Charlie Kaplan on the alchemy of music-tech, how a single falafel changed his life, and the chasm between boyfriend and husband (#2)

"You can’t get caught up in the ego of your own imagination. It’s very easy to fall in love with an idea...and pursue it even though the evidence is showing you that you're wrong."

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Charlie Kaplan is the VP of Product at Audiomack, a streaming music service with tens-of-millions of MAUs that draws the shortest line between artists and listeners. Prior to Audiomack, he was CEO of Cymbal, a music social network for iOS and Android described as “Instagram for music” by Forbes, VICE, and others. Charlie has written about music and technology for Pitchfork, NPR Music, CMA, and others, and has written The Retrographer, an album guide and new music monthly published on TinyLetter, since 2015. Charlie plays in the band Office Culture and released his first solo album Sunday in 2020, which was named one of the top 50 albums of the year by Across the Margin. He is a member of the Recording Academy and advises companies operating at the intersection of social networking and music.

Below you’ll find a lightly edited transcript of our conversation.

Edem Oladele-Kossi: I appreciate you hopping on, Charlie. How are you doing? Are you in New York?

Charlie Kaplan: Yeah, I'm in New York, and I’m doing well.

EOK: How are you feeling?

CK: You know, I feel very, very fortunate. My family’s been healthy. I've stayed healthy. I have lots to be thankful for. This pandemic has really been an exercise in counting your blessings.

Two weekends ago, I went with my fiancée and her dad to go visit her grandmother. My fiancée’s grandmother is 100 years old. So we fly down to Florida to see her, we’re all masked up, vaccinated, and we have a good time—all is well. We’re on our way coming back, sitting in the lobby of the Palm Beach airport, when all of a sudden our flight starts getting delayed. One hour, three hours, four hours, six hours. Finally, it's like 10:30 at night on a Sunday, and we’re still in this airport, waiting. Then suddenly, our flight gets canceled and we’re told there are no flights back to New York until Thursday. This is Sunday night, mind you.

So the next morning, we get up, rent a car, and drive from Palm Beach to Fort Lauderdale. We check into another airport and end up getting a connecting flight through Atlanta back to New York. But the whole time I kept thinking, You never know how good you have it until you start seeing things fail. And then you realize that you have to be grateful for the things in your life that seem small or even unnoticeable, like a flight taking off as scheduled. In a way, I’d say that’s been the theme of this pandemic for me. I try to notice the things that are breaking right now, so that later on when they’re not breaking, I can be thankful that they’re not broken.

EOK: I love that spirit. Coincidentally, I've been trying to work on a similar thing. I had a Bible study two weeks ago, and funny enough, the lesson was about gratitude. The guy teaching that day told us a story about a robbery. Some man was robbed and literally, the moment after everything went down, he fell on his knees and started thanking God. You know, at the time, I was like, I don’t understand, where is this story going? But the guy leading the discussion said, The man fell on his knees to thank God for three things: first, that he wasn’t the robber; second, that he still had his life; and third, though he was robbed of his wallet, he wasn’t robbed of everything he had. He still had his wife, his kids, his house, his job—the more important things.

CK: That's really powerful. It makes total sense. You have to count your blessings.

EOK: You really do. I’m curious, what blessings are you grateful for right now?

CK: Well, on top of the fact that I’ve somehow managed to make it through this last year with no one in my family really getting sick, I’m grateful that a lot of the go-to markers of stability have stayed stable for me when I know that for so many people, that hasn’t been the case.

Something else that I’m also grateful for is that me and my fiancée Emma are getting married next month. So now more than ever, I'm thinking a lot about our relationship, what it means to me, and also thinking about the sort of structural stability it gives in my life. So yeah, I would have to say that on top of the fortune to have made it through the pandemic healthy and safe, I’m taking a look at the relationships in my life, and working to be super grateful for the people around me.

EOK: When’s the big day?

CK: May 22, 2021.

EOK: Okay, let’s fast forward. It’s May 22, 2022. What kind of husband do you want to be?

CK: Hm, that's a great question. And part of the reason why it's such a great question is because Emma and I have been together for 12 years, basically ever since college. So part of what I’m looking to learn is, What’s the qualitative difference between being a 12-year committed boyfriend, and being a husband? 

