"When Silicon Valley starts seeing itself as the glamour capital rather than Hollywood," he said, "that's when I think we're taking ourselves too seriously and heading for another period of irrational exuberance."
To run Valleywag, Denton wanted someone who had no bridges to burn, a Silicon Valley outsider. Douglas grew up in Lima, N.Y., with a population of 4,500, where the hottest thing going is the annual Crossroads Festival and a related lima-bean cook-off. His father designs fuel-injection systems; his mother works as a library clerk.
Denton and his associates call Douglas "Little Nicky," for his slight build and boyish face. Without the thin red beard the writer sometimes sports, one friend says, "he'd look like he's 16." Douglas says he's "just a kid having fun." When discussing his choice of hand-held computers, he earnestly quotes Bill Gates' 1995 book, "The Road Ahead."
While slogging through a tedious data-entry job last summer, Douglas began writing for Blogebrity, a navel-gazing blog that writes about what other blogs are writing about. Among his subjects was the long-standing public feud between Denton and Jason McCabe Calacanis, who ran rival Weblogs Inc., now owned by AOL.
Denton had long been considering a tech gossip blog in San Francisco. He liked Douglas' style and approached him about the job. Only a few credits shy of a bachelor's degree in English, Douglas thought the idea was nuts. But, after a visit to San Francisco, he decided to drop out of school and take the job. He won't say how much he makes, just that it's not much.
"It was my dream job, writing for a living," he said.
He came out swinging. He revealed that Marissa Mayer, a much-quoted Google vice president, had dated co-founder Page until late last year. Douglas created a mock Us Weekly magazine cover of the two.
He exposed the identities of the Googlers each was then dating, posted photos from a company holiday party and let readers vote on whose date was hotter. Page's date, Lucy Southworth, beat Mayer's date, Dave Jeske, in a landslide, 1,405 to 1. Douglas later found the photos of Page and Southworth on the jet.
He also tackled Yahoo, even though the Internet giant distributes several Gawker Media blogs on its websites. After some Yahoo executives posted vacation photos for friends on Yahoo services but failed to secure them with a password, Douglas put some of the pictures on his site. With one, titled "Toby Coppel's hot wife," readers were asked to comment on her attractiveness.
Douglas typically works in his Smurf-colored room next to the coin-operated laundry machines he shares with 14 housemates. A battered dresser top holds a biography of Apple CEO Steve Jobs and a coin-filled mug whose inscription winks at the blogger's constant quest for traffic: "Link to mine, I'll link to yours."
Most mornings he rolls out of bed -- a mattress on the floor -- around 7 a.m. and makes the day's first post before getting coffee. Although his computer is an old Compaq laptop issued in his freshman year of college, one of his strengths is his ability to use the latest technology to cultivate sources and find information. Most of his tips come in via e-mail and AOL Instant Messenger -- he has 210 people on his buddy list.
In many cases, such as with the Yahoo executives' photos, the services being created by Internet companies make it easier for Douglas to dig up dirt.
He also eschews journalistic norms and practically begs for tipsters. In a post about police activity outside the mansion of the billionaire founder of Oracle Corp., Douglas concluded with, "If Larry Ellison's housekeeping staff is reading this, help the press out: ¿Que paso en la casa de Ellison el sabado?" ("What happened at Ellison's house Saturday?")
He's required to write a dozen posts a day, so the level of scandal varies widely. Sometimes he's content to mock a new Microsoft Corp. advertising campaign or a mainstream media story on technology. One day he trolled Craigslist for personal ads by tech-industry people and posted them, including one from a San Francisco software engineer who came up with this: "I don't make sex; I make love."
Douglas says he tries to check his facts before publishing. But he's willing to post inflammatory e-mails from anonymous sources with disclaimers such as, "Today's guest may be in the know, or they may do a great job of faking it. Your call."
He then publishes responses sent in defense of those attacked.
Douglas' approach has earned him some cold responses on the party and conference circuit where he goes to collect sources and rumors. At a conference in Austin, Texas, he ran into Google and Apple employees. His introduction was met with an icy reception.