Dennis Crowley

Whispering bots, crowd-sourced maps & the future of location-based experiences

Dennis Crowley is the founder and executive chair of Foursquare – a company whose location-based technology is used by Uber, Apple, and others. Dennis a pioneer in location-based social experiences – and an endlessly creative serial entrepreneur who knows how to navigate the ups and downs that go along with bringing new ideas to life. Tune in and hear Dennis’s thoughts on Pokemon Go, entrepreneur payback, and the future of location-based social experiences.

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Connect: LinkedIn @dens

Episode Transcript

[Amy Jo Kim] Welcome, Dennis, to the Getting2Alpha podcast.

[Dennis Crowley] Hey. Thanks, so much for having me on the show. I’m excited for it.

I’m thrilled to get to connect with you, and learn more about what you’re up to these days. For those who aren’t familiar with you, let’s start off with a whirlwind tour of your background. How did you first get started in design and tech? What were the key turning points for you, where you decided to pursue things along the way?

I’ve been in this building things for the internet space, really since I was able to get access to the internet. Which goes back to probably 1995 or so, I was a student at Syracuse University in upstate New York. Got really into web publishing, and making homepages, and stuff. Ended up moving to New York City after graduation. I got a job at an internet research company called, Jupiter Communications. I thought I knew a lot about the internet, and I wanted to be one of those talking heads that was really smart about the internet, so I went to one of the firms that was doing that stuff.

While I was there I got kind of bored with my day job, and I learned how to build prototypes of things, and taught myself out of a book. I built a city guide called, Dodgeball, back in, I don’t know, 2002, or something like that. Which then after all my friends got laid off on the dot com crash, I kind of turned it into a tool that helped people find their friends, on their mobile phones. I used that as a way to get into a company called, Vindigo. I worked at this Palm Pilot city guide company for a couple of years. Went to grad school, NYU. Resurrected that old Dodgeball project, during the days when Friendster, MySpace were all the rage.

It started getting some traction, we sold it to Google. I was at Google for a couple of years, trying to spin a grand tale about what you can do with mobile, and social, and location based services. We couldn’t get as much done there as we wanted to, so we left. We had to leave our Dodgeball project behind. About a year after we left we started another company called FourSquare. Now, we are eight years into it, and continuing to build all sorts of awesome, fun stuff.

Cool. I didn’t actually know that Dodgeball was something you were working on before you went to grad school.

Yeah. Dodgeball was in the early days of me being in New York. There’s a period of New York in 1999, 2000, where the only game in town was a city search. In terms of where we going to go, where are these places. New York was changing so much at that time, that there was literally a new street opened every week, that you could go explore, because it was now safer, because five things opened up. It was unbelievable. No one knew anything about these places, because no one was covering it. I was like, why don’t we just make, why does city search have to be controlled by these editors? Why can’t everyone just be an editor? Why can you not just add your own places and write whatever you want about it?

Which is a radical idea, back in 2000. I just started building that stuff. Dodgeball was the project that taught me how to code, because I tried to take computer science courses in college, and I couldn’t do them, I was kind of too dumb to do it. I didn’t have the math requirements to get into the other classes, so I eventually just gave up on it, and then years later just taught myself out of a book. Teaching yourself out of a book is really hard, but if you’ve got something that you want to build, I was just kind of hopping from chapter to chapter just hacking things together.

That’s awesome. You were really early in thinking about and pioneering location based services, particularly social services.

Yeah. That interest came from being in New York. In hindsight, all of this stuff makes sense, there is a nice drum beat through all of this stuff that I work on, but only hindsight. When I came down to the city, you are totally just overwhelmed. I’m from a super rural town in Massachusetts, and to be here where there’s what ten million people, and ten million things to do, it’s just like overwhelming. I had an interest in phones, and technology, and mobile, and I read Bill Gates’ book. I had read Nicholas Negroponte’s “Being Digital” book, which is like the Bible to me, in college, I read that five, or ten times.

It was predicting the future where these things were going to be possible with mobile and location, and I’m like, I want to build that stuff. When I was in New York it was just like all these kind of problems emerged, like I don’t how to navigate, where am I going to go? I have friends all over the city, how do I meet up with them? It just seems right for solving. You could make clever little things to help people do that.

When you started FourSquare, and FourSquare started to gain traction, it was very influential, and partially, I would claim responsible for launching Gamification. Because there were very visible game mechanics in particular in the onboarding. How did those come about? You’re not a game a designer, but of course you are comfortable with games. How did that happen?

