The Chainsmokers - Music & Markets - [Invest Like the Best, EP.430]

How do you feel about models training on your content?

I don't care.

Yeah, I figured.

Because it's like the cat's out of the bag.

We don't care about our music either. I ask because there's so much controversy around music and art.

Trip Adler has a pretty successful company, and he's starting something new. He's one of those founders where you're normally like, “This is a really successful second-time founder starting something in AI now.” I spoke to him, and he was like, “Yeah, it's basically licensing copyright rights that we find a way to protect and then get people paid.” And I was just like—

Yeah.

This feels—

It's like I'm going to stand in front of a tsunami, and I'm going to hold it off.

Yeah. I was like, everything here is hinged on the government protecting IP, and by the way, it's already too late.

I'd compare this phase in AI models training off of copyrighted data to the Napster moment, where the record labels couldn't figure out a way to sell music in the digital age. If they had been forward-thinking and accepted it, they would've created Spotify, and we wouldn't be paying an extra 30% to a DSP. But they didn't, and it had this whole moment where it's like, you can't really stop this from happening, so just embrace it and figure out how to harness it when it comes out the other side.

One person will get sued.

These models are going to train on this, and they're going to be able to do these things that everyone's feared about them doing. But then we're going to be able to make better art or different art.

Is there anything you do fear?

Loaded question that I want to answer correctly. My first instinct is to say no because, specifically, we're DJs. Fifteen years ago, the DJ-producer—and still to this day, you've seen the memes about how they're just pressing play or all of their music is software. I remember the first wave of that democratization of music software becoming available and accessible, and the barrier to entry coming down, and all of us being able to make stuff that we weren't able to create before unless we had access to a crazy studio.

I remember everyone saying that wasn't real music. I mean, here we are 15 years later. We and all our friends have had massive songs that have been culturally impactful, that play huge shows, that tons of people come to have a good time to, and listen to music that makes them feel euphoria or sadness or something amazing. It's the same impact of music because of a different set of tools.

I'm excited to see what happens next, and I'm excited to use those tools or for my kids to use those tools and to see how that enables people who might not have been able to express themselves with this medium.

I would argue that it's the same now. It will be worse in the future, but just lots of slop. It's just a larger volume of stuff that gets made every day. To Drew's point, 15 years ago was probably when DAWs like Ableton and Fruity Loops and all these things came into existence. Now on Spotify, when we started, there were 10,000 songs uploaded every Friday. Now there's like 190,000 or something like that.

That's not that long.

I imagine that in a few years it'll be 1 million, and that will definitely have an impact on how hard it is to break through. Maybe the importance of having a brand or an identity or a standing for something will mean even more. I just watched this Brian Eno interview with Zane Lowe, and he was talking about AI and whether it was scary to him. He was like, “No, because at the end of the day, it's still just a tool, for now at least.”

Is it maybe the opposite—that these tools make people like you, who are willing to go the distance and want it the most and are maybe the most talented, even more advantaged versus everybody else?

Who knows? I can't answer that question yet, and hopefully not, to be honest. I think what we're all going to have to do—and not just those of us who are established—is figure out how to use these tools. We have our way of making music, and I think what it does is actually kind of the opposite: it allows more people to be able to make music and perform music and create an experience that other people connect to.

I think music is just my personal favorite form of self-expression. With these tools, I'd assume that more people are going to be able to experience expressing themselves that way, and that's awesome.

And perform it. You can kind of look at the DJ as a microcosm, a blip on the radar of a version of more accessibility and what that gets you. But you look at how big the scene is and how fun the scene is now, and it's like, how is that a bad thing?

1. The Creative Process Changes

How does it feel most different now, creating a marginal new song versus when you started? What is the biggest difference you feel in the creative process?

I would say that's less technological. It's more my own brain that I'm still trying to reckon with. In songwriting, you're always trying to scratch this… It's not the same itch, but there is an itch you're trying to satiate. It's deep inside of you that makes you feel something that you haven't felt in other places, or maybe you feel that way because it's you making it at that time.

But as a massive music fan, I'm trying to make something that respects all of the things that have inspired me my entire life and still makes me feel like, wow, this is my statement now. You'd think that we'd have a formula now for how to write a dance song, at least, or write a pop song—forget about trying to write the truest song for you at that moment. It still can come from anywhere, and it's so difficult. I think I would be surprised if any artist told you that they weren't rewriting their process every single time they go to do an album or a new batch of songs.

Say a little bit more about the nature of those feelings that you're trying to get yourself to feel by making something.

Well, if I could say it, I wouldn't need to make music. It's us tinkering around, and it's really cool having someone that you've made music with your entire life because The Chainsmokers' music is what we both agree is fun and tasteful, and we want to play out.

But it's not just me or just Alex. It's a reflection of our friendship and what we've gotten super stoked about listening to as music fans over the past 20 years.

2. Inside No Shade At Pity

Is there a song that you remember making together where the creative process behind the song stands out the most in your memory as emblematic of what it's like to make something together?

You told me about “No Shade at Pity” one time and the process behind that. I thought it was so cool.

That's out on a day like today.

Yeah, I mean, it was probably almost a year to this day. That was an interesting song, especially for me. I'd just gone through a breakup or something, and we were pulling a lot of inspiration from that.

Just generally speaking, you go into the studio and you're like, “What interesting concepts or things that are happening in our lives can we talk about or expand on?” And then a lyric or something happens. We were thinking about New York City, which is obviously where we started, on a day like this, when it's 75 and sunny out and winter's over. You know what I mean? It's time to be feral and enjoy the city.

Enjoy the city. It's 60 degrees, but everyone's got their shirts off.

One of the best days of the year, yeah.

Yeah, and all those fun bars and restaurants with sidewalk space are just overflowing into the streets, and it's hard to find something that isn't fun. It was using that as a metaphor for coming out of a relationship. But then there are so many decisions and things you have to talk about: How long do we want the verses to be? Is it too wordy? Is it too dancey? Is it not dancey?

I wouldn't say that song was a runaway success for us by any means. I do feel like people keep coming back to it. I feel like we have a lot of songs like that where I'll get messages throughout the entire year. Once a week, someone will be like, “Dude, this song's really good.” And you're like, “Did you just listen to this? You're my friend. I put this out 9 months ago.”

I think that's what's cool about music: everyone has these moments with songs. I still have them with older songs from the ’60s, ’70s, or ’80s, as well as new songs that came out last week, where you're like, “Whoa, this dude's preaching.” You know what I mean? Or it just resonates deeply in some way that it maybe didn't before, just because of whatever mood or thing you're going through.

With songs like that, it's funny because he's talking about my breakup, but then we don't want to just make it about my breakup. We want to make something that's an experience that everyone can kind of relate to. Then he's figuring out clever ways to fit the story into a visceral scene that relates to both of us, which is a New York spring day. I'm trying to keep feeding the song with personal, sad anecdotes in it.

It's a funny process.

Yeah, and then it kind of goes back and forth in this way. I think Emily wrote that song with us, too—obviously, an amazing songwriter. It's fun, and then suddenly you're like, “There it is.”

I feel like when you make a song like that, you're so excited about it, to play it and to be like, “Is this it? Is this going to resonate with everybody?” At the end of the day, whether or not it met the standard of success for us on a metric level, it hit the mark as far as a Chainsmokers song on every level.

That's one of my favorite songs of yours, yeah.

Yeah. Thank you. I think that's a big part of what we've been re-exploring in the last year: dialing it back to the Chainsmokers fans and the Chainsmokers sound. Going back to the AI stuff, there are so many tools out there right now, so much software, so many ideas, so many genres, so much stuff happening every day that you almost have to constrain yourself a little bit to have success.

I forgot who was talking about this. The guitar has been the exact same instrument for hundreds of years, and yet people are still finding new ways to play it and create sounds and feelings from it. I feel like we go into our studio sometimes, and it's like, “Wow, we have 25 keyboards now.” It sometimes hurts the experience rather than helps it.

