The Chainsmokers - Music & Markets - [Invest Like the Best, EP.430]
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Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus Review along with all of our podcasts at joincolossus.com.

Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast.

To learn more, visit psum.vc. My guests today are Alex Paul and Drew Taggart. You might know them as the Chainsmokers. We explore their fascinating evolution from scrappy DJs to global superstars to serious venture capitalists with their fund Mantis. Drew and Alex share how the same high-touch relationship-driven approach that built their music empire now defines their investment philosophy. Their frameworks for backing founders mirrors their artistic approach.

They invest in obsessive individuals who will pursue their visions regardless of external validation, much as they've remained authentic to their sound despite industry pressures. We discuss parallels between creative iteration in music and venture investing, particularly around managing failure, maintaining intentionality in an age of abundance, and the importance of taste as a differentiating factor.

Please enjoy this fascinating discussion with the Chainsmokers, Alex Paul and Drew Taggart. How do you feel about models training on your content? I don't care. Yeah, I figured. Yeah. Because it's like a cat out of the bag. We don't care about our music either. I ask, is there so much controversy around music and art? Tripp Adler described a pretty successful company and he's starting something new. And he's like, you know, one of those founders where you're like, normally you'd be

you'd be like this is a really successful second time founder starting something in ai now and i spoke to him he was like yeah it's basically like licensing copyright rights that we find a way to protect and then get people paid and i was just like

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 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 is 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 that they would have created Spotify, 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 kind of embrace it and figure out how to like harness it when it comes out the other side one person will get sued yeah like soon these models are going to train on this and they are 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 because we're

Is there anything you do fear? Loaded question that I want to answer correctly. My first instinct is to say no, because I feel specifically us, we're DJs. 15 years ago, the DJ producer, and then still to this day, you've seen the memes about they're just pressing play or all of their music is software. And I remember the whole first wave of that democratization of like,

music software being available and accessible and the barriers to entry coming down and all of us being able to make stuff that we weren't able to create before we gave unless we had like access to a crazy studio i remember everyone saying that that wasn't real music i mean here we are like 15 years later us and all our friends have had massive songs that have been culturally impactful that play huge shows that tons of people come and have a good time too and listen to music that make them feel euphoria or sadness or something amazing it's like the still

The same impact of music has happened 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 be able to express themselves with this medium. I would argue this is 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 probably went

Jaws, like Ableton and Fruity Loops and all these things came into existence. Now on Spotify, when we like started, there was 10,000 songs uploaded every Friday. Now there's like 190,000 or something like that.

That's not that long. Yeah, yeah. And I imagine that in a few years, it'll be a million. And that will definitely have an impact about how hard it is to break through, or maybe the importance of having a brand or an identity or standing for something will mean something even more. I just watched this Brian Eno interview with Zane Lowe, and he was just talking about AI and is it scary to him and this? And 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 actually these tools make people like you, they're 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, and not just us who are established, we have our way of making music. And then I think what it does is kind of the opposite. It's like, it just 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 being able to express themselves that way. And that's awesome. And perform it. And you can kind of look at the DJ as like a microcosm blip on the radar of a version of more accessibility, what that gets you. But you look at how big the scene is and how fun the scene is now. It's like, how is that a bad thing? How does it feel the most different now creating a marginal new song versus when you started?

What is the most felt creative process difference? I would say that's less technological. It's more my own brain that I'm still trying to reckon with. Songwriting is 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 that time. But as a massive music fan, I'm trying to like

make something that respects all of the things that have inspired me my entire life, it still makes me feel like, wow, this is my statement now. And you'd think that we'd have a formula now on 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. And 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. I think that's quite a cool... 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 what Chainsmokers music is, is what we both agree on is like fun and tasteful and we want to play out. But it's not just me or just Alex. It's like a reflection of our friendship.

and what we've gotten super stoked on listening to as music fans over the past 20 years. 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? Every song I feel like is its own. You told me about No Shade of Pity one time and the process behind that, I thought it was so cool. That's a day like today. Yeah. Probably was almost a year to this day.

That was like an interesting song, especially obviously for me, I'd just gone through a breakup or something. And we were like pulling a lot of inspiration from that. Just generally speaking, you know, like you kind of go into the studio and you're like, what interesting concepts or things that are happening in our lives talk about or expand on or just talk about and then like a lyric or something happens. And we were like thinking about New York City, which is obviously where we started on a day like this, where it's like 75, sunny out.

winter's over, you know what I mean? And it's time to like be feral and enjoy the city. 60 degrees, but everyone's got their shirts off and the park pale as one of the best days of the year. Yeah. And like all those like bars, fun restaurants with the sidewalk space are just overflowing into the streets. And it's like hard to find something that isn't fun. And so it was kind of like using that as a metaphor for like coming out of a relationship. But then it's like, there's so many decisions and things you have to talk about or

How long do we want the verses to be? Is it too wordy? Is it too dancey? Is it not dancey? That feeling of it, I wouldn't say that song was like 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 nine months ago." I think that's what's cool about music is everyone has these moments with songs and I haven't still with like older songs from like the 60s or 70s or 80s to like new songs that come 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. So,

The songs like that, it's funny because he's like, we're talking about my breakup, but then we don't want to just make it about my breakup. We want to make something that's like an experience that everyone can kind of relate to. And then he's figuring out what clever ways to like fit this story into a visceral scene that relates to both of us, which is like a New York spring day. And I'm trying to

keep feeding the song with personal sad anecdotes. It's a funny process. Yeah. And then 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? But like at the end of the day,

I think 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, thank you. I think that's a big part of what we've been re-exploring in the last year is dialing it back to the Chainsmokers fans and Chainsmokers sound because I think going back to the AI stuff, there's 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 almost hurts the experience versus helps it sometimes.

