Description

Trevor McFedries (X, Instagram, Wikipedia) is a musician, technologist, and entrepreneur. Today he is the founder of Runner and 1/2 of electronic dance duo SoFTT. Previously, Trevor was co-founder and CEO of Brud, the company behind Lil Miquela that was acquired by Dapper Labs; Founder of FWB (Friends with Benefits); early artist in residence at Spotify; and a touring DJ who performed as DJ Skeet Skeet, was part of the rap group Shwayze, and produced for a range of artists.

Trevor’s work emerges from a tension he’s lived with throughout his career: the gap between who creates cultural value and who captures it. Growing up poor in Iowa and entering the dying music industry in the late 2000s, he witnessed firsthand how the instruments that capture value rarely benefit the creative people who generate that value. This has run across his entrepreneurialy work, from building virtual pop stars to a range of crypto projects that hope to give creative people more upside.

Trevor bridges culture and technology, art and capital, and high and low. I’ve met few people who are as consistently ahead of culture. His perspective challenges both the art world’s disdain for commerce and Silicon Valley’s shallow engagement with culture, arguing instead for creative people to play the game on the field and build the instruments that will make them rich.

Today, he’s focused on how that may end up being as much about predicting what’s next with stakes as it is actually making things. We also talk about authenticity and honesty, why he continues to spend time in crypto despite it being low status, why speculation is rational and selling out is punk, how power comes from consensus, his keen nose for weird—especially on the internet, briefly working with Kanye West, and his forever optimistic curiosity.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and the home of my new site where you can find all links and transcripts. My “What are You Building This Year feature with Notion on Instagram.

Timestamps

0:00: Opening Highlights
1:18: Intro to Trevor
4:12: Thanks to Notion
5:21: Start: Creative People Should Be Rich
12:03: Creative Ignition, Infrastructure, and Why Selling Out is Punk
21:49: Authenticity, Honesty, Divine Creativity, and Borrowed Nostalgia
30:15: Low Status Games and High Culture, Cultural & Financial Capital, and Crypto
42:08: The Belief Economy: From Making -> Framing -> Predicting
48:45: Markets, Power, Consensus, and Truth
58:22: Speculation is Rational
1:06:34: Developing a Nose for Weird, Being Early and On Time
1:19:06: Unfettered Cultural Spaces on the Internet
1:26:33: FWB, Community, and Exclusivity
1:31:02: LilMiquela, Online Storytelling and Celebrity, Touring as a Performer
1:45:41: Softt, Music as a Way In, Music as a Business
1:52:45: Culture & Business
1:54:38: Kanye
2:06:20: Optimism, The Next Generation, Parenting, The Stuff that Counts, and Cerulean
2:17:55: Thanks Again to Notion

Links & References

Transcript

Jackson: Trevor McFedries. We made it.

Trevor: We did it.

Jackson: Thank you for having me.

Trevor: Thank you for coming by.

Jackson: I’m very excited. This is overdue. We were going to try to do this six months ago, and here we are.

Trevor: We made it. I love it.

Jackson: I want to start with one of the main through-lines of your working life. You tweeted, “I think creative people should be rich.” It seems like that is your big quest.

Trevor: I think it’s probably because I’m old enough to remember a specific time. When I was 22, I joined a rap group called Shwayze. We put out a top 10 album in the States, and I was thrust into the dying corpse of the music business. I got to see a taste of wealth. I remember going to a record producer who had one hit in the 90s. He had a $5 million house in the hills and a sick studio. It didn’t compute because we had a hit, and I was still broke. I got a taste of what could have been, combined with a deep desire for information to be free, that I had as a product of the internet. There has always been this tension.

Jackson: Why aren’t creative people rich?

Trevor: There are a lot of reasons, but I believe there is an instrument problem. Creative people were producing a ton of value in Williamsburg 20 years ago, but the instruments that captured that value were properties. If you were a real estate developer or owned a massive amount of property, you got very wealthy. You didn’t produce any of the value in the day-to-day life of Williamsburgians. That is why I got deeply into crypto. It was an opportunity to create new instruments that can capture value and pass it back.

Jackson: How do you think about the instrument concept in the traditional capital versus labor framework? Is it the same, or are you getting at something more specific?

Trevor: I think about capital versus labor, but beyond that, I think about capitalists. I grew up super poor in the Midwest and was radicalized by Rage Against the Machine. I was reading Eldridge Cleaver in my fifth-grade English class, and my teachers were concerned. I was hostile to the idea of capitalism and interested in socializing things by redistributing wealth. Now, I am almost a creative supremacist. I think creative people should be billionaires, and people participating in this “Forever 21 economy” of ripping things off should be minimized. Ultimately, labor versus capital is a limited framing. I am interested in playing the game on the field. As the Black Panthers would say, “survival pending revolution.” It might seem crass to apply that to this modern, venture-backed technology environment, but there is an opportunity to play the game and create instruments that pass value back to the people who make life worth living—not just those who know how to trade derivatives, bonds, or stocks.

Jackson: What do you think the internet’s role has been in this? Do you feel the internet has failed its potential, or was our current situation the inevitable outcome?

Trevor: I’m old enough to recognize that it’s probably the most likely outcome. I’ve been through a few cycles of “this is going to change everything.” Whether it was dance music with Bloghouse, we thought we were going to reinvent dance music and change everything. Then we asked, “Wait, why is Will.i.am here?” Oh, shit. He took all the sound and made millions, while my homies are still broke driving DoorDash. They are effectively those participants in all kinds of culture. You recognize it in Silicon Valley, you see it in Hollywood, and you see it in D.C. Some people can understand what’s next and ride the wave. Obviously, the internet devalued media. That’s table stakes for anyone who’s a Dialectic listener; I’m sure they can appreciate that. But what is underappreciated is that there are these charlatans who often recognize an emergent trend and accelerate it. They create all this pomp about how radical it can be, knowing that it will effectively change things by more or less 5%. They insert themselves into that 5% and get ludicrously wealthy. I don’t want to sound like a doomer, but I think that is ultimately the game on the field. The people coming up with net new ideas and innovations should be that 5%, not the charlatans that insert themselves.

Jackson: You might sound like a doomer a couple of times today, but I think you are decidedly not a doomer.

Trevor: Decidedly.

Jackson: It’s important to establish that up front. On that last note about the extractors, a different take would be this: There is a cynical view that says the reason creative people aren’t rich is because of these extractors—opportunists who aren’t even the creatives themselves. There’s a less cynical view that says Drake is super rich. Depending on the medium—music is complicated for a lot of reasons—there are very clear ways to get rich in music. That path is probably less legible or obvious if you are doing something more esoteric, like if you’re a ceramicist or a fine artist. Maybe the less cynical view is simply that medium matters a whole ton. Some media are certainly much more commercial than others.

Trevor: The word “creator” is thrown around a ton right now. I would like to decouple this idea of “creative supremacy”—or whatever I’m coining now—from someone who is grabbing Tumblr graphics off the Internet and throwing them on T-shirts to someone who is truly innovating. When I talk about creative people, I mean founders, scientists, and artists who are creating net new things that are advancing this thing we call life. The challenge for me has always been that even in the culture industries, there was this commercial space. Then, there were institutions that recognized their role was to validate things advancing life that wouldn’t necessarily play nice in the commercial marketplace. Now you can go to a museum and see a KAWS show. KAWS has done financially really well in the commercial marketplace. You can walk into a Uniqlo and see KAWS. Do you need to go to a museum and see KAWS? I don’t think so. You have seen that proliferate everywhere across the culture industry. The challenge for me now is asking: if we have this opportunity to rethink what we’re doing, can we find a way to repatriate attention and value to people making net new things? Maybe not the people who have found a way to just package, repurpose, and use distribution to capture the upside. I recognize that probably isn’t going to happen, but if we can move the needle a 5% incremental amount, I would be elated.

Jackson: You mentioned a line to me a while ago: it’s easier for someone to raise $3 million than to raise $300,000, especially for creative people.

Trevor: Yeah.

Jackson: Maybe this is getting at part of your last answer. You’re talking about creativity through the lens of ignition, genesis, or originality. Why is that $300,000 over $3 million distinction important? What are you pointing at?

Trevor: There are a couple of things. One of the things we don’t recognize is the catch-22 where, in order to be given an opportunity, you need to prove that you can do things. That chasm often prevents really brilliant people from being able to capitalize and provide value to us more broadly. I grew up in Iowa and was lucky enough to move to Los Angeles. I encountered all these people who were celebrated and supposed to be really special. I recognized they were not that much different than the friends I grew up skateboarding with. But because they had peers, friends, or uncles who could get their foot in the door in a mail room or infrastructure, they could prove something. They were given a little more rope, then a little more. All of a sudden, they can raise a million-and-a-half-dollar seed round and take a big swing. The challenge is that getting that initial $30,000 to create a T-shirt company to prove that you can build something is really hard. People often don’t cross that chasm. The idea that it’s easier for folks, even an established creator, to raise a million and a half dollars to do something big and ambitious and fail than to do something small and prove it out is an interesting thought. That provoked startup ideas and other things that people could be solving for. There is probably something between venture and bootstrapping that needs to exist.

Jackson: I think agency is almost like an escalator, or a reciprocal relationship. One of my favorite ideas comes from C. Thi Nguyen. He talks about games and says that a game designer is creating a tension between your abilities and your goals that is not too far out of step. If you play level one of a video game and it’s really hard, you’re going to get bored. If it’s too easy, you’re also going to get bored. There is a dynamic that is part financial and part the world helping you—like having 100k to go do a little bit. Even if you’re Elon Musk building SpaceX, it wasn’t like, “Here’s a billion dollars, go nuts.”

Trevor: I have always appreciated complex video games that are able to introduce complexity to you step by step and walk you through it. I remember when Game of Thrones was massive, there was a dominant narrative that there were no more attention spans and people couldn’t focus on anything. I watched the first episode, and it was the White Wolves of the North. I had to take notes. Complexity done well is the most powerful thing, and people have decided to decline to even attempt it. I love it when games and films introduce all that.

Jackson: I like that a lot. There is a quote from Yancey Strickler that you quote-tweeted that points to something really interesting. I will read Yancey first. He said, “The idea of “selling out” implies a hopeful nostalgia of choice beyond market pressures. Among younger creators I talk to, in whose brains the algorithm is directly embedded, not selling out feels like an impossible luxury from a faraway time, too risky to attempt, but a fantasy they dream of one day indulging.” Then you said, “Increasingly feels like artists who opt out of the algorithm game and produce work that isn’t algo-friendly are seen as posh/nepo/trust fund. Playing the algo game to survive is optically punk and honest.” This is really interesting to me. When did that change? When did it feel to you that it changed?

Trevor: It has been a slow boil. I am old enough to remember the Beastie Boys being upset at their music being used in adverts. In my generation, I remember hearing Santigold in Budweiser commercials. There was a generation above me that said, “This is fucking selling out. This is terrible. Why would you do that?” Now we are living in this moment where I can’t afford to own a home, let alone have a family. Of course, I am taking the Budweiser check.

Jackson: Creative people should be rich.

Trevor: Creative people should be rich. In the last three to four years, the dominant understanding of how aesthetics flow and how ideas populate has inverted from the Bushwick model people are familiar with. In that model, an interesting art person makes something, it gets to a Vogue person like Anna Wintour who says it’s important, and it gets pushed down to a soccer mom in the Midwest. Now, we have this middle-out dynamic. I remember a TV executive talking about making the most inoffensive television possible—the kind that would keep people from changing the channel. It feels like “For You” algorithms perpetuate a similar idea. You can go to East Berlin, Bushwick, or Beverly Hills and see the same Alo Yoga outfit on the street. Culture is now middle-out. The most inoffensive person captures the most mindshare, and people optimize for being that person to get opportunities or influence. That isn’t groundbreaking. As a result, the only people who have been able to play this art game and opt out of the algorithm for the last four or five years are effectively trust fund kids. I don’t need to name names, but I love the meme: “Never ask a woman her age, and never ask an indie musician why their parents’ names have a blue link on Wikipedia.” To be truly indie and participate in a purely artistic environment while playing the culture industry game, you need to survive. It has gotten so dire that the only way to do it is to effectively be a trust fund kid. The most punk kids I know are playing social well, whether it’s Amyl and the Sniffers or Turnstile. They have been able to capture these mediums on their own terms, but they haven’t opted out entirely.