3. The Music Abundance Problem

If there are no barriers to entry, or fewer and fewer every day, for music creation, what are we left with? The same way I could play a guitar and sing a song that some other guy can, it might just hit differently when that other guy does it—or that girl does it—based on their background, the way they're holding it, or the way their voice inflects with that chord.

There's so much that comes down to brand. I hate to say brand when you're talking about art, but what is this thing that people are tuning into you to believe in? Someone brought up the point the other day: no artist knows what song they should play at their show. I don't know if you've ever heard that.

No.

I thought that was a really interesting point. And to what Alex is talking about—the success or lack thereof of a song like “No Shade at Pity”—how do you define success in an age of abundance of art? How do you define success with us, where we have a bunch of songs with over a billion streams, we've had chart-topping songs, but then what is the one thing that we do that no one else can do?

Can that even be replicated by AI? Can that be replicated by another person? When that person does it, it will be them doing it, and it'll be at a different time, and it'll look different, and it will feel different. When you think about AI, you can't be scared of it because it's just going to hit differently, for better or for worse, at some point. We just have to focus on being the most Chainsmokers possible.

Is art in a really bad place right now, generally, across the board? We have very few original movies being made: Avengers 25.

Slop everywhere. Everything's optimized for—

Yeah.

—various algorithms.

Exactly. What does that mean for art in general when anyone can do it and it's accessible? Are we in a golden age of creation, or is it different?

We work with R.Z.L. all the time, and he plays a song and it's like, “Oh, this is an interpolation of a song.” And you're like, “I have no problem with that stuff. I think it can be really interesting.” But you're also like, “It's already a hit.”

I think when you have an artist like Fred again.. come along, I think it has an even bigger impact than maybe in the past, because that originality is so refreshing.

I find him unbelievable. My son and I are huge fans. We've watched all his various sets. As fellow musicians in the same general category, what is it? How would you describe what he's done, effectively, to somebody else? Because he feels like the right example of this originality that we all want more of.

4. World Building Wins

Fred's a great example. There's a lot of standout artists from the past 3 or 4 years. If you look at Doechii or Charli XCX, and most notably probably Fred, they've all brought you into their world. It's bigger than just music.

What's so cool about music right now, and those 3 artists in particular, is they have songs that go viral, but they're not traditional pop hits like the ones we had when we came up 10 years ago. It's so much cooler now. It's so nuanced and just more niche than it was at the time.

We're seeing this in dance music especially, where the new stars of dance right now are blowing out Madison Square Gardens or basically doing festival-sized crowds for their own shows. If you looked at their Spotify monthly listeners, like we were talking about earlier, you'd be like, “Oh, this is an emerging artist. This is an opening act.”

That's what's so cool, and I think it kind of wraps up the whole point about if everyone can be creative: what else can you give them? You need to bring people into something more than just music. I think that's something we struggle with a lot, where we're hyper-focused on music, and we create this thing and we're like, “I crushed it this time. This is going to be it.”

But the world-building of the whole thing is something that doesn't come naturally to every artist, which I think will just be more and more important. As a fan, I want world-building. I want to participate. I think the album is God. I want to sit in your world for 45 minutes to an hour and 15 minutes. I want to put on the costume when I'm listening to something.

I read this amazing post this morning about the need to build heavy things, not light things, with light things being ephemeral. Make it fast, consume it fast, forget it fast. Something like the album approach, or something that takes a lot of time, heart, effort, blood, sweat, and tears, is what we need more of.

Such a good point. I think even the commonality between Fred, Doechii, and Charli XCX—these are people who have been grinding. Doechii's video, after she won the Grammys, went viral because she was fired from her job. “I'm just going to double down on music.” It was some crazy thing.

Charlie XCX has been writing songs for hit artists for 15 years. You know what I mean? Just in the background, waiting, almost fine-tuning everything, waiting for this moment. Fred, similarly, is literally a musical savant, but has been writing for Ed Sheeran and huge songwriters in the background. His story is equally as impressive.

Then you have that compared to the TikTok artists who, during COVID, made a viral 15 seconds of a song. Labels sign them, and then they're like, “What did we just buy? I don't know what this is.”

Oh, my God.

Totally. And it's not to say those artists can't break out and do great things. Addison Rae, I think, is doing a really great job of building a really amazing career right now.

I don't know Addison, and I haven't worked with her, but everything I hear from our songwriter friends who are in the studio is that she gets the world-building piece of this.

Yeah, you can tell.

What does world-building mean? Just define what that means.

Defining an aesthetic, a mood, and an attitude that you can participate in when you listen to the music. That's how I would see it.

The Chainsmokers

Some people do this super thought-out. They probably have boards and plans and branding and insane creative direction. I think some people are just themselves. They just build it inherently.

Like Travis Scott is rage.

But I would say, as far as lack of branding goes, Zach Bryan is Zach Bryan. When you go see a show, when you hear it, and you consider the amount of songs he puts out and the type of videos that he films, I'm just like, this is just a down-to-earth guy singing—I guess they call it Rust Belt country. Brilliant songwriting and no frills. You're just getting good-ass music.

I feel like Fred again.. might be the DJ version of that. This guy's just making really cool, innovative music and doesn't care how it's packaged.

He's so happy all the time.

How is he this happy?

There's this moment in the Boiler Room set that he did where a fan knocks the cable out.

Oh, yeah.

It stops the whole thing.

Yeah.

And his reaction to it—he instantly smiles and is happy about it, and then somehow uses it, weaving it into the music somehow.

The Chainsmokers

Yeah.

It was one of these moments where I thought, "Oh, my God."

I know the moment you're talking about. It's adorable.

It's amazing.

The guy's so embarrassed when he does it.

And then they start dancing together.

The Chainsmokers

Yeah. It's really nice.

You used the word "itch" before.

Yeah.

So many of my questions for you guys are metaphorical for other people building and creating stuff. We're both passionate about people who build companies. We'll talk about that plenty today, too. But getting in touch with the itch is actually a nontrivial part of making anything great, and I would love to hear from both of you how you originally found yours.

As a source of inspiration for people who want to find their itch, I think most people don't ever even know what the itch is. Where did it come from for both of you?

I didn't grow up wanting to be a musician, necessarily. I always had a really close relationship with music, but it was never a viable career path in my mind. For me, I was always a very visual, creative-type person. I was obsessed with Nike commercials back in the '90s and 2000s.

I would actually record them onto a VHS tape because I was so inspired by the feeling you got after you watched them, the visual storytelling, and obviously the personas involved, which were super cool. I was a huge NBA fan as a kid. I think most kids are. I started painting a lot when I was younger, and I think it was about trying to find a language: What is that language that I can speak that conveys these feelings I get from watching these Nike commercials?

As I got older, my dad was an art dealer, and he was fairly successful with it before he passed away. I think that when he passed away, it changed a lot of how I thought about the world and what my opportunity was going to be within it. I knew on some level that it was an out-hustle, outwork mentality. I wouldn't say that growing up I looked at the world like, "I want to be a musician," or, "I want to be a businessman." I only knew about the art world because that's where my dad was.

It kind of felt like growing up on a farm, where you're just like, "I'm going to be a farmer. It's what I know." Then you go out into the world and experience different things and different opportunities. I think the itch for me is about where your passions lie. What do you actually like spending your time doing? What do you find yourself being drawn to?

I think New York, going to school here, was the perfect place for someone with my ADHD because you're getting pulled in so many different directions—events and experiences, the art world. But you also have to survive here. If you can make it here, you can make it anywhere, sort of mentality. I always found that piece super inspiring.

But I don't know. It's a tough thing because the itch, to me, was something that was far away in the distance that I could see but didn't actually have the ability to do anything about. Then, when we finally started really building The Chainsmokers and things started to work, it was like, "Oh, my God, this is the feeling that I've been seeking out this whole time, and I've just been applying maximum pressure, grasping at different opportunities."