There's no barriers to entry or less and less every day. For music creation, what are we left with? The same way it's like I could play a guitar the same way and sing a song that some other guy can, but it might just hit different when that other guy does it or that girl does it based on their background or the way that they're holding it or the way that their voice inflects with that chord. There's so much different 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? And 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. I thought that was a really interesting point. And to Alex is talking about the success or lack thereof of a song like No Shaded Pity. How do you define success in a age of abundance of art? How do you define success with us where we have...

a bunch of songs 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? Because

When that person does it, it will be them doing it and it'll be at a different time and they'll look different and it will feel different. And so when you think about AI, you can't be scared of it because it's just going to hit different for better or for worse at some point. We just got to focus on being the most chain smokers as 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 like optimized for various algorithms. Exactly. What does that mean for art in general when anyone can do it and it's successful? Like, are we in a golden age of creation or is it different? We work with Ars O'Tan and play a song and it's like, oh, this is like a 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...

hit. So I think when you have an artist like Fred again or someone come along, I think it has 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

all his various sets. As fellow musicians in a similar category, what is it? How would you describe what he's done effectively to somebody else? Because it feels like the right example of this originality that we kind of all want more of. Fred's a great example. I mean, there's a lot of standout artists of the past three or four years. I mean, if you look at Adochi or Charlie XCX, 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 three artists in particular is they have songs that go viral, but it's not traditional pop hits like 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 a time.

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

That's what's so cool. And I think who kind of wraps up the whole point about if everyone can be creative, it's like, what else can you give them? You need to bring people into something more than just music. And I think that's something we struggle with a lot where it's like, we're hyper focused on music and like we create this thing. We're like, I crushed it this time. This is going to be it. But like the world building of the whole thing is something that doesn't come naturally to every artist, which I think just be more and more important. And as a fan, I want world building.

I want to participate. I think album is God. I want to sit in your world for 45 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, like light things being ephemeral. Make it fast, consume it fast, forget it fast. Something like the album approach or something that takes a long time, that takes a lot of time, heart, effort, blood, sweat, tears.

is what we need more of. Such a good point. I think even like the commonality between like a Fred and a Dochi and a Charlie. These are people that have been grinding Dochi'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 X has been writing songs for hit artists for like 15 years. You know what I mean? Just in the background waiting, almost like fine tuning everything, waiting for this moment. And Fred similarly is

literally a musical savant, but has been writing for Ed Sheeran and huge songwriters in the background. I mean, his story is equally as impressive. And then you have that compared to like the TikTok artists that are in COVID that made a viral 15 seconds of a song, label signed them, and then they're like, what did we just buy? I don't know what this is. Totally. And not to say that those artists can't break out and do great things. Like Addison Rae, I think is doing a really great job of building a really amazing career right now.

I don't know Addison and haven't worked with her, but everything I hear about our songwriter friends that are in the studio, that she gets the world building piece of this. Yeah, you can tell. What does world building mean? Just like define what that means. Defining an aesthetic and a mood and an attitude that you can participate in when you listen to the music. That's how I would see it. Some people do this super thought out, probably have

boards and plans and branding and insane creative direction. I think some people are just are themselves. They just kind of build it in here. Travis Scott is rage.

But I would say like Zach Bryan, as far as lack of branding goes, Zach Bryan is Zach Bryan. When you go see a show, when you hear it and the amount of songs he puts out, 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. And 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 and it stops the whole thing. And his reaction to it, he like instantly smiles and is happy about it and then somehow uses it, weaves it into the music somehow. It was like one of these moments where I thought, oh my God. - I know the moment you're talking about, it's adorable. - It's amazing. - Guy's so embarrassed that he does it and his reaction. - And then they start dancing together. - 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, creating stuff. We both are passionate about people that build companies. We'll talk about that plenty today too. But this getting in touch with the itch is actually a non-trivial 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 that want to find their itch? I think most people don't even ever 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 like a viable career path in my mind. For me, I was always like a very visual, creative type person. I was obsessed with Nike commercials back in like the 90s and 2000s. I would actually like record them onto like a VHS tape because I was so inspired by like the

like the feeling you got after you watch them. And like visually the storytelling and obviously the personas that they had involved was super cool. I was a huge NBA fan as a kid. I think most kids are. And I started painting a lot when I was younger. And I think it was like trying to like find a language. What is that language that I can speak that conveys these feelings that I get from watching these Nike commercials? As you get older, my dad was an art dealer and

And he was fairly successful with it before he passed away. And 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. And I kind of knew on some level it was an out-hustle, out-work mentality of things. I wouldn't say 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 my dad was in it. And so it kind of felt like that probably like growing up on a farm where you're just like, I'm going to be a farmer. It's what I know. And you go out into the world and experience different things and different opportunities. And I think the itch for me is about where your passions lie. What do you actually like spending your time doing? And what do you find yourself being drawn to?