Jackson: It is interesting. One question I found myself wondering is: are we going to get to the point where “slop” is punk? You are sitting inside this tension. At what point can you play the algorithm game while creating something actually new? Jackson: [00:13:46] Regardless of what you think about Warhol…Being commercial can be really interesting.

Trevor: Certainly. I’ve been hosting gatherings at my home to connect Silicon Valley friends and artist friends. There is a theme in Silicon Valley right now about taste and how important it is.

Jackson: That is almost becoming slop. That narrative is so regurgitated at this point.

Trevor: I brought all these artists together who aren’t on those X feeds and aren’t aware of this stuff, but have really important work. They were here, and the AI people assumed they would agree with the sentiment that AIs don’t have intuition, which is why they can’t do great art. All of the artists said, “I don’t know. I think a lot of that stuff is really good.” The AI people were surprised. I do think there is absolutely going to be a moment where “slop” is punk and interesting. You’re seeing some examples starting to emerge. But what is clearly interesting now are the models themselves and creating in latent space. As people begin to appreciate that, as they have the contextual awareness of how these models work, they’re going to really appreciate some of those things. It will probably be uncomfortable for researchers at the big labs to say, “I’m the artist. I’m making the most interesting work.”

Jackson: At least I’m making the medium.

Trevor: I’m making the most interesting cultural work of the moment. I think a lot of artists would agree. They might say, “I clearly made this cool wall work, but what you’re doing is the most important reflection of this current cultural moment.”

Jackson: Maybe I’m just on Twitter too much, but I would be shocked if most people had any intuition that “real” or serious artists felt that way. The midwit artist on the Internet is just complaining about AI. You say the words “AI,” and they have a meltdown.

Trevor: I would call that the “Capital A” Art World. I remember I really wanted to go to design school. I wanted to go to RISD; that was my dream. I was a football player, and I could go to college for free, so I ended up doing that instead. However, I would take these summer programs.

Jackson: There are so many possible timelines in your life.

Trevor: It is bizarre. I remember I went to Otis Design School here in Los Angeles for a summer program. I was really intrigued to see if I would meet artists who were just like me. When I was confronted with the people there, they would just draw anime, hentai, and dragons. They were really good at drawing dragons, but there weren’t really any new ideas. I found the people I was drawn to were actually in the corners of 4chan or random streetwear stores—places that were emergent and actually quite interesting. People who wanted to find net new forms of expression would huddle around there.

Jackson: What do you think the relationship between authenticity and creativity is? This is very related and also a can of worms. I feel that authenticity is almost ridiculous. At least when it became an aesthetic, is it even worth talking about? Maybe the other part of this question is: is there such a thing as pure art, creativity, or originality?

Trevor: Conceptually, yes. But when I talk about creativity or even authenticity, it’s like talking about nirvana. It’s an end state that I think you can aspire towards, but I’m not sure it’s achievable. I do think authenticity was the buzzword—the taste of five or ten years ago. Because we were doing Miquela at the time, that was often a question I was confronted with by new hires or VCs. I always tried to explain to them that authenticity can take a lot of different forms. Ultimately, what I’m looking for in great artwork is honesty. I am looking for a connection to you, who is themselves a divine bridge to something. This is a bit of a tangent, but during that Timothée Chalamet/Bob Dylan moment, I saw an interview with Bob Dylan where they were talking about his songwriting process. The interviewer noted that he wrote these songs so long ago, and Dylan more or less alluded to the fact that he’s not able to do that anymore. I thought that was really compelling. It is also terrifying, because as someone who wants to tap into that divine stream all the time, the fact that it can come and go is scary. I’m very aware of it in a songwriting room because you watch writers and think, “Whoa, where did that come from?” In building organizations and these marathon endeavors, it’s less clear. That said, regarding authenticity, there are creative people who do commerce explicitly. I always think about K-Pop. They didn’t write those songs. They didn’t style those clothes. They didn’t choreograph those dance moves.

Jackson: But what a beautiful machine.

Trevor: What a beautiful machine. I appreciate the machine. I often get into arguments with peers who say, “I don’t understand why you love Rihanna, but you hate these imposters and these people you think are taking attention from people that are actually creative.” I love Rihanna because she’s not telling me she’s making a two-Michelin-star steak. She’s saying, “Here’s a cheeseburger.” And I love cheeseburgers. This is fantastic. I get frustrated when someone says, “Look at this two-Michelin-star steak,” but I know all the references they are biting just because they are repurposing them. It is just borrowed nostalgia. I am seeing this interesting thing now where Silicon Valley has gotten into cultural critique, consciousness, and these more abstract concepts. The very uncool humanities are getting quite cool. There’s an emergent founder who has seen the Adam Curtis films and can paraphrase them, and the VCs are like, “Wow, how do you know this?”

Jackson: Naming McLuhan. We got it all. I’ve done some of that myself.

Trevor: That’s why you’re especially able to connect these dots. But you can do it in a very honest way, where it is in the interest of learning. There are people who say, “I have this new idea,” and it’s the first thing we talk about. That’s the frustration I often have. If you just want to get rich, sell real estate. Don’t purport to be some poet or philosopher and just repurpose ideas for people that aren’t familiar with them. That’s where I get all riled up.

Jackson: The borrowed nostalgia thing came up a few times in my research. What do you mean by that, and what is so frustrating about it? Specifically, you gave one example of Amy Winehouse. What is the line between borrowed nostalgia and the fact that nothing is truly new, but can be remixed in a way that feels really new?

Trevor: Some people act as a divine bridge. They can interpret their environment, share that moment, and reflect on it with people in really honest ways. I always use Amy Winehouse as an example. People say Amy was doing nostalgia, but she wasn’t. Amy was taking an interpretation and a style and parsing it through her lived experience. Talking about rehab through a jazz lens is new. She is standing on the shoulders of giants, but she is parsing it through her lived experience. That is really important. The reason the nostalgia piece is so tough for me is that, as a millennial, we had a generation that was effectively able to do that trick at scale. A bunch of Gen X didn’t know anything. We realized we had the internet. I could just put on a gold chain, reference some ’80s rapper and KROQ, and an A&R guy or radio programmer would say, “Whoa, this is a hip-hop aesthetic with a rock thing. This is crazy.”

Jackson: I’ve never heard anyone say it like that. That is so unbelievable. It was like you got the answers to the test.

Trevor: Totally. You could cheat in real time on the test and blow minds. There were all these people who effectively got to LARP different eras people weren’t familiar with and pass through these gates. Everyone wanted to tear down the gates. A bunch of millennials were saying, “This sucks. I want to make the decision because I can tell this is dishonest.” Then we removed those gates, and we thought, “Maybe some of the gates were good. Can you bring the gatekeepers back?” That is my war on nostalgia.

Jackson: Before we go into the next thing, I just want to mention the Bob Dylan thing. The optimistic part of that would be that you hear so many musicians say the songs come from God. It came to me in a dream, whether it’s Bob Weir or Rosalía. There is this loose grip on that. Thinking “I am Bob Dylan, I did it in the past, and I can’t do it anymore” is pretty tragic. I wonder if you have a looser grip—just that sometimes they come, and I want to be ready for when they come. It must be hard knowing that.

Trevor: I am of two minds. I don’t know much about soccer, but my friend Alonso was talking to me about Messi being this gifted savant and Ronaldo being a workhorse.

Jackson: This is like Agassi and Djokovic. I think it is a little bit similar.

Trevor: Totally. I find a lot of that in songwriting and artistic practice. There are founders like the Collisons, where you think, “I don’t have that gear. I’m not going to get there.” But maybe if I find other ways to create an edge, I can get to this thing that I’m really proud of. I respect both. To me, it’s almost like a spiritual thing. There are monks who I imagine have this divine light and are connected immediately. Then there are those who have to spend a lot of time getting deep into themselves and closer to God. That is how I interpret the practice, and I want to honor both. I am actually probably more aligned with Ronaldo. I am not a gifted musician. I just poke buttons and turn knobs until it sounds cool, and it’s a struggle. When I go into sessions and people say, “That flat fifth isn’t in that chord,” I don’t know what they mean. It is heartbreaking, but it is also a blessing. I get to find something and let it kill me in a lot of different areas.

Jackson: It’s like you’re not a native speaker, but you’re trying. Jerry Seinfeld comes to mind, though many creatives talk about this. I was speaking with Gabe Whaley about the work they do at Mischief; they schedule their brainstorms. Seinfeld goes into a room with a yellow legal pad. He doesn’t have to write, but he’s not allowed to do anything else for three hours. Scheduled discipline gives you the best surface area for inspiration to happen. That approach is maybe more Ronaldo. You aren’t walking into the room as Messi, but there is something beautiful about saying, “I’m ready for the inspiration if it ever comes.”

Trevor: You could argue both sides. Warren Buffett and Bill Gates don’t have calendars. They create space to do the work, but they are also creating space for divine lightning to strike. To me, this is very spiritual. The older I get, the more I relate these things to spiritual practices. Ultimately, they seem to be reflections of reflections; you can see the fractals.

Jackson: We talked about instruments at the very beginning. I want to set up our conversation about crypto with a couple of quotes from you that serve as an interesting backdrop. For many people, crypto is always low status; there is a lot of disdain. You wrote: “I’ve had such disdain for the hyper-financialization of our lives—blockchains, tokens, and so on. But if you invert that and try to create better instruments for capturing value, you can attribute that value and pass it back.” Here is another section: “After reading Debt: The First 5,000 Years by the late anarchist anthropologist David Graeber, Trevor found himself asking: What is value? He followed that destabilizing thought to a liberating conclusion: It’s whatever we collectively decide it is.” You went on to say: “One of the reasons I love crypto, or an Internet of value, is that we have really antiquated vehicles for representing value.” You believe crypto enables better instruments for assigning value to all things. The idea of value being something we can tinker with seems to be at the core of that. I am curious why you consistently find yourself drawn back to this, despite the arguments for doomerism, the disdain, the hyper-financialization, and the SBFs. There must be some hope or dream that you are seeing. What is that?

Trevor: There’s so much in there. I think there is a spiritual and psychological war. There is a desire to move people to a higher state of consciousness. There are plenty of people doing that. God bless them, they’re really good at that. A lot of people on the opposite end of the spectrum are looking at purely utilitarian ways to help people get to the next meal or the next moment. What I’ve uniquely been able to do because of my life trajectory is live what I say: from the squat to the yacht. I actively engage with shithead crust kids. I still have all of my tycoonian anarchist friends who are on no-fly lists. And I have billionaires speak in my house about AI. That was a function of moving from Iowa to LA when I was 16 and having art aspirations, but recognizing my place in the universe as being someone who can be this connective tissue. I’ve joked in the past that I’ve always wanted to be the chef who makes two-Michelin-star corn dogs. When I moved to LA, I had never had sushi until I was 19. I had a California roll, and I threw it up. It was too advanced. I was raised on not even Taco Bell. I was raised on Taco John’s—knockoff of knockoff. The idea that there were people who could contribute if they had some kind of connective tissue is what I was interested in. So there is this psychological and spiritual war. There needs to be someone to say, “I actually know how venture capital works.” You can say “2 and 20” to friends of mine in the art world; they have no idea what that means. I am also deeply rooted in the history of culture and music, and I’m interested in the right people winning. If I can effectively be a low-status person who can larp as a high-status person, and maybe a high-status person that can larp as a low-status person, I can be this translator and use this connective tissue. From the more utilitarian angle, low-status games are often the best way to repurpose value, historically. When I talk to my contemporary art friends, I tell them that if I was just a pure artist, I would be in Saudi right now. Where else are you going to find someone with $3 million to build a really compelling object or take a flyer? But I want it to be here. It’s déclassé, and people in America will say, “Middle East money.” But that’s what people in France were saying about America not that long ago. This was the déclassé. We are new money. We are low status. Ralph Lauren is a Jewish kid from the Bronx named Ralph Lifshitz who changed his name to Ralph Lauren and started pretending to be a kid from Connecticut. He was able to play this game so well that he created this whole fantasy that became real. That’s a tangent I’m also interested in. I love Lana Del Rey because her dishonesty is so internalized. It’s real.

