Often, at the end of a long workday, which is to say around noon, Frind plays war games. His apartment is outfitted with five computers for group play of Age of Empires and Command & Conquer -- and he has a substantial collection of board games. He is good, too: When I joined him for a game of Risk in October, he sat silently for almost the entire game before clearing the board in a single, virtuosic turn. He was still gloating the next morning. Frind approaches business in much the same way. "It's a strategy game," he says. "You're trying to take over the world, one country at a time."
Frind's account of his own exploits, published on his blog in 2006 under the title "How I Started a Dating Empire," says a lot about his worldview: "I spent every waking minute when I wasn't at my day job reading, studying, and learning. I picked out 'enemies' and did everything I could to defeat them, which meant being bigger than them. I refused to accept defeat of any kind." Around the same time, he returned to one of his old Internet hangouts, a forum called WebmasterWorld, and posted a brief how-to guide entitled "How I Made a Million in Three Months." It contained a blueprint for the success of Plenty of Fish: Pick a market in which the competition charges money for its service, build a lean operation with a "dead simple" free website, and pay for it using Google AdSense.
By 2006, Plenty of Fish was serving 200 million pages each month, putting it in fifth place in the United States and first in Canada among dating sites. Frind was making amazingly good money, too: $10,000 a day through AdSense. In March of that year, Frind mentioned these facts to Robert Scoble, a popular tech blogger whom he met at a conference in Vancouver. When Scoble wrote about the solo entrepreneur with the ugly website making millions of dollars a year, his readers were in disbelief. At the time, AdSense was seen as a tool for amateurs. It might cover your blogging expenses, but it wouldn't make you rich. Frind's website was also downright ugly. A search-engine-optimization blogger, Jeremy Schoemaker, wrote that Frind was a liar. "Give me a break, dudes," he wrote. "You look so stupid when you buy into his crap."
Frind embraced the controversy. He posted a picture of a check from Google for nearly a million Canadian dollars (or about $800,000) made out to Plenty of Fish. It represented two months' worth of revenue and implied that his site was making $4.8 million a year. But some thought the check was a fake, while others felt that posting it was a crude promotional stunt. "He came out of nowhere, and he didn't seem to give a shit," says David Evans, who writes the blog Online Dating Insider. But the stunt worked. Frind's site was the talk of the blogosphere, driving gobs of new users to the site. Plenty of Fish's growth accelerated dramatically, hitting one billion page views a month by 2007.
By the summer of 2008, with his site moving into first place among dating sites in the U.S. and the U.K., Frind began to wonder about his next step. He rented a 3,700-square-foot suite in Vancouver's Harbour Center, announced he was going to hire 30 employees, and bought a BlackBerry. But the plans were not exactly concrete. By October, Frind's own office was still empty: no furniture, nothing on the walls. He still hadn't figured out how to get e-mail on his cell phone. He had hired three people, not 30.
Frind seems untroubled by this disconnect. He says he leased an office because he was tired of working at home. He assumes he will one day need more employees, but he hasn't figured out what he would do with them. And he is in no hurry. He hasn't even bothered to offer a French language site for the six million French speakers living in Quebec. "I'll get around to doing that eventually," he says.
With all the free time on his hands, why doesn't Frind just start a second company? He says he thinks about that sometimes and has even toyed with creating a free job- listings site but finds the idea stultifying. "Sure, I could do it, but it'd be like watching grass grow compared to this," he says, gesturing at a traffic chart that shows Plenty of Fish's growth over the past few months. "It'd be like" -- he adopts a high-pitched, mocking tone -- " 'Whoop-de-doo, we got 100 visitors today.' Whereas with my site, every day there's another 1,000 or 10,000."
It's hard to know what to make of a guy who works an hour a day, who doesn't travel much, and who doesn't have any hobbies beyond war games somehow fretting about boredom. How is he not bored already?
But if Frind is guilty of a kind of sloth, there is also a wisdom to his passivity. Being ever careful takes serious self-discipline, and an aversion to doing harm can be more valuable than an overeagerness for self-improvement. If nothing else, it's impossible to argue with his success. Frind created his own game and wrote his own rules. As growing legions of lovesick people around the globe search for their perfect mates and advertisers fall over one another to write him ever larger checks, he just kicks back and smiles. And the money rolls in.
Max Chafkin is a senior writer for the magazine. He wrote the November cover story on Kevin Rose, founder of the social news site Digg.