Yeah. Interestingly, you just asked me to give you a run down of my career, and the version that I gave you it cuts out a bunch of projects I worked on in grad school. It cuts out a couple other jobs, that I worked at. Because everyone always wants to talk about the location services and geo-aware soide of my career. I mean, that is what FourSquare is. I was a gamer growing up. Hooked on Zelda. Hooked on Street Fighter. Sega Hockey, and pretty much anything else. In grad school, I took a class that was about game design, and I was like, I love this. Designing card games. Designing board games. I took NYU’s grad program called, ITP. I took a class with a professor named, Frank Lantz.

Oh. Frank. He’s awesome.

Yeah. He runs the NYU game center. This is when games weren’t taken seriously, and Frank was one of those guys it’s like, “Listen games are the future of entertainment. Not movies. Not TV shows. Games. Games cannot be just one class taught in this tiny division. It’s got to be its own thing.” He is like the captain of this movement. He taught a class, at NYU, at ITP, which was a crazy class at the time, it’s a game design course, but we’re not going to make games that you play on screens, or on a game board, we are going to make games that you play in the city. I was like, this is totally my thing. This is my wheelhouse.

We did a group project, the whole class did a group project. I think it was the first time this course was ever taught, and the group project was this thing called, Pac-Manhattan. We decided, let’s turn Manhattan into a Pac-Man game for an afternoon. If you look at the Google Map version of what the NYU area looks like, Washington Square Park kind of looks like the ghost house, it kind of looks just like the board, it’s really eerie. We played this awesome game of Pac-Man, where people dressed up, and they were running around, and there’s a little bit of technology, and a little bit of cell phones, and a little bit of app development that we did, but then there was a lot of just like, it was like performance art, you are running around in the street, being Pac-Man, or being a ghost, and playing this game. This was in 2004.

I remember we got a ton of media coverage for it, like, what are you grown adults doing running around in Pac-Man costumes? We were able to tell a story, like, “Hey. We took this class, it’s called, Big Games, we are bringing game development into the streets, blah, blah, blah,” I mean it was a really interesting story. Pac-Manhattan, it got people excited about this space. We went on to work on a project, me, Frank, and Kevin, and some others, called Conquest, which like a big urban scavenger hunt using 3D bar codes, basically QR codes, but before QR codes were QR codes, and doing it across five cities in the US. Frank and Kevin went on to start a company called, Area Code, that they basically, big games, like “big games”, games that take place in the real world. It had a company that was doing this for three, four, five years.

I actually worked for their company for a year. This was after I left Google, and before I started FourSquare. I was working with Kevin, who’s like a genius, creative person, and with Frank, who is like a genius game designer, and just through osmosis, I was learning about a lot of this stuff. Designing games for cities, and designing game mechanics, and that’s when I was like, “Listen. If Google is going to turn off Dodgeball. I’m going to go make another thing called, FourSquare, and I’m going to take some the game design, that I’ve learned here at Area Code, and apply it to this thing that we are building.” That’s where the game mechanics came from in FourSquare.

That’s awesome. When you think about game designing, adding game mechanics, do you think about it in terms of systems?

Maybe. I’m not a classical trained game designer. I think I could sit down and hold a discussion with folks that are and probably talk about the same things, but I’m not using those types of language. I don’t think I am using the same language everyone else is using. We do enough of this stuff at FourSquare, where definitely thinking about, “Hey. You want to design these systems that make sense to people.” Rules, that one user can explain to another user without having to look at a guidebook or rule book.

Certainly we want to make sure that all these things are balanced. I think through my experience at ITP, and my experience working on some of these games both at NYU, and at Area Code, and on my own, I’ve learned the bare minimum to make something that’s sustainable. I wouldn’t consider myself a game designer, or a great game designer, or anything like that.

Got it. The reason I am asking is that a lot of the folks I’ve been talking to from the UX world are very aware of systems thinking, and being able to deal with products as systems as key to their evolution, and also hard to recruit for. Paul Adams, told me that the hardest thing to find is UX designers who understand systems.


I was curious if that was something that you were running into. Given that you’ve got more game design background than most people working in design.

Yeah. I guess, system is not part of the vocabulary that I would use, normally. When trying to find the right people to work on this stuff, generally we go after people that are gamers, themselves. Because they understand, they might not be able to articulate it in an academic sense, of what they love so much about game X versus game Y, but they have kind of an intuitive sense that this is fun, and this is not, and this is easy, and this is hard, and this makes sense, and this doesn’t.