Jackson: Talk about authenticity.

Trevor: Lana can tell you she was living in a trailer park, smoking meth with the local rodeo guy, and I’d say, “I know it. I believe you with my whole chest, my whole heart.” Even though your dad was a domain broker and had hundreds of millions of dollars. You’ve internalized these things so deeply. Schizophrenia is real.

Jackson: There’s an idea I’ve struggled to articulate over the years, but I think identity can be a projector and a mirror. It’s intuitive that it’s a projector. If you dyed your hair green or have a mohawk, people are going to perceive you differently. But after enough time, you’re going to perceive yourself differently, which is pretty profound.

Trevor: Absolutely. We are who we pretend to be. That “fake it till you make it” thing is one of those things that’s so easy to articulate, but to truly live it and to become that is a real blessing to experience. Watching people overcome that imposter and just live it, commit—you see it in LA. You see the pirates; they’re still doing an 80s hair metal thing, and they live it. That rocks. Good for you.

Jackson: Do you think there are a lot of people who are really living it in crypto?

Trevor: There are obviously a lot of imposters but a lot of them have left. I like crypto a lot right now because most people are in AI.

Jackson: The weirdos are hanging around.

Trevor: It’s just freaks and weirdos and people that are probably unemployable in a lot of places. I haven’t thought a lot about it, but I’m sure you encounter it. The other day, I went to Shake Shack with my fiancé to get a cheeseburger. She’s pregnant, and I was carrying all these things, and this guy just went above and beyond and helped us. I started talking to him, and he was just so articulate, so curious, so thoughtful. I was asking him what he did. He’s going to school. I told him I work in technology. He had all these thoughts about AI—really poignant stuff. He could explain a transformer, which is what most of the VCs I engage with couldn’t do. There is this neat, Reddit, lost individual who’s deeply curious but maybe doesn’t have the tools to contain it or articulate it such that it’s parsable by whatever institutional powers that be. It’s just not quite legible. Some part of me is really interested in identifying those people, giving them power, and teaching them how to become legible. I think crypto is full of those people, which is so fun. That’s one of the reasons I love hanging out in a Telegram with a bunch of racists and insane anime PFP people.

Jackson: There’s somebody human underneath there.

Trevor: There is. There’s someone human underneath who read the wrong white paper.

Jackson: They read too much Curtis or whatever.

Trevor: Totally.

Jackson: There’s this thing that has been happening for a while that you are very interested in: attention and capital are compressing. This goes back to the idea of things being financialized. This is interesting through the lens of things being legible. Part of what the financialization of things does is bring things to the forefront. This is you: “This is the definitive mutation of the early adopter. The 2000s hipster discovered bands in basements and hoarded their finds like trade secrets, terrified of mainstream contamination. Today’s equivalent, what Nemesis calls the creative director, still wants to be early, but they want everyone else to show up too, preferably with liquidity. Creative directors aren’t gatekeeping; they’re shilling. Being first isn’t about protecting your scene. It’s about getting in at the bottom of the bonding curve and waiting for your idea to graduate to the DEXs. Cultural capital has merged with financial capital.” Great writing.

Trevor: Thank you.

Jackson: With that backdrop of the weirdos that the Internet has always been good at having a place for, I’m curious how you think about when attention and culture are fully financialized. Does something about them fundamentally change? One of my selfish frustrations with crypto is that the financialized part of it and the speculation part of it cloud everything else out. You have something that’s bubbling up to the surface, and all that weird stuff you were just talking about is hidden away somewhere.

Trevor: All of the stuff that’s being obscured needs to be obscured because we’re entering into a new era. It’s as uncomfortable as the move from modernism to postmodernism. Like the Duchamp urinal—saying, “No, this is art.” And people say, “That’s not a fucking art object. Where is the craft?” That is the great tension. I applaud people in Silicon Valley and the broader technology world for wanting to champion what they see as art. But what myself and other artists have been talking about behind the scenes is that the act of creation is not that different from the act of speculation if you squint. This idea that you have a belief about the future and you want to express it via a medium and have it validated by your peers or recognized in a market is something that all of the artists that people champion do. Because those models are so antiquated or laggy, by the time you get your work to an art fair, get the album out, or get the film out, it often feels dated. What is tough for people that are actually interesting is you watch the new Paul Thomas Anderson film and you think, “Oh, cool. A conversation about incels and civil war.” A bunch of 60-year-olds say, “How radical this is. This is a reflection of our time.” But we were having that fight on Twitter 18 months ago. What I’ve recognized is that in my group chats where my artists—visual, music, filmmakers—used to talk about prestige television, new films, or art fairs, we now talk about Fed rate cuts. You ask, “Wait, what happened?” I think what happened is they’ve recognized that there are instruments for expressing beliefs that now allow them to be right verifiably and with financial upside in the same way they could be with an art object, but now skipping the middle without a 50% vig to your curator. Meme coins and prediction markets are bad instruments. But the game before was that you could bet on wheat futures if you understood weather patterns. You had an information advantage because you were a meteorologist. Well, I have an information advantage because I’m a cultural savant. Why can’t I have a thousand-x asymmetric upside? That is the great tension. These people have very narrow ideas of what an art community is and what a finance community is. There are the Patagonia vests and the Bushwick babes. I’m interested in saying that instead of those people living in opposition, which is a fool’s game for the Bushwick babes, because these guys have nukes—

Jackson: Yes.

Trevor: They have financial nukes.

Jackson: Yes, yes.

Trevor: You have sticks, bows, and arrows. We can give you nukes, too. You can have a real, meaningful advantage against these people in markets and asymmetric upside in the yachts. Why not?

Jackson: So many of these things come down to “don’t hate the player, hate the game.” There is a lot of hating of the game. You talk about this idea of the belief economy. You have a specific framework moving from making to framing to predicting. That is partially encapsulated in what you just said, but it would be helpful for you to talk specifically about that. Danco has also written about this shift from postmodernism. What is that shift? I think it’s also worth hitting on the framing part. Most people feel like we’re still in that phase, but you are describing this new thing.

Trevor: I love Danco’s piece. There’s a group of friends I would call the “new models extended universe.” This includes Arthur at Trust, Joshua Citarella, Holly Hernandez, Matt Dryhurst, and the Nemesis folks. Dan Keller is here now, too. We’ve been deeply frustrated because we’re interested in progress. For us, technology has all this white space and incredible opportunity for progress. But post-Trump election, the artistic world saw technology as an enabler of dictators and tyrants—Russiagate and so on. We felt disenfranchised from both. We’ve had to talk in isolation about the world we see in front of us versus the world we encounter when we go to a Biennale. We see Aboriginal artworks, wall works, and sculptures that are not meaningfully different from those of 20 or 30 years ago. In the group chats, we’re trying to pull out this ethereal idea: the people who would have been articulating ideas about what’s happening and what’s going to happen have taken different forms in society over the years. The framing I used in that piece described the modernist era, where the thing you produced had all the value. Then came the postmodernist era, where we identified that the narrative and the framing around the thing had the most value. Now we’re talking about the belief economy, where the thing you were able to call or predict has that same value. It feels really uncomfortable for people because they think, “It’s all fucking gambling now.” You have to say, “Well, yeah, but it always was.”

Jackson: Always has been.

Trevor: There are always decisions being made, market forces, and outcomes that were more opaque. If you choose to make them more visible, it’s uncomfortable, but it’s very real. It allows for new champions to emerge. That’s the part we’re all really interested in: predicting is very similar to creating. If you squint, making a wall work or having an opinion about prestige television is very similar to taking a position or expressing a belief in a prediction market, a meme coin, or betting on a meta. Or betting on the thing I’m working on now.

Jackson: It seems almost that…

Jackson: Maybe a little less so with the making part, but especially the narrative, the framing part. We ran out of scarcity there. There’s nothing scarce in the ability to… I talked with Gabe Whaley about this: going viral is shots on goal. There’s no novelty there. There’s no magic there. It is interesting that consensus on the collective belief is relatively rare. That’s the thing that everyone’s seeking. One of the things I was thinking about as I went through this is that this feels very reactionary, even if you’re right. There are optimistic parts of what you’re saying. Don’t we still want to incentivize people to make things? Having all of our best people, all of our tastemakers, skip over everything to anticipating and reacting to what’s going to be next. Maybe we’ll horseshoe. If I were to guess the average thoughtful person’s reaction to what you’re saying, it is this: even if all of that’s true, are we just going to be in a world where we’re all speculating on made-up memes?

Trevor: There is a lot there. Talking about virality being shots on goal, the other thing I didn’t highlight in that piece that I should have talked about more is that discourse is probably the most important product of millennial culture. Like podcasts, everyone has “Clubhouse voice.” Every dinner party you go to, people are repeating the same New York Times podcast takes. We live in this sea of takes with no way to sift through what’s meaningful. Markets being a tool for seeking out information is really interesting.

Jackson: Yes.

Trevor: To speak to the part about making actual objects, I think it’s really important. I just think robotics and AI automation are going to devalue those things.

Jackson: So scarcity again.

Trevor: Having lived through technology devaluing things, I ask: Who are the people you care about? I care about creative people, and I want them to win. Where do you shepherd them? I shepherd them to where the value is going. What I appreciate about Silicon Valley is they want creative people to do well, but they are effectively pushing them to where the puck is, not to where it is going. That’s why I feel like, even if dissonant or uncomfortable, I need to actively speak up. This matters. Go here. Get the resources such that you can impose your will and point of view in the world. It’s important that you do.

Jackson: We’ll figure this out once you’ve won, almost.

Trevor: Yes, we’ll figure it out once you’ve won, but I also think we’re being quite thoughtful about it. Part of growing up is realizing that there are people who make decisions in the world, and you can either have a seat at the table and influence, or not. The All-In Podcast has extraterrestrial influence at this point. There’s a Space Force. If we can shepherd people from having conversations on Dialectic into having seats at the most powerful tables in the world, I would like that. In order to do that, they will need to have meaningful capital and meaningful amounts of verifiably correct takes.

Jackson: One of the things you said is that markets are a way to get to at least one kind of truth. Certainly, this is a pretty profound idea. It’s a market-driven truth. I’m curious if you have any thoughts broadly on what that truth is and if it differs from other types of truth we might have. Does that truth line up with what creative people are trying to get closer to? Maybe back to authenticity and honesty or whatever creatives are normally trying to get at.

Trevor: This is a sticky one. The framing I would use is that in a pre-enlightened world, there is effectively magic and a divine interpretation of truth. In this post-truth environment, where it takes so much discipline to find your truth in your research, there has been a return to magic. If you think about it in less contemporary terms, in a tribe, some people created magic and were able to define what truth is 100%. Obviously, the narratives and stories that control our lives define those truths, whether it’s capitalism or neoliberalism. The thing I’m interested in regarding truth right now, and markets being able to reveal truth, is that truth is subjective in a lot of ways. This is an uncomfortable reality. What you’re seeing in capital markets at the highest level is the unwinding of the efficient markets hypothesis. Retail is effectively running over some of these value investors and Steve Cohen’s of the world. You ask, “What is going on?” The idea that we can stay retarded longer than you can stay solvent is quite poignant. With the Wall Street Bets thing, there are PE ratios, and then there are a bunch of Redditors who say, “No, actually those don’t matter.” Effectively, at some point, there is a tipping point where a PE ratio—which is just a meme—is a collectively accepted truth.

Jackson: By the way, when we say truth here, I think what we mean is consensus.

Trevor: Exactly. At some point, consensus tips. That is the opportunity. That is what great creative people do. You can be Karl Marx or the Chicago School Boys or whoever you want. You can come up with a narrative that people internalize, manifest, and turn into real actions in the material world. All of a sudden, that is the dominant form of our everyday lives and truth. You’re pulling me into cancelable territory, but it is really interesting.

Jackson: We’ve been talking a lot about it from the lens of the creative person. One of the first interviews I did was with Jacob Horne, and he noted a difference between speculation and gambling along the lines of your belief economy. Speculation is putting weight or stakes behind something that you want to be more likely. I’m curious how you’re thinking about that now. How do hard incentives versus soft incentives from the crowd push the tastemakers in a certain direction? One instrument for this is meme coins.