I think that's why you meet these young founders who aren't necessarily saying, "I've always wanted to build this product." That's a great mentality, of course. Someone who's worldly, I think, offers a more interesting perspective to me about how they go about being successful in whatever it is they're passionate about, because it's not just a straight line anymore.

I think there are so many things that shape that great founder or shape a great company. I think it's more important to have that paranoia deep within you that forces you to live in fear your whole life, or something that allows you to be successful. It's tough for me because the itch was just a survival thing, or proving people wrong, more than, "Ah, I just want to do..." I stopped painting when I was 15 or something. It wasn't a sad day for me. I'm moving on. I'm out of paint. I just don't really want to do this anymore. It's more of a mentality thing, of how you search.

But it was a feeling you were chasing. There was some vector there.

Totally. There was a feeling of that. I felt like I was being chased, also, by people's expectations of what they thought things were going to end up like. Growing up in New York, too, you have a lot of people grow up to be super successful much faster sometimes. You're like, "Oh, my God. Half my friends have jobs at great banks now, and I'm a nightlife promoter. This sucks."

Also, in high school, I wasn't a loser in high school, but I definitely wasn't the super-popular kid.

Yeah.

The Chainsmokers

No offense to any of my friends listening, but some of y'all peaked in ninth grade. You know what I mean? I'm just glad that wasn't me.

To tweak the question slightly, because I want to hear the itch answer for you, too, I'm curious how the notion of happiness versus dissatisfaction versus paranoia figures into your answer.

I'm trying to figure that out with my therapist now. I grew up in Maine. Later in life, I'm very thankful to have grown up in Maine. I grew up in a small, pretty liberal society where everyone kind of did everything. Everyone was from a small town. Everyone was in theater. Everyone who also played varsity sports was super studious and all that stuff. It was a really great community to grow up in, but I felt super trapped.

There was something inside me from a young age that was like, "There's so much more going on in the world." My mom is a super-curious person. I think I inherited a lot of that from her genetically and through her parenting. My mom is just a great explorer and, still to this day, loves learning and seeing more things. I always wanted that.

There wasn't a lot of opportunity to leave Maine when I was a kid, and I think music was the thing that illuminated everything for me. I was super passionate about playing music from a really young age, and as soon as I developed my own musical taste, I was very obsessed with what I hadn't heard before.

I think that's what eventually brought me to dance music, because I had this transformative experience when I was 16. I did an exchange program in Argentina, and I heard the beginnings of David Guetta and Daft Punk for the first time, and this artist, Trentemøller, whom I fell in love with. I heard these sounds that were just—I had never seen colors like that.

That, in a nutshell, is my pursuit of the itch that I'm always trying to scratch. I'm trying to hear something new. It's quite torturous, to be honest, because once you've done something, you're like, "Yeah, okay, that's happened." Then it's, how do you innovate?

It's like The Innovator's Dilemma. How do I continue to create something that my fans really feel connected to and that I feel connected to, that really respects the core identity that is me, the music, and this thing that I've built, that's also innovative, that feels like it's still me, and gets me excited to go up and play new songs while my fans feel like it's fresh?

I think it's a pretty torturous pursuit. That drives me crazy a lot of the time. We have—I won't name names—but there are some artists in our genre and other genres that have just seemed to make the same song again and again and again. For a while, we were kind of like, "All right, we don't need to hear this person's new song because—"

Heard it already.

Yeah, heard it already. But when we look at what that looks like over 10 to 15 years, we're like, "Oh, my God, they're the only person who does that sound." All these fans are just amassing and telling their friends and all of that.

You look at someone like the Grateful Dead, and you look at what that's become. They're maybe the best people at making fans over time. Incredible musicians, but they've created this experience that's replicable, that people can tell, that people can rely on and tell their friends about, and that has great ethos.

I think that's really interesting to think about as we're asking, "What does the rest of The Chainsmokers look like for us?"

5. Redefining Product Market Fit

How do you think about a tech idea like product-market fit for you going forward?

You've had it in the past, just measured by streams or popularity or something.

The Chainsmokers

Yeah.

But if you think about it prospectively and you were to redefine what success would mean, how much is it for the audience versus for yourselves? It's such an interesting question.

A lot of artists would probably struggle with this question, us included. I'm trying to figure that out all of the time. Part of me wants to just get out of my own way and just be like, “Fuck it, I just have to make stuff.”

There have been a couple of records. We made this record called “Don't Lie” that our fans didn't connect to and didn't connect commercially. It came out just—what?—6 months ago. And when I hear that song, I'm like, “Fuck yeah, I did the goddamn thing on that.” From a writing and production standpoint, as a pop kid, I'm like, Kim Petras, an awesome artist, sounds amazing on it.

The whole vibe of the record, I just hear it and I'm very proud of it, but there's something about it that just didn't connect. Was it the marketing? Was it just that song from us? Was it that song in general? Maybe it didn't have enough of the essence of Alex and me in it. Maybe it didn't feel like we meant it enough. For some reason, our fans didn't connect to that song.

That other piece of the puzzle is what we're trying to figure out now. How do we show people we really care about this music without looking like some Gen Z on TikTok doing stupid videos that work for some people, but it isn't us?

A lot of it comes down to language, how you present yourself, and I think the same thing applies to companies and product-market fit. What is the story you're telling? Why should people care? How are you sharing it with the world? And if you don't care about it, then why would anyone else?

Intentionality matters more than ever. Your fans want to know that you love this thing that you created in a world of slop.

How do you show them that? Is it just the quality of the work?

I don't know. I'm really confused about this part, especially in this day and age, where I see artists that aren't us, that have a different vibe or are from a different generation, do it so effortlessly.

I think presenting stuff as art is always super important. One of my favorite bands is this band called Turnstile. They're a hardcore band from Baltimore. It just reminds me of so much stuff that I grew up on, but it feels fresh and repackaged. The videos are amazing, and the rollout, and there's so much intentionality behind it.

I'm realizing a lot of the projects that I'm really gravitating to are encapsulating all of that stuff. I don't know that we've ever intentionally gone after that. We've just been like, “We're making tunes. We're going to do all the shows we can,” and that inherently became us.

6. Work Ethic Builds Relationships

This really interesting thing about you guys to me is not just work ethic. Your work ethic, we could talk about that. It's obviously prodigious. It's incredible, the amount of stuff that you guys do, but it's this combination of the work ethic as a means to build relationships with more people.

It seems like everyone I know has some experience of you guys. They've met you somehow. Somehow you've met everyone. You've had a nice interaction with them. There's a high degree of accessibility that seems to come with the work ethic that allows for these relationships. How do you think about work ethic plus relationships as a key part of what defines you guys?

First of all, you have to want to do that. We love to throw parties, and we love to choose the music, and we love to curate the vibe. That was why we became DJs, pretty down the middle. That was always really inherently us.

We love making music. We love starting businesses. We love helping other businesses. The first thing that we went after was capitalizing on this desire to create a fun-ass time for people, and I think that is what we've continued to do at all levels. We're hyper-curious, and I think it's very gratifying for us to be able to pull people into our world.

Personally, it makes me really happy when you can include someone who's not typically included in either their social dynamic or work setting or whatever. When they come to our show or hang out with us backstage, if you can make 30 to 90 seconds and really listen to someone, look them in the eye, and offer them a drink in your environment or anything there, those are the little bits of magic that you get to pass around, and hopefully they keep passing them on to somebody else.

I think that's kind of the soul of what we do. Do that for 13 years, and it feels like you've met everybody, or people feel like they've had a great connection with you or with each other at your thing. That's nice. I think we like being those guys.

I was, like I said earlier, not the most popular kid in high school, but not the worst either. But I think my whole attitude was that I was just friends with everybody. I was a nice person who hung out with the varsity basketball team and the art kids later, and, ironically, I was school president. I never thought that was ever a goal.