The way I got to the decision of marriage was that I realized there are so many ways to tell someone you love them. Saying “I love you” is really just an abstraction of the feeling you have for somebody. But there are lots and lots of ways to actually demonstrate that love to them. And I think committing to someone for a lifetime is maybe the most profound way to show someone how important they are to you and how much you truly love them.

So yeah, a year from now, on May 22, my hope would be that I’m sort of manifesting and inhabiting that expression of love to Emma, that I'm committed, present, and supportive. I hope that my role as a partner is a demonstration of my love and how I see our relationship. I think that would be my hope.

EOK: That sounds incredible, but at the same time, extremely difficult.

CK: It is, but you have to hold yourself to a high standard. I think lots of people, when they're with someone for a long time, make their partner just another piece of furniture. They take them for granted, totally forgetting the fact that there’s this life-changing force they share with just this one person. I think in order to continue showing someone that you value them, that you appreciate them, that you’re still committed to them, I think you have to set the bar high. That’s how I see marriage. It’s like telling someone, I’m going to demonstrate over a lifetime just how meaningful you are to me.

EOK: Have you ever seen this kind of love expressed anywhere before?

CK: Yeah, I think so. The examples that come to mind are the loving relationships I see in my own life. I think of my dad and my stepmom, and my mom and my stepdad. I want to say my dad and my stepmom were together for 15 years until my dad passed. And my mom and my stepdad have been together for, gosh, almost 25 years now. So those are two examples of really sturdy, really committed relationships.

But definitely, too, there’s an element of my relationship with Emma that’s very aspirational. There are certain things I saw in my own previous relationships, and also in my relationships within my family and my friends that I didn't think were satisfactory. And I was like, What would a better version of a relationship look like? I'm very lucky to have a partner who's as in it as I am, who's just as committed to building this relationship, this shared space of commitment and love.

EOK: I had a super old wise man tell me once that who you choose to spend the rest of your life with, without a doubt, is the most important decision you will ever make. Do you think that’s true?

CK: Yeah, totally. I spend more time with Emma than I do alone. Also, we’re 12 years in. That’s over a third of my life that we've been in this relationship. It’s a trip. You know how people say you spend a third of your life sleeping, so make sure you pick a good mattress? It’s the same deal. If you're signing up to be with somebody for the majority of your time on Earth, then who you choose is more important than your job, more important than anything else.

EOK: I think there's something unique about you and Emma’s relationship in that you all have known each other for a really long time. Not a lot of people have that. I have a few friends who have gotten married, and there’s always this interesting moment where we’re talking about something they’re passionate about, and they realize, Huh, I don’t think my wife knows this side of me.

CK: That’s funny. Well, that's one of the reasons why you have other relationships, because everybody brings something different out of you.

EOK: That’s a good point. You know, a minute ago, you said you and Emma started dating about 12 years ago, right? Like 2009?

CK: Yeah.

EOK: I wonder, if you could go back in time and meet your younger self from back then, what would you tell him?

CK: Well, there would definitely be a lot of spoilers. But I’d probably say something like, “A lot of stuff is going to change. It’s going to be a real trip. You’re still going to be you, which is great news.” You know, back then when I was 19 or 20 years old, I knew what I enjoyed but I didn’t know who I wanted to be…Hm. I feel like I need to think about this question some more.

Okay, so 12 years ago, that would be my sophomore year in college. I was at a liberal arts school. I was in a heavily exploratory phase, taking classes that were interesting to me for the sake of taking them. I was making a lot of music myself and just trying to meet a lot of people. In the ensuing 12 years, I formed this incredible relationship with this person—Emma—who became an anchor for me in high highs, and all kinds of low lows, who I also had the honor of seeing grow and find the things she was really in love with.

Part of what I would probably say to myself back then is, “Look, amazing stuff is going to happen. You’re going to do a lot of writing. You’re going to work on really interesting, really creative projects. You’re going to work at this crazy company called Cymbal. And more importantly, you’re going to get into a relationship with someone who’s going to seek to understand you very deeply. And then a lot of terrible stuff is going to happen to you. You’re going to lose your father. You’re going to lose your grandmother—two grandmothers. There are going to be periods of time where you're not sure what the right path is. You're not going to be sure if what you're working on is the right stuff, or if things are even going to work out. And it's going to be incredibly important that you—number one—stay true to the things that you love and the people that you love. And—number two—that you don't lose your sense of possibility. Don’t lose your sense that if something is inspiring you, you should pursue it. That feeling should always be a part of your life.”

