The Love Techs

Max Krohn, left, and Sam Yagan, two of OkCupid’s founders. (Photograph by Dana Smith)

Floyd’s 99 Barbershop in the Back Bay is a chain, but it’s a “hip” chain—hip in the sense that it occasionally plays hip-hop and the stylists are all young and have complicated asymmetrical two-tone haircuts. The clientele is young, too: Berklee kids in skinny black jeans getting faux-hawks, Urban Outfitted frat boys from Northeastern getting Growing Up Gotti–style blowouts. I didn’t go to Floyd’s thinking about dating, but it’s nonetheless where I experienced an epiphany on the subject.

It began with my barber, Mike, a bearded guy whose good looks and laid-back nature made me think that if he lived in L.A. he would probably be a barber/actor. He was taking his clippers to the back of my neck when he started in on the success he’s been having dating online. The receptionist chimed in to offer anecdotes of her own online dating adventures. A manager type looking on chuckled knowingly. And it was in the midst of all this innocuous small talk that I realized what was going on. I was in a normal, relatively cool place, having a normal, relatively cool conversation with normal, relatively cool people. About online dating. And that sort of freaked me out.

Rewind your social-judgment clock to Y2K, or even to just four years ago, before the proliferation of social networking sites, and try to remember who you thought dated online. A quick straw poll of my mom—ever the pulse of the mainstream—provides a refresher: “creepers, child-snatchers, and geeks.” Harsh though that may be, what’s true is true. But if you think it through, the shift toward acceptance that online dating has undergone feels almost inevitable. As a generation of computer-using kids reaches dating age, the idea that the Web is just as natural a tool for finding a date as it is for finding an apartment no longer seems so crazy. And that’s not lost on Web entrepreneurs, who are finding good reason to tap back into what was not so long ago a maligned business: Experts project the suddenly booming industry could be worth more than $900 million annually within three years.

Such rosy prognostications, though, come at a time when analysts say interest in the industry Goliaths, sites like Match.com and eHarmony, has plateaued.

The growth is coming from upstarts, the most promising of which is plucky Cambridge-based OkCupid—a company hell-bent on changing everything you thought you knew about online matchmaking, and maybe matchmaking in general.

The site’s founders—math-majoring Harvard alums Max Krohn, Chris Coyne, and Sam Yagan—seem an unlikely trio to change dating norms. But such are their not-insignificant ambitions. Borrowing the insights that made the social networking behemoths Facebook and MySpace so popular, their OkCupid eschews the standard playbook for online dating sites (for starters, theirs is free) in favor of the novel idea that they ought to be, well, fun.

That the three founders were also the creators of a once-popular online community, TheSpark, explains their approach a bit, or at least their intention, which is to provide a site where users can just hang out, click around, and meet some people. If that sounds to you like the same sort of environment in which people form connections offline, you’ll perhaps understand why the site has more than half a million active users, and why OkCupid is creeping within striking distance of Match.com (which boasts some 1.3 million paid subscribers).

Nowhere is OkCupid more popular than here in Boston, where some 45,000 use it. Popularity like that not only makes sense—we are, after all, a city brimming with college kids and busy young professionals with serious tech know-how—it also explains the chatter at Floyd’s.

I am sitting in Kendall Square—arguably the techiest part of arguably the techiest city in America—and I am spilling soup. It’s a screw-Al-Gore-cold day, and inside Legal Sea Foods, among the aquariums and brown leather booths, sit the technologically articulate. Professorish guys in tweed perch at the bar, seeming in no particular rush, while biotech staffers make awkward chitchat in rumpled business-casual. The place reeks of world-changing scientific innovation (and clam chowder). The perfect spot, I figure, to meet Max Krohn, one of OkCupid’s founders.