Everyone likes you.

Yeah. You should obviously do this. Everyone would totally vote for you. You're friends with everybody, and I feel like that was such an interesting experience in life.

There wasn't a sense of, “We don't talk to that person because they're like this,” because I always felt plenty of times that I wasn't cool or whatever. And it meant so much to me when someone went out of their way to make you feel acknowledged or comfortable in something.

I felt like if you could continue to challenge yourself to be that person in all sorts of different scenarios, it wasn't with this long-term goal, like in Billy Madison, when he calls Steve Buscemi and apologizes, and then Steve Buscemi saves him later. No, it's not that sort of thinking where you're like, “One day this guy's going to put money in my fund.”

It's more like, it doesn't matter if you're the CEO or an SDR at a huge company or whatever. Just come and be a part of the world, and if you bring great energy, that's super interesting and exciting to me. I think we feed off of that experience that we give people, like Drew said.

We play Vegas hundreds and hundreds of times, and people are like, “How are you still doing this?” And it's because every weekend there's a new group of people coming, experiencing this for the first time, and they're so excited. You sometimes forget how lucky you are to be in that position.

The kindness that people have shown us in the past, from radio stations that supported us early on when they didn't need to, also means a lot. Life is so long, and I think if you take a second to listen, I've read this interesting—I think Chuang Fang, I'm hoping I'm pronouncing his name right—posted this interesting blog post from a wedding photographer who's been shooting weddings for 30 years or something.

It was 21 insights that she'd noticed about brides and grooms and different people who attend weddings and the personalities they have. Some of them felt a bit over the top, but a lot of them were like, “That's a super interesting observation.” And I think if you study people and study relationships, that's kind of all it is.

We're all just interacting with each other, and that's fundamentally what business is. It's fundamentally what relationships are. And so if you can put yourself in a position where people enjoy being around you and feel seen when they're with you, I think that's amazing. It's something we definitely struggle with as you get busier, too. I'm taking calls in August right now, and it kills my soul to be like, “I would love to speak to you in September.”

Right.

So it's just getting older and shit.

7. Running The Chainsmokers

If I think about Chainsmokers Inc., the enterprise around the art, what does it look like, and how has it evolved? This is maybe a good bridge question into talking about investing in businesses and stuff. But if you just think about your business first and foremost, how much are you thinking about it? How much of it is intentional—looking a certain way—versus just more of a residual thing that has evolved alongside your music?

It's evolving as we're trying to simplify it—

Mm.

—as much as possible. I mean, that means really looking at how we spend our time, how we enjoy spending our time, what we're getting the most out of, and stripping away everything else.

I think when our career was on the rise for the first time, we were so curious and we wanted to do, for all the reasons we've told you about us and our past, whatever, we wanted to try all of these different things. We said yes to way too much, and I think that through doing that, we have found the things that resonate with our core.

Making the music that we make is still the number 1. Our last 2 things will be venture and music, and we genuinely are in love with both of those things. Sometimes I regret having a situation where we have both, but if I had to pick 1, I don't know which one I would pick.

I think just trying to build processes through both of them, both of those businesses, so that we can do them in—I don't want to say effortless ways—but in the ways that are most synced to who we inherently are. Everything we said about intentionality and creating art that's really you, how do we open that process up so we can do that the easiest? That's what we're striving to evolve now.

When we raise money for our fund, we get asked that question a lot, and I always say that The Chainsmokers is the sun in our solar system because everything circles around that. If it's a really strong sun, it shines more light and creates more abundance and opportunity across Mantis and whatever, with tequila company and other things.

Whereas, I don't know if a strong Mantis saves our music career. You know what I mean?

Yeah.

Interesting turn of events.

Yeah. But what separated us and differentiated us early on—and, to Drew's point, what we're trying to turn back the hands of time on now—is that we did run The Chainsmokers like a business. As much as we obviously care so deeply about the music and the creative aspect of it, it was also, “This is a really unique opportunity that we want to make sure we're taking full advantage of.”

Whether that was doing too many things, playing too many shows, or whatever, we really controlled the biz. There is not a credit card statement that I have not gone through line by line still to this day, week by week. There's not a production budget that I haven't seen for a single show. The way that we organized our team set us up for success in a lot of ways.

COVID for some artists was pretty devastating, whereas for us, we were like—

Let's raise a fund.

Yeah, great. And so I think the problem with that, though, was that we became the CEOs of The Chainsmokers, and I think this relates to probably a lot of successful founders' journeys. I was talking to the founder of a company who's crushing it right now. He was like, “All I do is HR.”

Yeah.

He's like, “I don't build shit anymore. All I do is hire people, and it fucking sucks.” And I was like, “I know what you're going through.” We're on so many calls about the internal politics. I think we're actually making really solid strides to fix that, to go back to being The Chainsmokers instead of the CEOs of The Chainsmokers.

There's so many parallels between investing in and working with these companies and our own business, and it's really fun to have our own business because it's so easy to be the therapist for somebody else and have an X-ray into what they could be doing better and how to get out of their own way. And then when it's you, it's like, “This is how it's always been done. I came on this,” and you have all this shit in the way.

So it's been a great mirror, investing in these other businesses and then looking at our own and being like, How are we hitting these roadblocks or bottlenecks in our own situation? But that key one being: Be the founder, the CTO, or whatever you're best at. You don't have to be the CEO of your business. Hire someone that's great at that, that's going to deal with that. If you're the best product person, you're the best visionary of the company, don't be the CEO.

8. The Mantis Origin Story

Can you tell the Mantis origin story? What was the first conversation you had about it? What were you trying to do with it? Why did you do it in the first place?

Before Mantis, before creating a venture tech fund, we'd done a plethora of businesses. We're very avid investors, both privately and publicly, in the tech world, in public markets, and in real estate. At the time of our rise to, I guess, cultural zeitgeist status—probably 2015 to 2018—we met a lot of that class of founders: Drew Houston from Dropbox, Brian Chesky from Airbnb, and Michael Seibel, who was at Y Combinator at the time.

These guys were really amazing and opened our eyes to what private tech investing looks like. We didn't really know what venture capital was at the time, and we saw through their eyes that, for a lot of them, it was simple: “You guys can invest in all of these brands based on who you are. People want cool people on the cap table.” It started with something as simple as that idea.

As we got to befriend these people and get an insight into how they ran their businesses, we realized we had more in common with them than we did with most other musicians. We growth-hacked our first promotional platform and crowdsourced our first tour. We've always been doing the most to try and get our music out there.

When we worked with a lot of other artists, we found the majority of them were pretty disorganized and were just pursuing things in a different way than we were. There was some sense of familiarity, comfort, and like-mindedness that we found with tech founders that pulled us deeper into the space. So we did a bunch of private investing—

Just yourselves?

We did it ourselves, deal by deal, and then conceptualized the idea to start the fund. And then, as Alex said, we were putting it together in 2019, before COVID happened. I don't know what would've happened if COVID hadn't happened—

Yeah.

The Chainsmokers

That was because we were also prioritizing writing an album at that time, and all of a sudden we had time to raise a fund on Zoom and write an album in the studio.

Naturally, entertainers and athletes have these platforms that people are drawn to for different reasons, and I think when it relates to investing, you're seeing a lot of CPG and social creator-economy-type stuff. Initially for us, that was, “Cool.” I remember my business manager, Josh, was like, “Basically, you invest and you just hopefully make a bunch of passive income.” I was like, “Oh, how sick is that?” He also prefaced it with, “You probably will lose your money, but you could.”

Which we did, a lot of times.

We were really drawn to that entrepreneurial spirit. We're go-getters. We worked 24/7. If there's something that we could do now, we're going to do it now, not 5 days from now.

As we began to connect with these founders, I remember getting our first quarterly updates. I remember responding to one, and I was like, “I could help you with that.” And they were like, “Nobody responds to these.” And I was like, “What?” There were these little ways that we were able to make a real difference in these companies.