I think New York, going to school here, was the perfect place for someone like my ADHD because you're getting pulled into so many different directions of 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. And I always found that piece super inspiring. But I don't know, it's a tough thing because the itch to me is, I'd say it was something that was far away in the distance that I could see but didn't actually...

have the ability to do anything and then when we finally started obviously really building the chain smokers and things started to work it was like oh my god this is the feeling that i've been like seeking out this whole time and i've just been applying maximum pressure grasping at different opportunities so i think that's why you meet these young founders not necessarily being like i've always wanted to build this product is great mentality of course someone that's like worldly i think

I think offers just a more interesting perspective to me about like how they go about being successful and whatever it is they're passionate about, because it's not just a straight line anymore. I think there's so many things that shape a great founder or shape a great company. I think it's more important to have that paranoia deep within you that forces you to like live in fear your whole life or something that like allows you to be successful. So it's tough for me because the itch

It was just like a survival thing or like proving people wrong more than, "Oh, I just want to do things." I stopped painting when I was like 15 or something. It wasn't like a sad day for me. I'm moving on. Yeah, I'm out of paint. Like, I just don't really want to do this anymore. It's more of a mentality thing of how you like search.

But it was a feeling. You were chasing, there was some vector there that you could...

Half my friends have jobs at great banks now. And again, I'm like a nightlife promoter. You know, it sucks. Also, like in high school, I mean, I wasn't like a loser in high school, but I definitely wasn't like the super popular kid. Yeah. No offense to any of my friends listening, but some of y'all peaked in ninth grade. And I'm just glad that wasn't me.

To tweak the question slightly, because I want to hear the answer for you too. I'm curious how the notion of happiness versus dissatisfaction versus paranoia figures into your head. I'm trying to figure that out with my therapist now. I grew up in Maine and I later in life, now I'm very thankful to have grown up in Maine. You know, I grew up in a small, pretty liberal society that everyone kind of did everything. Everyone was small town. Everyone was in theater. Everyone that also played varsity sports.

It was super studious and all that stuff. So it was really like 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, like loves science.

learning and seeing more things and I always wanted that and there wasn't a lot of opportunity to leave Maine as 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 then as soon as I kind of developed my own musical stage I was very obsessed with what I hadn't heard before and I think that's what eventually brought me to dance music is because I had this transformative experience. I

when I was 16 and I did an exchange program in Argentina and I heard the beginning of David Guetta and Daft Punk for the first time and this artist Trenton Muller who I fell in love with and 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. And it's quite torturous, to be honest, because once you've done something, you're like, yeah, okay, that's happened. And how do you innovate? It's like innovator's dilemma. Like, how do I continue to create something that my fans really feel connected to and that I feel connected to and like really respects the core identity that is me and the music and this thing that I've built?

That's also innovative that feels like it's still me and it gets me excited to go up and play new songs and my fans feel like it's fresh. And I think it's a pretty torturous pursuit that drives me crazy a lot of 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. And I think for a while we were kind of like, all right, we don't need to hear this.

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, and you're like, oh my God, they're the only person that does that sound. And all these fans are just amassing and telling their friends and all this thing. You look at someone like the Grateful Dead, and you look like, what's that 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

has great ethos. And I think that's really interesting to think about as we're like, what does the rest of chain smokers look like for us? How do you think about like a tech idea, like product market fit for you going forward? Like obviously you've had it in the past, measured by streams or popularity or something. But if you think about it prospectively and you were to like 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, six months ago? And when I hear that song, I'm like, fuck yeah. I did the goddamn thing on that. From a writing production as a pop kid, I'm like, Kim Petras, 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 that didn't have the essence of Alex and I in it enough. 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. It's like, 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 for like 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 like 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 Turnstyle. They're a hardcore band from Baltimore. It just reminds me of so much stuff that I grew up on, but feels fresh and repackaged. And 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 kind of been like, we're making tunes, we're going to do all the shows we can. And that inherently became us.

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

and a nice interaction with them like 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 like 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. I mean, we love making music. We love starting businesses. We love helping other businesses. The first thing that we kind of 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. And we're hyper curious and

And it's, I think, very gratifying for us to be able to pull people into our world. Personally, it makes me really happy when you can include someone that's not typically included in a lot of their either social dynamic or work setting or whatever. When they come to our show or to hang out with us backstage, if you can make 30 to 90 seconds and really listen to someone and look them in the eye and offer them a drink in your environment or...

Anything there, I mean, that's the little like bits of magic that you get to pass around and hopefully they keep passing on to somebody else. And I think that's kind of the soul of what we do. Do that for 13 years. 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 a nice, I like, I think we like being those guys. I was, like I said earlier, not most popular kid in high school, but not the worst either. Not the worst. But I...

But I think that's like my whole attitude was like, I was just friends with everybody. Nice person, varsity basketball team I'd hung out with to like the art kids later. And ironically was school president. And I never thought that was ever like a goal. Everyone likes you. Yeah. Like you should obviously do this. Like everyone would totally vote. You're friends with everybody. And I feel like that was like such an interesting experience in life. There

There wasn't like, we don't talk to that person because they're like this. Because it's like, I always felt plenty of times I wasn't cool or whatever. And it meant so much to me when someone like came out of their way to like make you feel acknowledged or comfortable in something. And I felt like if you could continue to challenge myself to like be that person in all sorts of different scenarios. And it wasn't like with this long-term goal that's like Billy Madison when he's like calls Steve Buscemi and he apologizes and then Steve Buscemi saves him later. Yeah.

