PLAYBOY: Is that what got you interested in the mechanics of gossip?
DENTON: It’s possible. It’s a hypothesis.
PLAYBOY: So when were you fully out?
DENTON: With friends, probably in my late 20s. In Budapest I wasn’t out. I was in Budapest from 23 to 28, and it’s a pretty homophobic place.
PLAYBOY: When you eventually came out to your parents, was there any family strife?
DENTON: There was a lot of family drama. The thing that was sad was my mom became sick with cancer very soon after, so everything stopped. Everything was frozen, unresolved. No one wanted to upset her. That was a miserable period. I was on the West Coast. I’m kind of amazed I actually managed to come through that. My mom was sick, and we knew she was dying. She had two years from diagnosis to death, and I was in San Francisco. I flew back once a month. It was tough on my mom because my sister and my dad both shut down. That’s what they did. My mom was super strong. I never saw her cry. I saw her cry at other times, but not through that. She would say, “I’m not afraid.”
PLAYBOY: Is it safe to assume that was the worst period of your life?
DENTON: Yeah, and I was out of my depth doing two start-ups, First Tuesday and Moreover.
PLAYBOY: You did those at the same time?
DENTON: Yeah. I started First Tuesday while we were working on Moreover because the coding was going on and I didn’t really have enough to do during that. It was wildly overhyped. At one point they thought it was going to be a billion-dollar company. This was even after the Nasdaq had crashed.
PLAYBOY: How much did you sell it for?
DENTON: The nominal price was $60 million, I think. The cash component was less. The stock turned out to be worthless.
PLAYBOY: For something that was basically—
DENTON: A party. But cool people went to the parties. If you were in the venture market at the time, if you had a cool start-up or were a cool venture capitalist, you had to be there. At some point it got so big there would be 2,000 people and four or five TV cameras at the events. It was crazy. And I saw what happened. You get what you deserve, you know? In press coverage and attention, whatever you get undeservedly on the way up, you will pay a price for. If they put you on the front cover before you’ve actually done anything, they will pull you down as brutally as they were enthusiastic in pushing you up. There’s a kind of karma that obtains in media coverage.
PLAYBOY: What’s your relationship to money? What does it mean to you?
DENTON: Mainly it gives me the joy of being free. It gives me the freedom I always wanted. Everything I am is a result of not caring about social convention and not having to worry about money. I can say whatever I want. The times I’m holding back in this conversation are only to protect other people’s feelings. And not even that much. But you only have that kind of freedom, and our writers only really have that freedom—in theory—if they actually have the economic circumstances to allow that.
PLAYBOY: People have crazy ideas about what enough money is, though.
DENTON: Well, we have to be profitable, and I get paid a decent salary now. It’s very recent. For a long time I was taking $60,000 a year.
PLAYBOY: Until how recently?
DENTON: Until two years ago.
PLAYBOY: Gawker is famous for popularizing the ultra-low-wage model for journalism, paying writers as little as $12 per article for the first couple of years.
DENTON: That reputation has haunted me. At the very beginning there was no revenue, no advertising. This was basically money out of my pocket. So I would do a simple calculation. I would take the amount of money I had and divide it by costs, and I could keep going for 10 years. I didn’t need to make any money for 10 years. Remember, when we started in 2002 there was nothing going on. People had written off the internet at that point. It was such a cataclysmic collapse.
PLAYBOY: At what point did you become confident Gawker was a real company, a real business that was going to make you a fair amount of money?
DENTON: I resisted that. I never thought, This is going to make me a fair amount of money. I think at some point I realized, Oh, this can pay for itself.
PLAYBOY: How long will you keep running your current company before seeking what venture capitalists call a “liquidity event”?
DENTON: Oh, this one’s long. How long was Steve Jobs thinking about smartphones before he actually launched one? Twenty years? Twenty years waiting and waiting and waiting. It’s like the enemy is advancing, the guns are loaded, but the time’s not right yet. I think that’s what truly great leaders do. They marshal their resources, they train their troops and make sure they’re well supplied, and then they wait for the right moment.
PLAYBOY: Who are the great leaders in technology now that Jobs is gone?
DENTON: There are some exceptional people. Evan Williams is an exceptional person. He doesn’t present well, but he has an idea that is pretty much the same idea he’s repeated again and again with Blogger, Twitter and Medium, only with different wrinkles. He’s been the most influential person in web publishing, but I don’t think he’s ever done anything cheaply or cynically. He deserves the success. There’s nothing more to him. He’s just a believer in simple, awesome tools that help people communicate.
PLAYBOY: Who else?
DENTON: Marc Andreessen is obviously extremely smart and bold. I admire the fact that he’s all-in on this bet that the internet is changing everything, every industry. He’s an absolute extremist, but actually that’s a rational position to take. [Venture capitalist] Fred Wilson is smart and nice and probably in a position to be more truthful than any of the others. And Mark Zuckerberg, obviously: canny, determined, has retained enough power at Facebook. He’s going to have another 20, 30, 40 years of being productive, being in charge of the company and being able to do things.
PLAYBOY: Now that you’ve become part of the establishment, do you feel more sympathy for Gawker’s targets?
DENTON: I don’t feel like part of the establishment. I don’t even know whether there is an establishment. From up close, the establishment isn’t up to much. Celebrity was a better deal 50 years ago. There was a time, as long as you weren’t having orgies—or as long as you were discreet about your orgies—and as long as you weren’t a Communist, you were probably fine. You’d be lionized and could get all the pussy you wanted.