Very Fine Day #63: Kyle Chayka
"There's always a meme, there's always a new app, there's always a shift that's happening."
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“OK, you pay the New York Times your subscription of $300 a year, whatever, there's no way that you can talk back to The Times. There's nothing you're gonna get out of that. There's no way you can reach the people who are in charge, save for a letter to the editor or something. And that is kind of frustrating after a while.
It's like: I'm paying a lot of money! I really identify with this media brand! Why do I have, functionally, no interaction with it, besides just consuming what they make?”
The 2010s felt like a lot of things to a lot of people, but to me they’ll be a decade of media excess. We’re past that now. No more parties on the roof, no more company-wide Kanye West concerts with an intro from, I don’t know… Jeff Dunham the puppet guy. We have run out of cute puppies to surround celebrities with, and counter culture isn’t something worth talking about anymore. The cold drip is still on tap, but you have to get in before it runs out. Be wary of the pizza party - it rarely coincides with good news. And while the dream isn’t over, you were chosen as one of the many to be shaken awake. Welcome! The water’s warm.
But there is progress to be made. And innovation, too.
Kyle Chayka, our guest today, is the co-founder of DIRT, a newsletter and (stick with me) media company that funded itself solely using NFTs (please, continue to stick with me) and recently raised $1.2million to expand. It is very interesting to me - even if you don’t understand all of the words and workings just yet. It is important to encourage new things, new seeds, new attempts at breaking out of a mould that is clearly broken. That’s what Kyle (and his partner, Daisy) are doing.
Kyle and I talked about what it means to try and build something that gives back to the audience more, as well as the Brooklyn art scene, the cyclical nature of internet culture, and getting a gig at the New Yorker. Not bad, I rkn.
Welcome to our new subscribers, so-long to the old. Thanks for reading, writing, sharing. It all means so much.
See you down the road.
VFD: Hey, how you doing?
Kyle Chayka: Good, how are you?
VFD: I'm good. Is your day good so far?
Kyle Chayka: Oh, yeah. I live in DC, but I was just down in New York with my girlfriend, partly to do Dirt meetings and stuff. We just drove back this morning.
VFD: How long is that drive, a couple hours?
Kyle Chayka: Yeah, it's like a good four and a half hours. Five and a half if you're not lucky.
VFD: Yeah, shit.
Kyle Chayka: I've done it probably too many times.
VFD: You can get a train, right?
Kyle Chayka: Yeah, it's very easy. But we have a puppy — Who's right here.
VFD: Big puppy.
Kyle Chayka: Yeah. So she can't go on Amtrak, unfortunately.
VFD: Fair enough. Well, thanks for doing this man. Appreciate it. Especially after a five hour drive, or 10 hours round trip. You've been busy, then, with the Dirt stuff, which is not surprising to me. Tell me what's going on?
Kyle Chayka: So I mean, Daisy Alioto — who's the co-founder of Dirt — and I were meeting a bunch of our investors who are in New York. And we did all the fundraising over Zoom. Super long distance. So we wanted to set up a bunch of actual face-to-face meetings.
VFD: That's probably a good idea.
Kyle Chayka: Daisy lives in upstate New York, I live in DC. New York City is the central spot, obviously.
VFD: How did you two meet and start working together?
Kyle Chayka: I think just over the internet. The other company I co-founded, Study Hall — Daisy… I got to know her a little bit through that, I think. But then we just started talking about our own writing and ideas, and what we want to see in publishing or in digital media. And eventually we knew we wanted to work on something together at some point; Dirt became that thing.
VFD: How long has Dirt been going for now?
Kyle Chayka: Since December 2020, it started.
VFD: Wow, so not not a huge amount of time. And did you always start it with the idea of making it something bigger? Hopefully, maybe?
Kyle Chayka: That's the freelancer hustle, right? You try some experiments and then see what hits.