I think that's how I've lived my life over these last 12 years, trying to be there for me but also trying to be there for my siblings and my family and my friends. At the same time, though, it’s also been important to kind of—I don’t know if this is the right word—flower? I mean, investigate the things that are interesting to me, let myself daydream when I want to daydream or work on a project when I want to work on a project. I try to keep that sense of possibility and inspiration open. 

I think those would be my lessons to pass on to that Charlie. But one small footnote to all of what I shared is, You can tell anybody anything, but they got to live it themselves to really know. So I could go back and tell 2009 Charlie, Hey—this is what you have coming. But he’d still have to go through it to really learn it.

EOK: If someone took everything you just shared, the highlights and lowlights: 12-year long relationship; many loved ones passing away; seeing several ideas from ideation to market; working on a small team to leading one. If someone were to take all of that, and throw it up on a whiteboard, and ask a stranger, Look, here are some life experiences of a guy, how old do you think he is? I feel like most people would say, 40s, maybe late 30s. Am I right? 

CK: Probably, yeah. I guess you’re right.

EOK: Obviously, you’re not there yet. You just crossed 30 not too long ago. But I wonder, what does it feel like to compress twenty or thirty years’ worth of life experience into ten? What has that done for you?

CK: Hm, that’s a great question. So when I was a senior in college, everyone around me was figuring out what they wanted to do for their first job when they graduated. But me, I felt like I was looking at an hourglass, like my time in college was limited. There was no guarantee I was going to go to graduate school, so I felt like there might not be another period of time in my life where the focus of my waking hours would be dedicated to just learning. So I rolled the dice. I basically said, I'm going to spend every moment that I can while I’m still here to read books, write stuff, and just soak in the experience. And I did that and loved it. Mind you, I knew I was probably going to be unemployed for a little bit after I graduated. But I was okay signing up for that.

So as luck would have it, that spring break I was in New York City and I was making a little EP with a couple of my friends, and my friend Ian asked me, Do you want to go get some lunch? And I said, Okay, sure. So he took me to this place called Mamoun’s Falafel. Have you been?

EOK: No, I haven’t.

CK: Yeah, I hadn’t been either. Ian took me there and we got falafels. And mine had this very spicy sauce on it. And it was the best falafel I ever had in my life. I was just sitting there eating this falafel and I had this mind-expanding moment where I was like, Here’s this friend of mine, who's not even from New York, who took me down to get the best falafel that I've ever had in my life. And if we hadn’t been in New York City at this time, I never would have known this place existed, and we never would have ended up here. And Edem, right then a light bulb turned on for me. I started to think maybe there should be an app for the iPhone that’s a little like Foursquare, except instead of checking into locations, you’d instead see a heat map of all the places your friends had been to. And you'd see all your friends in East Village really like to eat out at these certain restaurants. And all of your friends that really like falafel, here’s where they go.

EOK: That sounds pretty awesome. Did the idea ever get off the ground?

CK: (laughs) No, I never ended up making it. But here’s what the experience did: for the first time in my life, I had this sense of creative possibility. You know, I loved making art but I also needed a career. And those things had never really emerged together for me. But right then at that moment, it suddenly did. And I was like, Okay, I want to be an entrepreneur. And for me, what that meant was, I want to have a job where I get to come up with exciting ideas, actually make them, and then see people use them. That would be the most thrilling thing for me.

So I graduated college, and just as I planned, I'm unemployed. But I’m not really fully unemployed, because I interned at NPR for a while, but I didn't have a real full-time job for almost a year and a half. But the whole time I was itching every day, wondering: how am I going to find a way out of here? How am I going to find a way to do this? And by this, I mean start working on a creative entrepreneurial project. 

Then in January 2013, I got a job at the Webby Awards, writing about technology. And on nights and weekends, I was trying to work on different startups, but nothing was really happening.

EOK: Just to pause real quick. Most startups require technology. Did you have any coding skills?

CK: None. All I had was a sense of what I as a user wanted. And also some sense about what made some apps good and others not so good. But I was really hitting the pavement, man. I was going to the New York tech meetup in the Skirball Center. And I was reading all these blogs and newsletters, just trying to get up to speed, trying to get literate in the space. And I was doing all of this while working at the Webby Awards. That was a really cool first job to have, because I got to use my skill, which was writing, and at the same time, also deepen my relationship with technology. But the problem with that job—by no fault of anybody's—was that my work was incredibly siloed. So I was just writing every day, in my own corner, and I’d look across the room, and there’d be folks working on video marketing, sales, and a number of other things. And I realized I wasn’t going to get the opportunity to understand those things working at a job like this.