No. And he's like, thank God I called that guy. It's not like 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, like a huge company or whatever. It's like, just come and be a part of the world. And like, if you bring great energy, like that's super interesting and exciting to me. And I think we feed off of that experience that we give people like Drew said, and we play Vegas hundreds and hundreds of times. And

People are like, how are you still doing this? And it's like, because every weekend, there's like a new group of people coming, experiencing this for the first time. And they're so excited. And you sometimes forget how lucky you are to be in that position. And also like the kindness that people showed us in the past from like radio stations that supported us early on when they didn't need to. Life is so long. And I think if you take a second to listen, I've had this interest, I think, Chewang fan

I'm pronouncing his name right, posted this interesting blog post from this wedding photographer who's been like shooting weddings for 30 years or something. It was like 21 insights that she's noticed about briding grooms and different people that attend weddings and the personalities that they have. Some of them felt a bit over the top, but like a lot of them were like, that's super interesting observation. And I think if you like 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 like put yourself in a position where people enjoy being around you and feels seen when you're with them, I think that's amazing. And it's something we definitely struggle with as you get busier too. I'm taking calls in like August right now. And it kills my soul to be like, I would love to speak to you in September. So it's just getting older and shit. Yeah.

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

It's evolving as we're trying to simplify it as much as possible. I mean that in the ways of like just 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, I mean, we were so curious and we wanted to do for all the reasons we've told you about us in our past, whatever. Wanted to try all these different things, said yes to way too much.

And I think that through doing that, we found the things that resonate with our core. Making the music that we make is still the number one. Our last two things will be venture and music. And we genuinely are in love with both of those things. And I think sometimes I regret having a situation where we have both. But if I had to pick one, I don't know which one I would pick.

And I think just trying to build processes through both of them, both of those businesses that like we can do them. And I don't want to say effortless ways, but the ones 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? What's our striving to evolve now? When we raise money for our fund, they get asked that question a lot. And

I always say that Chainsmokers is the sun in our solar system because it's like everything circles around that. And if it's a really strong sun, it shines more light and creates more abundance and opportunity across Mantis and whatever, Tequila Company and other things. Whereas like, I don't know if...

a strong mantis saves our music career. You know what I mean? But what separated us, differentiated us early on and kind of to Drew's point is what we're trying to turn back the hands of time now is that like we did run Chainsmokers like a business. As much as we obviously care so deeply about the music and the creative aspect of it, but it was also like this is a really unique

opportunity that we want to make sure we're taking full advantage of. And whether that was doing too many things, playing too many shows or whatever, really control the business. I mean, 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, it set us up for success in a lot of ways. I mean, COVID for some artists was pretty devastating. Whereas for us, we were like, let's raise a fund.

Yeah, yeah, great. And so I think the problem with that, though, was that we became the CEOs of Chainsmokers. And I think this relates to like probably a lot of successful founders journeys. I was talking to the founder of the company who's crushing it right now. He was like, all I do is HR. He's like, I don't build shit anymore. All I do is hire people. And it fucking sucks. And I was like, kind of know what you're going through. We're on so many calls about internal politics.

I think we're actually making really solid strides to fix that, to go back to being chain smokers instead of the CEOs of the chain smokers. There's so many parallels between investing 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, how to get out of their own way. And then when it's you, it's like...

This is how it's always done it. I came up with this. You have all the shit in the way. And so it's been a great mirror investing in these other businesses and then kind of looking at our own and being like, how are we hitting these roadblocks or bottlenecks in our own situation? But that key one being like, be the founder, the CTO or whatever you're like best at. Like 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 that comes to me. Don't be the CEO.

Can you tell the Mantis origin story? So 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, creating a venture tech fund. We've done a plethora of businesses. We're very avid investors, both privately and publicly. The tech world in just public markets, in real estate. And I think...

At the time of our rise to, I guess, cultural zeitgeist time, which was probably 2016 to 2015 to probably 2018, we met a lot of the class of founders that was Drew Houston from Dropbox, Brian Chesky from Airbnb, Michael Seibel, who was at YC at the time. And these guys were really amazing and opened our eyes to what private tech investing looked like. We didn't really know what venture capital was at the time. And we saw...

through their eyes. Like a lot of them, it was simple. It was like, you guys can invest in like all of these brands based on like who you are. People want cool people on the cap table and started with something as simple as that idea. And then as we got to befriend these people and get an insight into how they ran their businesses, we realized we kind of had more in common with them than we did with most other musicians.

We growth hacked our first promotional platform, crowdsourced our first tour. We've always been doing the most to kind of try and get our music out there. And when we work with a lot of other artists, we found the majority of them are like pretty disorganized and we're just in pursuit in a different way than we were. And I think there was some kind of sense of familiarity and 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 discussions.

Just yourselves. Ourselves, deal by deal, whatever, conceptualized the idea to start the fund. And then like Alex said, when COVID happened, we were kind of putting it together in 2019 before COVID happened. But I don't know what would have happened if COVID didn't happen 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. Yeah.

Naturally, entertainer 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, social creator economy type stuff. And initially for us, that was like, cool. I remember my businessman or Josh was like, basically you invest and you just hopefully make a bunch of passive income. Oh, how sick is that? You know what I mean? He also prefaces like, you probably will lose your money, but like you could. Which we did a lot of times. Yeah.

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 five days from now. As we began to connect with these founders, and I remember getting your 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?" And then it was like these little ways that we were able to make a real difference in these companies.

And then to Drew's point, the people like Brian Chesky and Steve Huffman and the Kahn brothers were like, why are you investing in fucking water companies? Well, water companies are doing quite well. Yeah, yeah, yeah, yeah. There's a few good ones. And we've made some decisions, but there's a whole world of opportunity investing out there into like really exciting companies. And I remember like doing the Uber Series S. I thought I was like in early. I think I've made like $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 Poppy. And Poppy, 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 and forward thinking and messaging.

