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Markus Frind is pale, bespectacled and six feet tall, a regular dude who has the desire to do the least possible work for the best possible outcome. He has a feline grin, an even keel and lanky arms emerging today from a formless short-sleeve shirt—a cross between golf garb and something a tad dressier. It's a style meant for men twice his 33 years, boomers whose only exertion is to toddle to the first tee. But evidently, the shirt is to Frind what the Adidas shower shoe is to Mark Zuckerberg.

It gives him the look of a true coder. With just a diploma in computer systems from the British Columbia Institute of Technology (BCIT), Frind—the son of German farmers—has applied his prodigious talents to, the free dating website he founded in 2003 on his home PC. Today, it's the most popular such site in the country, and a top global concern—a business that relies on advertisers (most of them his competitors) reaching millions of people looking for love. Or to hook up. Frind doesn't judge.

We are inside his company's glass-walled boardroom, like specimens in an aquarium: a long, thin sturgeon (Frind) and a pufferfish (me). He sits with his back to his workforce, 20 or so young techie types in jeans and sneakers, hunched over their keyboards, their knotted eyebrows signalling their intent to be productive—but not too productive. Down the hall, photos of a staff cruise have the hint of a college bacchanal. In years past, Frind claimed he worked just an hour a day, simply because that's how long it took him to get the job—any job—done.

Efficiency is his modus operandi: Do everything in the most streamlined way possible; abjure all bells and whistles, because they'll just complicate your life; don't dwell on aesthetics; and get the most out of your team—which, just a few years ago, was nobody. Now, he says, with live bodies accumulating in two offices on two different floors of the Harbour Centre in downtown Vancouver, "it's completely useless to me to hire people to do just one thing. I have programmers doing marketing. I have customer service people working on the product."

When he built the site, there was no shred of a business plan, just a basic offering. The text was crude, full of random bolded words, and photos came out like distortions in a funhouse mirror. Not one to spend time on making a site look pretty, Frind's focus then, as now, is the program—his "Behavioral Matching Engine." It was featured on a 2007 segment of The Today Show, as he writes in his exceedingly boastful blog, "years before any other dating site even knew that kind of stuff was possible. I feed it with nearly 20 billion pieces of data." The database is everything.

"When I first met Markus at a conference in 2006," recalls Mark Brooks, a New York-based consultant for the Internet-dating business, "he said, 'I'm going to be the biggest dating site in the U.S.' I pooh-poohed his hokey little site. Then he made me eat my words." (Frind became a client of Brooks that same year.)

Because it's the Internet, and nothing makes sense, the site's original aesthetic laziness bolstered its credibility. "It was underpromising in its looks and overdelivering in its service," says Brooks. "It sent the message, as a Craigslist does, that here's this one guy doing us all a favour."

Since then, Frind has expanded his audience as

quickly and eagerly as tetra fish mating. He has launched a paid dating site, called eVow, for those into serious partnering; a PlentyofFish mobile app; even a deal-of-the-day venture called Offeron modelled on the blockbuster Groupon. PlentyofFish is loaded with Offeron ads because the dating site has a captive audience of more than five million users who log in at least once a month.

Markus Frind understands the winning potential of numbers.


In online dating, which attracts roughly 1.4 billion consumers globally, Sundays are particularly fruitful—the day when single people feel most alone. And so it was that, on a Sunday in May, PlentyofFish hit a record 6.2 million log-ins in a single day. (The site has since jumped the seven-million mark.) The breakthrough moment allowed Frind to post a soaring fever chart on his blog. "Hard to believe after eight years PlentyofFish still has non-stop growth with no signs of slowing down any time soon," he wrote.

In person, it's hard to believe that Frind is remotely incredulous about his triumphs. He speaks quietly but with unwavering conviction, making little shrugs as if to signal facts I should already know—the gesture equivalent of "aber natürlich," the German "but of course." And he is swiftly dismissive of his rivals: "Oh, we left them in the dust long ago," he crows. According to the media tracker comScore, PlentyofFish draws a staggering 2.8 billion page views per month, compared to 723 million for, and has 6.3 million unique visitors, about the same as its Dallas-based arch-nemesis. And the newly launched PlentyofFish mobile app, Frind claims, has been downloaded by one million users. "It didn't really exist before Christmas and now it's half of PlentyofFish usage," he says. It irks Frind that a recent Financial Times piece gave props for enabling 1.2 billion e-mail exchanges over the past six years. He declares that PlentyofFish users send 5.5 billion e-mail messages to one another in a single year.