And then, to Drew's point, people like Brian Chesky, Steve Huffman, and the Khan brothers were like, “Why are you investing in fucking water companies?”

Our water company's doing quite well.

Yeah, yeah, yeah. There are a few good ones.

It's got a—

And we've made some good decisions, but there's a whole world of opportunity investing out there in really exciting companies. I remember doing the Uber Series F. I thought I was in early. I think I've made $6,000 on this investment. But at the time, I was like, “This is the coolest company ever. It's actually changed my life and my friends' lives. I want to find more stuff like this versus another beverage company or something like that.”

We were very lucky with Poppi, and Poppi, to its credit, reinvented what the soda category looked like and will probably look like in the future. That was a really nice blend of technology, forward-thinking, and messaging. And then, as it relates to marketing and distribution, I think a lot of CPG is just distribution and marketing.

Tech investing, you just get a front-seat view of the future. It's the most stimulating show you could watch. It favors the optimistic, which we are as artists. We like to dream about things that don't exist yet and build a world, and I think we didn't know it would be a lot of cybersecurity platforms, but now we gotta secure all those things.

It kind of reminds me of being in a school assembly in middle school or high school, where every now and again, they would bring in a professional, and they would speak about their career to the audience for an hour. You'd be like, “That guy actually did this shit. This is really interesting and exciting for me to learn from,” versus if it's a teacher who's just like, “Here's my perspective on something that happened or a career.”

In venture, you get to sit down for half an hour, an hour, hopefully many, many times with a founder who's like, “I've studied this space. I've lived and breathed this business, and I'm going to tell you everything about it right now.” For someone like me, that's the coolest thing: to spend 5 or 6 hours a day learning from an experienced person in a technologically exciting area.

Obviously, Mantis has evolved a lot. I remember on our first partner call, they were like, “So how much are we going to raise?” Someone was like, “$100 million.” And I was like, “Is that a lot? It feels like a lot.”

Turned out to be a lot.

I just want to start, and I think a big part of anything is just starting. To me, that is probably one of the things that sets us apart and makes our partnership so unique: We push each other into these areas where, on your own, you'd be like, “I don't know where to begin, so I'm not going to begin.” That's the cold-start problem; obviously, it's the hardest part of any process.

But I think with us, we're very comfortable putting ourselves in those uncomfortable situations. Also, because of how we interact with people and the relationships we've had, we're just listeners. We spent the better part of those 3 years doing 10 hours of calls a day with any investor or founder that would speak to us, just asking questions and learning through their experiences, the mistakes they made, or the things we should think about.

A lot of it began to contradict each other by the end of it, but there were definitely some patterns and things there. I think through those conversations we were like, “Wait a minute, this does feel like an extension of what being a good investor means, is an extension of what made us good in The Chainsmokers.” And it gave me a lot of confidence that we were right to get into this space.

But I think fighting the preconceived conceptions—and rightfully so, a lot of them—about being a celebrity investor was important. I’ve told this before, but on the fund announcement date, it wasn’t a positive vibe. People weren’t like, “Finally, The Chainsmokers are...” It was the opposite. People were not stoked about it at all.

To me, we saw that as—as much as it was a hill we were going to have to climb—A, the bar was clearly low, so maybe we didn’t have to do that much to be that much better. But it was also a market opportunity. It was like, “Wait a minute, people think we’re going to be fucking useless,” and that’s based on a lot of other people who have come before us and their experience with them. If we do this right, there’s a lot of white space for us to be unique and different. That’s the kind of product-market fit that we found in our music early on, and I think that gave us the confidence to start Mantis and take it really seriously.

9. From Artists To Investors

What are the things that map over most from what has worked for building The Chainsmokers to what you’re feeling early on is working as investors?

Being comfortable losing is a weird one. No one wants to lose, but I think it’s a power-law game. You build a career off of a couple of huge songs, hopefully, and then there’s lots of other great music. Only very few artists, like Drake, will constantly deliver smash songs for 10 or 15 years. Bruno Mars is probably the most notable one from a percentage basis.

You have to learn from each song, iterate and grow, and feel comfortable with that. Venture is very much the same thing. You’re hopefully going to back a couple of extraordinary companies, but most of your companies won’t go on to be super successful, and you can’t think you’re a terrible investor. Each of those opportunities paves the way for hopefully more future success to come.

I’ve been thinking a lot recently about how the relationship between an artist and a record label is basically the same as that between a founder and their investor. We’re now in the other seat, on the label side, investing in these companies.

We’ve been really fortunate to work with Columbia Disruptor for 9 years, and they’ve done an incredible job for us. But you see all the ailments of people having a bad relationship with their label, and a lot of times we try to think about how, now that we’re on the label side and we’re an investor, we can support these founders.

That’s become a brand for our fund. We want to be the utility player, because every company is different, every founder is different, and everyone’s needs are different. How can we help you? I think that’s the same for every single artist with their label. A lot of labels want to be helpful, but they just don’t know how.

All you can really do when you’re in that position is get in the game and be like, “What can I do? Be straight up. This is my area of expertise. I don’t know that person, but I know a guy who does. I’m going to try to make an email introduction for you. We don’t hire that type of employee, but I’m going to hit up these 3 recruiters.”

Just putting in the effort and showing these people that you support them. To Alex’s point, things that felt like tasks that we saw our founders needed from us, and that felt so far out of our grasp, were actually much more attainable. You realize there was a level of high-touch responsiveness that we—primarily Alex—could provide.

We don’t have to go into the history of how we built The Chainsmokers and how instrumental Alex’s thoroughness in being in touch with people has been to our success. It’s about being the partner that we see every artist wishing they had at a label.

I have a collaboration question. I told each of my kids this morning on the drive to school that they should come up with 1 question for you guys. My daughter’s question was about the song “Jungle” with Alok—

Alok.

—which is her favorite, I guess. She wanted to know how one of those works, which in this world is so common. You see multiple—

Collab, yeah.

—DJs, collaborations, et cetera. Literally, how can 2 people independently do the thing, come together, and work on a shared thing?

It’s always different. We’ve done tons of collabs, and we’ve worked with tons of writers and tons of producers. We’re always collaborating with people, and your job is to get into the room with someone with whom you hopefully have mutual respect for each other’s music. You see some kind of vision that your sounds could work together, or you have some great idea around what this song could be together. There’s some basis for you guys doing a session together, hopefully.

Your job as a great songwriter, producer, or artist is to figure out how to get on the same page as quickly as possible. That’s a fascinating thing about songwriting. You get in the room with someone, and sometimes I try to preempt this. I try to figure out where this person is at before we get together.

Alex and I are the type of people who don’t have a lot of time, and we want to make the most out of every session. Having 3 beat starts of an idea, which could just be a small piece of music, chords that feel a certain type of way, or a vocal that’s really great with the drop or the dance part not being great—and maybe that would be great if that person came and did the drop. This goes both ways.

Typically, we’re pretty specific about the lyrics. We like to write them, and “Jungle” is actually one of the only songs recently that we did not write. I don’t think I wrote anything on that topline. That’s maybe 5% of The Chainsmokers’ songs.

But Alok brought that song to us, and we were like, “Let’s make this a big-sounding donk, 140 BPM record,” which also isn’t our core sound. This was an opportunity for us to go and make something that doesn’t fit in the typical Chainsmokers bucket.

I feel like we got that topline, and it was fairly stripped back from him, and we were like, “This is cool.” Because you don’t write it, you listen to it and you’re like, “I like it.” But the fact that we didn’t write it adds this level of friction, but you put it to the side because music is very subjective in terms of how you’re feeling in that moment, on that day.

Are you frustrated? Are you in a rush? I think we played it a couple of times for different friends of ours, and everyone was like, “This is sick.” And you’re like, “I know.” You know what I mean? We love him, and obviously he’s a massive artist, especially in Brazil, which is a really important market to us. You look at these things and think, “Well, this is a guy we get along great with and who has a tremendous fan base.”