So at the beginning it was kind of still super-intense-COVID. So I was like: oh, people would definitely like a daily newsletter that's about what everyone's watching on Netflix and looking at on TikTok and stuff. So I thought it would be a good newsletter, and I think it was a good editorial format. I wasn't sure if it would be an actual coherent business or not. But as I got into NFTs and web3.0 stuff, I wanted to experiment with that and see how it works and use Dirt as a vehicle for that. And I think the fact that we did sell NFTs to fund a newsletter - and start working in that space - is why investors were interested in us. Because investors hate media. They cringe at the word media.
VFD: Not always. There was a golden time, which all ended… well. So I can't see why they're trying to pivot there. Did you have reservations about the web3.0 part of things and the NFT part of things when you did it?
Kyle Chayka: I definitely… I wasn't sure what it all was. I think you learn by doing, especially in that world, and I wanted to understand it and I thought trying something out was the best way to do that. I definitely think the environmental cost of the technology is really bad and can't be ignored. That’s my biggest reservation about it. Though, to me, I do believe the argument that a lot of the demand on the Ethereum system is from people mining it versus people using NFTs. But yeah, I think another concern about it was there's kind of… a stigma.
VFD: Oh, really?
Kyle Chayka: Yeah. Some people just don't want anything to do with this. They don't want to — very understandably — they don't want to dabble in weird crypto, they don’t wanna be in a strange Discord chat, but I've always been interested in whatever the new forms of culture are and where stuff is bubbling up. And I think there's so much energy there, in part because there's so much money floating around, that I was interested in how it worked and what was happening.
VFD: So is it like a community ownership model, then? Would that be the most regular way to explain it?
Kyle Chayka: Yeah. To me, it's like web3.0 is hopefully about community ownership and community participation in the project. So whatever you're doing, it's allowing people to have a stake and a meaningful way to participate in it, not just pay a subscription fee and consume the content.
I feel like this is sounding too sales pitch-y.
VFD: No, it's good, sell it.
Kyle Chayka: One conversation we kept having was: Okay, you pay the New York Times your subscription of $300 a year, whatever, there's no way that you can talk back to The Times, there's nothing you're gonna get out of that, there's no way you can reach the people who are in charge, save for a letter to the editor or something. And that is kind of frustrating after a while. It's like: I'm paying a lot of money! I really identify with this media brand! Why do I have functionally no interaction with it, besides just consuming what they make?
So I hope that web3 tools, in the future, will allow a better relationship between publications and subscribers. Because right now it's kind of bad.
VFD: Yeah, well, it’s very one-way as you mentioned, and the onus is on you. Your only avenue of value is like… more content.
Kyle Chayka: Which is, as you know, a horrible thing.
VFD: Yeah: we're not hiring more people! Instead, we’re just asking the staff to do more. You know how you wrote that thing? Well, now you make a podcast about that thing. Yeah, it keeps going.
Kyle Chayka: I mean it's like with this your substack. The subscribers want what you put out. But it feels one-way. I hope that there are ways to have it be more collaborative or something.
VFD: Yeah. How did you get started with finding investors? Is that something you've done before? Or did you google, like… “investors”?
Kyle Chayka: Goodinvestors.com? Yeah. I mean, Daisy Alioto deserves much of the credit for doing fundraising. She had many more first meetings with investors than I did. But I think a lot of the successful pitches and relationships came out of NFT-world people and web3 people who we had gotten to know through the newsletter and through topics that we had covered. And so it was nice. It's nice that it came from that community. They wanted to support this thing and see where the experiment led. I think the larger tech VC firms were not as interested. I think it was a little too strange, or different, or offbeat for them.
VFD: Yeah, and also not chasing a trillion dollars. I assume, maybe it is?
Kyle Chayka: Well, this is the problem. The early 2010s, the media pitch to VCs was like: we're going to be the biggest website brand in the world! Everyone on the planet will know what BuzzFeed is! Which maybe they do, I don't know. But that was the VICE pitch, that was the Vox pitch, that was the BuzzFeed pitch.
VFD: Yeah, I think what it revealed is that people knowing who you are is not everything. It's cultural capital, it's great, it's influential. And there's a little thing called ‘media ethics’ that really pisses off a lot of tech investors when they’re like: we’ll just sell it?!