Across the table from me, he’s wearing a gray zip-up sweater and those small rectangular glasses favored by the users of MacBooks. His nerd-cool look is paired with an impressive résumé that he’ll cap with a computer science Ph.D. from MIT later this year. The architect of the Web server that powers OkCupid, Krohn fell in with Yagan and Coyne when they were all freshmen at Harvard in 1995. This was at the outset of the Internet boom, you’ll recall, and the meeting was one of those serendipitous, find-your-genius-partners deals that were oh-so-popular in Cambridge when the Web was first minting millionaires.

Employing their complementing talents—Krohn the technical wizard, Yagan the businessman, Coyne the creative visionary—they launched TheSpark in the spring of their senior year. The youth-centric site was a grab bag of early Internet standards, including SparkNotes (knockoffs of the ubiquitous CliffsNotes) and random humorous articles. It also included what Krohn describes as a “very rudimentary” dating service, SparkMatch. Within a few weeks of SparkMatch’s debut, Krohn says, pausing to take a bite of his crab cake and then smiling, “we had 100,000 people using it.”

TheSpark’s irreverence was big with the college set—in 2000 it was honored by Maxim magazine as a “Site of the Year”—and particularly among students in Boston. Less than a year after its birth, the trio sold the site to the Web community iTurf, which then flamed out as the Internet bubble burst. When that happened, SparkNotes, the site’s most marketable asset, was sold to Barnes & Noble (which still peddles the print version in stores, much to the delight of layabout students everywhere). The rest of TheSpark was scrapped. “They knew we had all these other features, but they didn’t care,” Krohn says. “The dating part fell by the wayside.” The guys took gigs with Barnes & Noble, but eventually realized they hadn’t become Web entrepreneurs in order to work for a bookstore. The partners parted ways. End scene.

Five years ago, convinced they might have been on to something with SparkMatch, the trio decided to get the band back together. “The idea was to be extremely focused on dating and not worry about the other stuff,” Krohn says. But dating sites aren’t simple to get off the ground. As with all networking sites, their creators have to surmount the so-called cold-start problem: In order to get people to visit a dating site to find other people, you need a bunch of people already on the site for the finding. The solution available to Krohn, Yagan, and Coyne was a convenient one. They reached out to their old Spark fans, and, with minimal marketing spending, took the site live. Within a month, it had 100,000 users.

Even if you’ve never been to an online dating site, you can probably imagine how they work. On the whole, the genre is still not far removed from the AOL and Yahoo chat rooms of the mid-’90s that were online dating’s murky wellspring. Those places were, by today’s standards, awesomely crude social networks: Just pick a screen name, make sure no one is on the telephone, and join the fray. Once in, you could while away the hours in a “singles” chat room, a bizarre den of possibility where you could engage in hilarious/confusing/alarming conversations with boys pretending to be men, men pretending to be women, and men and women pretending to be attractive.

The one important update to the business model came in 1995, when Match.com went live as a subscription-based website. As this was back in the heady days when companies like AOL were still charging by the minute for Internetting, the pay-to-play service seemed a logical way to go. And for years, that general approach has held sway: Users create unique profiles, add pictures, and—depending on the site—fill out some sort of compatibility survey. Then, in order to search through other users’ profiles and find potential matches, they throw down a credit card.

A significant stumbling block that bedevils the large sites is the “lightning-rod effect,” wherein the bulk of the attention is slathered on a few attractive users, while the unwashed masses grow frustrated and bored. What a user finds on OkCupid, on the other hand, is based on what made TheSpark so successful (aside from its plot synopsis for Madame Bovary, I mean). One of the old site’s signatures was a series of quirky personality quizzes, and when the trio launched OkCupid, they decided it should have the same. Then they started letting online daters write and submit their own. In Internet parlance, this is the kind of thing that characterizes the thrust of Web 2.0, in which the users of a Web space are also encouraged to generate its content. Aside from making the experience fresh and more reflective of the people who visit OkCupid, the strategy has the added benefit of being dirt cheap. Today, more than 30,000 of these surveys float around the site, scoring users’ tastes and desires on everything from tolerance for erotica to devotion to the Red Sox.

