Derek Sivers | Breaking out of Berklee, Making it Big in Music, and Building Key Relationships

Derek Sivers has been a musician, producer, circus performer, entrepreneur, TED speaker, and book publisher. He started two companies called CDBaby and HostBaby a number of years ago which were quite successful and later exited them. 

Derek refers to himself as an ambitious hustler and ‘a monomaniac, introvert, slow thinker, and love finding a different point of view’. He is a California native based in Oxford, England and he studied at Berklee College of Music in Boston. 

In this episode, Derek Sivers is interviewed by John Corcoran about how he connects with people and keeps his relationships strong. He also shares what it was like to perform with Ryuichi Sakamoto and Kimo Williams, his experience at Berklee College of Music, and what he learned about the music industry.

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Here’s a Glimpse of What You’ll Learn:

  • Derek Sivers shares the story he refers to as ‘The power of one delivery pizza’
  • How Derek landed his first job at Warner Chappell Music Publishing
  • How Derek became friends with a bigwig in the music industry in Las Vegas and what he learned from it
  • Why Derek changed his thoughts, his self image, and the people he chose to surround himself with
  • How Derek keeps his relationships and connections going strong
  • Derek discusses the super connector philosophy and the  effects of the COVID-19 pandemic
  • Derek shares his story with Ryuichi Sakamoto and how he got to perform on stage with him
  • How Derek’s ambition and attention to detail has contributed to his success
  • How Kimo Williams influenced Derek and helped him complete a Berklee music course in record time
  • Derek explains what he means by ‘learn from your heroes, not only theirs’
  • The people Derek acknowledges for his success

Resources Mentioned:

Sponsor: Rise25

Today’s episode is sponsored by Rise25 Media, where our mission is to connect you with your best referral partners, clients, and strategic partners. We do this through our done for you podcast solution and content marketing. 

Along with my business partner Dr. Jeremy Weisz, we have over 18 years of experience with B2B podcasting, which is one of the best things you can do for your business and you personally. 

If you do it right, a podcast is like a “Swiss Army Knife” – it is a tool that accomplishes many things at once. It can and will lead to great ROI, great clients, referrals, strategic partnerships, and more. It is networking and business development; and it is personal and professional development which doubles as content marketing

A podcast is the highest and best use of your time and will save you time by connecting you to higher caliber people to uplevel your network. 

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Episode Transcript

Intro  0:10  

Welcome to the Smart Business Revolution podcast where we ask today’s most successful entrepreneurs to share the tools and strategies they use to build relationships and connections to grow their revenue. Now, your host for the revolution. John Corcoran.


John Corcoran  0:40  

All right. Welcome, everybody. John Corcoran here. I’m the host of the Smart Business Revolution podcast where I talk with CEOs, founders, entrepreneurs, authors, speakers, and many you know founders and CEOs of companies and organizations like YPO, EO, Activision Blizzard, Lending tree, Opentable x software and many more. I’m also the co-founder of Rise25 where we helped connect b2b business owners to their ideal prospects. 


I’m very excited today, because my guest is someone who has been reading and following for quite some time. His name is Derek Sivers, and he’s been a musician, producer, a circus performer and entrepreneur, a TED speaker, a book publisher, he started a little company called CDBaby and Hostbaby a number of years ago, which were quite successful, and ended up exiting those businesses. And you know, he’s learned a lot and shared a lot. I love his philosophy towards relationship building. He’s got some great stories to tell about the pivotal relationship in his life, how he built those relationships. He calls himself, and these are his words not mine, ‘monomaniac, introvert, slow thinker, and loves finding a different point of view’. So that sounds great to me. He’s also a California native but now is based in Oxford, England. 

So before we get into that, this episode is brought to you by Rise25 Media Now if you’ve been listening for a while, you know how passionate we are about podcasting content marketing, to uplevel your network and I am a podcast evangelists because for 10 years have been saying everyone should start a podcast or at a minimum and was going to be talking about, you know, in your experience, Derek, you should reach out to people, you should build relationships proactively, whether you use the podcast as a tool to enable you to do that or not. I think that you should be doing that. And so we’re gonna be tall telling some stories about that. But really, for me, a podcast is a Swiss Army knife. It’s a tool that accomplishes so much at once. It can and will lead to great clients, great referrals, great strategic partnerships, great relationships, networking, business developments, all of those things at once. If you want to learn more, go to or email us at [email protected] 


Alright, so Derek, super, super excited to talk to you having followed your work for so long, and I just reached out cold to you having known of you for a long time and thought, you know what, now’s the time, you know, why not reach out? And so I’m really excited to talk to you but you’ve got this great story about the power of One, delivery pizza in your life is amazing. All the great things that came from that, but you were a freshman at the Berklee College of Music in Boston and a guest speaker came in one day and said he was hungry. And you didn’t just take that piece of information and sit down in your seat. You actually did something about it, which I love. So tell us a story.


