Why Is This Man Smiling?

Wales will need to duplicate what Google has already done before he can try to improve on it. He needs machines to generate search results before humans can look them over and tweak them. He's starting out by relying on the free open-source search projects Nutch and Lucene, which have successfully replicated a lot of the vital under-the-hood mechanics. But he's going to need more, which is perhaps why Wales takes the long view. "If you're growing community, a healthy community Web site, it takes time," he says.

As a personality, Jimbo Wales, 40, is full of fascinating contradictions. The biggest mystery may be how a former options trader and self-professed follower of objectivism, the philosophy of Ayn Rand--a combative elitist who glorified the heroic, capitalistic individual and denigrated the envious, ignorant masses--became the guiding force behind a collectivist Web site that's often criticized for its "mob mentality." Wales is such an objectivist that his daughter Kira, 6, was named after the heroine of Rand's first novel, We the Living. Yet he has been criticized for being the Web's equivalent of a Maoist, and he playfully likes to wear red silk Mao jackets at public appearances.

During my time with Wales, he slowly reveals the different layers of his personality: At the base, there's the gentle geek who uses the word "fun" or "funny" in nearly every paragraph and seems genuinely driven by the pure intellectual challenge and the public-spirited idealism of his projects. He carries a Sidekick, because "I'm kind of a noncorporate-y kind of guy. It just seemed so--I don't know, I'd have to get a suit if I had a BlackBerry." Yet he says this while wearing a dark chalk-striped blazer, very Wall Street, having just come from an appearance on MarketWatch. (He did subvert the look with a purple turtleneck.)

He checks email and instant-messages obsessively, even in the moments when he's waiting for the barista to make his coffee. "If I'm stopped at a red light, I'll look at the news headlines, although I try not to do that too much. My wife doesn't approve of that kind of thing in the car while driving." In this way, he's like his techno-nerd friend Craig Newmark from Craigslist (who gets wide-eyed with awe about Wales, saying "Craigslist is for the moment, but Wikipedia is for the ages"). But unlike Craig, Jimbo is socially comfortable and adept, a quiet charmer and effective communicator.

But that's just the start of his apparent contradictions. Jimbo is wealthy, having made enough money on Wall Street by his early thirties that he wouldn't have to work again, yet he's a confessed cheapskate who lives in a modest single-story house in St. Petersburg, Florida, and he has spent the past half-decade working for nothing for a Web site dedicated to free access to human knowledge. He's both an outsider and insider. "All of our social world revolves around my daughter," he says, but "professionally, I know more people in London than in Florida." And he clearly relishes consorting with celebrities from business, politics, and popular culture, as he did that week on Richard Branson's private island: He was thrilled when his daughter flew on a helicopter with the Carters, and the ex-president said that he used Wikipedia every day.

Wales talks about Wikia and his new search project as if it's his rich-man's toy, his version of playing golf. "As long as it's fun, I don't care," he says. "As long as we're having fun," he repeats, "and it's an interesting project and once people are interested, let's take a shot at it. Search can pay for itself even if you don't become the market leader. Well, why not?" Go deeper, though, and he betrays hints of the tenacity and ambitiousness of a true mogul. When Wales talks a lot about the public good and just having fun, one can forget that he's the founder of a startup that runs paid advertisements alongside the content created by its communities. Although Wales still sits on the board of the nonprofit Wikipedia Foundation, he gave up its chair to focus on Wikia, a separate and independent for-profit company, working with Penchina, who used to run eBay's European businesses. (Penchina is more of the inside-operations guy, while Wales is the public figure.)