We’ve been able to find some amazing visual graphic designers along the way, who just happened to be a huge video game nerds. It’s like, we are trying to make something awesome with this Swarm game that we have, just make something that you want to use. Make something that you think your friends would want to use, which is kind of the thinking that we’ve applied to make Dodgeball back in the day, let’s make something that our friends would want to use, to make the early version of FourSquare. Let’s make something that our friends really love using, and so we are kind of teaching that internally here at FourSquare, the company. It’s okay if you’re not classically trained in some of this stuff, or formally trained, but just make stuff that you are passionate about, that you think other people are going to be really jazzed about, too.

Awesome. Do you have much interaction with entrepreneurs who seek you out, and want your advice?

It is. You know, I try to make a lot of time to meet with folks. I just came off of paternity leave. I just had a baby daughter. I haven’t done so much since the last two to three months, but normally I have a nine to ten am, coffee slot, on my calendar that I just leave open, and sometimes I meet with reporters, and sometimes I meet with students, and sometimes I meet with high school kids. I’m happy to talk to anyone that is just looking to get started with stuff. The reason I do that is because when we were doing Dodgeball, we had this moment, we’re at NYU, and it’s like, “Oh. My gosh. Instead of us going and getting jobs at someone else’s company, like Dodgeball could be our company.”

We didn’t know how to take it from an idea to a job. We didn’t know about venture capital. We didn’t know about pitch decks. We didn’t know any of this stuff. New York, at that time, 2004, 2005, was a very different place than it is now, there just wasn’t infrastructure of entrepreneurs that had done this before. You could ask for help. I try to help people on Twitter, or on email, or over coffee, as much as I can, because I think a lot of times you just need a little push in the back, or pat on the back, it’s like, “You know, you’re doing the right thing. It’s okay if you don’t have a paying job, right now. You just push through this and maybe this thing will work out, or this fish tank is fine, sorry you got five no’s, but most people get thirty no’s. Just keep doing what you’re doing.” We certainly needed that at some times in the past, and I feel like I can help people even just a little bit, and maybe I can help push them just a little bit further in what they are doing.

That’s awesome. It also gives you some really interesting patterns to just, it keeps you in touch with what’s happening. I’m really interested, what are the common mistakes that you see, first time entrepreneurs and designers making, not so much about the business, and raising venture, because that’s one, but when they are in the early stages of bringing their ideas to life. This is something you’ve been through multiple times. This is the core of the work I do, helping entrepreneurs bring their ideas to life. What are some of the really common mistakes that you see people make?

Good question. I could probably give you ten different answers for it. On the top of my head, one question I always get every time I give a talk about entrepreneurship stuff is, how did you come up with the idea for Dodgeball and FourSquare? Did you write down a hundred ideas on a whiteboard, then go through the market size of each one? I’m like that is absolutely the opposite of what we did. What we did was we built something that we wanted to use that we thought our friends would want to use. We built a small, little shitty, crappy prototype of it, and we let them use it as soon as it was usable.

Then, we got feedback, and we refined it. Along the way, everyone told us, this is a stupid idea, this is never going to walk, no one is going to want to use this. You should just go get a job. We just kept building, and tweaking, and building, and tweaking until we turned it into something interesting. There was no mathematical formula or analysis to help us figure out if it was a good idea. We just kind of passionate about it. When everyone told us that it was a dumb and stupid idea, we said, “Well, we don’t think so. We want to keep doing it, so we will just keep working on it.” I think there’s some people that might take criticism too seriously early on, “Yeah. Maybe this is a lousy idea. Maybe I won’t do it. Maybe I’ll just go back to not working on this thing.” I think that’s a danger.

You said something really critical there. That was in the subtext. Which is that, one, you solved a real need. It was a need you had, but you were solving a real need. Not creating technology in search of a problem. You were getting that need in to the world in super crude form as early as possible.

Yeah. That’s always been the way that we do it. It’s like, our thesis has been, if you can build something that you, yourself want to use, there’s a good chance that your friends would also want to use it, and there’s a good chance that their friends would want to use it, too, now if you build something and you are like, “This is so dumb. I wouldn’t even use it myself.” Then you got a separate set of problems. If you build something that you like and your friends don’t get it, then you got to go back and refine it. That’s always been the main thesis, like, do I want to use it? Do my friends want to use it? Can they explain it to their friends in a way that their friends want to use it. If you got that going, then you’ve got something good happening.

The “build quickly, and ship quickly, and iterate often thing,” that’s also tied to my skills as a programmer. I’m not a very good programmer. I’m a really awful programmer. I can build stuff that gets the point across, but it only works seventy-five percent of the time. If you can do that in such a way that gets people excited, and you get people to join you, and help out, and like, “Oh. Yeah. This is great. I want to work with this thing you do, and I can help make it better.” Launching quickly was, launching bad code quickly wasn’t a choice, it was kind of like a necessity, like that was the only thing I knew how to write.

