The Exchanges

Q Um, all right. So you graduate, you're 18, and you're not going to go to college. Um, so what, what did you do? I mean, where did you, did you get a job right away?

A I did. I graduated and then I applied at, This very, like, cool local record store, and I was very adamant about my application and, like, calling, did you get it, you know, and they got back to me a couple weeks later, and they said, hey, we really appreciate your enthusiasm, but You need to have some prior record store experience to get this job. Um, so I said, wow, where can I get that? Where can I get that? Where I can also get a job. Um, but the mall of America had just opened. So I went down to the mall of America. I applied at the music land store. I was in like that and worked there for the minimum amount of time, six months before I went and reapplied at the other, you know, what was the name of that record shop, by the way? It was called Down in the Valley. It's still there.

AI assessment note: “I did. I graduated and then I applied at, This very, like, cool local record store”

Q So how did you come up with Pitchfork?

A I came up with Pitchfork. I was, I was watching Scarface as teenagers do. And there's a scene in the movie where Al Pacino is being interrogated by a The feds or something. And, um, they, they noticed this pitchfork tattoo on his arm, and they're like, oh, what does that mean? That means assassin. And I'm like, oh, that's cool. That's cool. Like, I needed a new name, and I needed a new, a new name pretty fast. You know, I'm like living in rural Minnesota. I kind of like the angry mob connotations, which at that time were not so Tea Party affiliated. You know, it was more just general angry villagers kind of vibe. But I liked, I liked all the connotations. And I thought, you know, it's sort of like, It's sharp, and, um, I really wanted Pitchfork to be more aggressive in its review style, to be harder on music, and, I don't know, have a higher bar.

AI assessment note: “I was watching Scarface as teenagers do. And there's a scene in the movie”

Q Did you, were you, I mean, did you start to become actually profitable?

A Yes, uh, started to become quite profitable, um, quite profitable. So, you know, I was like, okay, well, I can afford to hire the right person for this job now, and, uh, once again, I just went the same route that I always did, which is putting out You know, a call on the site saying, hey, you know, um, we're looking for a person who's an ad salesperson, and let us know, you know, apply here, send your resume. And then I found, um, the very last application that came in was from a salesperson at The Onion, and he had in his resume all these, like, benchmarks, and, like, I took sales revenue from, you know, I increased it, like, 25% in this way, and I did this and that and there, and, like, he actually could, he quantified his results in, in the resume, which I was like, oh, this is it. This is the guy. Like, don't even need an interview. Like, this is him. So, yeah, and his name was Chris Caskey, and he went on to basically become, like, he ran the entire business of Pitchfork from that point on.

AI assessment note: “Yes, uh, started to become quite profitable, um, quite profitable.”

Q Did, did you, would you hang out at record stores in high school?

A Oh, constantly. Oh my God. It was like the only place I ever went. And I would spend hours, hours at the record stores. I got to know all the people at the record stores. You know, I'm like 15, 16, like, asking them. For recommendations, and I like this, what should I listen to next, and how's this? Have you heard this new album by The Cure? How's that? And just constantly digging and, you know, looking at all the artwork, and they had like, actually at my local record, record store in Minnetonka, we had, at that time, it's no longer there, but there's a big record store chain, um, in Minneapolis called Cheapo, and, um, I just, I spent all my time there. They had a listening station in the back.

AI assessment note: “Oh, constantly. Oh my God. It was like the only place I ever went.”

Q In terms of, like, the school side of things, how were you? Was school hard for you? Did you not care?

A School was very hard for me. I was neither a good student, nor was I, like, at all socially adept, so I was definitely... You know, kind of a loner. I was also sort of a sort of textbook ADHD case, so I was always sort of acting out a bad combination in general. But, you know, but at the same time, you know, I was actually also really fortunate because my parents actually really instilled a lot of self-confidence in me. So if I would get rejection from my classmates, um, I always kind of had a sense. It's like, we're not close. You don't know me. You don't know what, you don't see the parts of me that I see.

AI assessment note: “School was very hard for me. I was neither a good student”

Q What was the genesis of, of how you came to, to the idea of starting your own zine-like thing?

A So while I was working at the record store, this is 1994, um, I had already been on local bulletin board systems, these, like, Services that you could call up that a person would host a computer and it would be sort of like a local regional message board. But in 1994, one of these people introduced me to the internet. He was online already and. Showing me all, you know, websites and showing me how everything worked. And he had made a website and I was like, how do you do this? You know, he's like, it's actually really super easy. If you know, Photoshop, which I'll teach you and you know, five HTML tags and you have an FTP client. I'm like, this is the sounds complicated. He's like, no. So he actually walked me through it and it didn't take long to learn. So I basically just started learning that software and you don't even really need to know that frankly. I just wanted to make sure that we had images and, you know, that it was visual as well as text. And then I started to see other publications kind of popping up online.

AI assessment note: “in 1994, one of these people introduced me to the internet.”

Q You, you see these kind of like this scene kind of scene pop up around you. I mean, how did you, I mean, did you start to think, you know, I want to make one myself?

A Yeah. I was actually really drawn to the idea, but I just, I had no, I mean, working in a record store doesn't, you know, I was fortunate to be able to live at home while I did that. So my expendable income, I could, you know, whatever it was, there was not much. Um, it's certainly not enough to support, um, Even something like creating 203 hundred copies of something to distribute around town. The overhead was just kind of out of reach for me. Um, so yeah, there, there was always kind of like an instinct, like, oh, I could do this. Look at the, look at these kids doing this. They got like 10 minutes on the phone with like, you know, Ian Mackay.

