Let’s start at the beginning. You were one of the very first people who worked at Hooksexup.
Apart from the founders and Joey, I was the second person hired with Lorelei. Almost immediately after Lorelei.
What was your position when you were hired?
I think I was nominally the senior editor. [laughter] It was Rufus, me and Genevieve doing the editing, so by virtue of there being nobody else, I got to be called senior. Very exciting. I was a grad student. My options were teaching Chaucer at East Bunghole State or working for a hot sex magazine in New York. Right. So, it took me a long time to decide what to do.
How did you know Rufus?
He was one of my best buds in college. We had always planned on working together, or at least that’s what I always say. More to the point, probably, I had always hoped that I’d be able to use him for contacts. He knew that I was a Midwesterner and would slave for nickels, so it made sense to hire me.
What was the state of the website at that time?
They were publishing two things a week. They had already published a fair number of quality writers. I was impressed that their initial sort of letter blitz had reeled in quite a few big names. When I started working there, my ambition was to publish something new every day. It took me a while to ramp us up to that, and it certainly cost a lot of blood and tears.
That must have been wildly ambitious at the time.
What frequently happened is I’d have a hole on my editorial calendar. I’d see that there wasn’t a piece. So I would write one. In some ways, this led to me developing a freelance career. I would start my column [Jack’s Naughty Bits], which became weekly. Out of vanity, I once figured out how many pieces that I had written for Hooksexup, and it was well over 400.
How would you describe the magazine at the time?
Very ambitious. We had that super-slick front page. That was badass—there was no text on it, just this awesome living-room scene that you would have to drag the mouse around. This was back before we understood marketing. [laughter] We understood aesthetics, but not marketing. Clearly, that’s how we operated for a long time.
We tried to be really smart. That was the brand-building stage. When we were finally called the New Yorker of sex by somebody, we about wet ourselves with happiness, because that’s what we had been hoping to be the whole time.
What was the work environment like?
It was pretty fucking funny. We were all working in the loft Rufus and Genevieve were living in at the time. They had a little back bedroom. Until we had maybe seven employees other than Rufus and Genevieve, we all worked at desks around the side walls of this office. Every time Joey would go into the kitchen to make himself a cappuccino, I could block the exit and make him listen to lectures about literature. [laughter] That was fun. And we all loved dancing. Even when there were fifteen of us, every single person utterly loved dancing. So we would frequently have little dance parties. I thought, “How is it possible that thirteen editors and computer programmers can dance?” [laughter] “How is that possible?” The comical thing is, none of us were particularly sexually savvy or active. But when you have a dancing soul? That’s the precondition for good sex.
The way that this office is—people have never talked about their sex lives. Almost none of us had any sex lives! That I would write tons of articles about sex and that Emma and Lorelei would advise people about sex? This could have not been further from imaginable at the time. But Hooksexup gave us a little license and loosened us up.
What shocked you?
I don’t think I shock very easily, but one thing was kind of disturbing. We were compiling a huge database of sex- and sexual-health-related websites. I was nominally spearheading this. One website was all cartoons of exceptionally buxom, bright pastel pixies with those little wings and whatnot, flitting about in inappropriate outfits. But they were all snuffed. They were hung and mutilated and chopped up, with plastic bags over their heads. That was someone’s thing They have the internet so they can talk to each other.
What was your family’s response?
Oh, my family doesn’t really know I exist, so that makes it easier. My family hasn’t read anything I’ve ever written regardless. If I’d been publishing in Spaniels and Labradors Quarterly, they still wouldn’t have read anything.
What about reactions from friends?
I was—and to some extent, still am—a medievalist. So I scandalized my department, because some of my colleagues were telling my very Christian professors that I was writing for a porn magazine. That didn’t go over very well. But I did think that combining the occupations of medievalist and pornographer would have made for a very good business card. My friends just kind of chuckled. I probably was a little bit randier than most grad students, which doesn’t say much. But compared to any New York scenester, I could not have been more lame. It was just a matter of perspective.
What were some of the unique challenges of being a Hooksexup editor?