Jackson: I think a lot of people look at that and ask, “What is this? There’s nothing here.” What is a version of this that is good for creatives—for musicians, visual artists, and cultural tastemakers? What does it look like when regular people can be at home speculating on their favorite creator or artist in a way that goes beyond just investing in five likes?

Trevor: To set the state of play right now, Jesse Walden describes this current meme coin moment as the 4chan moment. There is an emergent Reddit or Twitter moment coming that will allow people to have these takes pseudonymously or anonymously, find community, and do all the things social media and those evolved “chans” enabled us to do. The current state of meme coins is a bunch of degenerates in the Wild West, effectively launching tokens that represent some idea or meme, with people speculating on how much attention they will get. The pros, in my opinion, is that we’ve created an instrument that allows creative and cultural people—or at least people aware of how information flows—to bet.

Jackson: Bushwick Girls or whatever.

Trevor: Right. Maybe it isn’t Bushwick Girls yet, but it’s the…

Jackson: Frank, the Telegram guys, the weirdos.

Trevor: Honestly, it’s like Fortnite kids.

Jackson: Yes.

Trevor: I think it’s really unsexy for people to look at a bunch of “spergy” Fortnite gamers betting on whether Elon’s AI companion will get enough attention. It feels bleak. However, it has opened the aperture. You can squint and see a world where, if you have an information advantage on whether skinny jeans will become popular again, you can express that belief and have the asymmetric upside that Bill Ackman has. Bill Ackman has takes. Why do we listen to Bill Ackman more than ever? Because he has billions of dollars from taking asymmetric bets. Why does he have influence? And why couldn’t the Bushwicks be…

Jackson: The internet may have memed that into being a real thing now.

Trevor: It actually probably does bang. If I were a single man, I might go out there and see who is as “brain-rotted” as me at the local bar. But what we need are attention instruments that can persist. The time horizons for meme coins right now are so small. Even if you think Mamdani is going to be mayor and there are 400 Mamdani coins, you’re not able to pick the right one. Even if you do, it might pump and rug in two hours. If you aren’t your average Fortnite enthusiast, those attention spans are too small for you to pay attention and win.

Jackson: On that note, I think most people who hear that example immediately think, “Obviously, it’s prediction markets.” Could you share an example of something better served by what you’re pointing to? Something more nebulous, rather than sports and politics, which are pretty deterministic?

Trevor: I think prediction markets are great for deterministic things with discrete outcomes.

Jackson: I think skinny jeans is a…

Trevor: Skinny jeans are a soft one. I think there are soft things that don’t have resolutions that everyone can agree on.

Jackson: Tip the scale a little bit.

Trevor: The question for me often is: if this thing is soft and squishy and we can’t get an elegant resolution, that is probably better served as a market where people can vote with their dollars. You can just see a real-time scoreboard. The illiquidity of prediction markets and the lack of fungibility create interesting challenges. Beyond that, bonding curves are magic. If you play with meme coins, it is a very regular occurrence for people to bet $10 and make $100,000 because of the convexity of those bonding curves and the way they are shaped. On the other hand, a 20% return on a prediction market is fantastic. A 2x or 3x return is fantastic. Most of the liquidity in these books—whether sports or politics—involves sharps that are so advanced that the edge is often 2%.

Jackson: It’s interesting you say that. Most people’s intuition is that a 20% return in a prediction market is the correct thing. They think turning $10 into $100,000 is actually a broken, novel feature of the market being weird and immature.

Trevor: Yes.

Jackson: You are almost saying the opposite. You are actually saying that is the feature.

Trevor: To me, this is as bizarre as Duchamp’s urinal. The broken and immature nature is the alpha. Artists are great at this. Duchamp said, “This thing you piss in is art.” That is not something a market would typically value. It is like the Warholian soup can. Effectively, bonding curves allow people to create a market and say, “No, actually, this is important.” Someone else might say, “That isn’t important. That’s slop.” But the creator says, “No, trust me.”

Jackson: This goes back to slop becoming punk.

Trevor: Totally. Great collectors have historically been able to take the other side of that bet. They say, “I want all these Warhols and this Basquiat guy that can’t draw. I think it rocks.” That is the opportunity on both sides of the market.

Jackson: I want to talk a little broader about speculation. It feels like gambling and speculation in culture are out of control, and people are starting to talk about it. Your big counterpoint cutting through a lot of this is that it is rational to speculate. All the crypto ideologues will tell you that “the trenches” are the death of crypto—that it’s all extraction and brainless. But they are wrong. From my point of view, the trenches are filled with people making very rational decisions about how to spend their time and energy to create the best outcomes for themselves and their loved ones. I also think they are underserved. Lots of people are building for devs, creators, or vibe coders, but not a ton of people are building for someone trying to turn $20 into $40 to buy Chipotle. There is obviously a silly, micro version of this, as well as the broader financial nihilism aspect. What are you seeing? What is happening for 20-year-olds, and why is it rational to speculate?

Trevor: I often get frustrated because the things happening for 20-year-olds today are the same things that happened when we were 20. We were young people who wanted to make a mark on the world, and to do so, we needed to prove ourselves. Often, we went to low-status domains to build up enough XP to get a shot. In parallel, you need to survive. Whether it was flipping sneakers for a generation or, for me, building eBay auction pages for my grandparents, you look for alpha. That is happening now. What’s really awesome is that a version of the internet I was drawn to as a young person, reading Kevin Kelly, is finally here. Whatever is happening, there is effectively an entirely online economy. People are spinning up meme coins and paying others in digital currencies all over the world without permission to manage a Discord or a Telegram or to bag work. It’s a totally different online behavior being paid in an online currency. I think it’s what people dreamed of.

Jackson: The irony is it’s not metaverse-shaped enough. As a result, people think that because it doesn’t look like Eve Online, it doesn’t count.

Trevor: Totally.

Jackson: Or it’s uglier than I wanted it to be.

Trevor: I had similar sentiments until I started talking to the people in the trenches. I’d ask, “Who are you?” They’re 21, living in the middle-of-nowhere Missouri, working at a bookstore part-time. While they are there, they “reply guy” Ansem with tokens he should buy. They are able to turn twenty dollars into a hundred dollars. They make twelve bucks an hour working at the bookstore. They could work eight hours, or they could just “reply guy” Ansem for an hour a day and be up 100 bucks. Absolutely, it’s rational. You should be doing those things. It speaks to what will come, but it’s uncomfortable because it’s new.

Jackson: And because we don’t believe in the underlying thing. To go back to the earlier point: most people in the world don’t believe being ahead of consensus is productive.

Trevor: It’s easier to be out of step when you’re already low status and perceived as déclassé. That is often where the alpha is. Of course, if it’s consensus, there is no alpha. Like any great investor, you have to be contrarian and right.

Jackson: A lot of great investors these days aren’t that contrarian.

Trevor: No.

Jackson: Which is maybe part of the problem.

Trevor: The momentum moment speaks to the tipping of this efficient market thing. What a lot of really intelligent investors have learned—we don’t need to name any of them—is that you can create media arms and shape consensus. You can make yourself right by having the hordes follow you. You can take gigantic bets, shape consensus, and be right. That is what Hollywood was so good at forever: manufacturing consensus.

Jackson: Hollywood forgot that, or they just lost their leverage.

Trevor: They’re still fantastic at it, but they’ve lost their leverage. What they had was a corner; they had a monopoly on distribution and media. Now that other people can do it, those with capital and media arms realize they don’t have to try to pick. They can just king-make and be right long enough to get an exit.

Jackson: It’s funny, when you say it like that, it sounds very similar to the new thing that’s happening.

Trevor: It’s exactly like that.

Jackson: One last thing on this. There is an excerpt from the piece I referenced earlier that Danco wrote, calling prediction the successor to postmodernism. He gets at something interesting I am curious for your take on. He says, “How early or late you are to something is now an essential component of your relationship to that thing. The timelines and reels represent what is going on and are increasingly about a single meta-topic: Are you predicting it or is it predicting you? This has become the main thing that you feel, and it is a complete break from the postmodern aesthetic where your consumption was wrapped in an unthreatening fuzzy blanket. It doesn’t matter what time of year you arrive at Whole Foods to buy strawberries; the farm stand simulacra is recreated faithfully. The prediction aesthetic is a new thing and rejects postmodernism: ‘I want to feel something, even if it hurts.’” This sits next to the idea that it is rational to speculate. Is there something else happening here? We all want to feel something again. Gambling is rational, but in a flat algorithmic society, it is also volatile.

Trevor: The idea that gambling is rational is provocative. I am aligned with a lot of that Danco piece, though there are other parts I am not. However, I think he is pulling exactly the right thread. One of the things you are pulling out here that I like is kind of dark. I remember getting on an airplane once and thinking I should look at my tweets to figure out what my last tweet would be if the plane went down. In the exact moment after that, I had this thought: “At least no more email.” We live in a life that lacks finality to an extreme. The thought at the end of my life was, “Damn, at least you would not be able to send an email ever again.” It was a bizarre thought, but it reminded me of the lack of finality in our lives more broadly. All of your ex-girlfriends and your eighth-grade friends are in your cell phone and in your Instagram feeds. We lack finality in a lot of our lives, and it is tough. Everything is so ambiguous; everything is frictionless. It is really comfortable to watch a basketball game and watch it resolve. Things that provide finality, like a scoreboard, are actually really comforting. So there is something about staring at a hyper-liquid perp and saying, “Damn, I’m up,” or “Damn, I’m down.” It is concrete. There is a difference between gambling and how people understand it. There is a misconception that people go to the slots in Vegas to win or to lose.

Jackson: To be in the machine zone?

Trevor: They go to be in the machine zone. They go to disappear. That is very different from being confronted with the finality of being up or down. Vegas does a good job of obscuring that.

Jackson: Is crypto more the machine zone, or is it more the actual simulacrum of finality?

Trevor: I find that the finality of crypto and the machine zone blur, which is concerning. People have recognized that there are opportunities to implement more of the machine zone into these things.

Jackson: But that is probably more common in fantasy sports.

Trevor: You could argue DraftKings or mobile games are places to get lost in the machine zone.

Jackson: But that said, I think Instagram Reels, for that matter.

Trevor: When I talk about the finality, the Hyper Liquid perp is compelling because I’m up or I’m down. But there is also the scoreboard of “I was right” versus “I was wrong” on a belief. In a messy world where everything is so subjective and ambiguous, Bitcoin hitting 100k was sick because I was rich, but it was sicker because I was fucking right. That is something people feel across the board.

Jackson: I love that answer a lot. I want to shift a little bit, though it is still connected. I’ve explained you to people many times over the years, and I always refer to you as the person who is most consistently ahead of culture. You are on the frontier of both technology and culture, which are orthogonal things. You were early on so many things: music, crypto, and Lil Miquela. There was a tweet from you in November 2020 where you said gaming is replacing music as the linchpin of emergent social scenes, and it makes everyone over 30 really uncomfortable. You were the first person to ever mention Politigram to me. Critically, the edge of culture partially means what is going to become consensus, but it also means “weird for now.” What do you think has caused you to develop such a nose for the weird, particularly the kind that actually resolves to consensus?

Trevor: It’s a good question. I will say I’m actively trying to be more “on time” now. This is important for people that I care about. This is a tangent, but I’m going to have a child in March. It provokes a ton of thoughts, but one of them is what you hope to offer them. To me, it is clearly curiosity. I don’t care what he is going to be into, but I want him to be deeply curious. I could probably psychoanalyze myself. I was a poor black kid who was good at sports but put in the alternative and gifted classrooms in middle-class white Iowa. I was consistently “othered” and wanted to find places to impose my will to create suffering for other people that made me feel uncomfortable. That is why I played football. It was partially to be good and loved, but also to break a quarterback’s ribs when I came off the corner. It was also the reason when we did times tables in math class, I was going to win. I wanted to feel good, but I also wanted to let you know that you are not better than me. That was also a sport. That’s what Nemesis was talking about. In some respects, I grew up in a pretty anomalous era. I’m 40 years old. I was 15 in 2000, and I lived through a moment that I have reflected on. I actually want to write something about it; maybe I should. It has been pretty detrimental to a lot of millennial men. Historically, I would watch Saved by the Bell when I was young. It was weird that the really buff jock was the cool guy, because I was 14 and the cool guy was the angular art guy. The coolest movie in America was Garden State. Zach Braff was a sex symbol. Pete Wentz was on the cover of Rolling Stone with his shirt off and was the coolest guy. When I went on LiveJournal or these dating apps, the mode was effectively: you put the five books you like, I’ll put the five books I like, and if you like the same books, we should date. I was like, dang, that may

Jackson: It has been correct, honestly.