This’ll be fun. Yeah.

Yeah. What is there to lose here, really? We do like this topline. If we can produce it in a way that feels interesting and connects back to us, I think that’s where, in the past, in the few times we’ve done it, people are like, “I love this song.”

And you’re like, “What does it mean to you?” And you’re like, “You know, it sucks.” And you’re like, “It doesn’t mean any—” You know what I mean? We didn’t write this. That’s why I think we’re really not drawn to that type of thing, because we really want to be able to tell people why this song’s important, has meaning, and has purpose. It does have meaning and purpose to someone.

Yeah, it was a fun one to make, and then we finally got to play it. I think we played it at Ilha Solteira for the first time. He has a whole vibe. I’m not sure if you’ve seen him online. He looks like he’s living in 2080 stylistically, and he’s done some incredibly big shows. I think he’s, other than Anitta, one of the biggest artists in Brazil.

Yeah, he’s huge. I just went to Carnival with him. Blast in Bahia. It’s crazy. He played for 2 million people on a bus that drives through the street for 5 hours.

That’s what’s exciting about collaboration in general—

A taste of other parts of the world, yeah.

—how other people approach their art. Even the team, from a promotional standpoint: How are you selling this record? What tricks do you have up your sleeve? Who are the directors that you like to work with for music videos? It’s exciting.

With Zurb, the song “Addicted” was his second big song, and you felt like you were a small chapter in what will probably be a really long, successful career for him. But we were a big feature of that, the same way that Coldplay is for us, or Halsey is for us, and we are for them.

I think that’s a really interesting way to build a career and also give you fresh perspective on how you’re approaching your process and your music. Similarly, you sit down and you’re like, “Man, everything must be great for you.” Then you sit down with an artist, and they’re like, “Dude, I’m stressed the fuck out. I’m upset about this.” And you’re like—

Well, it looks amazing.

Yeah. So we’re all kind of—

Yeah.

—not happy, really, or stressed about stuff. And it’s nice to see that. I think that’s probably why founders love founders. I feel like in venture there’s that trope, or motif, that founders love founders, and they love venture capitalists who were founders of some sort, because you understand the process and struggle a bit more than someone who hasn’t gone through that journey.

On that specific point, you mentioned what it takes to win early on and growth-hacking your way through the promotional and early efforts that drove some of the initial success. What were those things? I'm sure this is something you're looking for in people and companies: the ability to scrape their way from nothing to something and then build on that. What were the things you were referring to a couple of times?

I think we were just really scrappy. I quit my day job. He moved down from Maine and lived on his ex-girlfriend's couch, which was probably really uncomfortable. We were just like, "This is it. We have to put all of our eggs in this basket, and that will hopefully push us to work those extra few hours every day."

Yeah, there's definitely something to that. I was $150,000 in debt. You gotta—

Yeah.

—wave the white flag.

It was a comfortable job. My boss was like, "You're what?"

He was like—

"You can come back."

"When this doesn't work out, you know..."

Yeah, which I appreciated, but I didn't want to go back. I think that was a big part of it for us. We spent a lot of time trying different things. I think that iterative process, but also being really honest about it, was important. I remember making a song that sounded very much like an Avicii song, tonally, and we were like, "This is fire." But then we were like, "Is it, though? Because it's just Avicii, but not Avicii."

At the beginning of our career, we were trying to emulate people like Zedd, Avicii, Skrillex, Calvin Harris, David Guetta, and Swedish House Mafia. There were so many exciting things happening in dance music. I was a novice producer, and you were just getting into it. We'd DJ gigs around the city, and we grew up on indie music, so we would go on this website called Hype Machine. I don't know if you were ever aware of it.

Yeah, of course.

It was like the first viral chart on the internet, and it was all music that wasn't being officially released. There were tons of dance remixes. Remixes in general were a new concept. We'd go on Hype Machine and look at the top 50 tracks, and they were all tracks that we loved. They didn't have a presence in dance music. A lot of the DJs we just mentioned were remixing Rihanna, Lady Gaga, and whatever was on pop radio at that time.

We were like, "Well, we love indie music, and we grew up on indie music and hardcore music and all this stuff that doesn't really have a presence in the dance world. These songs are already trending." Alex would find the contact information for every artist that was on this chart and send them a hilarious, personalized email. We would get a response, and in the beginning, we were just taking what we could get. No one really would respond to us. He'd give me the stems, I'd do the remix, and then he would go into the backend of Hype Machine.

He would find every writer who wrote for every blog that Hype Machine scraped music from, and he would send them a hilarious, personalized email. What we realized was that all of these kids were college students who wanted to be closer to music, and they were getting these blanket press releases that were generic. No one reads them. They were coming from a label and weren't even attached to a personal email, versus Alex being the guy who made the song and sending you the song. It's a song that you're already posting about, so it's relevant. It's a dance remix, which was the trendiest, newest sound at the time.

He wrote this really fucking funny email that everyone related to, and within 3 emails they felt like they had a personal connection with us, which they did. I think within the first year of our career, we went from 0 to 30 number ones on Hype Machine. That took us out of DJing at Pink Elephant and all the great times of the 2012 club scene in New York. We were doing colleges here and there, and that was our first step.

Eventually, that process of building up a distribution channel with all of these blogs transferred into putting out original music, and then we had to do it with radio. You do a show in San Francisco, and then you have to drive to San Jose that morning. Any DJ from every station who wants to talk to you, you'd go and form a relationship with them. Then you go to Oakland and do that there. You go to San Francisco and do San Francisco at night, and then you go do your shows.

The next day, you fly to Chicago and do the same type of thing. You get a couple of extra spins for those things, and you get everyone rooting for you. I think that's the kind of grit that we want to see with our founders. Do you have the tenacity? How badly do you want it? Sometimes people think you just put a hit song out and it becomes a hit.

I think all the things we talked about today are those little pieces that you don't see people doing. Once something is successful and you try to trace back to how it started, you're like, "They just put it out, and the whole thing worked." It's like, no, you can't look at this shit retroactively. There's a grind story behind everybody. People grind to product-market fit. Sometimes they just stumble on it, make it, and it works forever.

But usually, I'm sure if you talk to any long-lasting, successful CEO or founder, there have been moments when they're like, "Fuck, my strategy is not working anymore, and I have to go back to eating shit, making phone calls, begging people, and finessing relationships to get myself through the next hurdle."

It seems to me like so much of the ability to do that grind requires that you love some core element of the thing you're doing. You've talked about it with music all day today. If a song doesn't work, it's fine. You still love making music. You're going to make another one.

How much does that matter to you when you're talking to a founder? Maybe the broader way of asking the question is: what are the things in the first conversation with a founder that are nonnegotiable for you, that you have to see to be interested?

The Chainsmokers

I feel like Alex Porter at Redpoint said this to me in a really simple way: invest in people who are going to do this idea no matter what. Even if it fails, they're going to start it again from a different angle.

I think then the question becomes: is this a step-function better, or is this something that can potentially reshape the way that an economy, business, software, platform, or service is used? Union Square Ventures does a really good job of thinking about investing at the edge of ideas, and then those ideas hopefully become more central. Then the TAM question answers itself, because if we figure that out, it's going to be humongous.

That obsession is really important to us. Going back to the anecdote just now, we weren't just like, "Dance music's big." We were obsessed with dance music. I was downloading songs from blogs before we even learned to produce with Drew—hundreds of songs a day that I would put in a folder because I loved discovering new music.

I also threw parties everywhere here in New York City for 6, 7, 8 years. I understood how to fill a room. I understood that, as a club owner, you don't give a shit about what the DJ's playing. You just want your club to be filled and making money. So we understood the business side of how to be successful as The Chainsmokers within a venue and what was important to them.