We would just constantly just push out prototypes. We would do this even when we were at Google. Just push out little features of Dodgeball, and see how people like them. I always think that’s lot’s of fun to do.

Totally. I cannot resist, you’re a pioneer in the field, and you’ve got this great perspective on gaming, and social local. What do you think about Pokemon Go?

I think the Pokemon stuff is awesome. I was a gamer in, I was, I mean, I still am, I don’t have very much time to play, now, but I played Pokemon and Game Boy, years ago. I understand the franchise, I understand the value in the IP in the franchise, and so when the game comes out, and you see people running around the real world, trying to catch these things, and everyone is like, “What are they doing? They are just wasting their lives trying to get these Pokemon.” I’m thinking, I’ve spent ten years of my career, trying to build software that encourages people to do things they wouldn’t normally do. I’m like, all my gosh, these guys that designed Pokemon, have kind of cracked the code. They made a version of this that tens of millions of people are now using.

That’s awesome, because it pushes the whole space forward. One of the things that I’m excited about, now, because we’re in a post Pokemon world, and this is important point, I’ve been telling people when I first heard about it, the reason that Dodgeball worked, when it did, is because we were able to say, “It’s like Friendster, but for your cell phone, and when I say that, I mean like, Friendster did all the hard work of teaching people about asymmetrical friend graphs.

Now, there is a whole bunch of startups that are like, the Twitter for this, or the Uber for that, because Twitter and Uber did the hard part of teaching people about big parts of infrastructure. In the next six months, or so, there’s going to be lots of, it’s like Pokemon Go, but for this. What that means is it’s a game that’s built into the real world. They’ve communicated a very, very tricky topic, there’s a game board on top of the map of the world, and they’ve just taught that to tens of millions of people.

Now, it’s just pop culture, and people understand it. I’m thinking, “Hey. Everything we’ve done with, we have a location based game called, Swarm, which is also very successful, here, but we can start pitching that, it’s like, “Oh. Swarm is kind of like Pokemon Go, but for places, instead of Pocket Monsters,” and it’s just like an interesting way to get to describe the space. I feel like, everything got moved forward, ten or twenty yards, I’m using a football analogy. Now, people can start building on top of this shared cultural literacy that Pokemon helped create.

That is a fantastic perspective. I completely agree. I think the game is brilliant. It’s highly imperfect. It’s brilliant.

It’s going to inspire kids that are playing it, to like, “Holy cow. I want to make a Pokemon Go, when I grow up.” It’s going to inspire game developers to be like, “Okay. I want to make something like that. Who would have guessed it’s a hit?” I’m wearing my chief executive chair at FourSquare hat, right now, but a big part of our business is licensing technology to enable people to build amazing location based services.

It’s like our business development team, has been very, very busy this past week, being like, people are like, “Can you help us make something like this?” It’s like, “Yes.” We’re very, very good in helping people build strong location, and contextual aware products, so if you would like to build a game, of course we can help you do that.

You’ve got the database.

We have the database, and we have the technology that we’ve made is, if you look at Pokemon, as awesome as a game as it is, and I love it, and I’m only level nine, my wife is now level eleven, and I don’t think that I’ll ever catch up. It really saddens me.

How is she getting all those steps in?

Because she’s home with the baby, right now, and so, she’s like, “I’m going to take the baby for a walk,” and I’m like, “You are not taking that baby for a walk. You’re taking your Pokemon guy for a walk.”

We go for Poke-walks at our house. It’s a special kind of walk.

Meanwhile, I’m at the office. Which is basically like Pokemon jail. There is no creatures running around here, so I’m at a huge disadvantage.

I see. The office has become Pokemon jail. Now, that’s a mental model.

Yeah. I got to break out, so I can go level myself up a little bit.

Oh. My God. That’s so funny, but yes. Yeah. Tell us a little bit more about Swarm and FourSquare, and just the fundamental assets that you’ve developed. How long have you been doing FourSquare, now?

I think it’s like eight years, nine years.

Yeah. You’ve split the product.


For those who aren’t aware. Swarm is the game.

The company is called, FourSquare. We have two apps, one is called FourSquare which is probably the best app in the world for helping you find great places to go anywhere in the world. Then, we have our check-in game, which is called, Swarm. Where if you go to bars, restaurants, cafes, gas stations, whatever, you check in, it takes you ten seconds, you win coins, you can spend the coins, you can become the mayor of a place, it’s like an item collection game, sticker collection game.