AI assessment note: “Yeah. I was actually really drawn to the idea, but I just”

Q And what was the, what was the turning point? How were you able to do that? Cause that's got to pay rent and you've got to get office equipment and internet connections and phone lines. What, how did you have the cash to do that?

A Well, by the end of 2001, I had a very healthy network of advertisers. And so I started to be able to put some of that money back into the business. But the first thing I wanted off my plate was the thing that I liked doing the least, which is the ad sales. And once we already had a client roster sort of, of, you know, uh, we had a lot of people in rotation. Um, I was kind of like, okay, I think I could afford to pay one person a salary and I actually offered one of my brighter friends from Philadelphia who had wanted to move to Chicago. I like offered it to him because I was like, he would be fun to work with. Not because I thought he would necessarily be great at selling ads. I was like, oh, it'd be fun to work with him. So he came, he came out to Chicago. I got us an office. I gave him a little salary. We did that for, I guess, almost a year.

AI assessment note: “by the end of 2001, I had a very healthy network of advertisers.”

Q He's a writer, ok. Um, that had a huge impact. I mean, right? Record stores weren't selling the record, and it was, I think, one of the first moments where it was clear that you, you could actually make or break artists. Do you remember that moment?

A I do. I mean, I actually kind of remember very early on trying to, um, write reviews of artists that, like, were not, Not in the press at all. Like going, sorting through the stack of promos that we would get to find something deeply obscure, but that looked interesting. And I would pull out and just listen to these CDs, like really pour through the stack, try to find something nobody else was covering. But we're also still kind of tied up with this kind of, you know, super, uh, irreverent, snotty, goofy publication at the same time. And so we like to do things that would You know, get attention or be outrageous in a way. And that was one of those moments that was like, you know, I was like, we haven't given a zero point zero. Like, have we ever done it? We should do it. You know? And, and unfortunately that was also the point at which I realized when I realized that pitch work could, could break careers, could like break artists in the bad way. I was like, yeah, that really gave me pause because the reaction to that, I did not, I mean, I didn't, Expected to end his career, for God's sake. You know what I mean? So when that happened, we took a beat, you know, and we're like, okay, we need to reevaluate how we're using this authority that we've managed to accumulate, and we, we've got to be a little more responsible with this, because that, you know, that doesn't feel, that does…

AI assessment note: “I do. I mean, I actually kind of remember very early on”

Q And, and just, I'm just curious, like, from a business perspective, was that good for your business? I mean, it's good in the sense that you really become a cultural, well-known festival, but is it possible to make money relatively easily on a festival?

A You know, we found out kind of the hard way pretty early on that first year. Um, I mean, Mike already had understood like, you know, the finances of it the first year, and he kind of had explained it to us and walked us through P&L for that. Um, so we were always kind of like, okay, this is clearly not going to be the major revenue driver that you would think it would be. Um, there is so much overhead that it's also like kind of a A delicate dance where all of these things have to just happen just right. You know, you have to have a reasonable artist budget with which you can attract talent that's not going to the competing festivals, say Lollapalooza, Riot Fest, et cetera. Um, you've got to, you know, make sure that the ticket sales are like Fair, reasonable, that you can attract a big enough crowd. Um, you've got security concerns, vendors. Um, there's just, there's so many moving parts. If one of those things doesn't come together, if you have like inclement weather all weekend, because it's an outdoor festival, I mean, these things can really crash the festival enterprise altogether, like kill the business. So it's a very, very high risk business. Um, and one that we fortunately, um, By staying mid-sized and not trying to scale up and not trying to compete with the Lollapalooza's and Coachella's and Bonnaroo's, um, we were able to manage to make it profitable, break even. S…

AI assessment note: “this is clearly not going to be the major revenue driver that you would think”

Q I know that you're writing a book, uh, written history of the, of Pitchfork, which will come out in a couple years. Do you miss that daily interaction, all those people being steeped in that world, um, meetings, talking about, I don't know, ideas? Do you miss that day to day?

A Oh, it's, it's hard not to miss, you know, like all the activity and excitement of a newsroom. Yeah. I mean, it's the most thrilling for me. So like, it's the most thrilling thing in the world at the same time, you know, kind of like having this sort of more isolated, like for one thing, I stopped writing in 2004, just mostly stopped doing it publicly, um, and stopped doing it almost period. So it took a while to kind of get back into the swing when I started kind of writing Kind of mapping out, like if I was to write a book, what, what, what would it look like? Um, and writing is something that I've just recently realized is kind of, it's totally my calling, but also, you know, the idea of running businesses that are innovative, that do help kind of change in the landscape, I mean, is, is just as much a part of who I am and what my interests are as it's been since, since the beginning of, of the web.

AI assessment note: “Oh, it's, it's hard not to miss, you know, like all the activity”

Q By the way, were you into any of that?

A No, I wasn't. What's so funny is I was not, like, I would sometimes have to go back and work the head shop counter, and they would, they're just slinging terminology, you know, and I'm like, they're like, uh, give me that dugout and that one hitter, and I'm like. Can you, could you just point that out to me? To me, like I was insane. But yeah, so we had people who were like into all kinds of music working there. Lots of, you know. Personalities. Of course, we were like, all snobby, you know, like, I don't think we were like snobby to the customers. Like, you know, that's sort of a record store, a record clerk stereotype. And for good reason, because I've been, I know I've experienced it to like no end also, right? Like being on the other side of the town.

AI assessment note: “No, I wasn't. What's so funny is I was not”