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Venmo, a mobile-payments company co-founded by 26-year-old Andrew Kortina, allows users to pay for goods and services via text message and also encourages people to trust vendors (the first one in New York is the Simple Kitchen, a café in Chelsea) to take the money owed to them directly from their accounts. The idea, says Kortina, is “it feels good to be trusted.

“I think everyone wants to be a regular somewhere,” Kortina says. “It’s more poignant in New York than elsewhere—there’s an innate desire to connect with real people. Say you’re going to the coffee shop every day. It feels good to know the people who are on the other side of the counter. It feels good when they know your name. If we can help make it easier for people to establish that connection, I think it just makes people feel good.” The technology is being used to enrich urban face-to-face interactions—a better New York, if you, as a New Yorker, can believe that.

Crowley’s original start-up, Dodgeball, resembled a primitive version of Foursquare. When users checked in to a location, their friends received a text message; the premise was that people would be going to multiple places in an evening and their friends would want to meet up with them at different spots along the way. But Dodgeball was in many ways ahead of its time; it came out not only before the iPhone but also before Twitter and the Facebook explosion. The idea that people would want to share, constantly, the minutiae of their lives was not one that had permeated much beyond the early-adopter crowd; Crowley estimates that Dodgeball had 75,000 users at its height— barely a Facebook rounding error.

But the promise of location-based social networking was appealing, even then, to a company like Google, which had launched a beta version of Google Maps in February 2005. Crowley and Rainert had started trying to get venture-capital funding, but instead sold to Google in May 2005 for an undisclosed sum and went to work at Google’s New York office. The idea was that Google’s software-engineering prowess would help bring Dodgeball to the masses, but almost from the beginning it seemed like a bad fit. Crowley’s reluctant to talk about it, but he says, “It was just after their IPO. The New York office had just opened. A couple weeks into it, we were like, ‘Where are those engineers?’ We were hoping to have more of a team, but it was hard to get engineers.”

By April 2007, Crowley and Rainert were gone, and Google announced it was shutting down Dodgeball in January 2009. Two months later, Crowley and Naveen Selvadurai, a 27-year-old, launched Foursquare. (Rainert recently came onboard as the head of the product team; he’s also an original investor in the company.) People in the tech world have decidedly mixed feelings about Google: How can something that big not be at least a little evil? At the same time, there’s no denying that having those 1,000 engineers here has led to a ripple effect, by establishing that New York—not just Silicon Valley—is a place that’s hospitable to technologists. “They’ve taken the Silicon Valley culture and infected hundreds of engineers with it, and those engineers are not likely to want to go work for Morgan Stanley or Goldman Sachs,” says Union Square Ventures’ Wilson. “It’s not in their DNA. That’s not what they’re going to do. They’re more likely to go into one of our start-ups.”

And then the city itself becomes a draw. “There are people who wouldn’t move from San Francisco to, say, Pittsburgh or Austin, but they would move to New York,” says Hunch co-founder Caterina Fake, who sold Flickr to Yahoo in 2005.

“The stuff is, first and foremost, meant for our friends,” says Crowley. We’re sitting with Selvadurai in the lobby of a Cooper Union building, across the street from the Foursquare offices, one afternoon. “The same thing happened with Dodgeball. We were just building tools that were making New York more efficient for twenty of our closest friends. A lot of the ideas we shoot within Foursquare are also themes that I think already existed in Dodgeball. We’re just bringing them back to life in new ways, with smarter phones. At the time, Dodgeball was a New York application. It was meant for people to start off with 25 friends who could easily jump to five places in one night, which is definitely an urban type of experience. Foursquare has been changed so that it rewards a one-player experience—it gets more interesting as you add friends to it, but it’s definitely a better one-player experience. And it’s designed to work in New York, and then we kind of tweak it so it works everywhere else. I think it works best in really dense urban areas.