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“We have a two-year program here, and we try like hell to hire women into that program,” says Union Square Ventures’ Wilson (whose office, except for his assistant, is all male). “We tell the world we’ve got this opening, and anybody who’s interested can apply, and it’s 90 percent men who even bother to apply. I mean, I don’t know what the problem is.”

The first time I visited Foursquare’s office, the company had six people. In a matter of months, it’s ballooned to sixteen. (Still, Crowley says, it’s not enough: “We just need to hire more folks. But if we hire more folks, we need to get another desk and some chairs.”) Everyone is leaving the following day for South by Southwest. The walls are covered with whiteboards and sheets of paper with various checklists; one says “SXSW Knocklist: Badges, XP, Venues, Design.” Also hanging on the wall is a framed quotation that says, “It’s not a bug, it’s a feature”; a single-speed bicycle leans up against a table. On the inside of his left forearm, Crowley has three temporary tattoos in the shape of Foursquare badges; one is special for SXSW. It’s a hookup badge, Crowley explains, for stops at three or more hotels in a night.

Since our first meeting, Foursquare has been busy—and growing. There were deals with several big companies and brands—including Starbucks, Bravo, Lucky magazine, the New York Times, and Marc Jacobs—that encouraged people to check in to places associated with them and earn special badges or get “tips”; Crowley sees this as a potentially important revenue stream. But with only one employee doing business development, it’s one that the company isn’t fully equipped to manage yet. “We have all these companies calling us, and it’s a little bit problematic—we have so much inbound business development that we can’t capture it all,” he says. Foursquare, he says, could eventually turn into not just an app that tells you how many bars your friends went to the night before but a more ambitious project about social relations. “You build a game of it,” he says. “The first person to do ten crazy things wins. It expands it beyond consumption. Maybe you get badges for meeting people or bringing people together.” So on Foursquare, based on the bands you saw in one week, maybe you met more people, and so maybe your happiness and your productivity is higher. So check-in is just the first part of this story.”

Crowley wants to build a whole community—the consumerism embedded within it is an afterthought. Of course, Foursquare’s utility increases with the number of users it has, and its 900,000 or so users don’t come anywhere near Twitter’s 100 million or Facebook’s 400 million. (Crowley says it’s projected to hit 1 million users on April 21.) There’s still a psychological barrier that Crowley has to encourage people—not just early adopters—to cross. When I first joined in January and asked Foursquare to search my Gmail contacts to see who was registered, a relatively paltry 80 people showed up, most of whom were business contacts who don’t necessarily need to know the bars I frequent and where I get manicures. At a dinner party recently, I asked the ten other guests—none of whom worked in anything related to tech—how many were on Foursquare. None of them was, and only four had even heard of it. “Look, I could check in to your apartment building,” I said to the party’s host, showing him my iPhone as the name of his building—a high-rise in midtown—came upon Foursquare’s list of locations. He looked horrified.

Foursquare’s success is breeding imitation. Facebook is expected to launch a feature this month that will allow users to share their locations with their Facebook friends. “There’s enough of a unique user experience within Foursquare that I don’t think someone can come along and replace it,” Crowley responds. “It’s a different type of sharing. When Facebook changed its status updates, it didn’t kill Twitter. It might make us a little more focused.”

Focused, indeed. With Twitter now running sponsored tweets, everyone seems to be getting more serious about the search for a business model—selling ads, selling to Google, earning a living by any means necessary. The wide eyes of the tech romantics—seeing a world where everything is changing, drinks are free, and a hangover at 11 a.m. is a small price to pay for being young in New York City—are evolving into the gimlet eyes necessary to survive in the long term. Working for free is about as popular as it ever was.

Foursquare’s first round of investors included Twitter co-founder Jack Dorsey, Silicon Valley angel investor Ron Conway, Union Square Ventures, Digg founder Kevin Rose, and O’Reilly AlphaTech Ventures. Crowley is currently considering a second round of funding—reportedly for about $10 million, which might value the company at as much as $80 million. When I ask Crowley about the Yahoo-acquisition rumors, he doesn’t deny, them, exactly. “We’re trying to figure out what the best thing is for us going forward,” he says. “We’re raising financing and meeting with tons of different companies. Don’t read into it too much.”

They’re not necessarily opposed to selling, Crowley says—but “it’s a business that can be a real business.” In the last boom, companies that were barely out of diapers were rushing to IPO, which led to the nasdaq’s becoming a graveyard of start-ups that peaked too soon. Today, people seem wary about selling too soon, as though they need to prove—to themselves, to the world—that they can create a viable business that actually affects people’s lives. Sure, everyone wants to be a millionaire, but to be a millionaire while also saying that you fundamentally changed the way people interact and engage with one another is, if you take their word for it, perhaps an even bigger badge of honor.

“We could make it work as a stand-alone business, or it might turn out that there are other companies that would find us valuable,” says Crowley. “The future is rosy.”


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