Why did you decide to start an online sex magazine for men and women?
I was a young editor at a small publishing house, and I realized my affection for serious literature was a liability. So I started thinking, maybe the intersection of a subject everybody's really interested in with serious introspective personal essays and fiction could be economically feasible. I started talking with some friends and with Genevieve about what existed in the sex/culture magazine space, and it seemed like Playboy had been eroding for decades. I'm led to believe in the '50s and early '60s Playboy was actually a cultural force, but they never found an appropriate response to the rise of the feminist movement in the '60s and '70s; the publication never really evolved. So we thought, the vacuum of what was once Playboy offers an opportunity. So that's how the early conversations went, and one of the first things I did was to have those conversations in the presence of rich people, because I really hoped that eventually one of them would say, "Hey, I really like that idea. Here's some money."

Online magazines were brand new, so you basically had no template to follow. How did you know how to do it?
We didn't. But what I did know a little bit about was how to publish books, and we thought, if we could gather this great collection of writers and get them to write powerfully and professionally about this subject, I think we could sell a book to defray the costs of the online magazine. And sure enough, six months after we launched, we sold a book to Doubleday for enough money to pay for most of our expenses, though we still lost money those first few years. The other factor was, we were friendly with the founders of Feed magazine, Steven Johnson and Stephanie Simon, and Word.com, which was Marisa Bowe, and we spent a lot of time buying them lunches and dinners and picking their brains.

How did you get these big-name writers to write for an unknown magazine?
We just wrote letters to all our favorite writers, fawning and ass-shellacking, saying, "Hey, we started this magazine. We're sweet, wide-eyed young people. Will you please contribute to it? Even just ten words?" I remember spending two months doing nothing but writing these letters — letters in the mail. At the time, I had just read Nicholson Baker's The Mezzanine. He had this incredible description of a date-stamper that librarians use that pivots and kisses the paper and then retracts back up like a lunar lander — there was something slightly perverse about the way he described all this nonsexual stuff, and I basically accused him of that in this letter, really poured my heart into it. So we're sort of tapping our fingers thinking, What if nobody responds to these letters? This is all we have. And I remember receiving a ten-minute message on our answering machine from Nicholson Baker, and he was like, "Rufus, I'm traveling with my family in Spain and I got your letter forwarded by my agent, and I want you to know that it's really one of the most wonderful letters I've ever received, and your magazine sounds great and I really want to do something for you . . . " And I almost wept. I was just so elated. It was the first response we got back from anyone. And as it turned out, Nicholson Baker never wrote anything for us. I wrote him another five letters and he never responded to any of them. But he left that one message, and I'd like to thank him for that. It buoyed me and drove us forward.

What was the response to those letters generally?
We got a tremendous response. Rick Moody had just written Purple America, he'd just become the hot novelist of the moment and he agreed to write something. Joycelyn Elders had just been fired as Surgeon General for talking about masturbation and we got her to write something. And then we got this out-of-print interview with Norman Mailer, and so the list of early writers we could list, that's what made the Newsweek and the Time pieces come out.

Can you recall any gaffes from those early days? Things you look back on today and think to yourself, I can't believe we did it that way?
Well, really the whole original homepage design was, in retrospect, this bizarre, distorted, mistaken, now very dated vision of the future. We were like, "Oh, it's almost like virtual reality, like you're in this living room!" It was incredibly naïve.

Like Tomorrowland at Disney World. It was supposed to be the future, but now it just looks like the '70s.
Exactly. It was like, "The future will be soap coming out of the showerhead." It was that kind of mentality.

What was the atmosphere of the "office" when Hooksexup was still being published out of your loft in Tribeca?
I would say it was very fun and very funny. It seemed like every two weeks there was a magazine doing a shoot or a TV show doing a segment on us — we got an absurd and unwarranted amount of press attention in the first two years. If you picture nine friends in somebody's house doing something they consider to be fun, that was the environment, more so than a business environment. And there was a lot about that that was naïve, but it worked for a while.

What was funny about it was that we were really — I wouldn't say prudish people, but a collection of people who were prone to blushing. And that was by design. The original premise was, what's interesting about sex is the discomfort, the blush zone, and if you hire editors who haven't blushed in a decade, then this isn't going to work at all. And this is the way we were most misunderstood. People assumed after the '70s that anyone focusing on the subject of sex was necessarily going to have a political agenda, whereas we just wanted to gnaw on taboos like squeaky dog toys. The taboos are what make it interesting, and the second that everyone in the country acts like they're in some pro-sex commune in California, the subject will be completely uninteresting. And I think that's somewhat true to this day.