Tech, Entrepreneurship, and Soccer: The Genius of Dennis Crowley


Few names carry as much water in the lower leagues as the name Dennis Crowley. The outspoken tech genius who helped create the app Foursquare, founded the NPSL’s Kingston Stockade four years ago. With slick kit design, solid play on the field, and progressive approaches to fan engagement, the club has quickly become one of the better known names in the league. While trying to build a strong club in the present, Dennis is also seeking to change the future of the American game, by co-filing a still-pending suit in the Court of Arbitration for Sport against USSF for the lack of promotion/relegation in the American pyramid. While that suit has not been settled yet, the ramifications could be ground breaking in this country. He’s an outspoken iconoclast who is shaping the sport of soccer in the United States and a voice worth hearing.

How do you feel about the health of soccer in the county right now?

Great question. I like to think that, in terms of global soccer and the global game, is on the rise. It’s easy to watch matches from around the world, easy for people to watch the best stars from around the world. It’s crazy to see that in the last ten years, you can go any part of the country and people are wearing Barcelona and Real Madrid shirts and jerseys. That’s awesome. That’s all going in the right direction. I think there’s things like the men’s national team fails to qualify, which I think robs US fans from having that moment in participating in that global conversation. Seeing the women’s team go out there and crushing it is awesome and inspiring. I think that for the regular everyday fan, awareness of soccer is growing, I think awareness of the MLS is growing, I just think it’s unfortunate that the U. S. Men’s National Team didn’t make the World Cup this cycle, that didn’t really help.

I think if you really dig into it, from a soccer nerd perspective and the business growth and evolution of the game, it’s pretty stagnant. To hear the reports come back from the Yedlin issue, the training and solidarity payments case, it’s not super inspiring. We haven’t heard a lot of resolution on the CAS case that we filed around Article 9 and promotion and relegation. You continuously hear about new leagues starting and trying to compete with other leagues. What is continuously frustrating to me is that there doesn’t appear to be any leadership from the USSF, saying like “hey, we realize that there’s a lot of instability in the US Soccer pyramid, so we’re want to and fix it. Here’s our ten year plan to fix it. Someone just has to step up and do that. It’s super frustrating that there’s no one at USSF that is capable of doing that. And there may not be anyone at the USSF who is interested in doing that. I find that to be really frustrating.

So, beyond that, from where I sit, as a board member in the NPSL and the chairman of a lower level club, one just got off the phone with someone in Connecticut who wants to start a team and just had coffee two days ago with someone who wants to start a women’s team in Brooklyn, there are people who wants to build these things around the country. I talk to a lot of them because I’ve written a lot of stuff about this. People seek me out on the internet and I’m happy to grab some coffee or talk on the phone for a half hour. And there’s a lot of people out there that want to do this because it’s a fun process and they want their community to have it and they just love the game. I wish there was also a real entrepreneurial take on it, where hey, if you start this club, you can build, invest, and win your way up, you can establish yourself and there’s business opportunities there. We’re just starting to scratch the surface of those things, but we haven’t really realized them yet.

That was a really long answer for a very simple question. Sorry about that.

There are some soccer fans that view club over league, how do you see that relationship, which is the priority for you? The strength of the league or the club? How are they connected? Which is more important?

Clubs, right? The leagues are the containers for the teams. The leagues should be set up and anchored in their spots and then the clubs should just move through the leagues as they evolve. That’s the way it works everywhere else in the world. Just in the US, you have these individuals that own these leagues, so the leagues are being entrepreneurial, as opposed to the clubs. And that’s the thing that’s broken. If the leagues could just decide, we’re a D4 league and we’re going to be a D4 league, this is where we belong. We want clubs to come in and we want clubs to go out. We want them to come in as amateur clubs and we want them to leave as professional clubs, that’s great, right? But not all leagues see it through the same lens.

As far as Stockade is concerned, you’re in your fourth season now, what is easier now versus four years ago?

I’d say that now the gameday operations run like a well-oiled machine. Stockade world headquarters is based in my garage and I load up a whole bunch of stuff into my car and I drive it to our rinky-dink stadium in Kingston. There’s always an army of 15-20 volunteers that know, once I park my car and open the hatchback, everyone unloads it, everyone sets up - we’re a well-oiled machine when it comes to gameday operations. That’s great, because when that works it allows us to do other things. Now we have time to think about food trucks, beer tents, an iron-on jersey station, let’s do our livestream in English and in Spanish, let’s try to be part of a tournament we weren’t a part of. It just frees us up to do those other things, which is awesome. So there’s that part, which is the off the field part.

