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. 

To learn more, go to or email us at [email protected]

To learn more, book a call with us here

Check out Rise25 to learn more about our done-for-you lead generation and done-for-you podcast services. 

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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.