What up world. It’s your homeboy Wordplay by T. Jay, and I’m back with another video for you in this three-part series.
I have a timeless talk with Derek Sivers. We talked in length about a number of topics around music, life, and culture. We had a great conversation.
If you don’t know who Derek Sivers is, he is an entrepreneur, a writer, a producer. He’s a book publisher. He’s a TED talk speaker. Most notably, he is the founder of CD Baby. He’s not doing anything with CD Baby anymore. He’s focused on writing books and being a publisher and writing his blog and his podcast. The most important thing that he’s focused on is being a dad.
How’s it going, Derek?
Hi T. Jay. Thanks for the call.
I appreciate you taking the time to talk with me. When I when I got this interview, I was super excited about it. I didn’t think that it would actually happen [laughter]. It says a lot about your mystique in the music world. Personally, I think very highly of you, and so I really appreciate you taking the time to respond.
Thank you. I don’t mean to be mysterious [laughter]. I had a kid and went off to be a full-time dad for a few years and disappeared.
That makes sense. There should be more full-time dads.
I agree. The reason I did that was because of John Lennon. When I was a teenager, I remember reading that when John Lennon had his first kid, he made a huge mistake by not being there at all for his kid. This was during the height of Beatlemania. So, when he had his second kid, he told his manager, “I’m saying ‘no’ to everything. I’m going to disappear for five years. Don’t even ask me. The answer’s ‘no.’ I’m going to be a dad for five years.”
I remember thinking, “If John Lennon can do that, I can do that.” And when I had a kid, I said, “It’s time to say ‘no’ to everything for five years and disappear.”
For the audience that is not familiar with you, can you talk a little bit about how you got here and where you are today?
Sure. I’ll give you a little context. What I’m working on today is my writing. I’m working on a few books, but for a little context, I’m old. I’m 52.
In the mid 80s I decided I wanted to be a full-time musician and I was dead set, monomaniacal, focused on that. I went to Berklee College of Music in Boston from ‘87 to ‘90, graduated in 1990, moved to New York City, and threw myself into the heart of the music industry. I had a day job inside Warner Chappell Music Publishing for two years, which was amazing to see the music industry from the inside. So often as musicians, were given advice about how to get contacts inside the industry, so it was amazing to be inside the machine and see how it works from the inside.
I felt like a spy. That’s what my next book is about. It’s called Your Music and People, and it’s about what I learned from the inside of the music industry. During my time at Warner Chappell, I was still a part-time musician, during nights and weekends. After two years, I had saved up enough money that I could quit my day job, so I quit my last job in 1992 and became a full-time musician ever since.
I made my living in New York City as a musician by doing the hustle. The only way you can really make a full-time living as a musician is by saying “yes” to everything.
“We’re looking for a bassist for this metal album.”
“Yep, that’s me. I play bass for metal albums. That’s what I do.”
“We need a jazz acoustic guitar solo.”
“Yup! That’s me.”
“Can you score an indie film?”
Exactly. Whatever it is, you say “yes.”
Actually, first you say, “What does it pay?” [Laughter].
I did that for a number of years until I put out an album of my own music in 1997.
It sold pretty well. I sold around 1,500 copies and I wanted to sell it online. But at the time, there was no way to sell music online. Nothing. Unless you were signed to a major label with major distribution. So, I built my own little shopping cart on my band’s website and then my friends asked if I could sell their CD through my band’s website too. I said “yes,” and then friends of friends asked, and that turned into CD Baby by accident. So for the next 10 years, from 1998 to 2008, I ran CD Baby, which became the world’s largest seller of independent music with 150,000 musicians and two million buyers.
I left in 2008 after feeling very done with it and that’s when I disappeared and had a kid couple years later.
What’s the best song that you heard by an artist on CD Baby?
Oh, God. You’re probably going to guess what I’m going to say, which is almost cliché. You can’t pick one favorite. But I think about my favorites in a bunch of different genres. I used to put together these old compilations of my hand-picked favorites.
I’d make CD Baby compilations and spend a bunch of stupid money to print 50,000 of them. We’d stick them automatically into every single order. No matter what you ordered, you’d also get this compilation.
I’m so proud of that. But of course, I eventually had to stop. What I learned is to value the quality of the song. You could create the most amazing song, but it doesn’t mean a damn thing if you take the wrong approach to your career. Music can’t speak for itself.
