The Upside Newsletter
The Upside Newsletter
🔥Upside Chat: Dennis Crowley, CEO of Street FC and Serial entrepreneur (Dodgeball, Foursquare, LivingCities)

🔥Upside Chat: Dennis Crowley, CEO of Street FC and Serial entrepreneur (Dodgeball, Foursquare, LivingCities)

This week we had the honor to interview Dennis Crowley the CEO of Street FC, building the biggest football club on the planet by making it easier to play in cities.

Street FC operates a football club to make soccer accessible to as many people as possible. It develops a technology that specializes in connecting a community of players online and offline by organizing fast-paced street soccer games on hard surfaces. The company was founded in 2018 and is headquartered in New York.

Dennis Crowley is a technology entrepreneur working at the intersection of the real world & digital world to create things that make everyday life feel a little more fun and playful.

He's also a Co-Founder at LivingCities ("reflecting the real world into the mirror world"), and is the Co-Founder/Co-Chair at Foursquare, one of the world's leading location technology platforms (and early pioneers of using game mechanics to drive real-world behaviors). Previously, he founded Dodgeball, one of the first location-based mobile social services (acquired by Google in 2005) and PacManhattan, one of the earliest "big urban games" (2004). Dennis is also the founder and Chairman of Kingston Stockade FC, a semi-professional soccer team out of Hudson Valley, NY that competes in the 4th division of the US Soccer Pyramid.

He has been named one of Fortune's "40 Under 40" (2010, 2011), a member of Vanity Fair's "New Establishment" (2011, 2012), won the "Fast Money" bonus round on the TV game show Family Feud (2009), and was worth $400 on Jeopardy (2020). He was previously an Adjunct Professor at NYU's Interactive Telecommunications Program (ITP).

Here is a picture of the Street FC app:

Here is a video about Street FC: 

Video: Street FC

📝Show Notes: Through this interview, we touched on his background, his company and product. Then we discussed his plans for the next 12 months.

Best Quotes: Here’s some of the key discussion points and best quotes from our conversation with Dennis:

  • On his background:

    • “ I've been doing tech and startups for about 20 years. I really started my career building things for mobile phones, and building software that would connect people, using real world and digital tools”.

    • “I had a company way back in the day. It was called Dodgeball, which was one of the very first mobile social networks out there. We sold it to Google many years ago and I worked at Google for a couple years. Then I started another company called Foursquare right after that, which started as a game that you would play on top of the real world that uses mobile phones and location and social networks. This startup has been going on for 13, 14 years and now it's turned into this big location technology platform”.

    • “But my interest has always been in building software that connects the real world to the digital world and helping people have fun”.

  • On how he got the idea of starting Street FC:

    • “Recently I got connected with Kyle Martino, who's a legendary soccer player in the MLS and for the US Men's national soccer team. He was running to become the President of the US Soccer Federation several years ago”.

    • “Meanwhile, as a side hustle, I run a semi-professional soccer team. This is a men's semi pro team up in the Hudson Valley of New York. And Kyle and I started talking and he pitched me on this idea that he had where he wanted to build the equivalent of SoulCycle, and its fitness classes on bikes, but we wanted to do it for pickup soccer”.

    • “So I had built a soccer team. I also built tech startups and I knew how phones and apps and social networks worked. So Kyle and I just started hacking away, trying to build this thing. So that's one of the things that we're working on now which is: How can you build the biggest football club on the planet?”.

  • On what Street FC is:

    • “What I mean by that is. A million people that all play on the same team and they all play under the same crest. They all feel like teammates all around the world. And we think that you can do that by making it super easy for people to play soccer specifically in cities where turf and grass are sometimes hard to find and the density of the city makes it difficult to play”.

  • On how the Street FC app works:

    • “ It's all driven by an app, available on the iPhone and on Android. Right now we're up and running in five different cities. So we're in New York, Austin, Atlanta, Philadelphia and in Minneapolis. But the plan is to take it to many, many more cities”.

    • “You need to download the app and sign. We ask you a couple of questions about your playing history. We give you a player rating. The whole thing revolves around having this player’s rating. You have a card that has your picture on it, and your rating, and how many games you played”.

    • “At the end of every game that you play, people rate you and you either move up a rating, you move down a rating and it depends where you're rating. You can get into beginner games or advanced games or you unlock the ability to play at different locations. So we've built this fun gamey thing into it”.

    • “And then there's a big community of people on the backend. We also have a Discord channel that has hundreds of people in it from all around the country that are talking about where they play. They talk about anything related to football culture and life in general”.

    • “So we're trying to build this community of people online and then we bring them out so they can kick a ball together in real life. It gets them to hang out with each other in real life outside of soccer”.

    • “We play on hardcore. For example we'll play on a basketball court, we'll play on a rooftop, we'll play in a parking garage, and the format is very quick. You're not playing for 90 minutes (..) we're playing these four minute games that move very quickly (..) And for us it's like this: you sign up in the app, you get to play a game for free. We're running 20 games a week”.

  • On their partnerships with clubs like the NY Redbulls (MLS) and how they are trying to work with clubs:

    • “We're still trying to figure that out in the spirit of it being a startup. So we've talked to some teams from the MLS and we've talked to some teams from other leagues. We've also talked to rec leagues in the city. We've talked to soccer brands like Nike and Adidas. We've talked to places that host indoor games. And we think that’s the best way to spread the product and spread the magic of Street FC”.

    • “We don't have a rigid format yet. But what I should say for people that are listening is that we're actively working to figure this out. So if you have ideas on how to bring Street FC to your city, if you have ideas for how you can partner with an organization that's building a giant community of soccer fans and players, you should reach out to us. You can reach out to me at”.

  • On his plans for the next 12 months:

    • “To be honest, I was literally just working on this before I jumped on the podcast with you, I was putting together a presentation to give to the team about what are we doing over the next year or so, on what are the goals, who's responsible for what goals, and how we define success”.

    • “Right now we're in five cities in the US (..) By the end of next year we should have our strategy defined to expand to those cities (..) we should have a much larger online community that we have now. We should be getting better at bringing people from the online community into the offline world to play (…) It's really one of the things that I've just been very passionate about in my career: Building tools that allow people to move from the real world to the digital world and then back into the real world again. Street FC is the perfect example of how to do that”.

    • “I don't feel like we need to add another 10 features to be successful. People love the product. People love to play. We need to host more games, we need to get more players, and we need to bring it to more cities”.

    • “We've raised a little bit over $2M, which is a good amount of money for a company of our size and it will give us a lot of ability to grow and try new things and to expand. So we're very fortunate to have found a great group of investors to support us (..) If you want to learn more about us, you can go to, which is our website or we're also on Instagram and Twitter.

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