You’re still at the New Yorker, right?
Kyle Chayka: Yeah. I got on staff there last June, I think.
VFD: How does that happen?
Kyle Chayka: Well, in my case, at least, I was freelancing for them quite a lot, starting in the early pandemic. For whatever reason, I'd kind of began pitching them, or my editor Rachel Arons came to me with this one idea to do a piece on architecture during COVID. And I think I worked on that for a long time. And I made this feature that I thought was very nice and it’s a cool discussion of what happens to architecture in the pandemic.
And I think that piece, in its success, kicked off a really good relationship with Rachel. A year later, as I was figuring out what my next career steps were, I started asking: would it be possible to be on contracts and is David Remnick interested in me being on staff? So it's just a very long-term conversation.
VFD: Yeah. Intimidating conversation, at least it would be, for me. I'd be like: please, if you like, maybe… I just thought.
Kyle Chayka: Oh my god, yeah, a little bit. I really like my editor, so much. Rachel is just fantastic. I just wanted to continue having that set up. Selfishly, I was like: Wow, if I could only do this, I’d be super happy.
VFD: It seems like you have a lot of projects going, right? And have done for a while. Is that the story of your career?
Kyle Chayka: Pretty much. I had staff jobs, in the early, early 2010s. So I graduated college in 2010, and I did an internship for a while in Beijing at this art magazine, called Leap. And then I got a real media job in Brooklyn at this art blog called Hyperallergic, and so I was kind of the classic, young, 23-year-old blogger writing three posts a day.
VFD: Yeah. Skinny jeans…
Kyle Chayka: Yeah, absolutely, living in Williamsburg…
VFD: Yeah, very cool.
Kyle Chayka: Back in the bygone days of the hipster boom, you know? So I then worked at this website called ArtInfo, which — now that it doesn't exist anymore — I can say is a terrible place and was owned by a negligent billionaire.
Kyle Chayka: So, left there and was kind of like: okay, freelance, I'm gonna be freelance!
VFD: It was that bad?
Kyle Chayka: Oh yeah, it was that bad. At one point, the entire tech department left because it turned out there was money embezzled or something.
VFD: Very cool!
Kyle Chayka: So that was cool. At that point I was like: Okay, I had two jobs squarely within the art world, doing art criticism and art reporting and stuff, I'm gonna work to go outside of that and just write about broader tech stuff and business stuff and whatever.
That's how I started expanding my range of work. And then there's pretty much freelance. I didn't have a real job from 2012 to 2021, until I got started at The New Yorker.
VFD: Where does the art thing start from? Did you do that at college? Or just a general interest?
Kyle Chayka: I did a lot of art making in high school. I was super into the art studio and was one of the kids who just hung around those classrooms all the time. And then I took an art history AP class in high school, where you get fake college credit. And that teacher just blew my mind. I didn't know that art history was a thing. Like, I didn't know that you could study the story of art and artists and what they made and how they made it. So I think that kicked me off, just being interested in the story of art and how things develop. I ended up writing art gallery and museum reviews in the Tufts daily student newspaper and did an internship at the Boston Museum of Fine Arts, but I hated it because it's mostly updating card catalogues by hand.
VFD: Oh, cool.
Kyle Chayka: I was like: wow, I thought this would be more about things that are happening in the present day. But it definitely wasn't. So I found that writing was the best way for me to engage with my interest in art. Then I got into covering contemporary art and hanging out with artists in Brooklyn…
VFD: That's not a bad scene. Interesting scene, I'm sure.
Kyle Chayka: Yeah. Fascinatingly, the tech/artist scene in Brooklyn in the early 2010s is now exactly the same as the NFT web3 artist scene.
VFD: Shocking. Same people or the same vibe?
Kyle Chayka: Same people, same vibe. A few are opting out completely and don't want anything to do with it. But for lots of people it's the first time the public has noticed what they're doing.
VFD: And there's money involved in a more open sense, I guess, which is nice.
Kyle Chayka: When you have to survive in the world, it's nice when someone buys your pixels.