There is millions of people playing it, every day. Which is great. As people are having a fun time playing Swarm, every check in teaches us a little bit more about the real world. Is this place still open? Is this place still interesting? Is this place open at 11pm, or does it close at 10? Every check in that we get, we get about eight million per day, I think we’ve got about ten billion total. Every check in teaches us something about some place in the world. It’s just this engine that is constantly learning.

You’ve built dynamic database technology among other things, but let me tell you why I’m bringing this up. I just read Kevin Kelly‘s new book, The Inevitable, which is very thought provoking, and it reminds me of you talking about reading Nicholas Negroponte’s book. It blew open some doors in my mind. It talks a lot about managing dynamic situations. Moving form nouns to verbs. Lots and lots of examples. Data sets, and databases are fundamental, and so many people are stuck with, managing content, and hoarding content. Especially, in publishing.

Mm-hmm (affirmative).

There’s this “new way”, but not new to you. Because that’s what FourSquare is. It’s a dynamic data set, and it goes back to you saying, “Hey. This restaurant is new, and it’s not in the city search.”


That is something that, maybe I’m not using the same terms you use, but as a company you’ve got to be incredibly good at that, and it’s a very, very hard thing to do.

Yeah. We would say it, the language we use is it’s a crowdsourced map of the world. You are exactly right. You just kind of blew my mind, because I’ve never even thought about the early version of Dodgeball from 2001 inspiring the databases in FourSquare, but you’re absolutely right about that. I never even made that connection, myself. Yeah. This idea that, hey, there’s places in the lower east side of New York that aren’t in city search, in 1999, 2000, is exactly the same thing as like there is new restaurants opening up outside of Istanbul, and Swarm users, and FourSquare users are telling us about them, so we can add them to the global map.

The FourSquare database is, there’s eighty-five, we have eighty-five million places in there. I mean, it’s literally every bar, restaurant, coffee shop, you could think of in the world, but it’s also like, every landmark, every hut that’s selling frozen drinks on some beach in Vietnam. Every bench that someones interested in checking into that happens to be on a college campus. Every place that someone has thought was interesting enough to check into is in our database, and it’s just this killer living map of the world.

Now, that is one asset that we have. Now, the Holy Grail, for me, in building all this stuff for the longest time, has been, we didn’t want to build, just like this thing that you have to check into, we didn’t want to build a check in button. What we wanted to build was a service that can teach you about the world as you walk through it, and in order for that to happen, you have to be able to understand when a phone goes inside of a place. How long it spends there. When it leaves. Where does it go next? Where was it before? Where does it go tomorrow? Does it go back to the place? You have to understand how phones move through the real world, but you have to also realize that people aren’t going to hit the check in button, every single place that they go. How do you build a piece of technology that just can basically check you in, in the background? That didn’t exist when we built Dodgeball, which is why we invented the check-in, it didn’t exist when we built FourSquare which is why we had to bring the check-in back in.

Over the last eight years, we’ve basically built this technology, internally we call it, it’s called Pilgrim. Pilgrim is this idea of, if your phone is running FourSquare technology, you can just go to the laundromat, and we know that you are at the laundromat. You can take your phone into the butcher, next door, or the cupcake shop, and we know that you were there for three minutes. You can take it into the Gap, and we know that you were there. You can take it into the coffee shop, we know that you were there. From this, we can start to understand, these are the places that Dennis, likes, and these are the places that Dennis doesn’t like, and we can use that to start making personalized recommendations and personalized maps.

Like my fantasy version of FourSquare is a version that you don’t have to use. It’s an app you never have to open it. It’s something that just texts you, once a week, or twice a week, and says, “Hey. Listen. I know, Dennis, everything about where you go in New York, and I found the perfect place for you and Chelsea to go for dinner, and it’s this place in your neighborhood, but it’s down a street you haven’t walked down in six months.” That’s why we started the company to build this thing. Coincidentally, now that I’m off of paternity leave, I have a group here, and we build this stuff. We have an app called, Marsbot, actually in the app store, now. Which is like a prototype of this version of FourSquare that you don’t use. It’s one that texts you with recommendations, depending on a better personalized, and based off of where you have been in the past. That’s our version of the future. We think, tens of millions of people are going to use software like that in the future.

Wow. That hits like four themes in Kevin Kelly’s book.

Yeah. There was a lot there, see if you let me go unchecked, I just keep talking.

I love it. As you were talking I was thinking, that sounds like the best interface for that would be a bot, and then lo and behold, it’s a bot.

The bot stuff is all the rage, right now. All the bots, are like a genie and a magic lamp. You have to summon the bot. You have to rub the magic lamp to get the genie to come out. Hey, Alexa. Hey, Siri. That bot is fine, but what we are trying to build is a different bot. It’s a bot that taps you on the shoulder, and says, “Dennis, go left, instead of right. Dennis, look up. Dennis, go to the ice cream place around the corner.” Just opened, and it’s awesome, and everyone is talking about it, and you’ve never even noticed it, before. I want that bot. That’s what we are trying to build, here.

