good friends, investors in Silicon Valley have millions of their own money in Wealthfront. So the question is why? Why is it so popular? Why is it unique? Because you can get services previously reserved for the ultra wealthy, but only pay pennies on the dollar for them. And this is because they use smarter software instead of retail locations, bloated sales teams, etc. And I'll come back to that in a second. I suggest you check out Take the risk assessment quiz, which only takes two to five minutes. And they'll show you for free exactly the portfolio they put you in. And if you just want to take their advice, run with it, do it yourself, you can do that. Or, as I would, you can set it and forget it. Here's why. 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