Meet Dennis Crowley, the Tech Entrepreneur Who Wants To Shake Up the US Soccer World
Photo by Terry McAleer, Courtesy of Kingston Stockade


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Meet Dennis Crowley, the Tech Entrepreneur Who Wants To Shake Up the US Soccer World

Dennis Crowley helped invent foursquare. Now he wants to reinvent the structure of soccer in America.
July 18, 2016, 1:30pm

When the Kingston Stockade take the field in a semi-pro soccer game, it looks like, well, a semi-pro soccer game. The level, the vibe, the surroundings, all of it is just about what you'd expect.

But this team isn't quite like the others. Sure, players are trying to win games and further their careers. Yet there's also something larger at stake. The Stockade, located about 100 miles north of Manhattan, is supposed to be a test case for controversial vision of implementing promotion and relegation in professional American soccer. If that sounds ambitious for a team that doesn't pay its players, it is.


A quick primer: in most every other soccer country, there's a pyramidal system between soccer leagues, beginning in the amateur ranks and rising all the way to the top professional tier. If your team wins a lot, it's promoted up a level; if it loses too many games, it's relegated down. Cinderella Premier League champions Leicester City, for instance, played in the third division in the 2008-09 season. Conversely, Portsmouth began its tumble from the first to the fourth tier the next year.

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The American hierarchy of clubs, however, is set in stone. There is no movement. No team currently not in Major League Soccer can be promoted to play in MLS. You can only buy your way to the top with exorbitant expansion fees. Below MLS, no matter how much you win or lose, there's no escaping the North American Soccer League (2nd tier) or the United Soccer League (3rd tier). Under that sit the semi-pro Premier Development League and the National Premier Soccer League, which have no professional sanctioning or designation. New pro leagues must apply for sanctioning to U.S. Soccer and are allocated to a level. As a club, getting into such a league varies wildly in cost. An NASL entry apparently costs somewhere between $3 million and $9 million. The USL, which includes several reserve MLS teams, will let you in for about $3 million.

Gameday at Dietz Stadium. Photo by Mario Rabadi / Fairplay Magazine

The logic that mobility between the leagues creates incentives to build stronger soccer clubs–unearthing and developing talent and growing smarter and bigger businesses–is sound. U.S. men's national team head coach and U.S. Soccer technical director Jurgen Klinsmann is a believer in this type of system, and plenty of savvy soccer men agree with him–as does the author of this article. But the American scene, thanks to the precedent set by the NBA, NFL, MLB and NHL, as well as MLS's single-entity structure and nine-figure expansion fees, just isn't set up that way.

So a small band of very loud pro-relegation advocates has been taking to Twitter and other media for years, shouting over dissenters and insulting anyone who doesn't wholly endorse them and their vision. The #ProRelforUSA crowd is a pain in the ass, and that's putting it nicely. This obsessive band of keyboard warriors is so obnoxious in proselytizing its good word that it poisons its own cause.


And then there's Dennis Crowley, a 39-year-old tech entrepreneur with Beatle-like hair, manic energy and a patter so quick his own mouth can barely keep up.

Crowley co-founded Dodgeball in grad school and then sold the social networking app to Google. When it got shut down, he left and basically built a better version of it–Foursquare. This spring, he built something else: an NPSL team in Upstate New York.

Crowley was one of the founders of the Foursquare. Photo via Wikimedia Commons

Crowley is an avowed advocate of promotion and relegation. So he started a semi-pro soccer club. He did so partly because he, his wife and his newborn daughter spend a lot of time at their house in Kingston–that is, when they aren't in New York City–and wanted to watch live soccer with friends. He also did it because he wants to create a template for a better soccer system, one that could ultimately buttress a stronger men's national team.

And so he worked out what it would cost, discovering that entry into the NPSL only runs $12,000 and that he could get through a season and come close to breaking even spending $50,000 or so of his own money. (The PDL, he says, would cost him around $70,000 just to get in). He found a stadium, had a friend design a logo and some sick uniforms, found a veteran coach, and held tryouts.

Soon enough, Crowley–who only got into and began playing soccer himself five years ago–owned a real semi-pro soccer club. (The players are unpaid, however, because NCAA stipulations say he can't field college players if any of their teammates are compensated. Because the NCAA …) Season tickets for eight home games run $40, and single games go for just $7. More than 800 people came out to each of the Stockade's first three home games. He'd projected 200-300 for the start of the season.


And then Crowley published his manifesto, explaining what he was doing, why he was doing it, how he'd done it, what his goals were and that he'd keep publicizing it all in hopes that others would copy him–albeit not before running it by Ted Westervelt, the spiritual leader, and vocal twitter proponent, of the pro-rel movement.

Crowley says he now gets an email a day from others interested in starting NPSL teams. Let me get through the first season, he tells them, and then I'll disclose my financials and impart my lessons in another post. He is essentially doing a PhD in soccer enterprise, with the goal of releasing his dissertation to the public.

"In order to get better players at the very top level, we need to have a lot more players at the bottom level," Crowley says. "And the only way to get more players at the bottom level is to get more teams for them to play for and more opportunities for them to get seen."

The Stockade have averaged almost 800 fans per game. Photo by Ed Diller / Stockade FC

More teams, argues Crowley, means more competition, begetting more academies and stadiums. But the trigger to all that is the possibility of upward mobility, the strong incentive to invest and improve. Letting market forces and human ambition run wild, rather than fencing off soccer's businesses, will draw more money and create better outcomes. Or so the theory goes.