Derek Sivers  3:17  

Yeah, thank you. I’m glad you know that one. I’ve always been an ambitious hustler. So


Yeah, I was in music school in Boston, Berklee College of Music. And the deal was that yes. As you said, the speaker came into the room and he was not just a speaker. He was like a high powered executive. He was the vice president of BMI music. And as everybody was taking their seats, I heard him say to the teacher, like, oh, are we starting now? I thought we were going to eat first. The teacher said, No, I just thought you ate already. So how long is the class? He said two hours anyway. Oh, he kind of grown. He’s like, Oh, man. So I had the phone number for Supremes pizza memorized. And so I dashed out of the room into the hallway quickly called Supremes pizza and said, Yeah, three Sicilian pepperoni pizzas. Berklee school room 325. Thanks. And sure enough, half an hour later, they showed up with three pizzas. And I went out and I paid the guy and gave one to the speaker and to share the class. And yeah, he just kind of, you know, finger guns at me like alright kid, I owe you one. And afterwards when he was done, he kind of said, All right, thanks, everybody. And that he kind of pointed to me like you, I need to talk to you.


That was a good move. We should keep in touch. Here’s my card. If you need anything, let me know. So


more importantly, I took him up on that, cuz you’ve probably found this to that. I’ve attended so many conferences where I’ve given my card to somebody that could probably really benefit from knowing me. And most people never follow up. Right? Right. It’s sad how many people never follow up, which I


John Corcoran  5:11  

mean, I’d say over 90% never.


Derek Sivers  5:13  

Yeah, yeah. Which means they’ve missed the whole point of the conference, you know, that note of going to conferences, not what happens at the conference. It’s like, that’s just where you make the initial connection, and everything happens in the follow up. So I did my follow up with this guy. I took him up on that offer. And like, every month, I’d say for the next two years, I found a reason to contact him. And God it’s funny thinking about this. This is before email.


John Corcoran  5:40  

So I would call him long distance, you know, from long distance charges and everything, right?


Derek Sivers  5:46  

I’m from Boston to New York City. I’d get his receptionist Holly and I talked to Holly for a minute and, and a couple times I took the bus down from Boston to New York just to go visit him on a Tuesday or whatever. take the day off of school. And go down just to keep that connection fresh because to me, this is like the biggest VIP I knew in my life. And I had an in, I was excited. This meant I could be a rock star someday. And, um, so yeah, I kept in touch for two years and also doing these little favors like one time we went to go visit New York, he took me out to lunch. And he just kind of give me random advice, but I heard him say something like, hey, do you know how to pick a good laptop computer? I need to get a laptop. Actually, this is a few years later, but I’m like, No, but I’ll look into it. And sure enough, you know, I spent the rest of the day researching what are the best laptops with you? And the next day sent him all the information I’ve gathered for him on what laptop I think he should get. And just things like that, like finding, listening carefully for a need. Anyway, here’s the real point of the story: two and a half years past, I graduated college and I wanted to move to New York. So I told him that and he said, Well, just give me your resume and I’ll get you a job. And I thought, okay, there’s only so much someone can promise I’ll get you a job. You know, that’s not like, I’ll take you out to lunch, like, get you a job is not a little out of his control. But, you know, I was 20 years old, I made a resume. Nothing on it, and get to them and yeah, about three or four weeks later, I got a call suddenly, like Monday night at 7pm Hi, this is Julie from Warner Chappell Music Publishing. Mark Freed said we should hire you. So, um, I mean, I guess you’re hired if you want the job. I’m gonna start on Monday. Yeah, I could start on Monday. Wait, sorry. What is the job? What does it pay? I mean, yes, I’ll take it but what is it? That was it? That’s how I got my first job inside the music business, and I started the next Monday at Warner Chappell Music Publishing, and we met in Midtown Manhattan. It was like minimum wage, but I was in. And it was all because of this guy that I bought a pizza for. Yeah. And people ask in the music business, like, how can you get in there? There’s a saying it’s the common English sign. It’s all who you know, right? So, as a teenager that didn’t know anybody, whenever I would hear it’s all who you know, it felt like the rest of that sentence was and you don’t know anyone so forget it. Yeah, it does. Right. And but um, it’s amazing to find out that you can go from not knowing anybody to knowing somebody in just a blink of an eye. It just takes the tiniest little connection in fact, if you don’t mind me telling another amazing similar story that without absolutely yeah, I love. I love these stories. I’ll prompt myself for a totally different one. Now, imagine In this, it’s now, let’s say, nine years later.


