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Frind's online dating company, Plenty of Fish, is newly located on the 26th floor of a downtown skyscraper with a revolving restaurant on the roof. The gleaming space could easily house 30 employees, but as Frind strides in, it is eerily quiet -- just a room with new carpets, freshly painted walls, and eight flat-screen computer monitors. Frind drops his bag and plops himself down in front of one of them.

He looks down at his desk. There's a $180,000 order waiting for his signature. It's from VideoEgg, a San Francisco company that is paying Frind to run a series of Budweiser commercials in Canada. Like most of his advertising deals, this one found Frind. He hadn't even heard of VideoEgg until a week ago. But then, you tend to attract advertisers' attention when you are serving up 1.6 billion webpages each month.

That's a lot of personal ads. "One-point-six ba-hillion," Frind says slowly, smacking his lips on the hard b. "There are maybe 10 sites in the U.S. with more than that." Five years ago, he started Plenty of Fish with no money, no plan, and scant knowledge of how to build a Web business. Today, according to the research firm Hitwise, his creation is the largest dating website in the U.S. and quite possibly the world. Its traffic is four times that of the dating pioneer Match, which has annual revenue of $350 million and a staff that numbers in the hundreds. Until 2007, Frind had a staff of exactly zero. Today, he employs just three customer service workers, who check for spam and delete nude images from the Plenty of Fish website while Frind handles everything else.