Somebody asked me once, “What does the average artist on CD Baby sell?” I used to post the numbers publicly on our About Page. I said something like, “We’ve got 169,000 artists and I’ve paid 85 million dollars to musicians.” One time, somebody did the math. They divided the total payout by the total number of musicians and said, “It looks to me like the average artist makes around $120.”
I thought about it a bit and realized that was completely wrong. There are two types of artists. I like to think about this in terms of a starting line versus a finish line.
For a lot of musicians, when they release their music, that’s the starting line. As soon as they release it, the starting gun goes off in a race and their quest begins. They do everything they can every day to promote the hell out of it after it’s released. They tell everybody. They do everything. They contact every outlet. That’s when it all begins for them. For those artists, I’d say the average amount they would make through CD Baby would be around $1,000. Some artists made $100,000, but we’ll go with the average.
The second type of artist is the person who sees their music release as the finish line. Things have been building up to this point for a long time. They’ve been working towards it and then they finally put out their music. “There you go world. I did it. I released my music. I’m done.”
Maybe the send it to some friends and send out a few emails. But for the most part, that’s the finish line. For those type of artists, the average amount of money they made through CD Baby was probably $20. A lot of them made nothing because they would just put it on CD Baby and do nothing about it.
So you asked about the quality of the song, but I couldn’t help but guess that that’s maybe where you were going with that question – how does the most amazing song affect your career? Does having the most amazing song that Derek Sivers ever heard at CD Baby, does that do anything for your career?
The answer’s no. It was weird how disconnected the quality of the song was from the outcome of their career.
People early on in their careers should figure out whether or not they’re just in it for the art, or they’re in it to bring some of the business into it, too. You have to make that defining factor, because if you’re not willing to do any of the business or touch it with a ten-foot pole, you’ve got to get somebody to help you.
Right. Or admit that it’s the finish line for you.
There might be some people listening to this right now that if they looked into their heart of hearts realize that they’re happy to just release their music. Maybe they’re doing this hustle because they think they’re supposed to, but they don’t really want to.
Sometimes that’s enough.
If I put out an album now, I’d probably be like that. I put it out, just to put it out. I don’t really care what happens. You have to be honest with yourself.
Are you currently working on any music?
No. But let me give you a better answer. It’s hard to admit when your identity changes. How old are you now?
So have you already had a major life transition where you thought you were one thing and then changed to another thing?
Yeah. At age 30.
At age 30, I thought, “Oh, no.” Looking back at it, that’s result of the album that I’m putting out next month.
Cool. It took me a long time. My identity was so wrapped up in being a musician for such a long time. Even during my 10 years at CD Baby, I thought, “I’m doing CD Baby right now, but really I’m a musician that’s doing CD Baby.”
Truth is, for those 10 years of CD Baby, I only made music during the first year. When I sold the company, I thought, “Now I’ve got free time. Now I’m going to make music.”
But it was only some other excuse why I wasn’t doing it. “I’ll do that right after I finish answering my emails, or after I finish this programming, or this book.” And then a few months ago, I started thinking about this metaphor that my old clothes don’t fit anymore. We all have a hard time admitting that these clothes we’re used to wearing don’t fit anymore.
I think it’s time to clean out my own closet [laughter].
Carrying the metaphor further, I was trying to put on new clothes, but the new ones weren’t fitting either. I realized it’s because I was refusing to take the old ones off. I was trying to put on new clothes over the old clothes. You can’t do that.
You actually have to completely take off your old clothes. And even then, if you keep them around the house, you’re too likely to put them back on again. So, I had to completely discard my old clothes.
Recently, I gave away the last of my musical instruments just a few months ago to a friend of mine. That’s a full-time musician here. It was a really weird thing to do, but it felt wholehearted and good. It was hard to get to that point.
Once I realized that’s just not me anymore, then getting rid of the instruments themselves was the last step because my soul felt torn. The guitars were looking at me, the keyboard was looking at me. I had the whole Native instruments set up with all the sounds and the keyboard. It was beckoning me every day and night. My soul felt torn, so I gave them away.
[end of pt. 1 of 3]
Were you inspired to make a blog and pursue other writing projects because you weren’t focused on music anymore? Was that the catalyst to this new creation?
No, I started that stuff 12 years ago when I quit CD Baby.
Writing words, not music, was always just a hobby. About a year ago, I started admitting to myself that writing is my real thing now. I’m not an entrepreneur. I’m not even really a programmer. I’m a writer.
I told myself this YouTube channel was something that I would do on the side and now it’s becoming the thing that’s taken off.
You know you’ve had a shift in values when you finally admit something that’s taken you a long time to say.
What’s your best piece of writing?