I’m inside the music business, but kind of In fact, I was still a self promoting musician that was still now attending these conferences to try to get my music heard by the executives so I could get a record deal, right. And so I’m at this conference in Las Vegas, all the music business bigwigs are there and it’s exhausting. It’s exhausting, mentally and kind of ego wise, like, you know, you just, you’re there, you’re so ambitiously hoping to get your music in the hands of somebody that could turn your career around and make you famous or whatever. And so in between these panel sessions, everybody, there’s like a 90 minute break for lunch and everybody goes outside and goes out and gets a bite to eat. So I go over to the pool, and I just take off my shoes and dip my feet in the pool and some guy sits down next to me. does the same thing he’s like, Yeah, that looks like a good idea, man. So he sticks his feet in the pool too. And he goes, you check out the bikini girls over there, aren’t you? I said, Yep. You notice to him, he goes, how could you not? And so we’re just sitting there talking about like, oh, man, this conference is pretty weird, Ani and we’re talking about the lady that put on the conference. And he said, Yeah, you know, you can’t really be a normal person and put on a conference, everybody who decides to put on a conference has something a little bit, you know, weird about them. And we joked about that. And we joked about, you know, one of the speakers that was speaking earlier that day, and I just assumed he was like a fellow musician like me. So I felt totally comfortable just shooting the breeze with this fellow musician, and making jokes about Vegas and the food and all that stuff. And anyway, after like half an hour of chatting, his name is Larry. And he’s like, Well, hey, man, I better get going. But he said, You’re cool, dude. Here’s my card. Let’s keep in touch. I like you. And I looked at this card. It was like vice president of a And records, I was like, well that I would have known that he was some bigwig, I will totally change the way you would have talked to him. Yes, I would have been paralyzed with fear. I wouldn’t have had a normal conversation, I would have been like, Oh, hey, wanna musician, you know, maybe there’s something, you know, I would have laughed too loud at his jokes and just been nervous, you know, but, but because I just thought he was a fellow musician. It turned into a real friendship. And I learned a really important lesson that day, which is to not put anyone on a pedestal, because that destroys any chance of a real relationship. And the best contacts come from the people that you’re actually just getting along with as a friend as an equal, you know, and the funny thing is, Larry ended up sending me my biggest clients at CD Baby A few years later, he’s the one that sent jack Johnson my way. And people like that and yeah, we just stayed In Touch, In fact, I just got an email from him out of the blue yesterday he stayed in touch now for whatever 25 years


John Corcoran  12:05  

jack Johnson used to play around UCSB where I went to college he used to be playing just in the in the area around there it’s really cool used to see him so but let me compare those two stories so that’s interesting because you know in the first story your even your lot younger, you’re a freshman in college and in sophomore and everything you remain in touch with this kind of big, weak person. How did you manage to suppress that instinct to put the the first individual, the New York City executive on a pedestal, and yet later when your musician you meet him at the conference, why do you think that if you’d known about that, Larry, if you’d known about it, you know what role he played at a&m that you would have put him on a pedestal. 


Derek Sivers  13:01  

I think as a teenager, when I met the first guy, Mark freed I definitely had him on a huge pedestal. I’ll bet I was incredibly awkwardly nervous at all times, even for years  afterwards. Like, that wasn’t a real friendship that was like a seasoned veteran who was just a really nice guy with a big heart and right up with this awkward teenager he wanted so badly to be a rock star.


John Corcoran  13:23  

Thank you made up for it with persistence, perhaps?