We had all of these pieces, in the same way that it's sometimes advantageous to invest in a founder who is a specialist in that field. "Hey, I was working at Salesforce. This is a problem that I always had, and now I'm starting that company. I think it's a problem that a lot of other people have. I've experienced it firsthand, and I know the solution that I need to build."

I think that really resonates with me versus the opportunistic, "AI's hot right now. I'm just going to build an AI company," or something like that. You might have short-term success, but as anyone who's been successful will tell you, it's a very long road of getting kicked in the nuts a lot. You have to love it so much that you almost enjoy the misery of those moments and know that it's ultimately just part of the process.

We're going through this with a company of ours right now that's doing a really terrific job. They just signed their first big enterprise customer. They've spent the last 4 months building out the integration, and I really admire how intentional they've been.

This is a guy who is 100% going to bring BYOC—bring your own cloud—to the forefront. This is his life's mission. I think he's built a really compelling platform, and he has a really compelling enterprise customer. But he and his team have been like, "What do you need? What is not working? How do we make this perfect? We really want to learn through this experience with you, as our first enterprise user, how to make this successful," versus being like, "Who else wants this?"

The same was true with us: "Let's just keep doing a million remixes." We would listen to these songs and be like, "Does this meet the requirements of what we love and think is a great indie song that should get remixed?" It wasn't always, "This is the number 1." Sometimes it was the 15th song, but we were like, "This song is sick, and we need to remix this song." I think that intentionality is super important.

You really want to find someone who has that experience, who knows exactly what they need to solve for. But you really have to be careful to make sure that person—what did they do before they worked at this company? Where do they come from? Do they have a self-starter mentality? What have they done? Do they just go and work here for a long while? What did you do before this that makes me believe that you're going to be able to fuck shit up when it gets hard? Keep rethinking things. Keep having the tenacity that gets you through the hurdles that we see.

10. How Investment Strategy Evolved

What is most different between how you're investing today versus when you started Mantis? What's evolved the most in your style, your preferences, the process, and the team? On the practice of investing—from ownership and stage to the discipline that goes into making the decisions make dollars—I think that's a really important piece that comes with experience, the same way that you've been lucky to have conversations with Peter Fenton, Bill Gurley, Alfred Lin, and prolific investors. There were certain commonalities that were just like, “You're going to think this. It's not the truth, but you're going to do it anyways, and then you'll be where I am right now,” you know?

So true, yeah. And they're totally right.

Yeah, if we're lucky. The funny thing is—

If anything, I feel like I've reverted back to where I think we're the strongest investor. Our goal at Mantis is to be the sixth man on every championship team. I want to work with the best investors who are investing in the best founders, and I want to absorb the things that both those parties are doing to understand how to make better decisions and build a better firm.

That doesn't mean we're not contrarian thinkers, and we're certainly not followers, but information is so readily available everywhere right now. You do see the best companies generally gravitating toward a specific group of investors that have been winning for a long time now.

Or identifying the new ones.

Yeah, or specific individuals within those funds, more so than the brand of the fund itself. For us, you just know when there's a really interesting, exciting founder. There's a hysteria around them in a lot of ways.

I think there's that part of investing which I find myself reverting back to. Some people might call it being a signal investor, but at the same time, I think it's just this pattern where it's the space, the founder, the team, the investors, the perspective of where they came from before, and the problem they're solving now. You're just like, “I don't know if they're going to be successful, but this has all of the ingredients of a company we should be investing in.”

Then there are the founders where you're like, “I'm going out in the woods on my own a little bit here.” I don't think this idea is so radically weird that no one else is going to be interested in it, but there's going to be a lot more alchemy than science initially. Those ones are kind of like the company I just brought up, Newon, before, where I think it's really exciting as an investor.

We're testing a hypothesis right now about where we think the future is going. This guy has the right pedigree. We have some solid people around the cap table with us. But the momentum to get this ball moving is going to be a lot harder than with the other company, which is just, “Hey, if Sequoia invested, someone is going to do that, even if it's just for no reason.”

I think that's what you have to learn through experience: How do you see through all the noise and bullshit of hype versus reality during certain periods? We've really seen a lot in the last 6 years, and it really changed my perspective on when you want to throw yourself into something and when something's not real in venture.

I think there are so many stages of, “Oh, my God, we got our company marked up to Series A. We must be really good.” There's so much further for this company to go before you see any liquidity or success. It's interesting how you don't want to get caught up in that part of the puzzle where you're like, “Well, I'm creating... My IRR looks pretty solid right now.” And it's like, what's your DPI? That's really the question you need to be asking yourselves.

We're all chasing that game of, who is our customer? Is it the founders or is it our LPs? The answer is both, obviously, but you walk this tightrope where you're trying to decide where you think you should be putting the most time in. For us, when we started, we were writing $25,000–$50,000 checks into companies. That was all we could get.

It was about proving ourselves and building a reputation. A lot of those companies are doing really well. It was like squeezing into a really important, hot round with great investors and great founders. Now that we're looking for bigger allocations, we're still having success, but it's a different conversation now where you can't just be like, “Yeah, we're going to put—

Nice to have you. Yeah.

Yeah, yeah, yeah. Exactly. So it's been really interesting. Also, we have a team of people now who are extraordinary, and everyone has their own identity and perspective on how they want to invest and evaluate things.

I feel like my job has always been to try to reel them in, like how we're trying to treat the Chainsmokers now: dumbing it down, keeping it simpler rather than confusing. It's so hard to get wrapped up in the minutiae of everything, and I've talked myself out of really good deals for that reason.

It reminds me of my son's question. He himself is an aspiring music maker. I thought it was a really interesting question in the car this morning: How do they know what the next skill is that they need to improve?

Ooh, that's a really good question.

Whoa. This is definitely your kid.

Yeah.

Yeah, exactly, right? The dad is proud. I thought that was so interesting because there are so many—I'm sure there are 15 things you could get better at at any given point in time. That's where he is, too. He's trying to figure out what he's good at and what he needs to get better at, and so that's what he wants.

Well, you can tell him I'm going to be thinking about that for the rest of the week. Right now, I'm trying to think about, back to the question of dumbing things down. We always feel like we're learning new stuff, and there are new practices. Making music is a never-ending ladder. My drum teacher told me that when I was 9 years old, and it's the truest thing I've learned about my musical journey.

At this point, we're always learning new things. But with the abundance of things that we have learned, how do they not get in the way of our success? There is something beautiful about a young artist who has their whole life to make their first album. There's a level of—they're just a little bit naive. Because of that, they're not overthinking shit.

Part of the thing is, when I make records that sound like this, it feels like me, and it makes me feel some type of way. When I hear it, that should be the visual. This artist is really cool. Maybe they'll do my cover art. We're just making music at the end of the day.

It's like heart and soul over mind.

Yeah, exactly, exactly. I think we're both trying to reconnect with that as much as possible. I mean, The Innovator's Dilemma, too, once you've reached this point and you're like, “Which way do I go? Do I keep trying to ride the wave of this thing that's kind of moved past me but I can hang onto it, or do you just stay steadfast in the thing that is inherently you?”

There's not really a right answer. There are a bunch of success stories for either side. But me personally, I'm trying not to let the lessons that I've learned—

Get in the way. Yeah.

Yeah.

It's because we're weird. I feel like I was thinking while Drew was talking about that, and in venture, I was googling words like TAM on my phone in my first month of coming into venture. I was like, “I don't know what—

I think we can say that now. It's okay.

—what are these fucking acronyms?”

Yeah, yeah. Ooh, the TAM seems—

—a big TAM's good, right? I was obsessed with acronyms in here.

Yeah, yeah. And I'm just like, “Get me in a room.”

And I feel like I'm constantly asking stupid questions. Honestly, I really am grateful to a lot of the people we've had a chance to work with and interact with. We approached this space with a lot of respect, and everyone, I think, hopefully acknowledges that now.