And then as it relates to marketing and distribution, whereas I think a lot of like CPG is just distribution and kind of marketing. Tech investing, you just get a front seat view of the future. It's the most stimulating show you could watch. And it favors the optimistic, which we're artists. We like to dream about things that don't exist yet and building a world. And I think we didn't know it would be a lot of cybersecurity platforms, but now we got to secure all those things.

Kind of reminds me of being in your assembly in middle school, high school, where every now and again they would bring in a professional. They would speak about their career to the audience for like an hour. And you'd be like, that guy actually did this shit. This is really interesting and exciting to me to learn from. Versus like, if it's like a teacher, that'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 like a founder that'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 five or six hours a day learning from an experienced person in a technologically exciting area.

Obviously, the evolution of Mantis has changed. I don't want to say changed dramatically, it just evolved a lot. I mean, I remember on our first partner call, they were like, so how much are we going to raise? And someone was like, 100 million. And I was like, is that a lot? Kind of 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 start doing it. That to me is probably one of the things that sets us apart and makes our partnership so unique is that we push each other into these

areas that you're like, maybe on your own, you'd be like, I don't know where to begin. So I'm not going to begin, you know, and that's the cold start problem, obviously, is the hardest part of any process. But I think with us, we're very comfortable putting ourselves in those uncomfortable situations. But also, because of how we interact with people and the relationships we've had, we're just listeners, you know, and we spent the better part of those three years doing 10 hours of calls a day with any investor or founder that would speak to us and just asking questions and like learning

through their experiences, mistakes they made or the things we should think about. And a lot of it began to contradict each other by the end of it. But there were definitely some patterns and things there. And 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 chain smokers. 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 investors. And I've told this before, but it's like on fund announced day, it wasn't a positive vibe. But you know, like people weren't like, finally, chain smokers or it was the opposite. People were not stoked about it at all. To me, we saw that as much as it was like a hill we were going to have to climb. Hey, the bar was clearly low. So it was like, maybe we don't have to do that much to be that much better. But it was also like a market opportunity. It was like, wait a minute,

People think we're going to be fucking useless and that this is based on a lot of other people that have come before us and their experience with them. If we do this right, it'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 that I think gave us the confidence to start Mantis and take it really seriously. What are the things that most map over from what has worked for building Chainsmokers into where 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 hopefully other lots of great music, but only very few artists like a Drake will just constantly deliver smash songs for 10, 15 years. Or Bruno Mars, probably the most notable one from a percentage basis.

You have to learn from each song and iterate and grow and feel comfortable with that. And it's like venture is very much the same thing. You're going to hopefully 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 paved the way for hopefully more future success comes.

I've been thinking a lot recently about how the relationship between an artist and a record label is basically the same as a founder and their investor. And I think about how we are now in the other seat and we are now on the label side investing in these companies. I think how I think about, we've been really fortunate to work with, we've been at Columbia Disruptor for nine years now.

And they've done an incredible job for us. But you see all the ailments of people like having a bad relationship with their label. And I think a lot of times we try to think about how to, okay, cool. Now we're on the label side. We are an investor. What can we do to support these founders? And that's become a brand for our fund is like, we want to be the utility player because every company is different. Every founder is different. Everyone's needs are different. How can we help you? And I think that's the same for every single artist with their label where

It's a lot of art labels that want to be helpful, but they just don't know how. And 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 expertise. I don't know that person, but I know a guy who does. I'm going to try to make an email intro for you. Like we don't hire that type of employee, but I'm going to hit up these three recruiters, just putting in the effort and showing these people that you support them. And to Alex's point,

Things that felt like tasks that we saw our founders need from us that felt so far out of our graphs were actually much more attainable. You realize there was a level of high touch responsiveness that us, primarily Alex, I mean, 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. But just being the partner that like 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 come up with one question for you guys. My daughter's question was about the song Jungle with ALOC, which is her favorite, I guess. She wanted to know how one of those works, which in this world is so common, like you see multiple DJs collaboration, etc.

Literally how two people independently can do the thing, come together to work on a shared thing. I mean, it's always different. And we've done tons of collabs. We've worked with tons of writers, tons of producers. We're kind of always collaborating with people. And it's always your job is to get into the room with this person that hopefully you 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 the song could be together, whatever. There's some basis for you guys doing a session together, hopefully. Your job as like a great songwriter, producer, just artist is like, how do we get on the same page as quickly as possible?

which is kind of a fascinating thing about songwriting that is like, you get in the room with someone and sometimes I try to preempt this. Like I try to figure out where this person is at before we get together. I think Alex and I just being the type of people we are, like we don't have a lot of time and we want to make the most out of every session. Having three beat starts of an idea, which could just be like a small piece of music

chords that feel a certain type of way or a vocal that's really great of the drop or the dance parts like not great and maybe that would be great if that person came and did the drop and this goes both ways typically we're pretty specific about the lyrics we like to write them and jungle actually is one of the only songs recently that we did not write i don't think i wrote anything on that top line of that song that's maybe like

five percent of Chainsmokers songs but a lock brought that song to us and we like let's make this like a big sounding donk 140 BPM record which also doesn't sound is an hardcore sound it's like an opportunity for us to go and make something that doesn't fit in the typical Chainsmokers bucket so I feel like we got that top line it was fairly stripped back from him and we were like this is cool because you don't write you

you listen to it and you're like, I like it. But the fact that we didn't write it kind of adds this level of friction, but you kind of put it to the side because like music is very subjective in terms of how you're feeling in that moment that day. Are you frustrated? Are you in a rush? And I think we like played it a couple of times for like different friends of ours. And everyone was like, this is set. And you're like, I,

And we love him. And obviously, he's a massive artist, especially in Brazil, which is a really important mark to us. And you look at these things being like, well, this is a guy we get along great with, has a tremendous fan base. This will be fun. Yeah. What is there to lose here, really? We do like this top line. If we can produce it in a way that feels interesting and connects back to us, I think that's where in the past and the few times we've done it.