Trevor: For nerds, candidly, it is. Then there was this cultural shift where you watched technology—the dominant cultural force—move from the nerds who talk to their shoes to the NBAs that took over. You watched dating apps go from writing books back and forth to Tinder, which is really normal. It’s like making eye contact at a bar: either we keep looking, or we don’t. Then there’s Instagram, where it was like, “Dang, you look good in a bikini. Lots of likes, yes.” I was knocked off guard because it was hyper-heteronormative, masculine, and sexual. I was taught that when I meet a young woman, I should tell her we should get married, and she’ll be my punk rock princess. Then there are Zoomers saying, “Hey baby, we should link.” I lived through this bizarre moment where nerds dominated culture. It was celebrated to go into a record store. I remember as a kid, I went to a Christian sleepaway camp in Iowa. My friend’s older brother was in an MxPx cover band, which is a niche pop-punk band. I watched him play and thought, “That was awesome.” I went to the CD store in North Park Mall in Davenport, Iowa, and said, “I want to get this punk rock thing. I think it’s something-FX?” They said, “NOFX?” I said, “Yeah, that’s it.” I got a NOFX album and got into punk. I went to the punk record store and said, “I like NOFX.” They said, “That’s fucking whack. This is what you should be into.” They pushed me into Fugazi and all this stuff that defined me. I’m still straight edge, I’m still punk. It was really celebrated to be deeply nerdy and inquisitive, so I wanted to win at that sport also. When I got into NOFX, I needed to get to grindcore. I needed to be at noise shows where they’re running vacuum cleaners through distortion pedals. That was the final boss I had to get to. I just don’t think that’s that compelling anymore.

Jackson: It’s interesting that I suspect if you surveyed five different generations, you’d get the pendulum swinging. It’s like a sine curve. One thing that’s weird about it is that while you’re living it, media and pop culture are lagging, so you’re sort of disoriented. I also wonder if being extremely into something is always going to win out. The extremely curious always wins out. I don’t know what stretch of your life you weren’t cool, but it probably didn’t take that long ultimately for things to resolve.

Trevor: That’s the interesting thing. Obviously, cool exists on different axes. But if you were to talk about pop cultural cool, it’s not clear to me that being super curious is the path. The people that I see winning the cool game right now…

Jackson: Maybe because those people are on time, to go back to your earlier comment.

Trevor: They are curious, but they’re curious about the contemporary moment and less interested in the historical context. I think it’s because things move so fast; it’s not clear that you need to have that. I remember the Charli XCX “Brat” moment. It felt like the last hurrah for the world that I knew. Here’s Charli, who I’ve honestly known since she was 16. We did some of our first sessions together in America in my bedroom in Silver Lake. She’s always been so knowledgeable, so bright, and so talented. She was finally able to make music that responded to people. More importantly, a lot of the Bushwick elite—the publicists, the people at Spotify—were able to say, “This is what it should be.” Someone making interesting, advanced, yet accessible music that references a culturally important moment, elevates it, and twists it. I remember going to look at the Spotify streams at the height of that. It was amazing to see. I looked and thought, “Oh, this song has 200 million streams. That’s crazy.” I just went to look at the most-streamed artists at the moment. Ahead of her was The Neighbourhood, a band that hadn’t released a record in a long time but made really play-listenable music. Or Charlie Puth, who, to me, is a savant but quite boring. I took it as an accomplishment. But I’m still well aware that there are tons of things most people have never heard of that are going to do far bigger numbers than that, which was able to capture the global Bushwick.

Jackson: You started that answer by saying you’re trying to be more on time.

Trevor: Yeah.

Jackson: It’s not surprising. Miquela is maybe the best possible example. But you’ve been early—arguably too early—to a lot of things. I have to imagine the honest version of you is way too early, and that’s awesome. But back to the commercial aspect: what is that feeling? Obviously, being on time has positive outcomes. It’s commercially resonant. Your things might actually get to go the distance versus just being the thing that the kids today are inspired by. I’m curious what the psychological thing is there.

Trevor: I think you also get old and tired. You hope that slows you down. Part of that Bob Dylan statement was terrifying.

Jackson: Yeah.

Trevor: I will probably go on a tangent again, but one of my best friends is Sam Teller. Sam and Elon were looking for a place for the Gigafactory. In parallel, around 2016 or 2017, I had been fascinated with the idea of getting all my favorite brilliant people to move to Iowa. I thought, “Man, it’s actually pretty awesome.” It has four seasons and is a two-hour drive to Chicago, where I’m from. What if we all went back and did what you did in Williamsburg or Silver Lake? You could own property. That evolved into a plan. I thought there was a way to reverse brain drain. It is kind of a cliché tech bro thing to say, “I’ll start a city,” but I thought we could work with economic development directors to get incentives to move there. Sam said, “You’re totally nuts. But we’ve been close to the people in Tulsa, talking about building a factory there. They’re really into these kinds of ideas. You should go talk to them.” Long story short, I went and met a guy named George Kaiser. He is a billionaire oil guy—an unbelievable guy. Famously, he was the first person to identify Obama and really back him when it was deeply unpopular. When I met him, he was in his late seventies or early eighties. He had built this Disneyland in the center of Tulsa with free buses going there. It makes me want to cry thinking about it. We went on a walk—he tries to walk multiple miles a day—and he talked about how he wants to make Tulsa a cultural center. He said, “I love what you’re talking about. We should do this. We should bring this here.” He told me, “I have all these consultants telling me what I can do to make this a center of culture. One of them said I should do an EDM festival. I don’t think that’s right. I think for a couple of hundred millions, I could move all of Broadway, theater, and ballet here.” I said, “You’re right. Don’t let these twenty-two-year-old McKinsey consultants tell you you’re wrong. You’re so right.” He’s brilliant. It is such an inspiration to me still.

Jackson: Wow.

Trevor: What I also saw in his eyes was a person saying, “What you want to do? I need you to do it, and do it now, because the clock is winding down for me.” It was deeply inspiring, but also somewhat terrifying because I’m someone who has endless ideas. I don’t know that it will just stop one day, but I do know that I’ll be confronted with a reality where…

Jackson: You’re running out of time.

Trevor: I’m running out of time. All that is to say, the Bob Dylan thing was terrifying, but also inspiring. Potentially, I could slow down and be right, and have enough resources to parallelize and do a lot of things to try to chew through this list.

Jackson: Yes, yes.

Trevor: Maybe you get satiated by the time the Grim Reaper comes knocking, or Bryan Johnson is able to extend me into perpetuity. But I think that’s part of the reason I want to be on time: this very human fear of the clock stopping.

Jackson: That’s quite an answer. On a lighter note—or maybe not—what are you obsessed with today? Outside of the speculation stuff we talked about, what are you obsessed with today that you think the rest of us are going to catch up on soon?

Trevor: Oh, wow.

Jackson: Is there anything else that’s been firing since? I know you were really interested in streamers for a little while.

Trevor: I’m absolutely interested in that. I’m trying to think of things that are maybe less obvious. I’m very interested in Telegram, not because of crypto at all, but because I’ve been able to stumble into these portals where teenagers seem to be very free. Because I’m anon, sometimes they let me in. There are these channels where they all upload MP3s and talk about the music they’re discovering. It’s really interesting to see the stuff they’re into and the revisionist history of what they think was important when I was twenty. Beyond that, these channels allow them to do what I was able to do on an internet that wasn’t so neutered. I often get really upset thinking about the overton window of what was acceptable on YouTube or any of these platforms, save for maybe X. I just don’t think Tyler, the Creator could release the “Yonkers” video right now on YouTube.

Jackson: Why?

Trevor: Because he hangs himself. I was playing a show in San Francisco with my DJ duo, and I was reminded of this band, Girls. They have a song called “Lust for Life.” It’s such a perfect encapsulation of San Francisco that I knew. It captures the 50,000 “art hoes” in San Francisco that used to exist. If you watch that music video, it’s an encapsulation of this radical band and these radical art hoes and queer kids hanging out in bathtubs, clapping and jamming. I forgot where I was going before the art hoes distracted me.

Jackson: You were talking about YouTube and what you can do.

Trevor: Right. I don’t even know if that video would be allowed because of young people’s nudity or whatever it is. But in these dark corners of Telegram, you’re seeing it. I’m watching them post, and it feels like Tumblr or blogs. There is horrible stuff, like “thinspo,” anorexia posting, cutting, and all the goth clichés of Tumblr that I saw. Those felt somewhat like rites of passage. I was misinformed to think that stuff had gone away and that we were living in this really progressive time. People are still dealing with all these demons. They are manifesting in the same ways I’m familiar with, but we pushed them to the margins where they still exist. What’s interesting for me is hearing them talk about culture and their experience. There are the clichés that I’m familiar with on YouTube, but when you talk to these people—and I’ve now kind of doxxed myself as a boomer in some of these groups—they’re able to give me unique insights. Maybe it speaks to a pendulum that constantly swings. The things I’m interested in now are these unfettered cultural spaces on the internet. It sounds silly and quite trite because a lot of us remember that, but most of the stuff we interact with now is mediated by algorithms.

Jackson: It’s really interesting you say that. The next thing I want to talk to you about has come up in so many conversations, including with Eugene Wei on the podcast. The consensus view is actually that there are no subcultures.

Trevor: On the internet anymore.

Jackson: The consensus view is that for whatever reason—lack of friction, so many other things—we have this total flattening. You’ve even talked about Iowa City being more culturally interesting than New York. I imagine that relates to something else you’ve said: New York is the soundstage for the Internet. Because of that, everything in New York is the other thing. Every Mexico City, New York—every coffee shop looks the same. It’s really interesting to me that you have found, obviously, for a while in Discord and now in this other place, where on the Internet can you actually not get in? That is what’s allowing for the fertile ground, the flowering, and the interestingness. By definition, it can’t be surveyed.

Trevor: That was one of my great gripes of the woke moment: inclusivity is incredibly boring. As the one black dude getting VC funding, I thought, “Actually, this sucks.” I think we should have boundaries. Boundaries are how you define society. People should be exceptional, and they should be of all kinds, of all walks of life. Absolutely. But we shouldn’t just let any old asshole in this place. Berghain’s not special because fucking suits get in. It is increasingly less interesting because some suits do get in. So I think boundaries are absolutely important. I want to write this thing in praise of exclusivity, but I was still the CEO of a company, so I thought maybe I shouldn’t get canceled. But I absolutely couldn’t agree more. Maybe that is at the core of what I’ve found. I have very fond memories of getting fake IDs to get into shows and go places. It made those experiences sweeter and richer. Maybe it’s all psychological, but maybe it is those boundaries.

Jackson: How do you find these Telegram groups? Is finding them sort of like getting into the party, or is it something totally different?

Trevor: I think what’s nice is I’ve developed a taste for the bizarre by doing the homework. When I buy artwork, I buy stuff that I love or that I hate. I often find that “I hate that” ends up being “I love that”…

Jackson: In six months. It’s doing something to me that’s causing a reaction. It’s not the middle.

Trevor: But I think ultimately it’s this narcissism of small differences. You think, “This is so close to the thing that I am, but watered down,” or “This is this thing that I hate.” I often find that. In some respects, the thing that got me into this Telegram group was some really wild, super ADD clip to an old breakcore song that I vaguely recognized, with just all kinds of anime and Wojaks and memes cut up. It was shared from this channel. You could see the forwarded thing in Telegram from “Armageddon.” I joined Armageddon, and it was all this. It’s people being blown up by drones and Ukrainian and Russian kids sharing Crystal Castles derivatives. You can just start clicking into the other things that are being forwarded. A lot of them sucked. Some of them were really interesting. I just keep clicking, and some of them get shut down.

Jackson: Curiosity is the engine, though.

Trevor: It’s about developing a palate for what is actually good. I don’t think a lot of people stop and think critically: “Is it good?” Often, people ask what they can do to be successful. You can simply stop and do the homework. Why is your podcast so excellent? You went and read all this stuff about me instead of winging it. Most people don’t have the time or the wherewithal to do that, but just don’t wing it.