Yeah. To get people to use that bot, they have to be super comfortable with surveillance.

I don’t think it’s necessarily surveillance. It’s just this idea that …

Let’s call it tracking.

Some friends of mine that work at Microsoft have this idea, they are called, listening machines. Machines that listen to what goes on in your life, and therefore they are able to make sense, or help out in certain ways. We already have this. Google, Gmail, reads all your email, and it surfaces various things, too. Like, Google, now looks at everything that you’ve done on the internet, and tries to figure out, this is what you probably want, right now.

We are already at this point, where the machines are aware of what we are doing on them, and they are trying to be helpful. I think what we are doing is we are taking it one step further, because we’re invoking location. What can the device, what can the software learn from where I take my phone? Does it know I that I like this neighborhood, over this neighborhood? I like cheap restaurants over expensive restaurants. I like sushi, but I hate cupcakes. We’re just solving one tiny sliver of the software enhancing your life puzzle, and we are doing it for places, because that’s the thing that we are really good at.

Yeah. That’s something that is interesting, but to me, the key is what you do with the data, and the interface you present. There’s a startup that actually just went out of business, that was formed a couple of years ago by my friends Siqi Chen, who comes out of Casual Gaming, and a lot he just comes out of viral manipulation. That part of Casual Gaming. They’re startup, was called, Hey, H-E-Y, and they did exactly that, Dennis, you didn’t have to check in and they tracked everything you did, and showed you little pictures, but it failed. It failed because it was, and then what? Okay, and then what? Which is kind of what takes us back to Pokemon Go. There’s been, a lot of people on AR gaming, are like, “This is not, new. I did almost exactly this ten years ago.” Pokemon Go is that magic combination of game played brand, and cultural readiness.

Yeah. I think that is totally right. With that said, Pokemon Go is going to have its “and then what?” moment. You know?

It already is.

Yeah. I’m level eight. Eighty percent of the monsters, and things that I catch, I already have them, and I’m not as enthralled with it as I was a couple days ago, last week. Any game designer will tell you, it’s very difficult to build something that holds someone’s attention for a long period of time. I feel, that we have gotten super lucky, and super fortunate with FourSquare game mechanics have made the jump to Swarm, and a lot of these things have lived on for eight years. People still love it, and they still play it, and the game resets every week, and people are digging it.

The Pokemon Go gym mechanic is right of FourSquare, or they’re both right out of the same thing, which is owning turf in the neighborhood.

Which goes back to Dope Wars, from Palm Pilot days, you can actually put it on your calculator way back in the day. You own turf, and you’re defending turf, it’s just a mechanic. I think, what’s interesting is you tie the mechanic to physical places in the real world. I think, what is also kind of nuts, is this space is small. The people that have been working on this stuff, over the last ten years or so, you could fit us all in a conference room, probably in some event. Everyone has been inspired by everyone else in a certain way. It’s fun to think, hey, we were inspired by Nike Plus, and then, Nike Fuel might be inspired by something else, and then Pokemon is going to inspire something else.

I hear from people that are like, “I was inspired by FourSquare game mechanics,” basically you’ve got this mix of creative folks, entrepreneurial types that have invented thing that whether they work, or not, succeed for a long time or fail, you basically put them in this mixing pot, and you kind of stir it around, and everyone reaches in there from time to time and they say like, “Now, I’m going to make FourSquare for X,” or, “I’m going to take Pokemon and combine it with this, and combine it with that, and we are going to have something new.” I think it’s great to look back and kind of see the lineage of, hey, there’s a hundred location based games of AR games, and GPS games that never hit the mainstream. You can see little traces of them existing in everything else that is successful, right now.

Absolutely. What trends are you following, right now? Whose work are you paying attention to?

I kind of just pay attention to a lot of the kind of the macro stuff. Like, are people using Twitter more or less, because of Instagram. Which people are using more or less, because of Snapchat, which people are using more or less, because of something else I haven’t heard of, yet. We are at this point now, where there’s a handful of these networks that are just super, super dominant. Besides, that if we did this interview a month ago, I’d be saying, “You know, there just hasn’t been something new that comes out in awhile.” Really, there hasn’t been a new disruptive thing in a bit.

