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After 10 years, eight South by Southwests, two startups, and zero dollars in profit, will Foursquare CEO Dennis Crowley ever find his way?

Will Foursquare CEO Dennis Crowley Finally Get It Right?

BY Austin Carrlong read

It’s 2 a.m. and Dennis Crowley is wired.

We’ve just left Foursquare’s South by Southwest party at the Hype Hotel, a warehouse-size space in downtown Austin where nearly 1,000 revelers were drowning in deafening club music and Tito’s Handmade Vodka. Crowley, 36 at the time in March, played host, quadruple-fisting Miller Lites and hanging out with his startup’s leadership team, including design director Ian Spalter, then also 36, who wore earplugs and a hoodie tied around his waist. “I’m getting too old for this!” Spalter yelled over the bedlam.

Outside on the sidewalk, streams of partygoers hail pedicabs and stumble home as the night comes to an end. Crowley isn’t ready to call it quits just yet. He’s leaning against a nondescript door, flanked by a small crowd of twentysomethings. Turning his head like a secret agent checking his six, Crowley flashes his trademark puckish grin. “You’re coming to the after-party, right?” he whispers. “Just play it cool.” The door suddenly pops open, and Crowley exchanges a few hushed words through the crack. Then the group races inside and up six flights of stairs as if a pot of gold awaited them at the top. (In reality: more bottles of Tito’s.)

That Crowley still commands such a following at the Austin tech conference is a testament to his willpower. It’s not just Foursquare’s fifth annual SXSW appearance but Crowley’s eighth–a point at which he might feel like the high school football star still grasping at the glory years. Crowley debuted his location-based service here in 2009 to much fanfare. The app lets users “check in” to venues via smartphone and share their whereabouts with friends–a tool perfectly designed for discovering hot bars and parties during the weeklong festival. Foursquare’s launch heralded the idea that broadcasting our location could unlock invaluable information–not only for users searching for a nearby coffee shop but also for merchants looking to entice them with instant deals and rewards. The press hailed Foursquare as the next Twitter, which also had blown up at SXSW, in 2007, and soon Crowley’s New York-based startup was rocketing toward superstardom.

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ABOUT THE AUTHOR

Austin Carr writes about design and technology for Fast Company magazine. More


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