Derek Sivers 13:26  

Yeah, exactly. Yeah. And, and I think he just kind of


Derek Sivers  13:30  

you must get these people to like, I get people still to this day that approach me. Y’all nervous, like, Oh, my God, I can’t believe it’s really you. Amen. I read your books. Yeah, you know, and you just, you just smile. You know how it is. And I’m glad that I was on the other side of that and was that guy, and I know how awkward and scary and weird it is. So yeah,


John Corcoran  13:58  

I think everyone was that One point in time, right? Unless you’re born into a famous family or something like that, you know, at some point you’re on the outside looking in. So you can relate to that. I get that from people when they come up to me and they want to ask me about working at the White House. I remember I was at a conference a year ago or something like that, in a fairly established, you know, person came up and brought his family up to meet me. I was like, geez, I was like, No, I wasn’t like bigwig at the White House. I was just one of many people who work there, you know, but he wanted to, like, introduce them all. To me. This is kind of my backstory. But it’s kind of funny. You know, you’ve got a great quote in this, the story that you said that you wrote up on your website, which, by the way is amazing, everyone go, we’ll link it in the show notes. Go check out your website. You’ve got years and years of great blog posts and, and you sum up the stories, they’re great stories, and then you’ve got great lessons from them. And one of the things you wrote in that story about meeting Mark Freed was the people you surround yourself With don’t just open doors, they change the way you think. And they change your self image of your capabilities. So talk a bit more about that about how you deliberately intentionally worked on changing the way that you think. Did you think differently as a child? Did that evolve, as you know, and you know, went into adulthood?


Derek Sivers  15:20  

Um, I think it’s just a constant, ongoing process that was influenced by the people that we admire. Sometimes even fictional people, you know, I mean, everybody knows that feeling of like, watching a certain character in a movie, and you’re like, I want to be more like him. I want to be more like her. And so I think that happens when we meet people we admire whether they’re famous or not. Sometimes it’s just like a person that you meet, you just think, Wow, like that. That person is so loyal. That’s amazing. Or that person is so empathetic. I wish I could be more like that or that person is really disciplined. I really like the way that she does. What’s the right thing. To do whether she feels like it or not, so I, I think I meant more like that, like, I like being around people I admire because it just makes me deeply happy to, to know them and to be influenced by them and to let their influence rub off. But yeah, that’s still happening. Um, just a couple years ago, I actually dated an Olympic athlete for a few months, and it was just amazing getting to know her so well and seeing how she lives her life with such like, massive discipline, just her set of values about like, you know, what her top priorities are and, and r&d was just yeah, just amazing to get to know her so well. And yeah, I still have that it with them. In fact, I mean, speaking of making connections, I still do this thing whenever I read a book that I love. I reach out to the author almost every time to say, Hey, I just finished your book and that was amazing.


John Corcoran  17:00  

You make their week when you do that.


Derek Sivers  17:02  

Yeah. And it’s amazing how almost every single one has replied back and have often turned Well, a couple times turned into friendships like when we find out that we’re going to be in the same city we meet up and you know, have a lot in common. And


John Corcoran  17:18  

So how do you keep that relationship going? You know, for me for many years, you know, sometimes it’s a challenge if you’re in different cities, and it was a chat, you know, is different. Back in the day before the internet before social media before email, things like that. It’s changed. I use podcasts. Obviously, you have conversations with smart people like yourself, but how do you do it? What do you do if you reach out, let’s say to an author whose book you really admired, and they live in a different city, how do you keep that relationship going?


Derek Sivers  17:48  

I’ve always been a phone guy.


I grew up in Hinsdale, Illinois, but then moved to Boston when I was 17. I moved to New York when I was 20. moved around the world a lot since Then. And so my friends are so scattered around the Earth right now. I was just talking to my best friend in Australia up until two minutes before this recording. So hold on, I gotta go. Yes, first thing in the morning there and see how my friends are spread out across the world. And yeah, and so I’ve always been, I depend on the phone. So yeah, my, the people that I’ve met like that there’s a certain point where it’s kind of, maybe you’ve emailed a few times, you’re like, Hey, we should talk. You know, some of them don’t get to that point. Some of them just stay as email contacts, you know, some of my favorite authors. It’s like we email a couple times a year. And, and that’s enough, it’s not really chummy enough to be a phone call. But yeah, for the ones that even or just the once a year phone call. Yeah, right. I think the phone is how I keep in touch is best.


