He created his first company in 1998: a networking group for the tech industry called First Tuesday, which he founded with three friends from London. They sold the company two years later for millions of dollars.
By 2002, Denton had founded his second company, Gawker Media, with Elizabeth Spiers. Denton ran the company out of his SoHo apartment and told a friend "If you run it out of your house, then no one expects anything." Gawker Media began as two websites — Gawker and Gizmodo. The company employed two freelancers who were paid $12 for each post.
By 2008, Gawker had grown so big that it needed an official office and the company moved into its official headquarters on Elizabeth Street in New York City.
After claiming they had worked for no pay, three former Gawker Media interns sued Denton and the company in 2013, resulting in a three-year legal battle. In March 2016, a judge ruled in favor of Gawker and Denton.
In the spring of 2014, Denton married actor Derrence Washington at the American Museum of Natural History in New York City.
In 2015, Gawker had outgrown its walk-up office and signed a 10-year lease in the Flatiron District in New York. By then, Gawker Media had grown to seven sites — including sports site Deadspin and women-focused blog Jezebel — with more than 250 full-time employees.
In March 2016, Hulk Hogan was awarded $140 million in damages after having sued Gawker for a 2012 article that contained a clip of Hogan, whose real name is Terry Bollea, having sex with a friend's wife. Bollea initially sent Denton a cease-and-desist letter over the article, but when Gawker refused to pull the story, Bollea sued for invasion of privacy. Denton has stood firm in his belief that the site should have published the video and plans to appeal the verdict.
By May, it was revealed that billionaire tech investor Peter Thiel had been funding Bollea's lawsuit. Thiel says he was outed by Gawker's now-defunct Valleywag site in 2007, adding that Gawker has published stories that have been “very painful and paralyzing for people who were targeted.”
In June 2016, Gawker Media filed for Chapter 11 bankruptcy. The move helped the company avoid having its assets seized as it continues to appeal the verdict.
In August 2016, Denton filed for personal bankruptcy to protect himself from Hulk Hogan's lawsuit. Denton is personally liable for $10 million of the $140 million judgment, and is jointly liable for another $115 million. In a memo to the company, Denton said: "It’s disturbing to live in a world in which a billionaire can bully journalists because he didn’t like the coverage."
On August 16, Spanish language media company Univision agreed to pay $135 million for Gawker Media. Denton said of the deal: "We could not have picked an acquirer more devoted to vibrant journalism." It's unclear whether Denton will stay on after the sale is finalized.