Can you talk about some of the promotional stunts you pulled in the early years?
My gosh. There were many, many funny times. We had this succession of parties, each wilder than the last. The first party maybe cost us $700. We had big prints of photos that had been published on Hooksexup on the wall, so it was just a little bit edgy. JFK Jr. showed up in a low baseball cap; that created some buzz. The parties became progressively larger and wilder, and we started having these exhibitionist booths where people could do whatever they wanted. I remember sitting at a party — which were both fun and stressful for me because we tended to have investors show up — and we had a thirty-foot-high projection on the wall of what was going on in the exhibitionist booth, and I kept trying to steer this investor to face me because I could see our poetry editor getting a blowjob from his wife on the wall. The investor kept getting ready to turn around to use the restroom or something, and I kept trying to more furiously engage him in conversation.

Another crazy thing we did was, we had this very interesting negotiation with 60 Minutes II, which was doing a segment on Silicon Alley. And they would say, "Of course, we don't want to influence anything you do, but if you did happen to do crazier things it would be more likely we'd run the segment." So we had just launched the HooksexupCenter, and we thought, wouldn't it be great to run around completely naked and pass out cards inviting people to become members of the HooksexupCenter community? So we rented this white van, and we had a big disco ball on the end of a pole, and we would pull up to street corners, open the doors, pop out the disco ball and light and crank the tunes, and go running out in the buff. We were wearing hats, scarves and running shoes — some of the women in the office were wearing very wide scarves. We'd originally hired other people to do this because we weren't sure how well this would go over with grandma, and because it's national television. But we had a bottle of whiskey in the back and ended up doing it as well. And my thinking was, this is CBS, there's no way they're going to show our butts or genitalia, so who cares? And after this thing aired, a friend of mine said to me, "I saw your Johnson on national television." We went back and froze the frames, and there were about three frames of that.

You and Genevieve were the very public face of Hooksexup. When your relationship ended, were you worried it would affect the image of the company?
It was definitely a worry, but I think Hooksexup had enough traction that it wasn't a huge issue. And also, mercifully, Genevieve was a really grounded, wise person. I think it was extraordinary that we were able to work together for another year after that, and pretty smoothly. The New York Times Magazine did a page on the breakup. That's the reason everybody says not to work with your girlfriend, boyfriend, spouse — it can be apocalyptic for a business with two founders. But I think it was not unlike the situation where you divorce with a baby and you don't want the baby to be hurt.

What about the ill-fated HBO reality show?
We signed a deal with HBO in '99. It was supposed to be a show that would be interlarded with reality segments and shots of the office. We said to them, "This is a magazine. We spend most of the day typing, it's not particularly exciting footage." It was also true that this was right around the time the internet bubble was imploding, there was no more funding, we were about to have to contract the size of the staff and I was really thinking, We need this show to work. Had the economic situation been different, we would have said this is not for us. But it was a really interesting idea, and there were portions of it that I think were quite good and others that were not so good. We had veto power — we could kill the whole show. That was really the only leverage we had, and we almost did it. It ended up running as a one-time special and they aired it like fifty times. It was a period of identity crisis for us.