John Corcoran  18:50  

Now the other thing Another thing you wrote about is that used to tell people that you need to move to a big city because everything that’s where it happens, right and that’s obviously what you did move to Boston then New York. But now you wrote everything’s happening online so and you use this term you write about super connectors and I, I not crazy about that term people refer to me as it sometimes my business partner people refer to him as a super connector as well. I think the reason I don’t like it is because it feels intimidating, and I want others to feel like they can do it too without the label of it. But regardless of the term, you know, you say that the reason that super connectors reason people know everyone can get to know everyone is number one, they keep creating great stuff and posting it online. Number two, reach out to say hello to the people they admire. So you want to talk a little bit about that philosophy.


Derek Sivers  19:42  

Hmm. It’s funny, I’ve been wondering how our current you know, well, I guess we’re in April 2020. Now, wondering how the current situation is going to affect the importance of being in a city. I want If being a virtual being, you know, on video is going to be, is this going to be like a temporary thing that we all stopped doing in a few months? Or is it just going to become the new normal, where it’s not so important to be in New York, LA, San Francisco anymore? I don’t know. What are your thoughts on this?


John Corcoran  20:20  

It’s a great question. I think the jury’s still out on that one. I don’t think we know yet. You know, it depends on if I did a great interview with a client who is an expert in COVID-19. And, you know, he didn’t have answers, and he’s got a medical degree and advising the governor of California. So I think at this point, we don’t know. I mean, personally, I like it because you can live in a small town and it doesn’t matter. You can connect with someone who’s on the other side of the globe, like yourself and have a great conversation.


Derek Sivers  20:48  

Right? It’s, I mean, we don’t know what’s going to happen with the virus. We don’t know if it’s gonna be a few months for us. But regardless, I wonder about the things the culture change that might have just had happened where I feel like Do you remember even back in the mid 90s, like, or let’s say late 90s Wired Magazine, or Tom Peters would talk about, you know, hey, now thanks to the internet, we can all just move out to the countryside. This is the death of cities, right? It didn’t exactly happen though. Ready? Quite the opposite just kept getting more and more and more concentrated and important. But I wonder now, if now that there’s actually maybe a health downside, or I was actually so right now I’m living in Oxford, England. And I was planning on moving to New York City in a few months. We’re kind of like making that family decision. And I think I’m changing my plans now. Because when I talk to all of my New York City friends and contracts, even the ones that are there that say like okay, personally, I wish you were here because I miss you, dude. But don’t move here. Now then. And, and a couple different people said, Yeah, all the good people have left like anybody who can leave has left. A lot of people who maybe had one foot Out the door before are just gone and they’re not coming back. They’ve moved up to Vermont. they’ve sold their brownstone in Brooklyn, they’ve moved down to North Carolina. They’ve moved here. They’ve moved, you know. And I wonder then, if enough people do that are cities not the concentration point that they used to be?


John Corcoran  22:18  

Yeah, I personally, I think it’ll wane for a little bit, but then they’ll come back. You know, I think I’m an optimist. So I think we’ll come up with a vaccine or something that will help with this virus and eventually we’ll get back to it you know, because you know, after 911 after 2008 there was this period of time, wherever and felt like oh my gosh, we’re never going to go back to normal ever again. But eventually, we kind of did you know, so like, right just kind of feel like eventually it’ll be at that point. I want to ask you, I don’t know how to pronounce his first name, but Ray Yuichi suck a moto is that is really cheese like


Unknown Speaker  22:55  

a moto? Oh, yes. That was another. I can’t.


John Corcoran  22:58  

I can’t let you go without asking about the stories. This is a great story. So let me just prompt you let me prompt you here. So, so, you know, you get a copy of his new unreleased album. So explain how you got that. And you, you know, one person maybe would just listen to it be like, wow, that was awesome. What a great opportunity to give it back. Right. But you had it for a day. And you listened to it because there was an opportunity for you possibly to work with him as a guitarist. And you decided that you would help him out in a sense, that talk about how you took initiative in this instance?


Derek Sivers  23:32  

Sure. So yeah, set the scene. I’m 21 years old. I’m living in New York City. And I want very, very badly to be a successful musician. And so I was just doing the hustle man at that point. I think I had already No, I hadn’t yet quit my day job. But I was just hustling saying yes to everything. And I was just going over the top to make everything happen. You know, I really believe that. If you just get a little whiff of an opportunity. You just want to jump on it and Just conquer it, you know, like, I don’t do anything casually. If it’s something I care about, I do it all the damn way. So, yeah, this situation was Ryuichi Sakamoto, who was like the Peter Gabriel of Japan, you know, kind of like making sophisticated music, but it’s a very famous thinking man’s musician. Yes, exactly. So really, he was recording his new album in New York City, and my roommate was the minimum wage assistant engineer, which meant the guy plugging in microphones in the studio,


John Corcoran  24:37  

which by the way, actually, I want to point out that little detail because it is really about who you surround yourself with, even down to your roommate was also in the industry because that led to this opportunity.