Jackson: You also have to care. Clearly, the reason you can do this is because you care.

Trevor: That’s absolutely right. The Paul Graham Bus Ticket Theory of Excellence rings true. I do love this shit. I want to find new things.

Jackson: Speaking of exclusivity and some of the things you were early to—Friends With Benefits, DAOs, and building Dapper Collectives—I want to talk about the exclusivity part specifically. But before we get there, what stands out from that era? It was a mix of crypto highs and lows, building during COVID, and getting deep into Discord to build the cultural DAO. Now that you have some distance from it, what stands out?

Trevor: I’m still a member and still very excited about FWB. What stands out is that crypto was effectively speed-running the history of markets and organizations. It was clear to a lot of us that most of these trials were going to end up in the exact same place that we were. However, it was important with this new coordination layer of the internet to ask, “Maybe things go differently?”

Jackson: Let’s give it a go.

Trevor: Let’s give it a go. We can run these experiments pretty rapidly. FWB was interesting because I was still of the belief that people would fork things, copy ideas, and iterate on them. At that moment in the crypto cycle, we were more of an extraction layer. The idea was to come up with a primitive. This was before crypto was even remotely mainstream. You’ve only known networks where all the value accrued to the people in the middle: the VCs, the founders, and the employees. There is a world where you can create a network where the value accrues to the people who make it interesting.

Jackson: Yes.

Trevor: We created super dumb tokenomics.

Jackson: By the way, I got a message from you in the fall of 2020. That was pre-NFTs and pre-Web3. It was really primitive for people.

Trevor: The idea was just to create a spark. That’s been the bummer of Miquela and this. We said, “Here’s a primitive. It’s exciting for you to go expand on it.” And people were like, “Eh, we just want this. I’d rather just cash out on this thing and move on to the next thing that has momentum.” There is still plenty of room for people to create spaces where value accrues to the people who make them interesting. FWB is doing a decent job of it now. One of the challenges was that in the Gensler era, it was pretty impossible to accrue value to a token without getting into trouble. Their hands were tied, but now is a better time than ever.

Jackson: What a time to try to do a new version of that. It’s maximally commercial. On a related note, what is the relationship between community and exclusivity? Are those two things necessary for each other, or are they eventually at odds?

Trevor: It’s a good question. I haven’t interrogated it deeply, but on the surface, I think they live in harmony and tension. I like to optimize for tension. Using Bartle’s taxonomy of play, you need grifters to fuck with the achievers so they have something to play against. I often get frustrated when people talk about politics. They complain about AOC or Tucker Carlson, but you absolutely need those things. You need that dialectic. Communities are places where boundaries can emerge. They are like petri dishes. You have this primordial soup that turns into a community, and the community can spawn a lot more primordial soups that turn into boundary communities. I’m not totally sure how one emerges or begets the other, but that’s how I see it in my head.

Jackson: Can these things scale? Maybe part of what you’re saying is that scale doesn’t mean getting infinitely bigger. It means spawning off new replicas or remixes.

Trevor: At the height of FWB, I loved that there were people who only hung out in the trading channels, and then there were the parenting bros who were just sharing different parts of their lives. To me, it felt like there was the Greenpoint crew and the Red Hook crew. That is how I view it. Those communities should have active tension and outlets for resolution. That tension begets really important and interesting things.

Jackson: We talked about this a little bit. I met you when you had just started Miquela. It was very early on, and even then, you had two prescient ideas. First—and maybe this is controversial—the artist is the bottleneck. You were feeling around that, particularly on the music side. Conversely, something you said more recently is that celebrities are a team sport. It is interesting to think about that in the context of 2014. We are in a world today where we use the word “creator,” yet what we mean is the person who controls the distribution. We live in a world completely dominated by the individual who is the leverage point of distribution. Even if there are other creative people behind them, they have no leverage. Bands are dead. I am curious what was in your head back then. More importantly, it feels like things have gone in the direction you were a little worried about, even more so. Do you have hope for creativity feeling like a team sport again?

Trevor: I was responding to the idea of the artist being the bottleneck. There are diminishing returns, creating a “crabs in a barrel” dynamic that I don’t think is positive. I saw opportunities to create what I think of as “pass-through vehicles.” You could view Rihanna as a giant, rent-seeking middleman. Everyone is on set waiting, and she is smoking another blunt in the trailer. The idea is to have pass-through vehicles where value is created by an entity on behalf of the visionaries behind it—whether they are storytellers, choreographers, or technologists. Mickey Mouse is 100% an example of this. I like to pursue things that are spiritually exciting because they poke at something important to the creative community while meeting a specific tech moment. For me, it was less about the technology stack and more about ideas like zero marginal cost reproduction and aggregation theory. I felt these concepts were radically changing the world. I wanted to “judo” that—to use those forces against themselves to reward the people being dismantled by them.

Jackson: That’s cool.

Trevor: More often than not, when you start trying to do those things, other elements emerge quite elegantly. You start moving in that direction, and suddenly, companies are spending a ton of money on AR. All this infrastructure emerges that I can use. Spatial computing, digital goods, and generative media—these ideas I cared about just started popping up. Hugging Face emerged, and I connected with Clem. I thought, “This is fantastic.”

Jackson: Like 2016, I think?

Trevor: Yes, back when they were still a conversational chatbot tool.

Trevor: When you can identify things floating in the ether that are becoming dominant parts of our lives—whether in technology or culture—you can let the ball roll in the right direction. The challenge, as you highlighted, was that people interpreted our behaviors at the surface level as just “virtual influencers.” Because we were so attached to the bit of being in the story for the Miquela project, we didn’t want to break the fourth wall. Ultimately, we should have made it clear that we were building Disney, not virtual influencers. The reason people care about Manolo Blahniks is not because Carrie Bradshaw was just shilling them. It’s because she was rad. She made you want to be her, and you could be her by buying Manolo Blahniks.

Jackson: I have that quote in front of me, which is awesome. Unfortunately, because of the timing, people took Miquela as a gimmick. It was almost as if it could never go further than that because of how new it was. One of the first things you ever said to me was, “I’m building Marvel for pop stars.” Specifically, you’ve talked about how it ultimately came back to the narrative.

Trevor: Certainly.

Jackson: One challenge of the modern Internet is that there is very little linear. Everything is constellation. It is fragmented world-building. You are speaking to a moving army, and you are moving while the army is moving. One thing that came up when I was talking to Gabe was this piece Brad Troemel wrote called Athletic Aesthetics.

Trevor: No, but I love Brad.

Jackson: It’s worth reading. I’ll send it to you after. He describes where we’re going with this. It isn’t really about what you’re saying or making as a creative or influencer. It is just about having the audience keep up with you. Yet I think you were really thoughtful about trying to tell true narratives with Miquela. I’m curious what you think great Internet storytelling looks like now.

Trevor: There are some contextual things there because it’s easy for me to forget. I started making Miquela in April of 2016. There were still chronological feeds. We were pre-Trump, so there was a lot of adoration for tech. When Miquela first started getting traction, Dazed and all these outlets were saying, “Look how fucking cool and interesting and smart Trevor is. Visionary guy. Wow.” The Trump moment really inverted the politics of celebrating technology. The change from chronological feeds to algorithmic feeds presented a wrinkle for us as storytellers. The thing I always try to elicit with people who are hiring is that this is panel-by-panel storytelling. It is the same as comic books.

Jackson: People are keeping up with us.

Trevor: It is the same as a comic book where you are reading panel by panel. How can we create a behavior where people learn to start from the beginning? Can we do some of these things? When you go buy The Sopranos, you don’t just start the last season; you kick it off at the beginning. By the time we were starting to get some of those things worked out, it was like, “Surprise.”

Jackson: No way.

Trevor: Oh, wow. Okay. So the challenge shifted to how we can participate in this more dynamic social media that brought stars like Cardi B to life. She is so good at a clapback. She is the opposite of Cary Grant to me. He just stands up and performs the things that were written. Her whole skill is, “Fuck you.” Cardi B says, “Fuck you, bitch. Suck my dick.” And you say, “Yeah, wow.” You can’t script that. That is amazing. That is Cardi. And so the challenge begins.

Jackson: She is a highlight reel, almost.

Trevor: But also, how can you be dynamic? In borrowing things from Hollywood and game studios—where they are working on long time periods and producing a finished product—can you instead try to develop systems that can be dynamic? Weekly bibles, all those kinds of things?

Jackson: Almost interactive.

Trevor: Almost interactive.

Jackson: This is related-ish to Miquela and the experience of being a touring musician or a person on the road. You said one of the things you were trying to do with Lil Miquela was create a model where people who were disenchanted with being public figures could share their work without having to deal with what it means to be a public figure. You noted that it can be miserable; the court of public opinion will try to destroy you as fast as they’ll champion you. The idea that you could create this avatar to share your creative wares was really intriguing to me. Then there was another tweet I found, I think on the day Bourdain died, where you said: “What strikes me most is his passing while on the road working. The loneliness I felt while professionally DJing was such an isolating experience. How do you vent to anyone about a job or a life that is viewed as the dream?” You’ve since been a touring musician after you wrote that—granted, with a buddy. What has your relationship been like to touring, especially with those musical bookends in your life? Do you have any reflections on that idea?

Trevor: Life is largely a game of luck to me. It’s funny how you stumble into things. I was really lucky in that when I turned 19, I dropped out of university. They created this software called Final Scratch Pro, where you could install Linux and then DJ with MP3s on traditional turntables. I thought that was crazy. Then Serato came out and made it easier. It created this dynamic where I was in San Jose. That’s a long story, but I ended up going there because I wanted to be close to Silicon Valley.

Jackson: This was for school, for football?

Trevor: Yeah. I went to San Jose to play football and ended up hating it for lots of reasons. I won’t go into that. But I was very lucky to be in San Jose at that moment because I was interested in tech and business. I was reading a lot, and I was frustrated that I couldn’t raise capital to start a business. I was reading books about brand building and thought, “Man, I’m actually pretty good at that.” I had pirated Photoshop and Illustrator. I knew how to build a website. I could do that part, but I didn’t have the capital to create a product. Then Serato came out, and I realized I could download MP3s for free, make myself the product, and brand myself. I created a MySpace and a blog, and I did all these things. I think I was also very lucky in that I’m very good at being isolated. I can sit in front of a computer for 10 hours a day and get lost in it; I’m very comfortable with that. As I became quite popular, DJing was a lot of that. It was just me driving to the airport, parking, walking in by myself, sitting on a plane for six hours, saying hi to a promoter, going back to my room, preparing a set, and playing the show.

Jackson: It’s a barbell: almost complete isolation, and then you’re in a mob.

Trevor: Yeah. But the bizarre thing—and I don’t think I was able to elicit this with the Bourdain tweet—is that the really difficult part is getting all this attention. It’s almost like empty calories. You’re the center of attention, and everyone is looking at you, but they’re kind of looking through you.

Jackson: It’s like, “Hey, monkey, dance.”

Trevor: Kind of. There are millions of times I’d be DJing, and someone would ask, “Hey, do you know where the bathroom is?” It’s a nice reminder. It’s like, “Yeah, I work here. I’m an employee.” You can think of yourself as talent, but you realize it is that way.

Jackson: Sorry.

Trevor: You encounter very bizarre things. This is maybe too crass for the pod, but you’d be DJing, and there would be some rich guy in a booth. He’d say, “Hey, man.” Then he says, “I don’t know what you’re doing later, but I’ve always wanted to see my wife fuck a black guy.” You’d just react with, “What?” I think he understands you’re contained here. You are effectively the monkey on stage. You say, “All right. Very beautiful. Not interested. Thank you.” It’s this very specific dynamic.

Jackson: He doesn’t treat you like a person.

Trevor: No, you’re dehumanized, but you are also getting all this attention. It’s very hard to come back to your friends and say, “I’m living the dream.” I was twenty-one, flying all over the world to play music and making more money than my friends who were doing investment banking. But I was also deeply unsatisfied in a lot of ways. That was the really tough part with the Bourdain thing. You could ask people what the dream job is—traveling the world, eating the best meals, meeting amazing people, and being famous. I think it can be really, really tough.

Jackson: What did you learn about identity through the Mikayla process, either running that account or thinking about the different personas you guys were going to create?