People are like, "I love this song." You're like, "What does it mean to you?" You're like, "You know it's not just sucks." You're like, "It doesn't mean anything. 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 is important, has meaning and purpose. It does have meaning and purpose to someone. But yeah, it was a fun one to make and then getting to finally get to play it. I think we played it at Il Sun Miik 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 one of the, other than Anitta, the most... Yeah, he's huge. I just went to Carnival with him, a blast in Bahia. It was crazy. He played for two million people on a bus that drives through the street for five hours.

That's what is exciting about collaboration, I think, in general. A taste of other parts of the world. Yeah.

you felt like you were a small chapter and will probably be a really long, successful career for him. But it was like, we're a big feature of that. The same way that Coldplay is for us or Halsey is for us and we are for them. And I think that's a really interesting way to build a career and also give you fresh perspective about how you're approaching your process and your music. Similarly,

You sit down and you're like, man, everything must be great for you. And it's like, you sit down with an artist, like, dude, I'm stressed the fuck out. Like, I'm upset about this. And you're like, well, it looks amazing. Yeah. Oh, so we're all kind of not happy, really, or stressed about stuff. And it's nice to see that. I think that's probably why founders, I feel like in venture, there's that trope or a motif that's just like founders love founders and most venture capitalists, or they love venture capitalists that 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 on the promo thing or the early things that drove some of the initial success. What were those things? And I'm sure this is something you're looking for in people and in companies, the ability to scrap their way from nothing to something and then build on that. What were those things that you're referring to a couple of times? I think it was just really scrappy. I

I quit my day job. He moved down from Maine and lived on his ex-girlfriend's couch, which is probably really uncomfortable. We're just like, this is it. We have to put all of our eggs in this basket and that will hopefully push us to work that extra few hours every day and stuff. Yeah, it was definitely something to that. I was like $150,000 in debt. You had a way to our world. Yeah, I mean,

My boss was like, you're what? He was like, don't do this. You can come back. When this doesn't work out, you know. You know, it's what I appreciated. But didn't want to go back. But I think that was a big part of it. I think for us, we spent a lot of time trying different things. I think that iterative process, but also being like really honest about it. I remember making some song that sounded very much like an Avicii tonally song. And we were like, this is fire. But then we're like, is it though? Because it's just Avicii, but not...

not Avicii. The beginning of our career, we were like trying to emulate people like that. Zedd and Avicii and Skrillex and Calvin Harris and David Guetta and Swedish House Maffia. There's so much exciting things happening in dance music. I was a novice producer. You were just getting into it. We DJ gigs around the city and we grew up on indie music.

And so we would go on this website called Hype Machine. I don't know if you ever were aware of that. It's like the first viral chart of the internet. And it was all music that wasn't being officially released. There was tons of dance remixes. Remixes in general were like a new concept. So we'd go on Hype Machine and we would 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, whatever was on the pop radio at that time. And 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 go into basically find 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 would do this remix. And then he would go into the back end of Hype Machine. He would find every writer that wrote for every blog that Hype Machine scraped music from. And he would send them a hilarious personalized email. And what we realized is all of these kids were just college kids that wanted to be closer to music. And here, they're

They're getting these blanket press releases that are just generic. No one reads them, whatever, coming from a label, not even like attached to a personal email versus Alex being the guy who made the song, sending you the song. It's a song that you're already posting about. So it's relevant. It's a dance remix, which is the most trendy new sound at the time. So he gave people a lot of reason to, and then he wrote this really fucking funny email that everyone related to. And within three emails, they felt like they had a personal connection with us, which they did. And

And I think within the first year of our career, we went from zero to 30 number ones on Hype Machine. That took us out of DJing at Pink Elephant and all the great times, 2012 club scene in New York. But we're doing colleges here and there. And that kind of was our first step. And eventually that process of building a distribution channel with all of these blogs transferred into then we started putting out original music and we had to do it with radio. You do a show in

San Francisco okay we got a drive to San Jose that morning and any DJ that wants to talk to you from every station you'd go and like form a relationship with them and then you go to Oakland and you do that there and you go to San Francisco and do San Francisco at night and then you go do your shows and the next day you fly to Chicago and you do the same type of thing and you get a couple extra spins for those things and you got everyone kind of like rooting for you like I

I think that's the kind of grit that we want to see with our founders is like, do you have the tenacity to like, how bad do you want this? Sometimes like this stuff, people think you just put a hit song out and it becomes a hit. But you know, I think all the things we talked to you about today are all those little pieces that you don't see people doing or once it's successful and you try to like trace back to how it started, you're like, ah, well they just put it out and the whole thing worked. And it's like, no, you can't look at this shit retroactively. They're

There's a grind story behind everybody. People grind to product market fits. Like sometimes they just stumble on it and they make it and it goes and it works forever. But usually like, I'm sure if you talk to any like long lasting, successful CEO or founder, there's been moments where they're like, fuck, my strategy is not working anymore. And I have to go back to like eating shit, making phone calls, begging people, finessing relationships to like 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. I mean, you've talked about it with music all day today. If the 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? Like,

