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.

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