So in 2014, a friend of mine told me that he was starting to work on a music social network. I was writing about music at the time, and he asked if I could help get some journalists on it. I said, Sure. Six months later, they raised a million dollars and they made me the first employee. And a year after that, they made me the CEO. And at that company—called Cymbal—I got the complete opposite experience from what I had at the Webby Awards, which was that if something had to happen, I had to do it. There were four employees at the company who handled everything inside the phone—the design, the front end, the back end—but if it was like, talking to journalists, or thinking about our social strategy, or about marketing the app, or managing the community, or talking to the investors who put money into the app, it had to be me doing it, because I had to protect the attention of our engineers and designers. I also had to product manage the team, which I had never done before. And I had to learn that stuff on a job.

EOK: That’s incredible. To be honest with you, I’m still stuck on the fact that you were hired as the first employee but became the CEO.

CK: Yeah, I know. That’s a whole other story that we can get into. But I want to get to your question about this idea of having a compressed career.

EOK: Bet, let’s continue.

CK: So half of the reason why I chose to work at Cymbal was that I wanted the opportunity to do this combination of creativity and career. The other half was that I wanted to grow faster. I wanted a position where I was responsible for some seriously heavy stuff. I wanted to be the person who stepped in at Cymbal and said, Okay, my job title is Head of Growth—which was preposterous by the way, because I had never worked in growth at any company ever, but I wanted the opportunity to figure it out. I had ideas and I wanted to put them to the test. Now, some of them worked. And a lot of them didn't. But it was all incredibly informative.

When Cymbal ultimately shut down, which was about three years after I joined, I got a job at Audiomack, which is where I am now. And I can genuinely say that what Cymbal gave me was honestly the most unbelievable set of experiences that I still cherish today, even though I’m three years into working at Audiomack. I rely on my lessons from Cymbal every day. There’s nothing comparable. There’s nothing like being put in the trapeze and having to figure it out for yourself.

When I stepped in at Audiomack and became the Director of Product Management and Growth, and then later the VP of Product, the whole time I was drawing on years of experience from Cymbal, years where I had already tried out a bunch of stuff that didn’t work. And I realized that that didn't kill me. Having the experience of trying something and failing, and then trying again and failing again, really pushes you forward. Cymbal was an incredibly informative experience for me.

So based on this question that you’re asking me, of how did I squeeze all of this learning into such a short period of time, I think it came down to the fact that I was really willing to accept a lot of uncertainty. I was willing to accept long periods of time where I might be doing work I found dissatisfying but I was doing this work with the belief that it’d open the right set of doors for me, and that those doors, or those opportunities, would then challenge me and grow me.

EOK: I feel like there are a lot of people who could say a similar thing about wanting to grow really quickly. I mean, there are many professional spaces out there that actually pitch people on the idea that they’ll work a crazy amount of hours—let’s say 80 hours a week—but by the very nature of putting in that much time, in a year, they’ll experience twice the professional growth that someone else does working 40 hours a week. What you’re saying sounds a bit like that.

But having said that, I think what makes your story unique is that there was also a lot of emotional and relational strain that exacerbated the professional weight you had on your shoulders. So I guess what I’m wondering is, how did those things play off of each other? How did the burdens you carried in your personal life translate over to the professional spaces you found yourself in? And also, how did this cycle of dissatisfaction and satisfaction, of growing and learning and stretching yourself professionally, how did that affect how you dealt with things in your personal life?

CK: Wow, that’s definitely the best question I've ever been asked in an interview. And it’s also a question that I’ve probably thought about the most in my own life, because from that falafel sandwich in 2011, for the next few years, my conception of what a career looked like, or what I wanted a career to look like, was really about finding an outlet for self-determination and agency. So essentially I asked myself the question, What am I going to do to not feel like I’m just another guy in a button-up shirt, riding the subway? What am I going to do to feel like I'm actually the captain of my own ship?