VFD: Yeah. Well, I actually came to know you from what I would call your writing on — I wouldn't say internet culture — but nostalgic tech culture. Writing about Tumblr, writing about old tech. And not even really all that old. But writing about my era, to be honest. 2010s era Internet and tech. How did you start doing that? How did you realise: "this is the thing that I can talk about and talk about in an interesting way.
Kyle Chayka: Yeah, it depends on when. I feel like I was writing about that stuff when it was happening for the first time in 2013. And I was interested in that collision of technology, digital and social networks, and culture/art, basically. And then it all came back around.
VFD: A different angle, though, right?
Kyle Chayka: Same process as the artists: I was there at the beginning, and now I'm here being the nostalgic critic who's seen the band. It’s like LCD Sound System fans from 2007. I feel like I’ve recycled a lot of things in my career that I just keep thinking about and keep returning to. So a lot of it is: how does culture persist through technology? And I think that question keeps coming back and coming back in all these different eras.
A few years ago we were squarely within “streaming is the future” + “everything is going to be Netflix all the time”. And in that, there was a lot to talk about: what is streaming TV? What does it mean that you can get stuff on demand?
And now we've come, passed out of that a little bit, and it's: “20 streaming services is way too many”, “I wish my websites were all just geocities”, “HTML”. I just find those shifts fascinating - the changing tastes in technology.
VFD: Yeah, it's all cable again. It's great. I think it's really cool.
Kyle Chayka: Like: no, no, no, now I don't want to choose! Don't let me choose!
VFD: I think about you having so many projects or doing so many things at once — even the nature of the New Yorker gig, right, is thinking of a certain amount of things every week, every month. Do you ever worry about it all falling apart?
Kyle Chayka: Yeah, absolutely. Journalists have a good “in” where you both document the rise and you document the fall — there's always something happening and you can always explain it to people or describe it to people. I was happy with the New Yorker. I was happy that we landed on a column about the internet, super broadly, because there's always something happening on the internet. As we all know: there's always a meme, there's always a new app, there's always a shift that's happening. And faster than in most other cultural spaces. So I thought that would be pretty good for prompting a weekly column. I do think doing a column is exhausting and it does like tire you out.
VFD: I've done it before. It does. And it doesn't make sense, because you're just writing one thing. I've had a job where I wrote, like, five things a day…
Kyle Chayka: Yeah, it's like maybe you run out of things to be interested in. It's not that nothing is happening, it's just that nothing sparks your brain as much. You've overdosed on the material. It takes something really shocking to really inspire a response from you.
But yeah, there was a while ago, a year plus ago, I had never used TikTok before. And I was like: Okay, it's February 2021, I'm gonna fucking download TikTok and see…
VFD: Real come to Jesus moment.
Kyle Chayka: The absolute worst. Winter 2021 was a pretty bad vibe. So I started using TikTok and I was just so obsessed with how it works. Like: how it suddenly just subsumes all of my attention and drove me in these different directions. I was like: Oh, my God, I just have to write something about this. And so I literally wrote for my own newsletter, what it feels like to use TikTok.
And that piece was super popular. I'm still not sure why — I think just because I was evoking feelings that other people were also having when they started using TikTok, because it is just crazy. TikTok, more than anything else, feels like a different form of technology or a different evolution of media.
VFD: Yeah. It's all encompassing. It's the most I've ever felt like life is completely helpless to the internet. I've always felt that I was born into this, that I can handle this. And then you read all this stuff about fake news on Facebook, and you’re like: I wouldn't fall for it. Wouldn't happen! And then TikTok shows up and takes over your brain for hours.
Kyle Chayka: Yes, clearly this young woman lives on a tropical island and has an idyllic life. Yes, I believe that, now I believe some other narrative. I don't know. The suspension of disbelief, maybe, is so total on TikTok. That's why it occupies your mind so much. This must actually be happening.
VFD: Well, thanks, man. I appreciate you talking. I’ll let you, I don't know, sleep or have a beer or something. But I appreciate it. Good luck with everything.
Kyle Chayka: Yeah, thank you.