"I'm wearing two hats now," Crowley says. "I'm wearing the chairman of the club hat–I want to sell t-shirts and merchandise, and I want the team to win, and I want to be in the Open Cup, and I want us to experience that glory, and I want us to get promoted someday. And then I'm also wearing the pro-rel, U.S. soccer-cheerleading hat. And 80 percent of the interests are aligned.


"I bet a couple of our guys actually get poached this season and get a chance to move up. And that sucks, for us, as an owner, but that's good for soccer in general. So let's do that. Let's have more of that. So long as people are seeing better playing opportunities than in the past, that's good. I do want to win, but even if we win, there's no end of the rainbow there. We win a trophy."

Laundry's done. Welcome to D4 soccer! — Dennis Crowley (@dens)May 23, 2016

If Crowley can develop a winning, profitable model, however, all of the American soccer scene could benefit.

One player who Crowley suspects might get an individual promotion is team captain Jamal Lis-Simmons. He's an interesting case in his own right. Lis-Simmons, who mostly plays in central defense, is 34. He played two years of Division I college soccer at SUNY-Albany before playing out his final years of college eligibility at SUNY-New Paltz when he was 30. He made his debut as a semi-professional at an age when others begin contemplating retirement. But then again, that was also the point of the Stockade: to give local players a showcase.

"I've been playing my whole life," Lis-Simmons said. "For this to all of a sudden happen in my backyard, in Kingston, was a really cool opportunity and I thought, 'What the hell, let's give this another shot.'" He isn't so sure that he'd move on to a higher level if given the chance. He has always lived locally, and he's just taken a job as the new head coach of SUNY-Ulster, a community college—he might well be the nation's only college soccer head coach who plays at a higher level than his players do.


But he's certain that if he wanted to move up, or if others do, the Stockade wouldn't stand in his way. "I'm sure he would be in favor of being able to make any sort of local kid being a standout player and move on to another level," Lis-Simmons says of Crowley. "It would be great for the individual and soccer as a whole."

There's already talk of other teams starting up in the area, who will compete for talent. So Crowley has begun considering whether he should look into affiliating with youth programs to create a pipeline. And this is exactly the point of his experiment: incentives fueling competition, competition powering innovation, and innovation leading to improvement and growth.

GAME DAY! (aka load up the back seat of my dad's car day!) — Dennis Crowley (@dens)May 22, 2016

For now, Crowley does most things himself, printing tickets and programs, ordering jerseys and merchandise, handling media, arranging sponsorship, roping in friends to do commentary on live streams of the games. Everything but the actual soccer side of it, which he leaves to the experts he recruited to help him–mostly volunteers. During a game, he runs around with his walkie-talkie, making sure everything runs smoothly.

"Dennis loves to build things," says Greg Lalas, Major League Soccer's VP of content, who has advised Crowley in a private capacity. "And he doesn't just say it; he actually starts to do it. That's how Dennis operates. I think about Dennis a little bit like the kid who gets a Lego set. And he says, 'I think I could build a rocket ship out of this.' And he just starts doing it. There's a structure in his mind. And he just starts putting Lego pieces together."


But what, exactly, is the end game? One team that still operates within a closed structure and, save for its underlying ideology, functions like most others, doesn't exactly drive the cause forward.

"I'd love to pitch this [to the other owners] next year: what if the NPSL is not 80 teams, but it's 200 teams? Or 500 teams? And there's three tiers that you move up and below?" Crowley says, adding that the tiers would be self-contained within the regional conferences that make the league's logistics affordable.

"Why isn't there promotion and relegation between two New England conferences?" he says. "That seems like it's a good next step. Let's do pro-rel in the Northeast, NPSL Division. And then teams that are in the top tier maybe we can get sponsorship and split it. Then the teams in the second tier want that sponsorship money and try to get themselves promoted up. The fundamental pieces that you need are that you should be able to move up, that there's an aspiration to move up, and that when you move up there has to be some kind of reward that you're chasing to get there. And above that level there should be another reward. I don't think there should be a ceiling."

NCAA rules forbid Stockade players from getting paid. Photo by Ed Diller / Stockade FC

Once he has perfected the Stockade's formula, he wants to help the NPSL expand through his model and collectively challenge the third-tier USL. In terms of the level of soccer, but also attendance, branding and relevance. "How do you make the NPSL the sexiest thing you can find in soccer?" he says. He seems to be implying that if you make a mockery of the tier system, you eventually force the hand of the United States Soccer Federation, which sanctions the various tiers at its discretion.

As is the case in tech, he says, you crowbar your way into the market by creating an attractive alternative to the established powers. Then they have to copy you, buy you, or work with you. He argues all are good outcomes.

It's a startup mentality. Disruption and all that. As Crowley lays all this out over coffee in a painfully hipsterish shop in Kingston's old Stockade District–get it? Stockade?–he constantly jots stuff down in a little notebook. Ideas. Memos. Things to do. "From doing seven years of Foursquare, you just have to have a plan and a strategy. And you execute until it's not a good plan and then you change it and you have a different plan," he says. "There's all sorts of shit [in soccer] that's broken that needs to be fixed. It will take years and years to fix them all but you have to identify the problems and then assign them to someone to go fix them."

After this interview, he has to go print out more tickets–over the course of its first full season, the Stockade would average a robust average home attendance of 756. First, he puts a box of pocket schedules on the counter. "We can sit around and wait for someone to figure out the promotion and relegation stuff or we can just take a stab at it and inspire people to do it," he says. "I don't know if the whole thing is going to work. But I just can't bitch about it on Twitter and not do anything."

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