Dennis Crowley, the cofounder and CEO of Foursquare, has been consumed with how mobile information and location can dovetail together for a decade—since his first job out of college, working on city guides for the Palm Pilot. So much has changed since then technologically, and so much is now possible on widely available smartphones, that you might think Crowley can see his dreams coming to fruition soon.
That would be a mistake.
"The things we think will be a rocket ship for Foursquare, we can’t launch yet," Crowley says. "The stuff we’ve built is going to be obsolete three, four years from now. We’re inventing and reinventing what we’re doing, because it wasn’t possible a few minutes ago."
He mentions an app that Foursquare launched last fall called Radar, to take advantage of iPhone 4s. "But it also drains your battery. Do people want to give up 40% of their battery life?" So while they wait for phones and batteries and sensors to improve, before they can put their full business vision into effect, "we launch other things," he says.
"We’re three years old now, about 150 people, kind of a big company," Crowley says. "But we’re reinventing the product on the fly. The product we have now is going to look radically different."
Crowley likes talking about Foursquare’s product plans, what they’ve been and where they might go.
With a little prodding, he will also talk about Foursquare as a company. "If we reinvent the product every couple of months, we have to reinvent the company too," he says. "Reorganizing a company is generally considered a bad thing. But we’re trying to get people to see it differently. It has to be built into the culture, the idea that we haven’t got it right yet—product or structure. The most challenging part is to keep executing as well as 100 people as we did at 50 people, at 20 people."
The system he has in place now, he says, "works well with 150 people. It wouldn’t have with 40. It might not with 200."
Foursquare was originally based around three groups: "discovery, loyalty, and engagement," says Crowley. "It worked great at 40 people." He’s now busted it down into 10 targeted segments, such as content creation and platform.
"It’s tricky," Crowley admits. "We’re transitioning from a top-down system to more bottom-up, we’re working on it." The company’s weekly all-hands meeting has been commandeered by the smaller groups, which use it to give updates. "Everyone knows what’s going on," he says.
About a third of the Foursquare crew used to work at Google, Crowley explains, and "we pulled a lot of what we liked from there." But there were also things "we didn’t like as much. Everybody is doing this their own way and is a little different."
"We have rock star designers who know how to code and engineers who want to design wireframes," Crowley continues. "If our management team locked a group in a conference room and said, "Build this," it wouldn’t work. Instead we focus on the idea of a North Star, a big, long-term vision of where we’re going. ‘We probably need 100 tricks to get there, you guys organize yourselves.’"
Crowley believes in creating a cadence of change. "Everyone is trying to kill us," Crowley says, referring to his company’s business prospects. "Local, social, mobile, everyone is trying to get there, Facebook, Groupon, Yelp and every new startup. What we’re doing now has to be ten times different, more evolved six months from now. We’re competing with the best companies ever built. And we want to be one of those standouts." He can’t afford to stand still. His only advantage is his next product, not his current one.
"We’re searching for the thing that gets us from 20 million users to 100 million, and probably isn’t possible yet [because of phones and sensors]," he says. Crowley cites this quote, from Facebook’s Mark Zuckerberg, as a favorite: "Technology is like fashion, in that it’s never finished."
Every day at Foursquare, says Crowley, brings something different. "Some days are up and some are down," he says. "I’m trying to guide people in a direction, without bringing a stone tablet down. We’re still in flux, and that’s a good thing."