When it comes to matching up would-be daters, OkCupid relies on a series of questions—as many as 3,000 of them—that users answer. But notably, unlike the massive and staid questionnaires employed by subscription sites like eHarmony (which purports to use a complex algorithm to systematically match people looking to find serious suitors), OkCupid lets you answer as many or as few of its queries as you like.

As simple as all this sounds, it’s a wild departure from the prevailing dating-site standard. To understand how, OkCupid CEO Sam Yagan says, it helps to know the difference between “transaction” sites and “destination” sites. Typical online dating services qualify as the former. Think of them as supermarkets: They want you to come in, find what you need (a date, ideally), and, as long as you’ve paid, get out. OkCupid, however, is a destination site. Like Facebook and MySpace and other free social networks, it makes money from advertising. And because advertisers pay according to page views, OkCupid has to not only get you to its URL, it also has to keep you there, clicking around. That makes OkCupid more like a bar than a grocery store. Drink specials and the lack of a cover charge may pull you in, but it’s what’s going on inside that’ll make you want to stick around.

Yagan likes that analogy. “When you’re single and you go out in Boston, do you just go from girl to girl, talking to them until you find one you might potentially like? Of course not. You might talk to some girls, but you’re also going to play some pool, talk to your friends, et cetera,” he says. “What we’ve tried to ask ourselves is: What does dating look like in the real world? And we’ve tried to replicate that.”

If OkCupid is like a bar, it’s one of those Faneuil Hall places where the shots come in test tubes. In other words, it’s set up to cater to the post-college crowd. In itself, slicing the online dating pool into easy-to-reach niches is hardly new. But going after younger daters is. Whether by race (BlackSingles.com), religion (popular Jewish site JDate), or gold-digging tendencies (Sugardaddie.com), plenty of websites are tailored to a specific audience, yet even within those populations the target customer is generally older.

This is understandable, since a) older people are more likely to run with a smaller crowd, thereby exhausting real-world dating options more quickly, and b) they’re suckers when it comes to paying for things on the Internet. It’s in a nod to this demographic that Match.com has made Dr. Phil the face of its site, signing him up to provide users with rhyming relationship advice. The well-advertised eHarmony, meanwhile—which markets itself as creating matches for people serious about finding marriage material—combines a socially conservative agenda (gays and daters with more than one divorce need not log on) with an extensive screening process involving so many essays and hourlong questionnaires that one former user told me the experience was a lot like filling out college applications and taking the SAT—at the same time.

The young daters OkCupid is after (Yagan says the company imagines them to have an average age of 26) arrive at the site expecting that the services they get online are not just free, but entertaining as well. Knowing that, Yagan and his cohorts have tried to re-create what works in the real world, and also what they’ve seen work elsewhere on the Web. On top of must-haves like the all-important profile pictures and the ability to flirt with other users (in OkCupid’s case, by sending a “woo”), their site allows you to mix with others in some pretty unique ways. Its new Wikiprofile feature, for instance, lets you edit a friend’s bio, changing his interest in the Rolling Stones to, say, Hannah Montana. Not only does this provide hours of laughs, it’s also an ingenious way to force users to stay active on the site, lest their defaced profile cut into their woo count. OkCupid is a Web space where irreverence is the lingua franca. (Want to see who’s viewed your profile? Click on “My Stalkers.”)
As we walk out of Legal Sea Foods and into the cold Cambridge air, Krohn points out the Gehry-designed building where he studies, then stops and chuckles.

“You know what I was just thinking about? Five years ago, you could almost see yourself going to Yahoo and saying, ‘I want to pay 10 dollars more a month to get 10 more megabytes for a 20-megabyte mailbox.’ And now you go to Google and you get a five-gigabyte mailbox completely free.” It’s the theme of perpetual technological innovation in a still-young Internet era. And it’s a story line that OkCupid fits into.

“Businesses just need to find a way to make money,” Krohn says. “It’s a new, completely different world. We understand that; Match.com doesn’t. We just hope it’s going to be us that takes them down.”