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“New York’s been critiqued for a long time,” he continues. “The critique is that you can’t do stuff like this here, but I think part of the reason that our product is interesting and special is because it came out of New York. It was designed to solve problems in that context, and those solutions tend to work in other parts of the world pretty well. I think the product is better because we’re based here.”

Crowley’s experience with Google in some ways exemplifies the complicated relationship that many in New York’s tech community have with the technology behemoth. Chris Dixon, the 38-year-old co-founder (with Flickr co-founder Caterina Fake) of Hunch.com, recently blogged, “Whenever I see a brilliant kid decide to join Goldman Sachs, McKinsey, or Google, I think to myself: a start-up just died, and as a result our world is a little less wealthy, innovative, and interesting.”

In early March, Foursquare redesigned its app and also announced plans to launch a dashboard for businesses that would make it easier for them to take advantage of the data Foursquare was accumulating about their customers. Occasionally, when you check into a location on Foursquare, you’re informed that there’s a special offer where you are or one nearby; these are generated almost entirely by users, often the “mayor” of an establishment, who encourages the owner or manager to set up a deal for Foursquare users.

“Usually what will happen is a user becomes the mayor somewhere and asks the manager, ‘What do I get for free?’ ” says Crowley. “The manager at first is usually like, ‘What are you talking about?’ They’ve never heard of Foursquare. Eventually, the manager will break down. It’s an opportunity for us to start turning users not just into evangelists but also salespeople.

“So the venues win—anytime someone checks in, it’s like a mini-ad. With the stats tools, you can find out who the most valuable users are to local businesses, like who’s sending their check-ins to Twitter. Maybe the owner wants to reach out to that person.”

To certain superannuated people—over the age of 35— this manic optimism brings a queasy sense of déjà vu.

Foursquare also allows anyone to use its software—or what’s called its API, the application-programming interface. So Yipit, which was launched a couple of months ago by Vinicius Vacanti and James Moran—both twentysomething Harvard grads and finance-world refugees—uses your location and your preferences to send you the best daily deal at area shops, restaurants, spas, and other businesses. And if you’re a Foursquare user, it pulls in everywhere you’ve checked in and lets you know whether there’s a deal at any of those places. When I signed up for Yipit, it informed me of two deals I hadn’t been aware of—including a happy hour at the bar I’d been to the night before. Depending on which deals I click on in the future in my daily e-mails, my Yipit account will get smarter and start recommending deals that will, theoretically, be tailored to my tastes. “New York is the perfect place to test new, local products, just because of the demographics and the density,” says Vacanti. Moran left Blackstone around the same time that Vacanti left Quadrangle, in July 2007; since then, they’ve been living off their savings. “In New York, people are constantly moving into the city. It’s such a confusing city, getting your arms wrapped around everything.”

Eventually, Yipit will get smart enough to know that if you’re interested in wine-tasting deals, you’re probably also interested in artisanal cheese. But these deals encourage social interaction; they take a DailyCandy or a Thrillist, both e-mail newsletters, one step further. Vacanti says that one of the most popular shared deals in New York was one that went out on February 18, less than three weeks after Yipit launched, for an $18 ticket to the “Taste of 7th Street” festival. At the time, Yipit had only 500 New York subscribers (currently they have 7,000)—but 40 clicked on that deal, and ten forwarded it to their friends. Tiny, tiny numbers. But imagine if, as they say, they’re scalable.

At this point in the game, not many of the latest wave of social media have any profits. This is the fun and messy business of collecting eyeballs, which then—somehow, some way—can be monetized. They don’t talk about it as much as, say, a Goldman associate would. Yet alongside their tech idealism is often an ecstatic vision of a liquidity event, the sale to Yahoo or Google or Facebook—at which point the tech dreamer becomes a guru, someone who can then mentor and invest in start-ups him- or herself.

Other companies—including Art.sy, a soon-to-launch online art service that will connect galleries with collectors—are living their arts-communitarian ideals. Kickstarter‚ which launched in April 2009, is a kind of community funding site for creative projects. One afternoon, I’m at their Lower East Side office, where they’d recently moved. Their eight-person staff is working at one large table in the front room. The floor-through office itself is badly in need of renovation—it looks like a long-neglected apartment—and some friends of Kickstarter’s two New York–based co-founders, Perry Chen and Yancey Strickler (a third founder, Charles Adler, lives in Chicago), are going to be taking on the project; in the back room are tools and plywood.


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