Trevor: I’ve expressed this a little bit before. Some of the seedlings of Mikayla stem from me being really intrigued with this idea that I could make a song, put it on SoundCloud or YouTube, and have someone talk about it. I really feel bad viscerally. You see one comment with no likes saying, “That snare sucks.” You think, “Damn, maybe I should change the snare.” I had also been able to live as a little script kiddie hacker in these spaces on IRC as a kid that were clearly very white. There were white people saying incredibly racist shit in chats, but I could live inside of them and embody this thing that was different. There was this idea that it would be interesting if people could effectively embody another person physically on the internet. You could feel what it means to have someone say, “You’re ugly.”

Trevor: What was bizarre is that the working model was very real. I’ve never been a woman on the Internet, and never in my life have I thought I should change my eyebrows. But people would say, “Look at her ugly eyebrows,” and I’d think, “Damn, should we change the eyebrows?” It must be crazy to be a woman on the Internet. People will say a lot of things about this podcast, but I doubt they’ll critique my eyebrows. There was a lot about identity. One of the things we tried to explore was this idea of post-physicality and us being post-physical creatures. Some of the best moments were getting messages from young people saying, “I’m 13 and non-binary and live in Missouri, and no one believes that I’m real. You’re not real, but you’re doing amazing things, and that inspires me.” That is so cool. When I look back on it, making employees rich and making fans of Mikayla feel seen and heard—the way X-Men was for me—that was always the dream. I was this weirdo kid thinking, “When I get my mutant powers, they’re all going to pay.” That was easily the best part.

Jackson: That’s awesome.

Trevor: With Mikaela, it was gnarly. We walked first through the door and caught all the arrows. I remember reading that and thinking it was so true.

Jackson: I think you’ve done plenty of that, too, in your life.

Trevor: Having a child has reframed a lot of this stuff. Before, it was just me against the world. We haven’t talked about my personal life, but it’s always been me against the world, and that’s been very liberating. There wasn’t a lot of collateral damage. I have my mom, so I could take risks because we were already at zero. There was nowhere else to go. Either Mom has a retirement plan, or she doesn’t. Let’s take a big swing. If I fail miserably, I was already supposed to be here.

Jackson: I want to talk a little bit about music. There’s an article on Soft—do you call it Soft? The South Florida Trance Team? The quote is: “We want to not think too much with our brains and just feel the music with our bodies.” You’re a brilliant dude who can brain blast with the best of them. Yet, both conceptually and physically, you’ve always done a really good job of navigating both high and low. I think that’s part of what’s in that quote. I’m curious how music has helped your ability to move between those spaces.

Trevor: It’s interesting because we’re a bit trolly, but there’s a tension that’s a product of being born when I was born. I never had anything. But I was very lucky that it was very chic to have nothing. The song “Common People” could blare through a nightclub when I was twenty, and it was very real. A lot of the rich kids wanted to be common people and go to the shithole dive bars and hang out where me and my actually poor friends were playing records. It was comforting in that I could just thrift clothes and still participate in high-status Los Angeles society. In parallel, it was a bit heartbreaking. One of my best friends when I moved here was a guy named Adam Moonves. His dad was Les Moonves, former COO of Viacom. We had tons of amazing interactions just from being in proximity to him. I remember us hanging out one day, and he told his dad, “You should give Trevor a radio station. He’s good at music.” I thought, “Honestly, I would crush a radio station.” I had no idea how to sell ads, but just being in proximity to people who could think that big was really comforting. But I also think the ability to develop a palette, to understand how some of these modes of thinking are superpowers, and the desire to pass them down was really interesting. It’s the same answer I’ve always had, but being good at music—and I’m realizing this now—provided me a lot of power because of exclusivity. Because I was the DJ at hot nightclubs, I would regularly have people walk up to the booth. They would say, “This is my business card. I’m a producer at Warner. I’d love to come back here sometime if you ever need anything.” I’d think, “Dang, that’s a power broker.” Then he’d say, “By the way, we actually need a DJ for a movie we’re in. We could definitely get you paid well.” I’m like, “Bet. I will text you and you will get back into the nightclub next week.” If you watch The Haunting of Molly Hartley, some weird horror movie, there’s a party scene that I got paid $5,000 to DJ for one night, back when $5,000 was an insane amount of money. For me, music provided a path for a low-status person to create something of value or scarcity that people of high status wanted. The ability to transact that would be a really crass way to view it, but I think that was increasingly important. Getting a job at Spotify early and being able to get people in North America onto Spotify was really cool. Lewis Hamilton or whoever wanted Spotify, and I was like, “Bet, bro, I got you.” They would say, “Thanks, man. If you ever need anything…” and honestly, I might. That’s probably a pro tip for anyone out there looking to do things: figure out places where you can create leverage and provide access to people of high status or high power. You can call in favors when the time is right and skip steps.

Jackson: This is, I’m sure, a can of worms. We don’t have to spend a lot of time on it, but I found myself watching and wondering.

Trevor: I don’t know.

Jackson: I worked at UMG ten years ago or longer. Music just feels like it structurally wants to be free, at least with the internet, more than maybe any other medium. If that’s true, is there a business model for music? Is it just real-world scarcity? Is it patronage? Do you agree with that at all? If so, does it tie into some of this other speculation stuff you’re thinking about?

Trevor: Definitely. Music maybe more than anything else. I always wonder if that was a function of file size.

Jackson: File size is obviously a huge part of it, but it’s more that you hear a song once and you’re not like, “I’m good.” You want to hear it more. Before you like it, you need to hear it five times.

Trevor: Good point.

Jackson: When you watch a movie, you’re like, “I saw it, I’m good.” So it has a little bit more of that feeling that you should have to pay $20 to see it once. Listening to a song is a way to build fandom with the artist.

Trevor: Obviously, I wrestled with this for a long time. Immediately, it’s not clear to me as a business model that makes sense for selling music. One thing that’s been great for SoFFT is that we’ve built a fan base that deeply cares about music, and they buy our stuff on Bandcamp. I make far more than I ever could have imagined through Bandcamp. Again, I can’t live in this home on Bandcamp, but I don’t have a good answer for that. What is starting to emerge is that if you can build universes, there’s lots of opportunity to sell things. The brightest of the bunch understand that. Whether they’re capable of doing it is a whole other task because it’s taxing. It’s not what you love. It can be really hard. What I think was most impressive about Charli in that Brat moment is that she’s so smart. She recognized the game on the field and was able to commit and do the thing. We’re not close—it’s daps and hi’s—but when I see her do big television adverts or Converse things, I’m like, “Get it.” You probably had to sacrifice a lot of emotional discomfort to commit to this bit, this story, and this world that you were building when you’re just a really gifted songwriter.

Jackson: On a much smaller level, this is even just the artists who love to make music and don’t want to tour.

Trevor: Totally. I’ve always tried to be a realist about this and told a story to musicians about when I was 16, playing in a hardcore band. There were two drummers, and one had a car. We were like, “He’s the worst drummer, but he’s got a fucking car. We can go play shows in other places.” So he’s the drummer.

Jackson: A lot of life is like that.

Trevor: In some respects, if you want to play shows, you gotta have a car. If you want to be a famous musician, you got to make the fucking TikToks.

Jackson: I got a handful of miscellaneous things before we wrap up. First, from our friend Alex Zhang. His question was: Is there any point where culture actually prices into tech and business in a real way? Beyond just narrative and marketing, does it actually become a core business driver?

Trevor: It’s a tough one for me. The immediate answer is I don’t know, but I understand that I probably think about culture in different terms. My friend Julie Young, who’s brilliant, understands culture more than almost anyone. I don’t think she would ever describe herself as such, but she is so adept at identifying things that matter, like OMG LOL dolls and those blind boxes. She was so good at identifying that. I think Silicon Valley will be able to weaponize the young girl to shape meaningful societal change in the way that Hollywood’s been able to. I think there’s a path there. It’s still not clear to me that Hollywood has been able to actually shift from the early adopter crossing the chasm model of technology and software adoption. I do see really intelligent investors thinking about that and trying to go downstream to shape the hearts and minds of young people, especially young women, and then having that work upstream. But for now, I still see: go identify early adopters and then work upstream. I’m not a buyer holistically of that just yet, but I imagine I have blind spots because I am somewhat of a fucking hater as well and probably refuse to see some of these things people are acknowledging.

Jackson: I promise this is not a gotcha, but you once described your involvement with him as, “Kanye collected me for three months.” And then you also said, “He’s the greatest of my time. He’s a genius. I will ride with Ye forever.”

Trevor: It’s tough, but yeah.

Jackson: Maybe especially up close, since you got to experience it, what is so magical about that guy?

Trevor: I’ll say what was magical for me. It’ll be a little bit of story time. I got a text message from a big venture capitalist that said, “Hey, Kanye’s doing some investing. Told him about you. He really wants to meet you. Is it okay if I give him your phone number?” I’m driving to the Beverly Hills Hotel counter downstairs—honestly, the spot—to try to win back my ex-girlfriend at the time, who was with me through the startup thing. You can understand how partners who are dealing with running startups can be miserable. She was like, “I’m not into it. I don’t want to date this version of who you are.” I’m like, “Yeah, cool.” I go to breakfast, and by the blessings of the Lord above, I’m like, “Hey, this is insane. I’m sorry, but Kanye’s texting me, and he says he wants to meet right now. Would you be down to hang with Kanye?” For added color, it was right after the MAGA moment, so there was the kind of first break of Kanye. She was like, “Yeah, of course.” So I’m texting Kanye. He’s like, “I want to meet right now. Are you in LA?” He’s like, “Yeah, I’m in Calabasas. Where are you?” I’m like, “I’m at the Beverly Hills Hotel.” He’s like, “Cool, I’ll be there in 30.”

Jackson: He came to you.

Trevor: We finished our meal, and I got a text: “I’m out front, silver Tesla.” I said, “Cool.” I told him I was with my ex-girlfriend, and he said great. We climbed into the back seat of the Tesla and dapped him over the top. There was a friend in the front seat. What I love about Ye is that he is like a thirteen-year-old boy who is so curious and excited. He was so excited to meet me. It was bizarre. He said, “I’m just excited to hang out with you. We can do whatever you want. If you want, we can go to Venice.” I think he thought tech people like Venice. I told him I didn’t need to go to Venice. He said we could go wherever, so maybe we’d just go for a drive. We started driving, got on the 405, and he said, “If you want, we can go to Calabasas.” I said, “Okay, cool.” We were just talking. My girlfriend at the time was in urban planning and an architect. He said, “You’re an architect? I love architects.” We started talking about that stuff and geeking out. He said we should get her to work on some stuff. I told him about Brad, and he said, “Kim just invested in some nuclear stuff. I want to be investing.” It was infectious. We went to the studio, and he played me a bunch of the record with him and Cudi, and we talked about it. His homies were there challenging him about the MAGA hat while he was there. It was very transparent. We went to sit down. I had been wearing these Vivo Barefoot shoes that I am still very into. He asked, “What are those?” I explained they were barefoot shoes and that I really fuck with them. He effectively went on this anti-nostalgia rant, which is one of my rants. My ex has seen me give that rant a million times. He said, “I love some new shit. I get so tired of seeing these fucking same old clones of Forces or whatever.” She just looked at me and said, “You guys deserve each other.”