Now, Pokemon is a thing that has everyone’s imagination, right now, and I think, I’m especially tuned into it, because I’ve been in this location based services, location based games thing, for so long, that I’m like, “Oh. My God, someone hit the jackpot with this. This is great.” I don’t know if other people are as inspired and excited about it as I am, but think about it, the Apple watch came out, and it didn’t really transform, anything. There’s no new sensors in the phone, for people to take advantage of.

We are kind of in this lull, right now, and there hasn’t been a big jump. People keep saying it’s going be AR, but it hasn’t been. I don’t think Pokemon is this start of this AR revolution. I still don’t know if AR is going to be a thing. There’s virtual reality. Wearing the headsets. You can now buy them at Best Buy, but I don’t see people playing those, yet. I think we are still in this, what is going to be the next big thing moment, even though there is a couple things that are fighting to be that, right now. Does that make sense?

Absolutely. What are the couple of things fighting to be it? There’s AR, and VR, but I completely agree with you that it’s not a done deal. VR got really over funded. My daughter is such a perfect example, she’s nine, and she sees VR, because she watches YouTube videos, where most education happens these days.


Sees her hero with VR, “I need VR.” A friend of mine is developing some Google cardboard VR games, so he did a play-test, he got a Google cardboard, so we could play-test my friends game. Then, we downloaded every Google VR game in the store. Twenty minutes later, she was kind of over it. The next day, she kind of picked it up, when a friend came over, she showed him. It’s just sitting there. There you go. It’s a bunch of demos. Like you said, it’s hard to drive long-term engagement.

It’s a new medium, and people haven’t figured out what to do with it, yet. Here’s a perfect example, in Snapchat, this is a toy. There is nothing interesting here. It’s a toy.

Ho, ho, ho.

You know? Then, as it starts to pick up speed, it’s like, no, this is the medium at which millennials, now, I cannot believe I just used the word millennials, but this is the platform by which they express themselves. It’s a brand new medium, and people have to learn how to use it. AR, is that, and VR, is that, and mobile is that, and whatever is next is that. When you ask me what’s next, it’s not one of these things. As soon as you asked that, I specifically thought back to, I remember I had, we were doing Dodgeball, before we went to Google. I had a pitch deck, and the pitch deck showed a mobile phone, plus Google Maps, plus Friendster. It’s like social plus mobile, plus location, that’s the thing. It’s not one of those things, it’s all of those things put together.

Whatever is next is going to be what are those three things? Is it, okay real world game, if you play in the real world, plus fitness tracking, plus AR, plus front facing camera. It’s like, I don’t know what does that thing even look like? Maybe we are too old to figure that out, and that’s something for your daughter to figure out, but that’s how it happens. There used to be this thing, in 2005, people talked about, it’s like remix culture, everyone is taking all this stuff and remixing it with everyone else. That just happens over, and over, and over again. Now, there is just the toolbox, it’s so much bigger and so much more advanced, and so much more sophisticated, and people can just make awesome things, because all this other technology has been getting built over the last ten years. FourSquare being one of the pieces that exist in that toolbox.

Yeah. One of the more sophisticated pieces.

Yeah. I think, so. That’s one of the things that we are super proud of. It’s so funny people always say, “FourSquare, I haven’t used that app in a long time. How are you guys doing?” And, I’m like, “We are doing just fine. There is fifty million people around the world that are using either FourSquare or Swarm,” and then we have figured out a way to basically monetize a lot of the data that is coming in, and the technology that we’ve developed so that we can continue to finance building and innovating great things, here. People are like, “I don’t check into places,” and I’m like, “That’s fine. Because there is still eight million check ins we are getting every day, and even though you don’t know it, FourSquare technology is inside of Twitter. It’s inside of Uber. It’s inside Apple Maps. It’s inside of Pinterest, and Yahoo, and Microsoft.” That’s great for us. It allows us to keep building the things that we are excited about.

Absolutely. That’s, again, so connected to the path that lead to Pokemon Go. That was not possible without years of Ingress tagging the world.

Yeah. Niantic has an interesting data system that Ingress game, and I’m sure they’re getting interesting data from Pokemon, as well. I think I mentioned this in an earlier interview, but one of the things that I’m really excited and inspired about is, if I was sitting on an airplane, I have to go to San Francisco, next week, and someone says, “What do you do?” And, I say, “I work at FourSquare, and we have this app called FourSquare and Swarm.” “What does Swarm, do?” I have to say, “Okay. Swarm is like a game you can play in the real world, and you go to places and you check in, and that is kind of the game, and as you check,” it’s a mouthful.

Now, I can sit next to someone and they are like, “What is Swarm?” It’s like, “You know what Pokemon Go is?” It’s like, “Yeah,” it’s like, “Pokemon Go but for places, instead of the monsters. You play it at the places that you go to,” and that instantly makes sense to people. Because of that cultural literacy that now exists. It’s like a different world, now in a sense. At least for us, because we don’t have to go out and explain all this stuff somebody has already done it for us.