There’s also the on the field part. When we started four years ago, people were like, who’s going to coach? Who’s going to play? No one’s going to come out and watch. No one’s going to care. Coaches were like, I’m not going to send you my players, I’ve never heard of you before. And now, four seasons in, we’ve won a conference championship and played in the U. S. Open Cup. Some of our players, every year, get picked up from our club and go play internationally. We have a reputation in the Northeast for being a good program - coaches want to send their college players to us. Talented players want to play on our team, because they see it as a doorway to play in a different league or even in a different country. That’s a huge luxury for a club like ours, where fans know what to expect when they come out, players know what to expect when they come, coaches know what to expect when they send us players, everything runs well and now we do four or five new things every year, which makes the fan experience more interesting.

The soccer team is kind of the same thing. It brings people together in Kingston, to have the most fun two hours of their week, that it just so happens to be a soccer team.
— Dennis Crowley

You’re pretty well-known for starting and running an app. What’s the difference between the starting an app and starting a soccer club?

I’ll correct you for a second, we’re not just an app, we’re a technology company that happens to have a couple of apps of our own.

My apologies.

No worries, people ask me that all the time. The soccer thing came out of left field, what’s the difference between tech and soccer. Really, when we started Foursquare, it was about building things that bring people together. To build software that helped people connect, so they could connect if they were in a new city, stuck in an airport, in a bar or restaurant. The soccer team is kind of the same thing. It brings people together in Kingston, to have the most fun two hours of their week, that it just so happens to be a soccer team. And so, they are closer than you would think.

Once you peel back the onion a little, it’s about community, about bringing people together, and about building a platform. These days Foursquare is a technology company. We are a technology platform, we build tools that let people build on top of our tech and data. Stockade is a community platform. We built this thing that enables players to come in, be seen, and then move to different parts of the world. That allows people to sing the national anthem in front of a crowd. That inspires kids to want play youth soccer or try out for the high school team. We’ve turned fans of the game into broadcasters – they now broadcast our games, they’ve become operators, they’ve become technical directors. It’s a platform that enables people to do cool stuff and that’s what we’ve made.

Kingston Stockade take their name from the Stockade District in downtown Kingston, NY.

Kingston Stockade take their name from the Stockade District in downtown Kingston, NY.

You’ve mentioned that you’re giving advice to start-up clubs. What is that first piece of advice that you give a new club?

Usually, people read my blog posts, and they think this is really expensive. To give people a sense of the costs is super helpful. So then I usually talk them down on the costs, because we spent so much money on merchandise and not every club is the same. Some clubs are going to have crowds of 1,000, while others are going to have much smaller followings. One of the main pieces of advice I give people is that every club comes with a founding group and every founding member comes with a super power. Now the super power might be that you’re a coach. Maybe you run a youth organization, so you have the field. Or you run a bus company on the side, so you have transportation. It could be that you’re really good at the internet, so the marketing comes easy. Every club has a super power, so you’ve got to find out what your superpower is, do that really well, and then bring in a bunch of other people that can help with the other stuff.

It’s a fucking joy to watch this team when they are clicking. It’s fun for me, it’s fun for them, it’s fun for the fans.
— Dennis Crowley

Currently, Stockade is third in the conference. What was your expectation coming into this season and what is your expectation at this point?

We didn’t have a good season last year. Not as a result of that, but we also had some turnover in our coaching staff. We brought in a new coach who was our captain for a couple of years. So there were a lot of unknowns. One of the things we did this year, we had a much larger roster, about 40 guys, that gives the coaching staff a lot of flexibility. I think that was one of the things we learned from the first couple of years. We have a much deeper roster, a coach who was a former captain, a lot of unknowns.

But the team has been playing very, very well together and that is a testament to amazing staff, amazing coach, and really dedicated players. My expectations were a little humbled from last year, which wasn’t a great year, but we are doing much better than I expected. It’s a fucking joy to watch this team when they are clicking. It’s fun for me, it’s fun for them, it’s fun for the fans. They play very, very well when there’s good chemistry on the field.

Earlier, you mentioned the suit that you filed in the Court of Arbitration. Where is that suit right now, at this point?

The CAS filing is a little bit of a black box, so I can’t really give you an update on that. There’s also other confidentiality things that we’re a part of. But we do see bits and pieces coming back which I can’t comment on. To be really honest, it’s a very black box of a process. We gather a bunch of statements, have a bunch of hearings, and then something comes out of it. So I’m very anxious and interested to see what the decision is. I really think it has the potential to start to change the landscape here, because we really need it.


What do you hope to accomplish with the suit versus what you think the reality of the result will be?