Trevor: You guys deserve each other. What was so special about Ye was that boy-like energy. I watched him meet Tyler, the Creator, and tremble. In this moment, Tyler is not the Tyler who has won Grammys; Tyler is this kid with a kind of cool thing. Kanye is shaking, asking him questions, really in awe. It’s like, “You’re the guy. You are Kanye. This is just Tyler.” But he approaches so many people that way. He is so curious and so funny. At the time, he had bought all this property in Calabasas and wanted to build a new Rome. He told me, “You can be the tech guy—the clothing guy, and the tech guy.” We flew to Italy to meet up with Vanessa Beecroft. I’m an insane Kanye fan, and we were at the private terminal at LAX, getting carted onto the plane. We flew ten hours next to each other; he was showing me stuff, and we were talking. I was giving him ideas. The thing I remember most about Kanye is that I’ve always had ideas that are crazy. You can’t say them out loud because they’re not feasible. With Kanye, it was this constant process of having an idea, thinking, “That’s nuts,” and then realizing, “Kanye would want to hear that.” I remember sitting at Axel Vervoordt’s castle in Belgium with Vanessa Beecroft, Tremaine, and a bunch of other people he wanted to be part of this new Rome to build this world. They were going through the designs of what the property could be. It was up against a mountain, and there was an airstrip there. I remembered the X-Men cartoon where they would take off—a mountain would open up, and the Blackbird would come out. I thought, “That’d be sick if the plane came out of the mountain.” I told myself I couldn’t say that, but then I thought, “Kanye would want to hear that.” So I said, “Damn, Kanye. What if the airstrip came out of the mountain?” He said, “We gotta do the out-of-the-mountain.” The architect looked at me like, “We’re not going to get the rights to have the plane come out of the mountain.” Kanye said, “I’ll call Donnie. I’ll call Donald. We’ll figure it out. The plane’s coming out of the mountain.” Honestly, it rocks. It’s just cool to be around someone who is so unafraid to be unabashedly nuts, say things, and get an eighth of the way there. There was obviously a ton of other madness. While we’re sharing all the alpha with Dialectic—and because it’s less precious now—there was a moment where he wanted to buy Brud and have me run Yeezy. Imagine going to Sequoia Capital and saying, “So here’s the thing. How do you feel about a Kanye West exit?” They asked, “What is the company?” I said, “It’s an LLC. He owns 100%.” It was amazing. Kim was brilliant, sweet, and so good with him. That part was tough for me because we’re not homies. I was part of his life for a moment, and then the acquisition didn’t go through, and we stopped talking. Four phone numbers later, we didn’t talk. But it was really incredible to watch Kim with him and the kids. All of it was inspirational in a lot of interesting ways. I can be quite complicated, and he’s complicated in a more extreme way, but in similar ways.

Trevor: It was interesting to see what worked for what he had built around himself and what didn’t.

Jackson: What an amazing thing to be someone who inspires other people to say their crazy ideas.

Trevor: It was like a blessing. It really was super special.

Jackson: Having watched the last few years, do you have any sense of what happened?

Trevor: Kanye is so good at intuiting what matters and where there is strife or problems to be addressed. He’s not very articulate verbally, and I think people struggle with that because you have to take a whole rant for 30 minutes. When you dig through it, you think, “Whoa, actually that was really brilliant.” But it’s tough to parse. In parallel, that boyish wonder is surface area for attack. I think there are people around him with good intentions. Rick Rubin was probably someone who, in a very unpopular time, had more libertarian beliefs in the music business. When people see Rick and Tyler Cowen do a podcast, they think that’s crazy. I don’t think it’s that crazy. If you’ve been to Malibu, there are a lot of people who are kind of hippies who lean more libertarian. They do classic lib. My read was that someone like Rick was able to show Ye what ideas are really important to him. Ye’s boyish wonder and curiosity were met with people who were able to exploit it for other means. It’s a tradeoff. What makes him so special is this ability to absorb, be deeply curious, take things at face value, and be childlike. But I think it also has caused him a lot of pain, and that’s hard to watch. It’s tough because some part of me doesn’t want to say that because it makes me a Kanye apologist, and he’s an adult. But spending time with him, I am aware of how impressionable he is. That is tough to watch. That’s a really hard thing for people to grok. Someone so influential, powerful, and wealthy—someone with so much bravado and confidence—can also be someone who will take something at face value. For example, Tyler, the Creator was so much smaller than he was at the moment. But Ye recognizes the aura. He can see you for who you can be and what you’re bringing to the world, not what you are. That combined with the boyish capabilities can be a dangerous combo.

Jackson: When you first started talking about it, obviously a lot is clearly different, but the other person who Kanye knew—who has a boyishness that can be really frustrating to me but also manifests so amazingly—is Elon. It’s interesting that there’s some similarity.

Jackson: I have a pair of separate ideas from you. One, you say a whole generation has come of age not knowing real criticism. I think that was a random tweet. And then: computers are creation machines; iPads are consumption machines. When you think about the next generation, are you worried? Are you hopeful? What are you most concerned about?

Trevor: I am long humanity, so I think we’ll figure it out and we’ll be fine. It’s funny, I randomly delete so many tweets. You found a lot of these ones.

Jackson: There were a lot that were deleted.

Trevor: Respect.

Jackson: I’m not holding you to it either.

Trevor: I lifted the consumption one from some book I was reading. I really do believe that. I would love for my child to spend time at a computer, hacking at stuff and trying to make things, versus passively engaged, consuming something. I’m really not that worried. If anything, I’m very inspired. Making sense of Gen Z has been beaten into the ground. Regarding Gen Alpha, there’s an artist named 2hollis. His mother, Catherine, is someone I’ve known for a very long time. Her other son is in a hardcore band called Start Today that I love. When I look at 2hollis and see what he’s built, it’s incredible. I look at his Instagram and he’s posting pictures of himself on main looking incredible with a song by 7 Angels 7 Plagues. That is a deep-cut hardcore band from Milwaukee, I believe, that I was into when I was 15. I think, “Man, there are still people that are deeply curious, and it is being rewarded.” I think that’s fantastic. Both of them are kids. Start Today and 2hollis—check them out.

Jackson: I know of 2hollis from Drew. It’s crazy when both your kids are that. Mom’s pretty cool. On a slightly related note regarding optimism, something is happening around the populist stuff—obviously, Zohran lately. You’re a weird anomaly for so many reasons, including being sort of a techno-capitalist and sort of an anarchist. I know you were a big Bernie guy. Any views on what’s happening and where that’s going?

Trevor: I feel like I’m taking crazy pills sometimes. It feels like a status quo issue: people who are comfortable with the status quo and people who aren’t. People can cut that a million different ways. To me, the Mamdani thing is not that dissimilar from any populist thing. Watching Marjorie Taylor Greene say things she’s saying in the last two weeks, people resonate. People are frustrated. That’s the hard part for me with mainstream DNC politics. People are very comfortable and they’ve had very good outcomes from the way things are, but most people aren’t. I really struggle with that. That’s a whole other rant about growing up in Iowa, seeing what most of my peers are doing, and having multiple friends’ parents kill themselves post-NAFTA. We had an Oscar Mayer plant, an Alcoa plant, and a John Deere plant. When those plants left, the hurt was palpable. People who were making 100 grand or 70 grand a year and could provide for their children in unimaginable ways, all of a sudden couldn’t get a job at 7-Eleven. I remember that feeling. Funny enough, the first time I used Claude 3.5, I felt that feeling. I thought, “Oh my God, this is going to displace a lot of people who move symbols on screens.” What white-collar NAFTA could look like is still really scary to me. Hopefully, people smarter than I are trying to figure out how to mitigate some of those pains.

Jackson: Conversely, we talked about this at the beginning. There are lots of potential black pills, yet you continue to lean on optimism. Why?

Trevor: I’m just a believer in the human condition. Maybe it’s silly and quaint, but I believe in us, and I believe in the goodness of us. To lose that is almost worse than death. I’m having a child, and I constantly get asked, “Are you going to have children?” A lot of people say, “I don’t want to bring kids into this world.” I tell them, “You have to bring kids into this world. We need people like you, who are good people, to create children raised right with the right moral compass who will go and make this place better.” Of course, everyone has their own beliefs, and I don’t want to push them on anyone. But anyone out there who is morally righteous and a virtuous person: crank them out. We need good ones—the good little ones fighting the good fight.

Jackson: On an old Young Skeeter blog, you wrote, “The only peaceful constraints I’ve known in this world are music and friendships that allow for freedom.” What did you mean? Any reflections on that? Do you even remember what you meant?

Trevor: I definitely don’t. That blog was such a great outlet for me for such a long time. I felt so much discomfort in my life, and music is again this kind of divine bridge. You can hear something and feel something. Loud music and flashing lights are so simple, so primal.

Jackson: That’s kind of what I was getting at with the high and the low, right?

Trevor: Yeah. The monkey in me is just like, “Wow.” Everything is fine. As for good friendship, because of the circumstances of my upbringing and my kooky family, I have been able to build different familial units. I’m always reminded around Thanksgiving that my Friendsgivings have been the most important Thanksgivings in my life. What a blessing. There is a DJ Boring song where he samples Bob Geldof. Bob Geldof is a popular figure; he did Live Aid back in the day to help Africa, getting all the musicians together. As I understand the story, his wife was an MTV presenter. She interviewed the lead singer of INXS, and they fell in love. He was a heroin addict. Bob had two daughters with this woman. She ended up overdosing, and the lead singer of INXS accidentally hanged himself. Later in life, Bob’s daughter Peaches—who I knew a little bit from partying in LA—also tragically passed. He is sampled in the song talking about grief. He talks about grief and life. He talks about being on holiday with his family, looking out from a dinner table, and seeing his grandkids and his kids dance. That is all that matters. It’s incredibly poignant. For whatever reason, that met me at the right time in my life. That is all that matters. It’s like a post-Hoffman me. In my startup days, my best friend Harley would ask, “You want to get coffee at 1:00 on a Tuesday?” I’d say, “No, I have work.” Now I say, “Yeah, let’s get a coffee.” I can get back to work later tonight. Spending time with loved ones is really important, so make time to do it. It’s so obvious, but it took me a while to get there.

Jackson: You brought it up a few times that you’re having a child. How do you hope to be changed?

Trevor: It’s changed in so many ways I can’t even imagine already. We read an ultrasound and they were showing parts of my son. They quickly moved over his brain. This thought of, “That’s the brain. You have to protect the brain,” was a primal thing where I was like, “I gotta protect the brain. I’ve got to protect that thing’s brain.” I’m really excited to be blindsided by those things. There’s the obvious stuff. I’ll never get to experience ice cream again for the first time, but I get to do it with him. That’s gonna rock to be like, “Wow. Ice cream. Welcome to fucking ice cream, dawg. There’s so many cool ice creams for you to enjoy.” That’s gonna be great. Other than that, I’m just excited to be blindsided by the whole thing. I can plan all I want, but there is no way to prepare. I will say, while we’re sharing nuggets of wisdom on this thing, I go to this conference that I love. It’s kind of an unconference where you sit around and talk about cool stuff. I go to the dad session every year and have been going for close to a decade now. One year, a gentleman was talking and asked, “How many of you think that you’re a better parent, a better father than your father was?” A bunch of hands raised. A bunch of hands didn’t raise. Then he asked, “How many of the hands raised have kids that are older than 18?” They all put their hands down. They said, “Yeah, when my kids were seven, eight, nine, ten, I was 100% a better father. By the time they’re 22, I don’t know actually.” The person who brought this up highlighted that everyone in the room were world beaters. You’re doing incredible things, impossible things. You make the world bend to your will. He said, “The thing I think is important for all of you younger parents is that parenting isn’t carpentry; it’s gardening. You may want this thing to be an oak tree, but it’s a lemon tree, and you just got to make it the best lemon tree it can be.” I was like, “Wow.” So I’ve just tried to sit with that. It’s easy to have expectations of what my boy can be. He’s in the 95th percentile right now, so I’m like, “We got a chance.”

Jackson: A chance at the league? Do what you couldn’t do?

Trevor: Do what I couldn’t do. But again, if he wants to be, God forbid, an artist, he can do that too.

Jackson: One last thing. You actually mentioned it. I didn’t know it was going to be a land project, but there’s an old email of yours that I followed the link on, and there’s a domain called actuallycerulean.com. The language on the website is just this: “Okay, I see you think this has nothing to do with you. You go to your closet and you select that lumpy blue sweater, for instance, because you’re trying to tell the world that you take yourself too seriously to care about what you put on your back. But what you don’t know is that that sweater is not just blue. It’s not turquoise, it’s not lapis. It’s actually cerulean.” Some people obviously know the reference, but what does that mean to you?

Trevor: It’s a quote from The Devil Wears Prada, which is one of my favorite films. But to me, I think it reflects the sentiment I’ve probably brought up far too much in this podcast: there are people that introduce important ideas into the world, and they can be discounted. They can be made to feel small or unimportant. I would much prefer a world that celebrated cerulean, because it’s not just blue. It’s actually cerulean.

Jackson: Trevor, thank you.

Trevor: Thank you very much, Jackson.

Jackson: This is great.

Trevor: A pleasure.