That said, numbers are a matter of interpretation. For starters, comparing PlentyofFish's five million regular users and's 1.9 million subscribers isn't exactly apples to apples, since the former is a free site, and the latter is not. And the online personals game is not unlike the news industry, in that a great deal of time is spent locating the precise figures to convince both users and advertisers that one's particular product is the strongest.

Several dating sites claim to be the most successful, citing any number of criteria—frequency of dates per user, number of marriages, number of "connections" the site has facilitated. Badoo, a site that requires users to log in via Facebook, actually has a running ticker tallying God-knows-what-exactly on its home page: "122,731,621 people are already here!" it read the last time I checked. Surf over to PlentyofFish and you'll see this claim at the top of the page: "More dates, more relationships than any other dating site." That's eerily similar to's ubiquitous campaign (which I notice during marathons of the TLC bridal show Say Yes to the Dress and, oddly, Hoarding: Buried Alive): "More dates, more relationships and more marriages than any other site."

Back in April, Frind wrote on his blog that "PoF is probably #1 in terms of marriages now." But when I ask him about this in person, he hedges: "The way I measure it is not scientific," he admits. "But we look at the number of people who say they're entering into relationships when they leave the site, and then, to get a ballpark figure, you take 12.5%—supposedly, that's the percentage of relationships that end in marriages." One can only verify this measure of worldwide domination, he concedes, by "doing a massive study," but he points to the absence of one.

As the consultant Mark Brooks observes, online dating is a "virgin industry." It's only been active since 1995, the year was born. If your entire sphere of reference is 16 years old, it's a challenge to weigh results.

Slightly easier to pin down is the money., owned by Barry Diller's publicly traded IAC, has the mightiest revenue—$400 million (U.S.) last year, with revenue up 20% in the first half of 2011. By comparison, says Frind, PlentyofFish's earnings, generated solely from advertising, are in the "tens of millions."

Any site can bring in $100 million, he assures me; he's just not so into that right now.


To captivate Markus Frind's interest, one has to place a problem in his way. When he was 5, his

parents moved from Germany to Hudson's Hope, an unforgiving landscape an 18-hour drive from Vancouver, in B.C.'s remote north. At first, the family lived in a trailer on a 1,200-acre farm. No electricity. No running water. Every night until he was 10, Frind, the eldest of two boys, played chess with his dad. Game after game, his father mercilessly defeated him. It was only after Frind diligently studied patterns and, as he says, "learned to see what would happen five, six or even 10 moves ahead," that his fortunes changed.

Aber natürlich, he started winning. "Of course," he says. And he didn't stop.

Frind left the "land of dinosaurs and dams" (town motto) for good after high school for two years at BCIT. After graduation, with the dot-com bust lingering, he flitted from one sinking ship to another, mostly doomed Internet marketing companies. In 2001, he was noodling around on dating sites "because I was bored and wanted to chat with people," when he was struck by the utter lameness of their sign-up fees. For what? he thought.

As he writes in his blog—under the fist-pumping title "How I Started a Dating Empire"—he could do better, and not charge anything. Frind registered the domain name, then did nothing until February, 2003, when he found himself on the deck of the HMS Imminent Unemployment. His latest employer had shrivelled from 30 staff to 15 in three months. He could be next to go, so he decided to do something more useful and learn the Microsoft website-building tool ASP.NET. Using PlentyofFish as his training ground, he built a few bare-bones pages, read up on search-engine optimization, and let everyone he could think of know about the site. By March, he had his first 40 users.

For a guy who'd probe forums asking questions like "I am interested in know [sic] how much money sites generate off advertising," Google AdSense couldn't have launched at a better time. Frind added the new program that summer, and, over time, it brought advertisers. By the end of 2003, as the number of singles using his site grew to 10,000, Frind was earning more than $3,000 a month in ad revenue—enough to quit his job.

In 2006, he posted a scan of a cheque for two months' earnings—amounting to more than $900,000—mostly to hush those techie bloggers who couldn't believe such payoffs were possible for an ungainly site like PlentyofFish. Two years later, the company was bringing in $10 million a year, with a 50% profit margin.