The thing that changed for me was in November 2013, my father died. And I definitely had a response to that. For me, it turned the initial impulse of waiting to ‘seizing the day’ into something more like, “You only have so much time left.” Either implicitly or explicitly, after that moment, I put on the afterburners, and I started to think about my life more like, Okay, you have to make the most of this while you have it. You know, this kind of thinking becomes very pointed when the number of memories you have with someone is suddenly capped because they’re no longer around. You end up realizing you only get a finite number of those. Ultimately, I think that experience thrust me into a modality in my life where I felt like I had to be highly exposed to opportunity. And I had to spend a lot of my time, on nights and weekends, trying to make something of myself. In other words, I tried to use my time in a way that treated it as valuable.

To bring everything full circle, in early March of this year, I actually cut back a lot on the things that were occupying my free time. And I did that because I realized I'm approaching a new stage in life that I want to be really present for. I want to be present for my wedding and my marriage. And then I want to start a family and I want to be present for that, too. I think there’s some circularity here. As I’m aiming towards hopefully becoming a father myself, I’m starting to let go of some of the things I stuffed my free time with as a way to cope with the loss of my own father. So I think it’s part of the healing process, though that may be the wrong word for it. Maybe it’s part of the process of me advancing in life and finding new ways to celebrate living.

EOK: I feel like that’s the challenge, How do we make the most of our time? I’ve always been amazed at people who are good with their time. I think it’s easy to talk the talk and say, “I value my time.” But I think it’s another thing to really live that. The people who best display it, in my experience, typically fall into one of three categories. The first group is people who are just extremely busy people. I think the second group is older people. Like, I have this professor in graduate school who sends these really blunt emails. And you read her messages, and you want to feel a type of way about her candor, but then you realize, she’s actually onto something. Email is not where life is.

CK: (laughs) That’s so real.

EOK: Yeah, and then the third group of people is, interestingly enough, people who are very family-oriented. 

CK: Hm.

EOK: Yeah, it’s like they intuitively understand that every hour they put into something frivolous is an hour they don't get to see their daughter or son mature.

CK: It’s true. You have to make choices, man. There are 24 hours in a day. Hopefully, you sleep pretty well for some of them. And then for the remainder, I think you have options. People express their priorities in all kinds of interesting ways, though. For example, there are folks who express their commitment to their families by working more. But there are also folks who express their love for their families by cutting back and trying to spend more time with them. The human psychology around this is very interesting. In a way, I think people create their own set of justifications for how they allocate their most limited resource, time. Once you get closer to starting a family of your own—which is something that I’m starting to think more seriously about—you have to figure out how you define value. It’s a profound topic.

EOK: I have a feeling you’re going to be a great dad, Charlie. I’m curious, do you remember how people used to talk about your dad when you were young?

CK: Totally.

EOK: What did they say?

CK: Well, so my dad was a journalist. His name was Peter Kaplan. He was the editor of a publication called the New York Observer. And he was a really legendary editor. As a father, he was an amazing person—loving, fun, very connected. And as a man, he was also someone who it was really easy to look up to because he not only had a unique point of view—as an editor that people sort of understood and appreciated—but he had also built up this organization of writers who were all these young folks, who looked up to him and learned a lot from him and then kind of launched their own careers elsewhere. So when you talk to folks who knew him from his job, you’d hear about how he was this guy who was like this leading light in journalism. And then when you talk to folks in his personal life, like the folks in the town I grew up in, they picked up on another angle: here’s a guy who’s building a career that’s not cookie-cutter. It really seemed like he was working on his passion. He seemed to be following a sense of inspiration. And that's definitely a big part of where my sense of agency comes from, his example of working on things that he really loved and believed in. I got a lot of that from my mom, too. I don't want to make it seem like this was a unipolar influence. But yeah, I think the simple fact that I still have my mom and I don't have my dad certainly changes the way I relate to his memory.

EOK: It sounds like the apple didn’t fall too far from the tree.

CK: Well, I would be honored if that were the case because he was a guy I admired a lot. He was definitely somebody who—I mean, the specifics about his career and his work are incredibly cool. He did some really great writing of his own. For example, he did this incredible interview of Eddie Murphy that was in Playboy in 1983 or around that time. And it was just him and Eddie Murphy driving around in Eddie's Corvette for like three or four days. And my dad writes that by the end of their time together, Eddie could do a perfect impression of him. It’s a great piece of writing, and my dad really captures Eddie, and how famous Eddie really was at that time. So yeah, my dad did incredible work that was really inspiring, a lot of it that I’d loved to return to. He was really the kind of guy who ran to his work rather than ran away from it, if that makes sense.

EOK: Yeah, that makes a ton of sense.