Derek Sivers  24:48  

Exactly right. It was because of my roommate, we weren’t even like good friends. We were just roommates. Right? But he knew that I was a good guitarist. And so he came home one night and said, Hey, man, uh, really she’s got a whole tour booked. And he’s got Peter Gabriel’s drummer Monica che. He’s got Victor Bailey on base from a weather report who’s like a legendary bassist. And he doesn’t have a guitarist picked out yet, man. So I told him about you. I was like, Oh, my god, yes, I want this. And so I said, Well, what are you doing? Like, can you give me some of his music? What are you recording with him? And he’s like, well, I got this debt in my pocket. It was like the digital audio tape master. He said, I can lend it to you for a few hours. But I got to go back to the studio at 8am. So I gotta bring it back with me. But yeah, why don’t you listen to it? And this is like 11pm on a Thursday night, right? And so yeah, john, not only did I listen to it, I literally didn’t sleep that night. I spent from 11pm until 8am. staying up all night writing guitar parts for his new album, putting them in Little home recording studio playing guitar along with his new album with the parts that I wrote for it, MIXING it back together into a new debt digital tape Master, which I said here in the morning when my roommate woke up and he was about to go out. I said, All right.


Unknown Speaker  26:15  

Give him this tape.


Derek Sivers  26:17  

Tell him I really, really, really want the gig. So yeah, my roommate brings him the tape. reel, he listens to it. He’s impressed. His first question is, what does he look like? He had to make sure I looked the part you know, yeah. This is all gonna be televised and everything so apparently I looked the part and but I still wanted to get like I wanted to make sure that like, you know, how can I go over the top to show him how much I want the gig. So that day I went and bought like six of his previous albums. And I wrote some guitar parts to those two and one had a really difficult cello piece in the middle. So I transcribe the cello piece on bass clef on sheet music, just to show him that you know, if you need that Any help transcribing parts, I can do that too. I’m a school musician. So once again, gave those to my roommate like here, please give the


John Corcoran  27:06  

show your utility really, ultimately.


Derek Sivers  27:09  

And so yeah, about two days later, I got the call from his agent saying he’d like to meet me. And I got the gig. And yeah, I was 22 years old. I got to go on this tour of Japan for six weeks. I got to be in the band with this like legendary bassist, legendary drummer and 22-year-old knee on guitar playing to audiences of 10,000 people each night. It was amazing. But yeah, again, it was all because I jumped on an opportunity that my roommate mentioned before bed,


John Corcoran  27:41  

right right now, you have another little detail here, which you wrote about the tiniest detail can degrade can derail everything. It was about an experience working with the World Expo in Seville, Spain.


Derek Sivers  27:58  

Yeah, I’ll never know. So yeah, I did the Japanese tour with him. And that went great. And if you search my name on YouTube, and if you search Sakamoto Derek Sivers I’m on a video in there somewhere with my long blonde hair playing guitar, and 1992. And so then yeah, the next year, really, he got asked to play at the World’s Fair in Slovenia, Spain. And so he called up the band again and said, We’d like to hire you to come back. So I did, and it was, you know, 20 minutes before we’re going on stage or like already, everybody, get dressed to get into your outfits. And I said, What outfits? And they said, the outfits we gave you in Japan from the last tour. You didn’t tell me to bring that I didn’t know. And they’re like, well, what did you bring? Then I said, Nothing. And I’m sitting here like wearing shorts and a Hawaiian shirt because it’s hot. It’s Spain. It’s August. Like and they just Well you can’t come out looking like that. I was like, I don’t have anything else. And it was too late so yeah, I went on stage wearing shorts and a Hawaiian t-shirt everybody else’s dressed in white rock star there’s no that john paul go to everybody else was wearing their jet black john paul co t outfits that he had designed for really cheap. Oh my gosh. T-shirt and shorts. And I never heard from him again after. Who knows? It could have been that I wasn’t going to hear from them anyway, but I had the feeling like, you know, that little bit of iral kind of knocked me down into my reputation.