There are no dumb questions. I'm always like, “Explain this to me like a golden retriever.” It's kind of something I say a lot. As we've gone deeper into the space, and obviously engineering is a huge part of any tech platform, I was like, “I want to try to learn how to code a little bit,” because I want to have at least a semblance of not just respect, but understanding when I'm discussing these things—the different processes and stuff.

And then now vibe coding, Cursor, and things like that exist, and you're like, “Okay, so I don't need to learn coding anymore.” Now it's back to taste, which I feel like I'm pretty good at. But it's an interesting process.

Even in music, I played guitar growing up. I didn't carry on very long. I remember a few years into our career, I was like, “What if I have a kid one day, and my kid's like, ‘Play ‘Closer’ for me’?” And I'm like, “Oh, I can't.” That's so lame. So I was like, “I'm going to learn piano.” I took 2-hour lessons of piano 5 days a week, and I still do to this day.

The purpose was to be like, “I can’t claim to be a musician if I can’t play our music.” Ridiculous. So I figured that the process of practicing and learning it opened up a whole understanding of how to communicate my ideas to Drew as we’re discussing music, and it really enabled me to be a much more critical, thoughtful musician in general.

But I totally agree with Drew, because at the end of the day, there’s an ignorance-is-bliss thing to a lot of this, where you can talk yourself out of any situation. Part of the investor’s role is to be like, “How many miracles am I comfortable with for me to back this? Is 5 miracles too much, or is it 2 or 1 for things to go right?” You have to look at it through that lens and think: imagine that world.

I feel like I’m probably a little bit more like this in terms of my angel portfolio stuff, where I’m just like, “Fuck it. Let’s do it.” We invested in this company, Radiant Nuclear. I remember talking to them on the first call, and it was like—

“We can’t do this, but fuck it.”

Yeah. And we’re like, “But if they do this and we didn’t do it, they’d be really pissed off.” A lot of it’s like that sort of stuff, even though it sounds really stupid. I mean—

Outside the fund—

Yeah, yeah.

Inside the fund, we have a process, I swear.

Doug has as good a pedigree, and Bob, as anyone to tackle this problem. It was just like, the timelines were like, “And then in 7 years, we’ll be able to test the first one.” And you’re like, “7 years, we’ll test it?” And you’re like, “All right. Let’s do it.” You know what I mean?

Now they’re absolutely crushing it. It’s obviously Monday-morning quarterbacking, but it was funny when you look at those things, when you’re just like, “We could have called Blake and Chad and had deep conversations with our friends who have experience in this space,” and they all would’ve probably been like, “Don’t fucking do this.”

What I was saying the other day, I don’t know if we would’ve invested in Poppy again, because we just don’t—we do stay away from CPG. That was a 30X, but again, completely YOLO. There is, again, some level of naivety where you’re just like, you’ve got to have faith. Venture favors optimism, and I hope we would’ve identified that Poppy had 2 incredible founders, but maybe not. Maybe it was just like, “Eh, another soda.”

I was talking to Alex once about some company in the portfolio. It wasn’t over Zoom or something; it was live, and he started rattling off the KPIs of the company. I was like, “Wait, you know the company’s KPIs?” And then he was able to do that for a bizarre number of the companies.

Yeah.

I asked him about it, and he said, “Yeah, no, I know all the numbers for all the companies,” which is surprising, back to your point about when you announced a venture fund, everyone’s like, “Oh, these jackoffs have a venture fund now.”

Yeah, we’re like, “We’ve got to know all the numbers.”

Yeah, exactly. But it’s an amazing way that you bridged the 2 worlds, and obviously it’s early days. Like you said, you’d probably do both these things forever. It’s such an amazing history for me to hear. I’ve loved doing it.

When I do these, I ask the same traditional closing question of everyone. I get to do it twice today. What is the kindest thing that anyone’s ever done for each of you?

It’s so funny. First of all, I obviously know that this is your final question, and I thought about this on my red-eye flight here for so long. I was like, “Nobody’s done any kind shit for me.” That’s the conclusion. I was like, “I don’t want to single out anyone in particular.”

I love how you were going to—

Yeah.

You were going to say there’s a caveat of, “I did think about this for 10 hours today.”

Yeah. The truth is, people aren’t that kind to me, at least in the ways that I’ve heard other people think through these things. Obviously, I have extraordinary friends and people in my life.

But I guess if I had to, I was trying to think of a clever way to answer this, because, funny enough, I think it was an unkind thing. I had this homeroom advisor in 6th grade named Mrs. Park. I think she liked me, but I think she also understood that I was at this really interesting crossroads in my life.

My dad had just passed away. I was 12 years old, super young, impressionable age as a young boy. I had a lot of friends, but I was also not a banging student by any stretch, and she was very clear. She was like, “This is the most important moment in your life, and you will probably not even recognize it until it’s too late,” either in a positive or good way.

She was like, “You are fully at a crossroads right now. One path will lead you down a road of success, where you’ll use this experience and pain and everything that comes with it to motivate you through life in a really positive way, or you will just become a total fuck-up, and everything will be derailed, and you’ll go on to accomplish nothing.”

Obviously, as a six-year-old, you’re like, “What?” You’re like, “Lady, it’s 8:15 in the morning. I’m going through some shit.” But it actually did really stick with me in a lot of ways.

From that moment forward, as I thought about the different decisions I made in my life, whether consequential or consequential, I would’ve had this thing in the back of my mind: “Which path is this leading me towards?” It really motivated me to get my shit together, become a good human and a really good student, and push myself.

Ironically, I think it’s funny when someone can offer you advice like that, and I think maybe too often in today’s day and age, people are offering advice like this all the time. People just don’t listen anymore. You acknowledge it, but you don’t really think about fundamentally what it means.

She was probably in her 60s, and this woman had obviously advised and taught homeroom to hundreds and hundreds of kids. I’m probably not even the first kid she’s had this experience with. I’m so grateful that she said that.

Did you feel like, when your dad passed away at a young age, it snapped you awake in some way?

I love my mom. She’s still around. She’s an amazing woman. And I had a really tough upbringing. They fought relentlessly. Insane fights are probably why I painted so much, because I just didn’t want to leave my room and interact and get in the mix of all that.

My dad passed away in the middle of the divorce, so it was a really dark period. To the point of what I just said, I had a lot of friends who came to my side and supported me then. More than anything, I think as you get older, you kind of distort memories.

Now when I look back on things, I have a completely different perspective than I did when I was a 13-year-old about who my dad was, how he treated my mom, how she treated him, and what my relationship was with him, or his with my sister.

After that moment, it was just kind of like, I have my family, but I’m really on my own to be my own man. It’s a weird experience not having grown up at all with anyone to be like, “Dad, look at this,” or, “Am I doing this right?” Or having the dad who’s like, “Hey, let me help you out with this or do that.”

So it’s been probably one of the strangely better things that has ever happened to me. But I’ve also never seen a functional relationship in my life, which is probably why I’m still single.

What’s your answer for the kindest thing?

The one that’s coming up for me is my mom buying me a drum kit when I was 5 years old. You know what it’s like to buy a drum kit for a 5-year-old kid in a 130-year-old farmhouse in Maine? You’re listening to me trying to learn, listening to me just smash drums, which I played all the way until I went to college.

My mom would sit in the kitchen doing grading papers and doing stuff she had to do for work or making dinner, just listening to it, and she loved it. She watched my whole musical journey and always supported it. But yeah, crazy move for a parent. Just tortured herself. She really loved it.

I’ve always been fascinated with business and with music. When I wanted to go to college for business, she really discouraged me from choosing a path that didn’t include music in some way, and it ended up that way. So thanks, Mom.

Well, your guys’ story is one of my favorites at this intersection of 2 of my favorite things, music and business. I’m so excited by the next chapter of what it might become and what it might look like, and I can’t wait to watch. Thanks for doing this with me.

Hell yeah. This is an honor.

Thanks for having us. Yeah.