UPDATE: Gawker Media filed for bankruptcy protection today and will put itself up for sale in an auction. The decision follows a ruling by a judge not to issue a stay of a required $50 million bond payment by Gawker pending its appeal of a jury's $140 million judgment against it in Hulk Hogan's invasion of privacy suit. We spoke with Denton about the suit for our February 2016 issue. 


Nick Denton shouldn't be talking to me. Any founder worth his cocktail peanuts knows that when in the midst of a massive lawsuit, one maintains one's silence. But that's not how Denton operates. The thought of being muzzled offends his principles. "I believe in free expression," he tells me over drinks on a sunny Thursday in Lower Manhattan--you can watch the video of our conversation above. "The idea that you have to shut up, lest your words be used against you ... " He shakes his head. Not happening.

Denton has a lot to talk about, too, because his company, Gawker Media Group, a collection of irreverent, news-breaking blogs that gather more than 100 million viewers globally each month, is in the fight of its life. Hulk Hogan, the former WWE wrestler (real name: Terry Bollea), has filed a $100 million suit against Gawker for running clips of a bootleg sex tape that Hogan stars in, claiming the company invaded his privacy. Screenshots from the video had already appeared on other websites, but none have pockets as deep as Gawker's (the company, of which Denton owns 48 percent, was profitable on an EBITDA basis in 2014, Denton says, on revenue of around $45 million). A trial is scheduled for March 2016.

If Gawker loses, and Hogan gets his full asking price, Denton's company may not survive. "I think it's clear we'll win this case," says Denton. "The question is how many rounds we need to go through to establish that."

And, boy, are those rounds getting expensive--so expensive that Denton has said publicly he is open to seeking outside capital for the first time since he founded the company in 2003. As if that weren't enough, in June part of his staff voted to unionize, and he recently announced layoffs and a major shift in editorial focus and strategy for the company's flagship property, Gawker.com, which has generated a flood of critical and, at times, personally insulting media coverage. Then, shortly after we spoke, a former employee published a blistering article maligning the company's treatment of its female employees.

A London-born child of a psychotherapist mother and an economist father, Denton was a financial journalist before he became an entrepreneur, with stints at The Economist and Financial Times. He's an ardent, some would say foolhardy, proponent of free speech and the rights of the media to publish the truth as they find it. "There are public aspects to our lives and there are private aspects to our lives," says Denton, who recently married his boyfriend, performer Derrence Washington, after a brief courtship. Hogan, he argues, made himself Gawker-worthy when he publicly and shamelessly bragged about his sexual prowess-- a claim refuted in the sex tape, Denton says.

But Denton is also an idea man, adept at spotting tectonically important trends that have been the basis for Gawker and his two previous companies (both sold)--First Tuesday, a networking and social events company, and  Moreover Technologies, an online news aggregator. He can feel the wind shift before anyone else knows it's blowing. Right now, though, he's in the middle of the sort of public storm that few private company CEOs ever experience.

The story is unfolding under the gaze of the schadenfreude-loving New York City media, which is obsessed with the minutest details of Denton's travails. Hard to find fault there, considering the scathing manner in which Gawker has covered the media. "We're in the attention game," says Denton. "We're used to being out there. We've played the role in the past and it's a role we will continue to play. I'm cool with it."

Indeed, Denton is preternaturally calm when we meet for lunch and drinks. By all appearances, none of it is touching him. I assume he's either so self-confident (or emotionally detached) that he truly doesn't care, or he's discovered the trick to compartmentalizing criticism. Turns out, it's a bit of both.

"Everybody needs to get used to an online environment where everything that can be said will be said," he says. "You have three alternatives. You either close your ears to it, operate in an atmos­phere of complete secrecy, or embrace the transparency that the internet has brought and say, 'That's what it is.' There are going to be people who like what you do and there are going to be people who don't. What matters is that there are enough people who like what you do."

"My interests tend to wax and wane. I'm not a particularly consistent manager. I need people around me to save me from myself, and to save the company from me, too."Nick Denton

But before you get too smug that you're not Nick Denton, get ready to join him--because if your company hasn't yet faced this sort of scrutiny, it very likely will. "Managing now is increasingly a question of managing in public," says Denton. "When you're thinking about what you're going to do internally, you have to think about how it's going to play externally, because organizations are much more leaky than ever before."

Denton has built an entire business by exploiting those leaks, and his media properties have been credited with breaking stories about crack use by former Toronto mayor Rob Ford and Hillary Clinton's private email server, and unearthing photos from Dallas Cowboy Greg Hardy's domestic abuse case.

In the past year, despite the controversy swirling around Gawker, Denton has focused mostly on an overhaul of his upper executive ranks--the people he wants to be managing the company's day-to-day drama and challenges. Considering his assessment of his own managerial skills, it's a smart move. "I don't think journalists are, by character, very good CEOs," he says. "My interests tend to wax and wane, which means that I'm not a particularly consistent manager, and an inconsistent manager is basically a bad manager. So I had to rely pretty heavily on deeper-level managers who are much more consistent than I am."

He pauses and adds: "I need people around me to save me from myself, and to save the company from me, too."

Getting someone else to handle the ugliness might explain Denton's serene aspect. We'll see if it holds come the Hogan trial in March. 


What Denton Likes

"I love the internet," he says. "I love following links and finding interesting things," like these:

1. Black Mirror, a British TV series on Netflix about a dystopian future."It's brilliant. Awfully brilliant. There's so much good stuff."

2. Sapiens, a book by Israeli historian Yuval Noah Harari. "A media-centric history of humanity--flattering, if you're a writer."

3. The Browser, a blog by U.K. financial journalist Robert Cottrell. "Economics, political science, evolutionary biology--he's interested in a lot of things I'm interested in."