This is cliché, but my best piece of writing is my next book called How to Live. I feel good about the other books I have written. But this one, I’ll literally scream with joy sometimes as I’m writing it.
I’ll write something and go, “Wow!!” I yell in appreciation at the ideas that I come up with while writing it.
That’s an amazing feeling. It feels like the best thing I’ve ever done.
Is the hallelujah praise is coming out because you lived it?
The title, How to Live, makes it sound like I’m being a know-it-all that’s going to tell you how to live. But no, it’s actually quite the opposite. The title’s referencing the fact that nobody knows. Everybody’s got strong opinions, and nobody knows.
Each chapter has a strong opinion on how you should live, and each chapter disagrees with all of the others. It’s a blast to write and makes me realize, “Yeah, this is actually how my head works and this is how life works and this is how advice works – it’s all conflicting.”
My favorite part is the great conclusion, but I have to leave that as a surprise for later.
Do you believe work should be play as independent musicians?
There is this idea, “Everything should be fun, or I won’t do it. I wasn’t inspired to write music. I don’t feel like making those phone calls.”
It’s a dangerous and harmful belief to hold that you need to wait to be inspired to do something.
I really like the metaphor of your muse as a beautiful woman that’s never going to make the first move. You always have to make the first move words the muse. If you go towards her, she will meet you halfway. I almost never wait for inspiration. I just sit down to start creating whether I feel like it or not. And then as I work, the inspiration comes.
How can musicians use that type of thought process to their advantage?
Don’t wait for inspiration to write a song. If you want to write a new song, sit down and very deliberately come up with something, whether it’s playing with sounds, or imitation.
Don’t underestimate the power of imitating a great song. It doesn’t have to be a hit song. Even if there’s a song buried in the back of an album you bought once that has a melody you can’t get out of your head, you can straight up imitate it.
We’re all imperfect mirrors. You’re never going to create a perfect imitation of that thing. Go ahead and copy it. Get inspired by your version of that melody. I don’t mean actually steal the melody where you now you have to go get licensing.
Try inverting it. Play the middle notes, add your own style, and now it’s your unique melody.
I wrote over 100 songs from the age of 14 to 29. A lot of them were just really deliberate exercises. I’d pick a certain technique that I liked and say, “I like the way he did that melodic jump. I want to do melodic jumps like that. What is that jump?” Then, I’d sit down and figure it out.
I wasn’t waiting for inspiration. It was a deliberate assignment that I gave myself to craft something.
I used to read every single interview I could with hit songwriters. I wanted to learn how to be like them. It was crazy that these hit songwriters often admit that their most successful hit song was one that they thought was stupid and not even worth recording.
I’ve read so many interviews with bands where they were almost done with the album, but on the last day of recording, they put together this stupid song that they wrote in five minutes and recorded it in two hours. And that became the big hit.
Do you know the song Who Let the Dogs Out?
That had to be written in five minutes.
Nobody crafted that song [laughter].
As musicians, we get into the nuance of what we’re doing.
We like a song because it has a certain production thing we’re really proud of or a lyric that we sweated over. But nobody cares about those things.
We feel like we need over overthink it.
Right. For example, you did something really difficult with the way you arranged your instruments and think, “Wow, everybody has to hear this song because I put so much work into that kick drum!”
But the stupid, fun, dumb things end up being the most memorable. When you ask about work as play, in that case, sometimes you should think of your songwriting quite often as play.
Ask yourself, “What would be fun, funny, or amusing to write?” Be ridiculous and have fun. I think it helps prevent you from taking yourself too seriously, too. Because I think most people listening to our music don’t take us very seriously [laughter]. We’re just another click on the screen. If you can be in that same lighthearted attitude towards it all, it’s probably healthier and more successful.
Did you ever make a song that you felt like it would be a hit?
Most people don’t notice, on the very first sentence on my website, sive.rs, it says, “I’ve been a musician.” Click the word musician. It’ll bring you to sive.rs/music, which is every piece of music I ever recorded in my life. It’s all there on one page, free for the taking.
There’s a song in there called Kiss Me Here. I loved that song. I thought it could be a big hit.
I was trying to imitate Low Rider by War, but dirtier, skankier. It was supposed to smell like smoke wafting out of an old beat up car window. I was going for this really janky junkyard sound that I never quite got. I never got the recording of what I wanted. But I liked the idea. The version that’s in my head should have been a hit, but oh well.
[end of pt. 2 of 3]
Should musicians focus on mastery? Which musicians have used mastery to their advantage?