John Corcoran  29:38  

Right, right. All right. I mean, we were running a little short on time here but a couple more stories. I want to tease out of your background here. So right I think it was right before you started at Berkeley. You called up a local studio owner and he ended up kind of taking a liking to you, in a sense, or at least he was nice to you showed a little promise and he said come on down. It turns out this is the way that he kind of tested local musicians. And so you go down and you meet him and talk a little bit about what that experience was like Kimo Williams was his Kimo Williams. Yeah.


Derek Sivers  30:14  

Yeah, again, I was just nervous. I guess I was 16 at the time, maybe seven mon. And yeah, I just said, Come on to my studio at 9am. Tomorrow, I’ll show you. It. His thing is he said, I think you can test out of Berklee in two years. He said it’s a four year college but it doesn’t need to be. I used to teach there. I think I think I can help you graduate in two years instead of four. So yeah, show up to my studio at 9am tomorrow, and I’ll show you what to do. And so you had nine 859. The next morning, I was standing outside his door. I looked at you know at the time and waited till it was nine o’clock to ring the bell. And he looked at me a little confused. And he told me the story much later that this is something that he says all the time to people that say they think they want his help? He says show up at my studio at 9am tomorrow and he said nobody ever does. Everybody flakes out, I believe it. And I was the one who did. Which is kind of funny. You know, there have been a lot of times that people Sorry, I’m taking a tiny tangent that people attribute the success I had with CD Baby to my skill as an entrepreneur and I say I was just in the right place at the right time. Like I started the business in 1997. Like Come on. It was just really lucky timing. And one of my friends pushed back on that same man No, there’s no such thing as luck. And I said, What are you talking about? Like, everything is luck. And he did that push back where he said no, it looks like it’s all these little things you’ve done over the years that add up like absolutely would have called Kimo Williams and flaked out and I think all right, I guess so. I guess I’ve always been super ambitious and just jumped on everything.


John Corcoran  31:57  

You see when you saw an advert opportunity You took advantage of it yeah there’s a lot of people who would have slept through the night instead of adding in carpet you know guitar parts to an album you know as an opportunity there’s a lot of people who you know wouldn’t have shown up when that local studio nurse had to show up you know, there’s definitely a clear pattern here but it’s that quote


Derek Sivers  32:19  

around whatever percent of success is just showing up right it just feels like well you know, that’s all i did i just showed up but anyway so sorry to the chemo Williams story is Yeah, he um, in basically six intensive two-hour music lessons, taught me two years of Berkeley’s required courses and just showed me how it can be compressed like yeah, you don’t need to sit in whatever 12 weeks of classes to learn this. I can show it to you in two hours. And he did and the most important lesson he taught me is that never accept the standard pace. He said these Schools have to set their curriculum pace to accommodate the slowest student in class. If you are ambitious, you can go 10 times faster than that. So um, he just I don’t know if he taught it as a life lesson or I just took it as a life lesson, that it’s like that and everything in life. Like there’s the standard pace that people tell you well, you know, takes about a year to write a book, or it’s gonna take a lot of work to start a podcast or whatever it may be 10,000 hours to get good at whatever it


John Corcoran  33:29 

Right, right. Yeah. And you can just, yeah, you can set your own pace. Right and your own abilities. Right. You said before I met Kimo, I was just a kid who wanted to be a musician doing it casually ever since our five lessons. I’ve had no speed limit. I love that.


Unknown Speaker  33:45  

Yeah. So


Derek Sivers  33:49  

yeah, he was just a massive influence on me. And 20 years later, or something like that, when I got married, I invited only three guests to the world. And he was one of them. Oh, that’s so cool.


John Corcoran  34:02  

That’s so great. I love that. All right, before we wrap things up, there’s one more story when I asked you about and it was going to go back about 12 years now, you did a talk to the first year students at Berklee in 2008. There are a number of different points in that talk and feel free to, if you can recall them. recall any of them but one you made, which I love. Point number four, you said learn from your heroes, not only theirs. And what I take from that is that others will hold out who their heroes are. And sometimes your hero might be different, like who you hold up as a standard, who you admire, who you want to learn from, it’s okay, if they’re different. It’s okay if it’s someone else, who maybe is a little cutting edge at the time, maybe it’s a little hasn’t, you know, isn’t like the Mozart or the Beethoven you know that it’s gonna be years from now before they’re recognized. So anyways, but I want to get your take on that point that you made.


