And the Money Comes Rolling In

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By early 2003, the technology economy in Vancouver had yet to bounce back, and Frind's sixth employer in three years was laying off half its work force. Worried that he would again find himself unemployed, Frind decided he needed to bolster his qualifications. He would devote a couple of weeks to mastering Microsoft's new tool for building websites, ASP.net, and he would do it by building the hardest kind of website he could think of.

Online dating was an inspired choice. Not only does the act of building an intricate web of electronic winks, smiles, and nudges require significant programming skills, but the industry has always been a friendly place for oddballs and opportunists. Industry pioneer Gary Kremen, the founder of Match and the man who registered the Sex.com domain name, cites rapper Ice Cube and the bank robber "Slick" Willie Sutton as important influences on his business philosophy. Another pioneer, James Hong, co-founded Hot or Not, a site with a single, crude feature. Hong allowed users to upload pictures of themselves and have other users rate their attractiveness on a scale of 1 to 10. Hot or Not was acquired for $20 million in cash last year by Noel Biderman's company, Avid Life. Avid, which has also courted Plenty of Fish, derives most of its revenue from Ashley Madison, a dating website for married people (tag line: "Life is short. Have an affair"). The site has 2.8 million members and revenue in the tens of millions of dollars.

Unlike many online dating entrepreneurs, Frind didn't start Plenty of Fish to meet women -- or even because he had some vision of business glory. "It was a burning desire to have something stable," he says. "And I didn't really want to work." Frind's eyes were also a factor. He suffers from hypersensitivity to light, and his eyes were not taking well to long days in front of a screen. Working a few hours an evening for two weeks, Frind built a crude dating site, which he named Plenty of Fish. It was desperately simple -- just an unadorned list of plain-text personals ads. But it promised something that no big dating company offered: free.

The idea had initially come to Frind in 2001, when he started checking out Canada's then-largest dating site, Lavalife, hoping to meet women or at least to kill some time. Online dating seemed like a good idea, but he was startled to discover that the site charged users hefty fees. "I thought it was ridiculous," he says. "It was this rinky-dink little site charging money for something anyone could make. I was like, I can beat these guys."

This thought was not exactly new. Since the mid-'90s, there had been dozens of free dating start-ups, but all had struggled to attract users, because they were competing with the outsize marketing budgets of paid competitors like Lavalife. Paid sites could afford to spend $30 or $40 in advertising to acquire a user. A free site could afford to spend perhaps 40 cents, making it exceedingly hard to attract daters and still turn a profit. Frind's answer to this problem was somewhat radical. Rather than try to compete directly with Match, the industry leader, he created a website that cost almost nothing to run and was aimed at the sort of people who wanted to browse a few profiles but weren't ready to take out their credit cards. In doing so, he had found a way to reach a large, underserved market. Even better, he had created a perfect place for paid dating sites to spend their huge advertising budgets.

Plenty of Fish grew slowly at first as Frind focused on learning the programming language and trolling Internet forums for clues on how to increase his traffic. There are a handful of half-literate posts from early 2003 in which Frind asks basic questions, like "I am interested in know how much money sites generate off advertising." Reading these comments in retrospect paints a picture of determination and naiveté.

Frind knew little about search-engine optimization or online advertising, but he was a quick study. From March to November 2003, his site expanded from 40 members to 10,000. Frind used his home computer as a Web server -- an unusual but cost-effective choice -- and spent his time trying to game Google with the tricks he picked up on the forums. In July, Google introduced a free tool called AdSense, which allowed small companies to automatically sell advertisements and display them on their websites. Frind made just $5 in his first month, but by the end of the year, he was making more than $3,300 a month, largely by selling ads to paid dating sites that were interested in getting his unpaid members to trade up. He quit his job.

"Have you ever met anyone like me?" This is both a boast and a genuine question: Frind has few friends in business, no mentors, and no investors. Moreover, he has taken a path that seems at odds with the conventional wisdom about Internet companies. Most websites with as much traffic as Plenty of Fish would have by this point raised millions of dollars from venture capitalists, hired dozens of engineers and business-development types, and figured out a way to keep someone as unconventional as Markus Frind from making any major decisions.

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Max Chafkin

Senior writer Max Chafkin has profiled companies such as Yelp, Zappos, Twitter, Threadless, and Tesla for the magazine. He lives in Brooklyn, New York.

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