We had that quality standard. I was a very aggressive editor and would make people go through draft after draft after draft. And we had no money, so I would always tell agents and writers that we were gonna ask for the moon and pay them peanuts, which is hard. It’s harder still when it’s for an internet publication, and even harder still when it’s for a sex one, so drumming up content in the early days was just not easy at all. But Rufus and Genevieve had a great model. They just wrote to a lot of writers that they liked, and sure enough, enough people would respond.
I would compulsively read Best American Essays and Best American Short Stories of previous years, and find a lot of smaller writers that way and write them. And frequently, they would be flattered. They weren’t getting letters from New Yorker editors saying, “Hey! Write for us!” I feel like I really tapped, for example, the writers of Ohio.
Were there any you’re especially proud of?
Before anybody had heard of Andre Dubus III, I wrote to him and told him that I had read one of his essays, and that it made me feel like I had gotten punched in the stomach. He wrote me back, flattered, and he said, “Well, I have this novel coming out, and maybe you want to do the first serial of it.” It ended up being House of Sand and Fog, which we did run a first serial of. Later it became an Oprah book and a best seller.
I did have a long back-and-forth with one of my favorite essayists in the country. He was all excited to write a piece. He said, “I’ve got this great piece; I’ll send it later in the week. It’s all about having sex with my students.” Two days later, I get another letter: “Um, it dawned on me that that might not be such a good idea.” [laughs] I never did get that piece.
Didn’t you have a postcard from John Updike?
I got some great postcards and rejections from Updike, Toni Morrison, John Barth and Umberto Eco—I tried about everybody. Rufus, too. We have some extraordinary little ones. They almost all make the same joke, which is something along the lines of, “I couldn’t possibly write for your magazine.” [laughs] I think that’s what Updike said. Rufus thinks that’s what Tom Wolfe said. It could be that they said the same exact thing.
Do you have other author stories?
This guy’s super-super-famous. A screenwriter. We were really excited to get a piece from him, which he actually sent. But it just wasn’t that sexy. So I wrote him back saying, you know, “Is there any way we can bump up the sex part?” “No I like it as is.” “But couldn’t we just, you know?” “No I really like it as is.” And, you know, it was clear that he was not going to budge at all. So I did what any editor would do and what I had done quite a few times: I wrote the sex scene for him. Very much in his idiom. And I wrote and said, “Well, all it would take would be a little thing along these lines.” [laughs] Thinking that he, like every other writer, would be lazy enough and would just say, “Oh yeah, yeah, yeah, that’s fine, you can just go and stick that in,” and instead he says, “Nope. I like it as it is.” And so I said, “Well, we can’t run it.” Which I think Rufus was going to kill me for. I don’t think that went over so well. But we were idealists then. We believed in venture-capital infusion. [laughs]
I think ultimately, my intransigency might not have been super-helpful for Hooksexup. I’m sure my standards were higher than what the readers’ were. They might have benefited from some of these big names.
Right.
But at the time, we really thought quality would help us fight the idea that internet writing was just bad. And most of it is bad. We wanted to have better copy than what you would find in print magazines. And it was hard. But we won a Webby a couple times while I was the editor there, so that suggests that maybe we were succeeding.
What changed the most about Hooksexup during your time there?
Oh, God. We went from a little magazine to this octopod of potential revenue streams [laughs], few of which brought in anything. We went from five employees to, at one point, close to fifty. The internet boomed, and I left right as it was dying. I didn’t realize it was about to burst, but it burst almost minutes after I left Hooksexup. In many ways I was there for the rise and fall. But the fall wasn’t that bad. And Rufus kept finding ways of having Hooksexup hang on, which I found very impressive. My departure was timed well, because the minute they had to start taking money more seriously, it made sense to have an editor-in-chief who was a little more pop conscious and magazine oriented and marketing oriented. You know, when money really matters, you don’t want an academic running the show.
What do you take away from your time there?
I learned that one can be both a medievalist and a pimp at the same time. I take away life’s caprice. Before Rufus made the fateful call, I had no ambitions of being a writer.
Nor did many of the former Hooksexup staff members, who went on to very successful writing careers. I’m kind of the big failure of the group. Everybody else went on to very impressive things. I think that’s amazing. It’s like, if you were part of a little Bloomsbury or some little cultural foment that had a magic to it, and it really facilitated people finding the best parts of themselves. How ’bout that?
