Foursquare founder Dennis Crowley wants to disrupt American soccer and improve the USMNT, one club at a time

Dennis Crowley
Crowley, co-founder of Foursquare, started his own NPSL club in Kingston, N.Y. (Getty Images)

NEW YORK – Dennis Crowley hunches over a laptop, plaid fleece hat covering his signature tufts of boyish hair. He sits at a nondescript desk in the SoHo headquarters of Foursquare, the location-sharing app he co-founded eight years ago. It’s the sort of tech office that feels more like a grownup playground, all beanbags and shuffleboard tables and red London phone booths and step-machines that charge your phone. By the entrance, one of several slogans on the wall implores the 160 workers to “Invent the future.”

The meeting rooms are all themed. One is decked out with snowboards, because, well, Crowley likes to snowboard. Another is being turned into a Stockade FC room, for the semi-pro National Premier Soccer League team he founded in Upstate New York in late 2015. Which is, of course, what brings us here. The unlikely link between a well-known tech founder and professional soccer, the next industry he’s trying to disrupt.

When Crowley decided he would like to dabble in sports ownership in late 2015, he did more or less the opposite of what other wealthy tech barons had done before him. Rather than buy into, say, an NBA team, he started a small-town, minor-league soccer team in a league without professional designation in about 100 miles north of New York City: the Kingston Stockade Football Club. Then he set about building it from the ground up, just like the apps he founded, Foursquare and Dodgeball – the former of which was at one time valued at $650 million while the latter was acquired by Google.

Crowley picked a name, designed a logo and uniforms, found a coach, recruited volunteers, held tryouts and secured a stadium. And then he set about washing jerseys, handing out pocket schedules and selling merchandise wherever he could set up a table around Kingston.

In its first-ever game in May 2016, the Stockade drew 852 spectators, four times what Crowley had projected. The club was even somewhat competitive in its inaugural season, going 5-8-3. But that isn’t entirely the point. Crowley wants to win things and compete, sure. He also wants his club to improve American soccer as a whole, and not just its own circumstances.

But to understand where the Stockade might go, and where it might lead the sport, you first have to understand where Crowley came from.

Raised in the Boston area, Crowley, now 40, was an entrepreneurial teenager. He ran all kinds of rackets. He started a magazine called Dystopia in high school to write about the things that interested him, Legend of Zelda and skateboarding. He tried to get people to subscribe via AOL. He and his brother rented out Nintendo games by the day. They flogged recordings of video games and published a fanzine called Power Play. At Syracuse University, he started a snowboard club so that he and his friends could fund their own season passes with huge group discounts. They threw house parties with kegs and bands and would charge entry. They’d make around $1,000 in a weekend and use it to buy upgrades for their house.

Dodgeball began as a tool for the hyper-social Crowley to more easily meet up with friends in New York City. He’d worked for several failed startups and gotten laid off when the tech bubble burst. That was the last time he worked for someone else. Dodgeball was bought by Google and then shut down. So Crowley and his co-founder left and started over, spawning Foursquare.

Almost a decade on, and newly settled down with a wife and a daughter on the way, Crowley got the itch to build something again. He’d learned that his own soccer team in Manhattan was constrained in its upward mobility in the Byzantine tangle of leagues and structures of American club soccer. What would it take, he wondered, to start a semi-pro team and see where its ceiling was? Not a lot, he learned. The NPSL let in teams for just a $12,000 entry fee.

If he started a team, he reckoned, he would have somewhere to take family and friends in Kingston, where he and his wife have a weekend home and there isn’t a whole lot else going on. But more than that, he was keen to prove his theory that starting your own club at a respectable level was doable and that more people should do it. Because if the United States, as a nation, was ever going to get anywhere in soccer, it needed more opportunities for its players.

More teams equal more places for players to develop, which, Crowley believes reasonably, will beget a larger number of better American players. If the U.S. is ever going to win the World Cup, it needs a larger pool of talent – this is universally accepted – but the professional game, as it exists, is a rickety structure that’s more solid at the top, where Major League Soccer grows rapidly, than at the bottom, in the morass of upstart teams and leagues that go almost as fast as they come. By creating a model for an affordable and sustainable lower-tier team, Crowley wants to shore up the foundation upon which the entire thing is built. For the good of the American game as a whole.

So Crowley scouted Kingston, found it to be fertile ground for his project and got to work. Never mind that he didn’t actually know all that much about soccer, since he’d only been into it for a few years.

“You get this false sense of superpowers from doing a project like Foursquare for many years,” he told Yahoo Sports. He’d learned the hard way to just keep going when he was overwhelmed and it all seemed hopeless. “You get used to tackling bigger problems. I just saw that we have 100 things to get done and 300 days to do ’em, so let’s get to work.”

“It’s the same type of hubris that you get when you say, ‘I’m not going to get a job so I’ll just start my own company instead,’ ” Crowley said. “That’s an awful idea. It’s never going to work. Well, maybe we can make it work.