The ad model endures to this day: If a PlentyofFish user is a younger woman interested in older, wealthier guys, for instance, up pops an ad for a paid site to entice her—say, Established Men, the sugar-daddy concern owned by Noel Biderman, president of Toronto-based Avid Life Media. Biderman—best known for the infidelity site Ashley Madison (slogan: "Life is short. Have an affair") and the rate-a-bimbo site Hot or Not—is a long-time PlentyofFish advertiser. He pays Frind on a cost-per-impression basis, which works out to roughly $150,000 a year.

Biderman once tried to buy PlentyofFish, in the early days, but he says Frind's "$100-million valuation" wasn't quite what he had in mind. "Entrepreneurs have to believe what they're doing and do it their way. We all put our heads down. But Markus put his head way down," Biderman says. "He might have tripled his traffic that way, but that doesn't mean he will triple his revenue. He has to figure out how to do that. Or he can look in the mirror and say, 'I've done the best I can. Now I need to find a true operator to take this forward.' "

But, of course, hell would have to freeze over for Frind to let go. Instead, he's investing in his new mobile app, diversifying into Offeron, and has a general plan to expand into the non-English-speaking world—to be "everything, everywhere, for everyone." That's one of Markus Frind's mottos.

For now, he still arrives at the office at 11 a.m., sometimes noon. "I walk around to see what people are doing. Of course, I already know what they're doing." And then a few hours later, after surveying the kingdom of his own creation, he will stroll three blocks to his three-bedroom Cole Harbour condo, to lounge and play video games (he likes Age of Empires). An inspiration to lonely hearts everywhere, Frind is married to a radiant blonde named Annie, a graphic designer he met in 2002 and married in Mexico last year. The Frinds are fond of skiing and travel. They toured 12 countries in four weeks earlier this year. Frind ticks them off: "Rwanda to see the mountain gorillas, South Africa for safari, the Maldives, Cambodia, Laos, Bhutan…"

When they returned, Frind's focus intensified on the mobile app. A PlentyofFish member's average age is 39, but mobile daters tend to be a decade younger at least, a group that can't do as much as breathe without their smartphones. The PlentyofFish app lets them go to a bar, see who else is single, load prospects' photos and profiles onto their phones, send messages and select from the following options: yes, no or maybe later. It's a brutal world of rapid-fire decisions, perfectly suited to the central Markus Frind tenet: "Adapt or die."


Any empire needs a fitting command centre. For Markus Frind, it's the Harbour Centre—a tower of waning manhood that used to be (past tense) the tallest in Vancouver. It has a pointy needle and a

revolving restaurant, the architectural equivalents of mutton-chop sideburns. Its elevator rattles flatulently all the way up to the 26th floor, where, at 2625, there is an unmarked door, a buzzer and a camera.

Inside, Frind and I discuss the need for security. Because this business attracts a lot of weirdos. In the first years of PlentyofFish, when membership was increasing by 500% annually, ad revenue was falling out of the sky, and Frind was CEO, programmer and everything else, the Vancouver police would periodically show up at his door. Most often they were looking for information on crazy boyfriends who'd posted bleakly cruel personal ads targeting their exes.

Now, the attacks are a bit more complicated. Hacking threats, says Frind, "are the price you pay for being so large." Many of his 29 employees spend their time on the lookout for these attacks, which are "24/7, nonstop attempts to take down the server. You have to write a ton of code to protect yourself and constantly monitor," he says.

This January, as Frind was on a plane headed to the iDate conference in Miami, a hacker tested the system for two days straight until he found a way in. The intruder, Chris Russo, later identified himself as an Internet security specialist from Argentina. After exporting several hundred accounts, Russo contacted Frind's wife by phone at midnight, Miami time. He demanded money in exchange for closing the breach.

It got nuttier from there. Russo claimed his associates included a former Washington Post reporter, and he suggested he was being chased by Russian thugs. Frind's team plugged the leak in the server, but for the next day or so, at all hours, Frind says Russo left frantic messages. "Let's just say when someone hacks into your accounts, then calls you up to say you should either fly to D.C. to meet with this journalist—who, by the way, might be working for the CIA—or go to Argentina to meet him, you know something is weird. It was a lot to deal with in the middle of the night—after a bottle of wine."

Frind and his employees (just three of whom handle security, besides the boss) went into a zone he knows all too well. "When you constantly deal with crises, usually hardware or machines breaking down, you learn to a) assess the situation, b) control the situation and c) solve it," he says, evoking the same methodology he used to annihilate his dad at chess. Russo eventually gave up, only to surface again several months later in relation to a far different matter.

