Hip to be Foursquare: A night out with CEO Dennis Crowley

I'm sitting in a dimly lit, slightly grungy bar in New York's East Village, where Dennis Crowley, co-founder and CEO of Foursquare, the white-hot mobile networking service quickly becoming de rigueur among bloggers and scenesters of a certain set in New York and San Francisco, is holding court. It's late.

An intermittent stream of well-wishers greets Crowley, who receives each compliment with a low-key smile and slight wave of his signature shaggy bangs. In addition to co-founding the five-month old startup, Crowley is also, as they say, a client, not to mention a bit of a man about town. In fact, he's probably the most influential "Foursquarer" in existence, so the stream of quite comely friends who have seen his "check in" and stopped by to say hello isn't exactly surprising.

Welcome to Dennis Crowley's life.
Foursquare, which allows users to "check in" at locations around town using their phones and find friends, is the 33-year-old Crowley's latest venture, following a less-than-satisfying two years at Google New York, which he joined after the search empire bought Dodgeball, Foursquare's predecessor, from Crowley in 2005. "We described Dodgeball as Friendster for mobile phones," Crowley tells me. "With Foursquare, users explain it to each other as Twitter with location."

It's a bold claim, but to see the speed at which Foursquare is taking root among the coastal digerati is to become something of a believer. (I will admit, I have "checked in" occasionally.) Since launching the service at this year's South By Southwest Interactive confab -- something of a rite of passage for new social startups including Twitter -- Crowley says Foursquare has expanded into 20 cities, including New York, San Francisco, and Los Angeles; as well as Minneapolis, Portland, and Atlanta. And Amsterdam.

Now, Crowley is leaning forward amid the chatter of the tavern, about to break some news: the latest version of Foursquare's popular iPhone application -- version 1.4 -- is about to be submitted to Apple for review, which means it could be available in two weeks. On Wednesday, Foursquare's long-awaited Google Android mobile app is being released -- Crowley says it's even cooler than the iPhone app -- and Blackberry users, ahem, can finally look forward to a native client in about a month. "I've seen the demo and it looks good," Crowley tells me.

With the new Foursquare iPhone app, Crowley says there will be several improvements: First, the ability to see who is at the same venue as you. "If you see someone you're interested in, you can reach out to them," he says. Second, a new feature incorporating promotions for local merchants -- whom Crowley sees as central to Foursquare's success. "There are probably about twenty venues in ten different cities that have reached out to us, and they give out free drinks and free appetizers or whatever," Crowley says.

Brooklyn bars Cornelius, in Prospect Heights, and Union Hall in Park Slope are giving out a free whiskey shots to each venue's "mayor" -- a highly coveted designation used in Foursquare to denote the person with the most "check ins" at a given venue over a 60-day period. Bowery Wine Company is offering a free glass of wine to its mayor during happy hour. And out in San Francisco, The Marsh Cafe will give you a free drink or two bucks off at the door. Good Hurt in Los Angeles will give you a round of drinks if you're its mayor. And so on.

Titles like "mayor" are examples of the types of "game dynamics" Crowley has introduced into the service to encourage certain types of activity -- others include badges for certain accomplishments like, say, checking in with three members of the opposite sex, a feat Crowley has managed in multiple cities.

"It's not just that people are more apt to check in, they're more apt to go somewhere because they want to regain a mayor title," Crowley says. "So we hear stories about people who were going to stay in on a Monday, but they go out because someone stole their mayorship. And I've been guilty of it myself. I've gotten emails saying I've just been ousted as mayor, and I was like 'Shit, I've got to go back there,'" he says. "I still get pissed when someone ousts me as mayor. People get very defensive about it."

For Crowley and his two employees, Foursquare's mission is simple: "We're trying to make cities easier and more interesting for people to explore," he says. "It's about helping you find where your friends are, exposing you to new places you may like, and rewarding you for being adventurous either in your neighborhood or in your city."

For now, Crowley says Foursquare is targeting niche demographics -- "people in dense, urban environments, people who socialize, and people who share with social media" -- but he isn't ruling out eventually "growing up" and embracing "the world" as his intended audience, like Google and Facebook, and for that matter, Twitter. And aside from being surrounded by very attractive people nightly, Crowley isn't simply running Foursquare for fun. He wants to make money, and he's focused on "connecting local merchants like coffee-shops, restaurants and bars with the people who frequent them the most."

There was some controversy after Crowley left Google, which had bought Dodgeball, Foursquare's predecessor, in 2005 for under $10 million in a combination of cash and stock -- some of which Crowley still holds -- in one of its first post-IPO acquisitions. But after messing around with Dodgeball, Google eventually shut it down to focus on its own -- and now competing -- geo-locational product, Google Latitude. Crowley wasn't about to stick around. He walked in May 2007, took one Google engineer with him, and began devising Foursquare. Despite gossip to the contrary, Crowley tells me there is no ill-will between him and Google. "I believe in Google and what they're doing in the mobile space," he says, pointing out that his favorite mobile Foursquare app is built for Android, Google's open-source mobile OS.

Now, five months after launch, Crowley says he is "close to figuring out what we're doing financially" and preparing to announce an initial round of seed funding. He says he's met with "everyone," but declines to name the VC firms he's been huddling with. "This is going to be a good September for us," he says with a smile

Update: Friday, Sept. 4, 2009, 6:00 p.m. EST: DailyFinance agreed to withhold the names of Foursquare's forthcoming seed round funders at Crowley's request, but thanks to a SEC filing, it is now public information that the five-month-old startup has raised $1.35 million in venture capital funding in a seed round led by Union Square Ventures. O'Reilly AlphaTech Ventures is also participating in the raise, which the company plans to officially announce next Tuesday, according to Business Insider, which noted that USV honcho Fred Wilson telegraphed the investment weeks ago when he confessed his infatuation with the mobile networking service.

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