Maybe the broader way of asking the question is, what are the things in the first conversation with the founder that are non-negotiables for you that you have to see to be interesting? I mean, I feel like Alex Porter-Redpoint said this to me in a really simple way, which is just invest in people that 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 or business or software or platform or service is used. Union Square Ventures does a really good job of how they think about investing at the edge of ideas, and then those ideas hopefully become more central. And then the TAM question answers itself, because if you figure that out, it's going to be humongous. That

That obsession is really important to us. And even like going back to the anecdotes just now, like we weren't just like dance music's big. We were like obsessed with dance music. I mean, I was downloading off blogs before we even learned to produce with Drew, hundreds of songs a day that I would just like put in a folder because I just loved discovering new music. And I also threw parties everywhere here in New York City for like six, seven, eight years. So I also understood how...

how to fill a room. I understood as a club owner, you don't give a shit about what the DJ is playing. You just want your club to be filled 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. And so we really had all of these pieces understanding the same way that sometimes advantageous to invest in a founder is a specialist from that field. Hey, I was working at Salesforce. This is a problem that I owe

always had. And now I'm starting that company. And I think it's a problem that a lot of other people have. And 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 is hot right now. I'm just going to build an AI company or something like that. And I think you might have short-term success, but as anyone who's been successful tells you, it's a very long road of getting kicked in the nuts a lot. And you kind of have to just love it so much that

that you almost enjoy the misery of those moments and know that it's just part of the process ultimately. 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 four months building out integration. And I really like admire how this is a guy that would 100%, he's going to bring BYOs, bring your own cloud to like the forefront.

This is his life's mission. I think he's built like a really compelling platform. He's a really compelling enterprise customer, but he's spent every, 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? And he's really being intentional. The same with us where it was like,

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've loved and think is a great indie song that should get remixed because it wasn't like always this is the number one sometimes it was the 15th song but we were like this song is sick and we need to remix this song and i think that intentionality is super important and

You really want to find someone that has that experience, knows exactly what they need to solve for. But you really have to be careful to make sure that that person, what did they do before they worked at this company? Where did they come from? Do they have a self-starter mentality? What have they done? Did they just go and work here for a long time, a 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. 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, the team? On the practice of investing, like from ownership and stage, the discipline that goes into like making the descents make dollars.

And I think that's a really important piece that comes with experience the same way that you've had the lucky to have conversations with Peter Fenn and Bill Gurley and Alfred Lynn and prolific investors. And there were certain commonalities. They 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. 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

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.

And 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 towards 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. And for us, you kind of just know when there's really interesting, exciting founders.

There's like a hysteria around them in a lot of ways. I think there's that part of investing, which I find myself reverting back to. I think some people might call like a signal investor, but at the same time, I think it's just this pattern where it's like the space, the founder, the team, the investors, the perspective of where they came from before and the problem they're solving now. And 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 into.

And then there's 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 this, but there's going to be a lot more alchemy than science initially.

And those ones are kind of like the company I just brought up, Nuon, before, where I think is really exciting as an investor. We're testing a hypothesis right now about where we think the future is going. And 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 the other company, which is just, hey, if Sequoia invested, someone is going to do that A, even if it's just for no reason. I think that's what...

You have to learn through experiences. How do you see through all the noise and bullshit of hype versus reality versus syrup periods? And we've really seen a lot in the last six years. And it really changed my perspective on when you want to throw yourself into something and when something's not real in venture. Because I think there's 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 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. And 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, 50K checks into companies. That was all we could get. And 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. And now that we're looking for bigger allocation, 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, exactly. So it's been really interesting.

And also, we have a team of people now that are extraordinary and everyone has their own identity and perspective on how they want to invest and evaluate things. And I feel like my job has always been to try to reel them in, like how we're trying to treat the chain smokers now. Dumbing it down, keeping it more simple than confusing because it's so hard to get wrapped up in the minutia of everything. And I've talked myself out of really good deals for that reason.

It reminds me of my son's question, himself an aspiring music maker. Great. I thought it was a really interesting question in the car this morning, which was, how do they know what is the next skill that they need to improve? Ooh, that's a really good question. This is definitely your kid. Yeah, exactly right. The dad proud. I thought that was so interesting because there's so many, I'm sure there's 15 things you could go get better at at any given point in time. That's where he is too. He's trying to figure out, he's 11. 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. It's like, we always feel like we're learning new stuff and there's new practices. I mean, like making music is a never ending ladder. My drum teacher told me that when I was like nine years old and it's the most true thing I've learned about my musical journey.

And I think now 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? Because there is something beautiful about a young artist that has their whole life to make their first album. There's a level of like, there's a little bit naive because of that. They're not overthinking shit. You know, I'm part of this thing. And 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. It's like heart and soul over mind. Yeah, exactly. Exactly. And I'm trying to like, I think we're both trying to like reconnect with that as much as possible. I mean, that's 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 like ride the wave of this thing that's kind of moved past me, but I can hang on to it? Or do you just be steadfast in the thing that is inherently you?

