Foursquare, Kingston Stockade founder Dennis Crowley builds a club from scratch

Foursquare co-founder Dennis Crowley speaks to SI's Grant Wahl about the challenges of starting his fourth-tier soccer club from scratch.

Dennis Crowley is no stranger to the startup world, launching and co-founding Foursquare, among his other tech ventures. But last year he turned his attention to an area where he had considerably less expertise: soccer.

Crowley created Kingston Stockade FC, a club in the fourth-tier NPSL, located in New York's Hudson Valley. Starting a soccer club from scratch is accompanied by a number of questions and challenges, which Crowley quickly found out and tackled. 

"It was tough. There's not a lot of material online. When you Google 'how do you star a soccer club from scratch' you don't really get a lot." Crowley joked to SI's Grant Wahl in this week's Planet Fútbol Podcast.

Crowley is all for full transparency of his process, which is why after learning what it took and executing it, he provided all of the information and data, from expenses to roadmap, for anyone to see in recapping Kingston Stockade's first season and launch.

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With the club in the fourth tier of U.S. Soccer's closed pyramid, the topic of promotion and relegation is naturally on Crowley's mind as well.

"By not having a chance to get promoted, you never have a chance to compete in a bigger market, in a bigger audience," he said. "You never have a chance to get a cut of sponsorship or broadcast revenue that may be associated with a higher league. This is how these systems work everywhere else in the world, just the infrastructure isn't here yet. 

"If you want that system to exist someone just has to get to work trying to build it. ... Why can't we help to push that agenda forward?"

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While recognizing the obvious differences between the two, Crowley likens trying to alter U.S. Soccer's pyramid to a tech venture, in that it starts with taking action and building small, not just sitting idly by hoping things happen.

"Instead of just sitting around and saying 'It has to be this way! It has to be this way!' Well, it's not that way right now," Crowley said. "So let's build the smallest piece possible and then let's go and make friends with other owners in our league, in different leagues and let's see if they think the same as us, and let's try to get on the same page and maybe we put a plan together and maybe that plan goes into effect a year or two from now ... It's about taking baby steps, and making friends, and building coalitions and getting kind of a shared vision around it.

"It's very easy to sit on the sidelines and say 'This is the way it is and I'm going to be mad until it gets fixed.' Or you can be like 'I'm going to raise my hand and try to do something–I don't know if what I'm going to is going to make a difference, but at least I'm going to try to do something.' That's the approach we're taking, because that's always what we've done with tech and startups, and it just seems natural."

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Crowley elaborates on the process of building Kingston Stockade from the ground up, his hopes for promotion and relegation, why he understands where MLS and its owners are coming from and why it can't work just yet in his full interview in the podcast above. He also details Stockade's rise in this mini-documentary with Kick.

After going 5-8-3 in its inaugural season, Stockade's second season in NPSL begins in May.