My hope is that FIFA says “Thank you for calling this to our attention. Yes, it does appear that MLS is not adhering to the rules of Article 9. So, we would like to work with USSF to come up with a timetable to get the US Soccer pyramid will be compliant and that will happen in the next 3-5 years.” I just want a roadmap. I want someone to step up and lead and say “Hey, this system is like no other in the world. We hear the fans. We know that we are non-compliant. Here’s our plan to fix it and it’s going to take 3, 5, 7, 10 whatever. Someone put a plan together and share it with the fans.

It’s super confusing and I wish USSF would help manage it and set some direction and guidance. In the absence of that, you’re left with a bunch of leagues jockeying for position.
— Dennis Crowley

Are you optimistic for that result?

It’s hard for me to read the FIFA statutes and look at Article 9 and say, “where does it say that it doesn’t apply to the United States?” 208 FIFA countries, I think that’s the right number, and two are non-compliant: us and Australia. The Australian Federation is starting to make the steps to open the pyramid and showing leadership to get it done. We’re ignoring it here. The leadership is pretending it’s a problem that doesn’t exist.

It’s hard to read it and not be optimistic about it. But I’m also very jaded on USSF and FIFA. Sometimes things aren’t done to the letter of the laws that they’ve written, and I think systems are made to convenience folks with favor. And that’s not fair.

Another league (CPL) was announced last week. We’ve got NISA, Founders Cup kicking off later this year. USL 2 is snapping up NPSL clubs. Are we in a new era of Soccer Wars?

When was the last era? Did it ever end? I think everyone is trying to figure out the problems at the bottom of the pyramid. What happens to amateur teams when they grow up? A Chattanooga, a Detroit, ten years in the NPSL and they are on the verge of outgrowing the league. So Founders Cup emerges as a way for NPSL to grow in the fall to help these teams that have made it. On one hand, I think it’s super interesting to see all these other products (I call leagues products) that allow clubs that are right on the edge of amateur and professional to find a home to play. On the other hand, it’s super confusing and I wish USSF would help manage it and set some direction and guidance. In the absence of that, you’re left with a bunch of leagues jockeying for position.

Has NISA even announced their teams? I don’t think they have, and they are kicking off in the fall? I’m interested to see how that comes together. Same thing with Founders Cup. They have some work to do before launch. CPL just announced they were forming. Well what’s this all about? How are they different from NISA? How are they different from Founders Cup? How are they different from USL 2? There’s a lot of confusion in the market. I’m knee-deep in this space, in terms of thinking about it, strategizing about it, and sometimes it’s really hard to articulate the difference between NISA, Founders Cup, USL 2, and whatever CPL is going to be. That’s not a good position for all those leagues in the lower level.

Is the solution to the pyramid’s problems top down or bottom up? How do we figure this thing out?

I think that either solution would work, but top down has to be driven from the USSF and I think the USSF is incapable and disinterested in solving this. Which I think does a disservice to fans, clubs, players, coaches, and anyone that follows the sport in the US. So in the absence of it coming from the top down, it has to come from the bottom up. That’s basically what you’re seeing when I rattle off those four leagues: NISA, Founders Cup, NPSL, USL2, UPSL, and CPL. What is that, six? These are leagues trying to fix the system from the bottom up. It’s like the landscape was dead before it and right now, a lot of the leagues and clubs aren’t working together and no one is incentivized to work together right now. And so, it feels a little wild west. But I do think if things are going to change, they are more likely to change from the bottom up than from the top down.

As a guy who works in tech, what role can technology play in the growth of soccer in the United States?

That’s a good question. As someone that’s been doing tech for twenty years, I’m also an investor, a board member, an advisor, for other technology startups. One of the things I’ve been looking at is autonomous broadcasting systems. We have 100 teams in our league and for a lot of those teams in the NPSL, it’s very hard for them to stream all their games because they lack the experience and expertise. So this idea that you could put a camera on top of the stadium that has computer vision algorithms that would understand where the ball is moving and would be able to pan and zoom appropriately, and maybe even add automatic graphics tied to jersey numbers, rosters, tied to out of bounds, corner kicks, shots on goal– basically automatic keeping of stats, automatic broadcasting, automatic pan and zoom of cameras. All of that would get fed into larger data systems that would facilitate scouting, measurements, evaluating of players, and hopefully aid those players as they move through the system. I think there’s a huge opportunity there. A lot of the same technology that’s being in self-driving cars is immediately applicable to understanding what’s happening on a soccer field, on a basketball court, or on a football field – it’s a very similar problem.

- Dan Vaughn

Header image courtesy of elevenneyyork with editing from NoaNoa Marketing.