And there's not really a right answer. There's a bunch of success stories for either side. But me personally, I'm trying to like not let the lessons that I've learned get in the way. Yeah. Yeah. Skills are weird. I mean, I feel like I was thinking, well, Joe was talking about that and

In venture, I was Googling words like TAM on my first month of college. I was like, I don't know what- I think we can say that now. What are these fucking acronyms? Everyone's obsessed with acronyms in here. A big TAM's good, right? Yeah, yeah. And I'm just like, they made me wrong. And I feel like I'm constantly asking stupid questions. And honestly, I really am grateful to a lot of the people we've had a chance to get to work with and interact with because-

We've approached this space with a lot of respect and everyone's, I think, hopefully acknowledges that now. There is 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 space. And obviously like engineering is a huge part of any tech platform. And I was like, I kind of want to like

try to learn how to code a little bit because I want to have at least a semblance of not just respect, but understanding of when I'm discussing these things, the different processes and stuff. And then now vibe coding and cursor and things like that exist. And you're like, okay, so I don't need to learn coding anymore. And 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, didn't carry on very long. And I remember like

few years into our career and I was like, "What if I have a kid one day and my kid's like, play closer for me?" I'm like, "Oh, I can't. That's so lame." I was like, "I'm going to learn piano." So I took two-hour lessons of piano five days a week and I still do to this day now. The purpose was to be like, I can't claim to be musician if I'm not, I can't play our music. Ridiculous. So I figured that, but in the process of practicing learning, it opened up a whole understanding of how to communicate my ideas to Drew,

or whatever as we're discussing music and it really like 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, where there is like an ignorance is bliss thing to a lot of this, where it's like 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 five miracles too much or is it two or one for things to go right? And you have to like look at it through that lens and think, imagine that world. And 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 and Nuclear. I remember talking to them over there on the first call and it was like, we can't do this, but fuck it. And we're like, but if they do this and we didn't do it, they'd be really pissed off. And a lot of it's like that sort of stuff.

Even though it sounds really stupid. I mean, outside the fun. Inside the fun, we have a process, I swear. But as Doug has got as good as pedigree and Bob as anyone to like tackle this problem. It was just like the timelines were like, and then in seven years, we'll be able to test the first one. And you're like, seven years, we'll test it. And you're like, all right, let's do it. You know what I mean? And now they're absolutely crushing it. It's obviously like Monday morning quarterbacking it. But it was like funny when you look at those things and you're just like, we could have called.

Blake and Chad and had deep conversations with our friends that have experience in this space. And they all would have probably been like, don't fucking do this. Why would I say the other day? Like, I don't know if we would have invested in Poppy again. Cause we just don't, we do stay away from CPG. That was like a 30 X, but again, completely like YOLO. There is again, some level of naivety that we're just here. Just like,

You got to have a venture favors optimism. And I hope we would have identified that Poppy had two incredible founders, but like, maybe not. Maybe it was just like another soda. I was talking to Alex once about some company in the portfolio. It wasn't like over zoom or something. It was live. And he started rattling off the KPIs of the company.

And I was like, wait, you know the company's KPIs? And then he was able to do that for like a bizarre amount of the companies. And I asked him about it and he said, yeah, no, I know like all the numbers for all the companies, which is surprising. Back to your point about like when you announced a venture fund, everyone's like, oh, these jack-offs have a venture fund now. Yeah, we're like, we got to know all the numbers. Exactly. But it's an amazing way that you bridge the two worlds. And obviously it's early days. Like you said, you probably do both these things forever. Yeah.

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 like so long. I was like, nobody's done any kind shit for me. That's a good religion. I was like, I don't want to like single out anyone that significantly. Yeah.

I love how you're going to say this with caveat. Like, I did think about this for 10 hours today. Truth is, people aren't that kind to me. At least in the ways that I've heard other people think through these things. I mean, obviously, I've got extraordinary friends and people in my life. But I guess if I had to, like, 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 sixth grade named Mrs. Park. I think she liked me, but I think she...

I also understood that I was at this really interesting crossroads in my life. My dad had just passed away. He's 12 years old, super young, impressionable age as a young boy.

I had a lot of friends, but I was also not like a banging student by any stretch. And she was just like, very clearly, I mean, she was like, this is like the most important moment in your life. And you were like, probably not even recognize it till it's too late, either in a positive or good way. But she's 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 like 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. And obviously as a six year old, you're like, what? You're like, ladies, I ate 15 in the morning. You know, like 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, would have had this thing in the back of my mind, which path is this leading me towards? And really like motivated me to like get my shit together and become like a good human and a really good student and push myself. So ironically, I think it's funny when someone can offer new 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 kind of like acknowledge it, but you don't really think about fundamentally what it means. She was probably like in her 60s. And this woman's obviously advised and taught whatever homeroom to hundreds and hundreds of kids. I'm not even probably 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, like it snapped you awake in somewhere? I

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. That's probably why I painted so much. I just didn't want to leave my room and interact and get in the mix of all that. And my dad passed away in the middle of the divorce. So it was like a really dark period. And to the point of what I just said, and it was like, I had a lot of friends that came to my side and supported me then. And more than anything, I think as you get older, you kind of distort relationships.

memories. And now when I look back on things, I had this completely different perspective now than I did when I was a 13-year-old about who my dad was and how he treated my mom and how she treated him and how my relationship was with him or him 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. And it's a weird experience not having grown up at all with anyone to be like, "Dad, look at this." Or like, "Am I doing this right?" Or the dad that's like, "Hey, let me help you out with this or do that." And so it's been probably one of the strangely better things that has ever happened to me, but also,

I've 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 five years old.

You know what it's like to buy a drum kit for a five-year-old kid in a 130-year-old house, farmhouse in Maine? You're listening to me trying to learn, listening to just smash drums, which I played all the way until I went to college. And my mom would sit in the kitchen doing grading papers and doing stuff that she had to do for work or whatever.

Making dinner, just listening to it and loved it. 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 two of my favorite things, music and business. I am so excited by the next chapter of what it might become and what it might look like and can't wait to watch. Thanks for doing this with me. Hell yeah, this is an honor. Thanks for having us, yeah. ♪

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