CK: I think that's one major takeaway from him. My dad allowed himself to be driven by inspiration, instead of being scared out of doing things that maybe were risky. He never really felt like he wasn't entitled to try. I think that’s a pretty great example to have.

EOK: You know, a friend once told me a similar story along these lines. He has a friend in Atlanta who works as a prison chaplain. One day, my friend asked his prison-chaplain-friend, How do you keep coming in to work? How do you keep showing up, knowing all the negativity that awaits you when you clock in? After mulling over the question a bit, the chaplain-friend replied that he “jumps” to work. In other words, he understood the space he was in was a space that was made for him, you know? Like there was no one else called to tend to that specific patch of the garden. He understood that deeply and that's what really helped him wake up each morning even while knowing the prison wouldn’t be all sunshine and giggles. There’d be trauma, pain, suffering, hopelessness, tragedy. Hearing you talk about your dad, he sounds like someone who knew on a very deep level what his calling was.

CK: Wow, that’s a great story. And yeah, I think you’re exactly right. But that was the hard thing for me as a kid. I didn't know what I wanted to be doing, you know? And I know I keep talking about this falafel, but it really wasn’t until I ate that falafel that I had a better idea of who I wanted to be. That’s kind of the core thing that I was observing in my dad, which was this sense of self-determination, of picking something that you really believe in, something you're inspired by, and then working on that, chasing that. For me, even though I love writing and got the opportunity to write for a bunch of publications, it wasn't my calling. It wasn't the thing that I woke up late at night thinking about—like, I have this great idea for an article. It was never like that for me. But once I started to get more into the space of knowing I don’t have to work on the exact same thing as my dad, that it’s more about “What’s the thing pulling you?” that’s when things really clicked for me.

EOK: So what is that today? What’s the thing pulling you right now?

CK: Yeah, so as you know, I love music. And even before I worked at Cymbal or even interned at NPR, music was the thing I was thinking about most of the time. And so at Audiomack, I’ve had the opportunity to build for both artists and listeners, which is interesting because I inhabit both of these roles. In my personal life, I make music and I also listen to an incredible amount of music. [Edem’s note: Charlie’s monthly newsletter, The Retrographer, is an amazing treasure chest of deep cuts and songs you’d love but would never find on your own or via an algorithm. I highly recommend it.] Because I inhabit both roles—artist and listener—when I go to my team at Audiomack and share what I think the product direction of the company should be, I get to draw from a very authentic source of experience. It’s a pretty neat circle. 

As one example, after I made Sunday—an album about the loss of my father—I went out to Bandcamp, Spotify, and Audiomack, and tried to get people to listen to it. So I have this sort of track line, where I can actually identify with what millions of artists out there are also trying to do, which is: resonate with folks and try to find an audience who feels the way you do.

EOK: You know, I love that a lot of our conversation has been grounded in words like self-determination and agency because I think there's power in abstraction. When I think about Audiomack and what its product really is, I don’t think about it in a way that maybe other people would. I think some people hear ‘product’ and think tangible software, tangible tools. But if someone were to ask me, What’s Audiomack’s product? I’d probably say, discovery. I feel like that’s what Audiomack does. Everything Audiomack is doing points back to discovery. It’s all about helping listeners discover artists, and helping artists discover listeners. Everything you see from Audiomack—Trap Symphony to Audiomack World—points back to this. It’s all in service of discovery. It’s all in service of bringing these two groups of people—artists and listeners—closer.

CK: I think you’re totally right. You know, there’s like an older vanguard of streaming music services out there—Spotify and Apple Music—that all music goes through. And each of them is trying to launch apps for artists, Spotify for Artists being one and Apple Music for Artists being the other. The unique thing about Audiomack—which is also true for Bandcamp, YouTube, and Soundcloud—is that on these platforms, the content actually originates from the creator. That is, the creators themselves upload their content directly to the platform. There are no intermediaries. So you’ve got this single meeting place where both the listener and the artist come to the same place at the same time. That’s where the real magic is going to happen in music, at this connection. 

Fundamentally, an artist makes music to take the feeling that they feel inside of them, and turn it into this thing that can be given to anybody else, and ideally, make someone else feel the same way they feel. And that feeling of being on stage and seeing other people respond to what you've made is like this incredible alchemy. It’s almost like an ESP connection, like music is a spiritual translator between individuals. Now, to be able to embed that into a product experience, I think that’s a really powerful thing. And I think that’s something we can do at Audiomack that not every other company in the space can. It's a very exciting thing, definitely. And the fact that I get to draw from my own experience to do it is amazing. 