“It’s very easy to get talked out of some of the crazier ideas you have. But at some point, you just get the confidence to say that maybe you see the world in a way that’s slightly different than everyone else and I’m just going to go ahead with it. I just don’t have the ability to sit on the sidelines when you have good ideas and wait for it to happen. It only happens when someone pushes for it to happen.”

Success came immediately, as Stockade FC tapped into an unmet demand for live sports and a rallying point for a community. In addition to the surprising attendance, the team’s merchandise became ubiquitous around town and local media covered the story eagerly. “When you walk around Kingston now, you see people wearing the hats and the shirts,” Crowley said. “It’s like a thing.”

And then, as promised, he wrote one Medium post at the start of the season and one at the end of it. He broke down his project in granular detail – the philosophy, the timelines, the lessons, line-by-line budgets, all of it. After building a pair of successful apps, he’d drawn up, in the span of a year, a blueprint for starting a semi-pro soccer team that, in his case, ran a $32,601 deficit in its first season. Although much of that is in inventory for the popular merchandise or went to equipment that will last for several seasons. Crowley anticipates that the Stockade should break even in 2017, or come close to it.

The idea was to be transparent. And to start a conversation – to open a discourse over ways in which our national soccer scene can get better. “This is one of the possible North Stars,” Crowley said. “Who else has one? Let’s build a consensus and find a way of getting there.”

He has gotten all the other NPSL owners talking regularly, beginning a Slack room. They used to talk once a year. But Crowley wanted them to think bigger. How could this high-turnover circuit – in 2017, 22 teams are joining while 15 are leaving, for a record total of 95 clubs – get bigger? How could it get so big that it might begin to make life uncomfortable for MLS teams and challenge them to be better? Where local soccer is at least as relevant as the national game? Or where local soccer lives side-by-side with the highest level?

“I saw this quote last night: ‘If you think you’re too small to make a difference, try sleeping in a room with a couple of mosquitoes at night,’ ” Crowley said. “The change will only come from the bottom up. What is the soccer version of the mosquitoes? My opinion is it’s a bunch of smaller clubs built in a bunch of markets that were overlooked, making products that people care about as much or more than their MLS team.”

So Crowley wants to at least get the conversation started about the path forward for the NPSL. He likens the trial-and-error approach to a tech startup.

“The first three years of the company [Foursquare] I spent at the whiteboard,” he said. “You draw a couple of things, you erase it, you draw, you erase it. You just do this over and over. Until you solve the problem. The league is just getting to the point where we’re drawing on the whiteboard.”

He wants to think ambitiously, about league-wide sponsorship and how to stream all games online. He found sponsors for his own team and streams all games on YouTube with a fairly professional setup. Stability begins with revenue.

But for all boats to be lifted, the tide has to rise.

“These are startup issues,” he said. “Big, logistical problems that are really hard to solve. You have to find someone that likes these types of problems. I like them. Some team that I’m never going to see play in person, I care about what kind of camera they’re going to be streaming with, because I want the quality to be good. That’s something that maybe not everyone in the league has.”

In order to make American soccer better, Crowley argues, you have to recognize its malleability. Perpetual reinvention isn’t just natural but necessary, just as Foursquare has remade itself from a social app to one that recommends places to go and things to do, and a company that provides location data and patterns for companies like Uber and Airbnb.

American pro soccer is in constant flux. Just this winter, the second-tier North American Soccer League nearly went out of business and the United States Soccer Federation finally gave in and elevated the United Soccer League from Division 3 to Division 2 status. Not that this matters much, since there’s no movement for teams between the tiers anyway. It’s mostly branding and artifice.

But it’s easy to forget that the top league, MLS, is only 21 years old and that it only really took off in recent seasons.

“Some of these big changes only started to happen in the last six to eight years,” Crowley said. “When you start thinking about where we could be in five years, whatever you can imagine you can go and build.”

The construction of his own team is complete. And in its wake may follow others. A new NPSL team in North Carolina, Asheville City, told him he and his Medium guides-cum-manifestos had inspired them to get started. Crowley says that in the last six months, he’s spoken to two dozen or so groups of people who were thinking of starting a team. Some will take the leap; others won’t. Either way, he’ll talk to them all. And at least one new team has gotten started, adding another place for serious American soccer prospects to play. An avalanche starts with a just a few rocks.

“Can you take a team, and if you do it right, can you drop it in an area and make soccer fans where soccer fans didn’t exist before?” Crowley asked rhetorically. “I think we’re finding that the answer is yes. Can that team, even if it’s amateurs, inspire kids to play and stick with the sport? And I think the answer to that is yes. If you’re transparent about the process and how hard it is, and you published a guide, would you inspire other people to do clubs? And the answer to that is yes.”

The Stockade is a proof of concept. And now it’s for others to take it and replicate it and then to improve on it. To disrupt the disruption. Because, Crowley believes, American soccer, like anything else, only gets better if you keep erasing the whiteboard.

Leander Schaerlaeckens is a soccer columnist for Yahoo Sports. Follow him on Twitter @LeanderAlphabet.