My introduction to music was in the mid 80s at the age of 14. There was a lot of fast, heavy metal guitar players with big hair and the fast fingers. I practiced finger exercises and scales and arpeggios up and down the neck as fast as I could for six hours a day for years.
Sure enough, by the time I was 17, I was really damn fast. I was on this mastery guitar path. I was drenched in that mastery mindset. I was all about who could be the fastest and the best.
That goes for everything. Historically, there a violinist a long time ago called Paganini who was believed to be possessed by Satan because he was so amazing.
I have mixed feelings about this virtuoso technique that I practiced for so long because now, I kind of hate listening to instrumental virtuosos. They have a, “watch me” approach and I don’t find it nice to listen to.
I prefer an amazingly well-crafted recording or song, or a great arrangement. It’s so tight – tight meaning that every note needs to be there.
I do still believe that the virtuoso path of mastering your craft is the way to go. Whether you want to be a writer, a producer, an engineer.
There’s a musician that I feel we’ll look back on and think, “This guy was the greatest.” He’s Jay-Z’s engineer and he Goes by Young Guru. He’s incredibly tight in his engineering.
He engineered the record that Empire State of Mind is on. He engineered Run This Town by Jay-Z. He worked on the new Rap City Project with a young female emcee from North Carolina.
Every time he touches the boards, I have to analyze his mixes. I think, “How did he do that?” I always compare my masters to his masters and think, “I want to get where he’s at.”
I love that. There was an engineer back in the 90s that called himself Flood. I would buy any record that he engineered because the sounds were so creative. His stuff was so twisted and different. I’d listen and think, “How did you get that? What is that?”
I would sit in my studio for hours trying to imitate these sounds. I love the underrated, behind the scenes heroes. For example, Max Martin in the world of pop. He’s a 49-year-old Swedish guy.
Nobody would recognize him on the street, but he wrote almost as many number one singles as the Beatles since 1990. He’s the guy that wrote Britney Spears’s Hit Me Baby one more time and many Backstreet Boys songs.
I think he’s still doing it with Katy Perry hits. All of these came from ONE guy. He also produces a lot of them. But as far as pop songwriting, that guy is a master.
In Nashville, there is a guy named Tom Jackson who’s a master at crafting a great stage show. He’s actually a stage show consultant. He directs concerts. When a pop star is putting together their show to go on tour for a year. He works with them to craft a great live performance.
Look up Tom Jackson Nashville on the Internet. I think you can get videos of him doing these workshops with artists where he shares all of his advice.
I really love this idea that we think of virtuosos as the fastest or the best, but many are really behind the scenes.
How can artists be in the now?
I’m actually a little stumped. If I ever said that in the past, I think I might disagree. Prior to when I said it, there was a great book called The Time Paradox about living in the present moment versus the future and the past.
I know that a lot of people who have written hit songs also like very deliberately sat down with the goal of writing a hit song. I remember reading some Beatles interviews. People would glorify them and think that they were all peace and love. But they said, “No. We would sit down and say, ‘Let’s write a swimming pool.’ Let’s write a song that’s going to make us a million bucks and get us a swimming pool in our house.”
And then they would write one of their great songs that everybody knows. Yes, it was a great song, but they wrote it in a very future focused, “let’s make lots of money” approach.
On the other hand, there are some people who are doing the same thing and not having any success and creating crap. There are people who live in the present moment making crap and people living in the present moment who are creating genius work, too.
I guess when the Beatles sat down to write, they’re thinking about the future in that moment.
That’s what I mean. They’re not really being in the now. So it can.
It’s completely disconnected. Whether you’re being in the present now moment or whether you’re future focused is probably unrelated to what you’re going to create. There are ways to create amazing music and there are ways to create crap.
Just have fun [laughter]. Guru says that when he sits down to engineer a record, he’ll listen through it once and get the vibe of it. Then, he’ll go through it again, have fun with it, and make adjustments as quick as he possibly can. Once he makes those adjustments, he has the confidence to stick with those first adjustments.
Where did he say that? Did you read an interview?
I’ve watched several interviews.
He doesn’t overthink anything. He mentions that he’s not in a space where he needs to think about what adjustment he needs to make. The only time when thinking is really involved in his craft, is when new technology is involved. He was one of the first to use Pro Tools.
He learned that process and then listened to his intuition.
Cool. And to show that there are different ways to do it, one of my favorite producers was Brian Eno, whose whole thing was to deliberately overthink everything. He would say, “Question every note. Does it really need to be there? Let’s see what happens when we get rid of it. What isn’t there that we could try to add in?”