In May, the Toronto Star reported that PlentyofFish might provide clues to the unsolved murder of Sonia Varaschin. The 42-year-old nurse, whose body was discovered in a field in Caledon, Ontario, had been a member of the site. Reports speculated that Varaschin had met her killer on PlentyofFish, or that a hacker had found her details there and hunted her down. In truth, Varaschin had not been active on the site for years, and Frind is adamant her personal information was never accessed by a hacker.

But in this business, perception is everything.

During the media swirl—as if summoned by the cyber-verse—Chris Russo rematerialized. This time, news outlets were reviving an old e-mail statement he made to the Vancouver Province, saying that he "discovered a vulnerability in, exposing user details such as user names, addresses, phone numbers, real names, e-mail addresses, passwords in plain text and in most cases, PayPal accounts. …This vulnerability was under active exploitation by hackers."

Frind countered, saying PlentyofFish "deletes all e-mails after 30 days, even if you are an active user. We don't collect phone numbers or PayPal accounts and never have."

Still, a few weeks after the flurry of news, I mention to an acquaintance in Toronto—a young woman in her 20s—that I'm working on a story about PlentyofFish. She winces. That's where that psycho met the woman who was murdered, she says.

It didn't help matters that, on the other side of the country, health officials in Alberta launched a campaign targeting the rise of syphillis with a parody site. Its name: PlentyofSyph.


When he was 25, Frind wrote a program that found 23 prime numbers in succession, meaning they are separated by the same number. The findings were cited in a paper that won the Fields Medal, math's Nobel. Of course, he notes, that was very hard to do, and he nailed it. "I'm very good at looking at chaos and picking out exactly what matters," says Frind.

Perhaps that explains why, on the surface, the site is the same old fish it ever was—full of ungainly grammar and unruly capitalizations—but that the program underpinning it, which Frind writes himself, is in continuous improvement mode.

The basics are this: On registering at, users are asked a series of questions that determine whether they should be placed in a "commitment material" bucket or a "casual dater" bucket. Then the match pools are narrowed down to "people you aren't likely to hate," as Frind puts it—as simple as keeping the non-smokers separated from those who smoke. From there, "every user affects another user's behaviour. You have to figure out how to measure the changes that result from this, and figure out what you've done that's important and helps the site grow."

Frind's data-crunching isn't anything mind-shattering. It's about determining cultural and personal preferences, just as on any other site, from on down. But he knows, for instance, that a guy in rural Manitoba considers it no obstacle to date a girl living 100 kilometres away, but that a girl in Manhattan wouldn't be caught dead dating a loser from Jersey. To put it another way, if I were single and on the system, I would answer my questionnaires so as to suggest I don't want profiles of guys who like to kiss their pecs (seen in alarming quantity on PlentyofFish) or lonelyTED from St. Catharines (too far!) or junglehiker from Markham (too sporty!).

However, if I were to repeatedly click on the musclemen anyway—and, better yet, if I were to actually send them messages—then Frind would see that, okay, this gal can't admit what she really wants. And he'd send me pecs. Similarly, if a man on PlentyofFish professes to want a long-lasting relationship with a woman 35-plus but is always searching the site for hot co-eds, then Frind will stop serving him up to marriage-minded women. Maybe he can also do something about the inordinate number of his male users who pose either standing in a pool, underwater in a pool, or freshly emerged from a pool. What's with the waterworks?

And it may be that the profile photos are looking quite a bit less squished than they used to—but they're still not radiating exclusivity. "It's a hookup site," one acquaintance assures me, regaling me with a story of a male friend who used PlentyofFish to arrange multiple dates on one night.

Then again, I know a lovely Toronto couple who met through Frind's creation three years ago. Victoria's 32, a chef; Scott's 29, an actor. She signed up for PlentyofFish mostly as a lark. "I didn't take it all that seriously," she says—though seriously enough to fill her profile with a list of everything that made her happy. Instantly, she was inundated with creepy guys referencing nothing from her profile, but instead offering her massages and threesomes—your basic online-dating nightmare.

In the middle of it all, she got a message from Scott, who was intrigued because her list of beloved things included the band Ween (how many girls like Ween? he thought). Soon, they discovered the myriad other reasons they should be together.

By all accounts, their August wedding in Northeastern Ontario was superb. Why did she pick PlentyofFish over the multitude of other dating sites on the Web? One reason alone: "It was free."

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