EOK: When you talk about past experience, in what way do you think your experience at Cymbal has been most informative? In other words, if Cymbal never existed, what lessons do you think would have been lost?

CK: That's such a good question. So with Cymbal, before I became the CEO—

EOK: Before you jump in, do you mind giving a short explanation of what Cymbal was for the people who may not know?

CK: Sure, so Cymbal was a music social network for iOS and Android devices. If you Google “Cymbal app,” what folks generally described it as was “Instagram for music.” So there was a feed and you’d follow friends. And everyone would share their favorite song, and the cover of your favorite song would sort of be like your profile photo. So essentially, your feed would become this constantly updated playlist of the music your friends are most into. And it was all built on the back of the Spotify, Apple Music, SoundCloud, and Deezer APIs. So ultimately, we turned it into a community of a few hundred thousand music fans who were sharing their favorite songs and connecting over music. And it was one of the most life-changing experiences that I've ever had. 

When we announced we were going to shut down in 2018, I got a torrent of emails from our users who were telling us how much they cared about Cymbal, and how much it meant to them. Some people told me they found their favorite songs on the platform. Other people told me they met their best friends on the platform. There’s actually a really good community of Cymbal users on Discord. Some people even told me they fell in love through the app. I got an email from someone who said they were moving from California to Australia to live with their girlfriend who they met through Cymbal. It was really profound.

Every month since Cymbal has shut down, someone has reached out to me and said, “Hey—I want to start a music social network. I read about Cymbal and I want to learn about your experience.” I think for me that has been the most incredible legacy to have from that experience because it's shown me that not only does music have this incredible power to bring people together and to connect, but there's still this huge surge of inspiration to try to move that mission forward. And even though we weren't the company to do it, I was able to briefly peer into just how important music is as a tool to connect folks. So that's what Cymbal was. It was a really amazing community and it certainly changed my life working on it.

But to get to your question about what's the most useful thing I learned from my Cymbal experience, here’s what I’d say: when you work for a small company—like a five-person company, which is what we were—if something's got to happen, and you don't do it, there isn't another person to make it happen. And that's especially true when you get into the leadership position as I did and become the CEO.

So if we had to go to [the record label] Def Jam, and give a presentation about why they should put their artists on Cymbal, there had to be a slide deck that convinced them that even though at the time, we had like a few ten thousand users, that we were a worthwhile use of their energy. You know, I had to figure out how to make that argument. I had to figure out what our perspective for the pitch was. I had to understand the audience, make the deck, show up, and present. There are a million examples of that, everything from “How am I going to get folks to follow us on Twitter?” all the way to really hard stuff like, “How are we going to figure out how to improve our product, and make it more inclusive, and build features that keep our community of folks here for the long haul?” That experience flipped a switch in my head that hasn’t turned off, which is this feeling that if something's got to get done, I just have to do it. I have to figure out a way for this to happen and not leave it to chance. I can’t assume somebody else is going to handle it.

So in my day-to-day at Audiomack, where that comes into play is that when you’re at a seed-stage company—like, a very early-stage company—you don’t know you’re right. That’s what makes it seed-stage. You have a lot of assumptions about the market, your customers, your business. The analogy I like to use is that you’re in a dark room, and there’s a timer. And you have to find the light switch before the timer goes off. The timer here is how much money you have left in the bank. So you have to learn to be very empirical, to try things and if they work, do more. And if they don't work, do less. You can’t get caught up in the ego of your own imagination. It’s very easy to fall in love with an idea that you're wrong about, and pursue it even though the evidence is showing you that you're wrong about it. In fact, plenty of folks don't even collect the data to see whether they're right or wrong about something. So that's another really key part of my job, this idea of figuring out what direction we’re supposed to be going in product-wise as a company. I try to be a very forward-thinking product leader and ask questions like: how can we build an even better experience for listeners and artists? What are the other companies in the music space not doing? What are they not thinking about? And ultimately, how can we make this a more rewarding experience for the listener and a more rewarding experience for the artist?

EOK: It sounds like you’re well on your way to finding the light switch this time around, Charlie. Thanks for coming on. I had a great time talking with you.

CK: For sure, man. It was awesome talking with you, too.

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