He tried to flip expectations musically and deliberately overthink everything. I think he felt that it was his job. That’s really cool to hear that Guru goes with the opposite.
Maybe Brian’s intuitive nature is to flip things upside down, while Guru’s is to not overthink.
Wow. I love this stuff!
I know. I’m having a moment [laughter.]
What’s your favorite hip hop song and what elements do you like most about it?
I’m embarrassed to say. I wish that somebody would turn me on to something new.
For anybody listening, please send me an email and turn me on to your new favorite song, because I need to be turned on to something new.
You have to understand, I moved to New York City in 1990.
To me, the sound of New York in 1991 is Low End Theory.
[Sings] “Back in the days when I was a teenager Before I had status and before I had a pager.”
A pager! It’s like a Polaroid photo. It reminds me of a past self.
I can try to listen some new stuff, but when Low End Theory comes on in the shuffle, I get so excited.
Q-Tip was good about using that base on his productions.
That was Ron Carter on that album, wasn’t it? He was a real jazz bassist and this guy that plays with Miles Davis.
But OK, you asked about the ingredients. I would love to listen to instrumental hip hop. There was a band called Disposable Heroes of Hiphoprisy with Michael Franti that later made Spearhead.
There was so much going on instrumentally and Michael Franti was on top of it all and his vocals were really high in the mix. I wish that I could get an instrumental version of that because I wanted to hear what was going on behind it.
I’ve never been into folk music because folk music seems like it’s all about the lyrics and strumming boring CGD chords behind it. But then you get hip hop, which is also all about the lyrics, except what’s going on behind it is so damn interesting.
Sometimes the lyrics are so distracting. As humans, we’re drawn to a voice, but I wish I could get an instrumental version of most of the hip hop out there. I do that with a lot of records. I try to find the instrumental version. Even if I like a song, I want to remove the distracting voice so I can focus more on what’s going on behind it.
When it comes down to it, I’m more of a music guy than a words and voice guy. When you asked what I love about my favorite hip-hop song, I love the nostalgia. Especially Q-Tip’s voice and Tribe Called Quest, and Low End Theory in particular. That’s a snapshot of 1991 and moving to New York City. Oh my God. It was overwhelming. I was only 20 years old.
And then your other reason would be the qualities of the instrumentals?
Is there one song in history that every musician or songwriter should study in order to get better at their craft?
No, and here’s why. I went to Berklee School of Music from the age of 17 to 20. My teachers would make us analyze their favorite music. They’d say, “Listen to this Cannonball Adderley solo. Listen to this John Prine song.” I never liked the examples they gave. It did nothing for me.
My teachers would say, “Listen to the harmony of this. Listen to his lyrics describing the wrinkles on the back of his grandmother’s hand. Isn’t that a masterpiece?”
I thought, “No, I don’t want to write lyrics about the wrinkles on my grandma’s hand. Sorry. That’s just not my thing.”
It reminds me of my creative writing professors [laughter].
It took me a couple of years to learn how to use their analytical techniques on my favorite music. Music that they would probably hate. I figured out how to dissect whatever moved me the most.
Don’t let anybody else, especially some guy that started CD Baby, tell you that there’s one song you should listen to become a better musician.
No. Ignore everybody else’s opinion and instead learn the techniques of how to dissect your favorite song. Here’s my best advice on that. If you want to understand how a car works. It’s not enough to just take apart a car. You can take apart a car in your driveway and break it into a thousand pieces and you’ll know a little bit about how a car works. But if you really want to know how a car works, you’ve got to put one together and make it work.
This also applies to music. If you want to understand how your favorite music works, you need to build it up yourself. You can take it down. You can dissect it. But you’ve got to go into the studio and imitate that song. Every layer of it. Try to get frequencies to this kick and try to even imitate the sound of the voice and the mic and compare it back to the original song.
Rebuild it yourself. That’s how to do it.
That’s what every A&R says.
They say go study the hit records and just mimic one of them and you’ll find it.
I’ve never heard somebody say that. Cool.
This has been great. I’ve come away from this conversation a little bit more aware and knowledgeable. I feel like I know you better now. This is some great content that I’m going to deliver to my supporters and give them some of these golden nuggets that you have given us and given me.
Thanks, T. Jay. I appreciate it. Anybody listening to this, please go to my website and introduce yourself. It’s the reason why I do interviews. I’m not selling anything. I just I really like the people that I meet from doing these conversations.
Thanks again for your time. I appreciate it.