Derek Sivers  35:01  

Sure, um, so listeners, you’re going to have to listen metaphorically, to this one, unless you are a musician. I’m just going to use a direct music example of this, attending Berklee School of Music. It was very much a jazz school. They were teaching jazz. That’s what it was known for at the time. And I also took songwriting classes, teaching you how to craft a better pop song. But the examples that the teachers used were often these like, Billy Joel, Celine Dion, old, you know, 60s or 70s classics by whatever, kind of free Disney but, you know, like lame acts that I wasn’t into. We’re holding these up as like now that’s a song. And so I had to think past that there was one, in particular, there was a teacher, who he was a Nashville. Country Music lyricist. And He really said you know, it’s not a good lyric unless you use all five senses, you know, describe the way the room smelled when you walk into it. Describe the dust that came off the, the curtains in the room as you went to go visit your grandmother for the last time. And I really at first as a 17-year-old taking his class believed that my lyrics were no good unless I use all five senses. And it took me about a year before I realized like wait, for one. I don’t like jazz that much. I mean, I can appreciate it from a distance but I don’t want to make jazz and I know that all my teachers love jazz, but that’s not what I want to do. And my favorite song lyrics definitely do not use all five senses. So what I did is I had to learn their techniques that they used to analyze their favorite songs, but ignore their Examples and extract the lesson and use that same technique to analyze my favorite songs. So now I’m analyzing the glitchy quirky electronic music of Bjork and why I like it. And I’m analyzing, you know, these weird talking head lyrics and why I like them. And my teachers would hate this music. But that’s not the point. I don’t need to emulate their heroes. I need to learn what I like about my own heroes. 


John Corcoran  37:31  

It’s a great lesson. All right, Derek, this has been wonderful. I want to wrap things up with the question I was asked: let’s pretend we’re at an awards banquet, much like the Oscars or the Emmys. you’re receiving an award for lifetime achievement for everything you’ve done up until this point, of course. And what we want to know is, you know, who do you think were the colleagues were the friends who are the professors were the studio owners who are the music industry executives, who are the roommates, he would acknowledge who’s the what pizza place would you agree knowledge and your remarks?


Derek Sivers  38:02  

Well, uh, those six intensive music lessons I had with Kimo Williams. Um, he didn’t let me pay him. He knew that I was just like a teenager. And I said, Well, you know, what do I owe you for these lessons? I think I asked him at the end of the first lesson. I said, you know, thank you so much. Oh, my god, that was amazing. What am I Oh, yeah. He’s like, don’t worry about it, you know? And so we had like, the fourth fifth sixth lesson. I’m like Kimo, what are you just doing all this as a favor? What do I owe you? And he said, someday, when you’re getting your Grammy Award, when you get up there on stage, you hold that award up in your hand. He said, All I ask is that the first two words out of your mouth are Kimo Williams. So for years, I’ve had the idea that, uh, I mean, not anymore, but, but I for years, I had the idea that if I get a Grammy Award, I would get up there on stage and I would just say chemo Williams. Thank you and walk offstage. Nobody’s ever asked me that before. But yeah, you just totally set me up for that answer that’s been prepared for 30 years.


Unknown Speaker  39:09  

There’s gonna be others as well. No, no, no, no,


Derek Sivers  39:12  

Hell no, no, I don’t even have dedications in my book or anything. I’m one of those kind of, you know, cool.


I love the fact that if you look at old Beatles albums, let’s just say when you would look at like, contemporary albums, I guess back when we would like still buy CDs, like the liner notes would be like 15 pages long listing, like everybody that ever, you know, brought a coffee into the studio. But if you look at the old Beatles albums, it’s just you know, songs written by Lenin McCartney song titles produced by George Martin. That’s it very simple.


John Corcoran  39:39  

Simple. Derek, this has been wonderful. And thanks so much for dropping by. And for this great conversation. Tell everyone where they can go and learn more about you and connect with you and read your writing and you’ve got your podcast now, which you’ve been doing for a little while. I hope you really enjoy doing that.


Derek Sivers  39:58  

Yeah, that’s funny. tell everybody where they can go. That’s a funny prompt. Go to That’s my site. And it is very plain on purpose. Yeah, that’s it. I put everything I do is So just go there and my favorite thing. The reason I do these interviews Honestly, I’m not here to promote anything as you can tell I’m, I really like hearing from people and connecting with people, as you can tell. So my email address is in a big font, right? So, anybody listening to this, send me an email, send a Hello. All right,


John Corcoran 40:35  

Derek. Thanks so much. Thanks, John.


Outro 40:38  

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