That is so interesting. Your perspective is just fascinating to me. On a completely one eighty degree different note, you’ve got a new startup project that is deeply rooted in the physical world. You are growing a local team.

Yeah. I started a soccer team from scratch. It’s something that I had in the back of my head for a long time. I would love to do this someday. We just kind of pulled the trigger on it, last fall, and we just finished our first season. It’s been a lot of fun to do. The club, the soccer club. It’s a semi professional team. We are in the fourth division of the US soccer pyramid. I don’t know if people follow the MLS, we’re a couple levels below MLS. It’s based in the Hudson Valley of New York, which is about two hours north of New York. The team is called the Stockades. Stockade FC.

What I am trying to do is take all the lessons I’ve learned from startups, Dodgeball, and FourSquare, apply them to building this community based soccer team, and then publish everything that I’m learning in an effort to encourage other people to start similar clubs in their own hometowns. Now, I’m advising like eight or ten different people that are interested in starting these teams. It’s like a fun noble thing, it’s also, I’m really enjoying putting a lot of the stuff together.

Wow. You really like helping entrepreneurs who are coming up. You are just doing the same thing as when you make your coffee hours.

Basically, advising people how to make these clubs. Soccer clubs. Soccer teams. Over email, and the same way I would try to guide an entrepreneur for getting financing. I’ll tell you what it’s like, it’s really empowering to have an idea that doesn’t exist, and to go make that. To see it work. I think there’s lots of people that have the ability or capacity to do that, but they don’t get the chance to do it. I think once you do it, and this sounds weird, but I’ve gone through so much shit in trying to build FourSquare that I feel that I could basically build anything, now, and get through anything, because nothing could be as hard as it was to build this company.

In building the soccer team, we had our share of drama, and stuff that almost caused us to quit, but I’m like, “Listen. This is nothing compared to how hard FourSquare was, let’s just keep powering through it.” Once you do that, a couple times, you kind of get the sense of I can just build things, and I can just get through problems, and I can just push forward. I think it’s really empowering. I’d like to help other people to feel the same way that I’ve been able to feel through building some of these things. It sounds kind of corny, but I would like to help people do more of that.

It actually sounds like that’s your super power.

Yeah. Maybe. I think my super power might be the fact that I have this sense of I can build it and I can do it. The confidence, that I can actually get some of that stuff done, because I’ve actually built a couple of things, and now I want to see if I can use that to inspire other people to build the things that they want to build. With the soccer stuff, it’s like I’m fan of the game, and I play, and I’m awful, but I don’t know anything about starting it. I don’t know anything about managing it, and growing it.

We had to learn all this stuff from scratch. I kind of want to make a big deal about we didn’t know what we were doing. We were the least likely people to ever make something like this, but we made it and it worked, and it was successful, and now we are going to teach other people how to do it, and I think, I mean there is something that inspires me in that. I want to help other people be able to get past the fear of not doing their own thing, and getting to go build the things that they want to see in their own world.

Did you use the same techniques of early prototyping and getting feedback to bring the soccer team to life as you do with software? Iterative prototyping process?

The thing about the soccer team was that it was so hard to get people excited about it, because there was no prototype. You are basically launching, V1, is like when the guys show up on the field, and they play for the first time. Instead of the thing crashing or not, it’s like, “Are these guys any good, or are we going to get beat six nothing?” It turns out that the team was pretty good, so that worked out pretty good. It was a good beta test. I had a hard time, early on, getting fans, and sponsors. We were lining up the fields, and people were like, “What? What are you doing? Can you show me a picture?” I’m like, “No. It doesn’t exist, yet.” You are basically building it from scratch. That’s tough. I did kind of run around a bunch and say, “Hey. I’m thinking about putting the soccer team here, making it from scratch. What do you think?”

By talking to people it helps refine your pitch, and it helps to spread the word a little bit, and it helps me get better about talking about it, and I find the things that really resonate with people. It’s not the same, but it was definitely similar. Even though, like you would think, there’s no overlap between a text startup and a soccer startup. You still got to inspire people, you got to actually get stuff done. There’s going to be people that want to help, and you’re going to have to manage them, and organize them. A lot of the skills are the same. Imagine, even if we did something else that was crazier than this, I don’t know what it would be, the skills would transfer that, as well.

Something from nothing.

Yeah. I think that’s the thing that I like to do. I think I figured that out, just a couple years ago. I just turned forty, this year …

Mazel tov.

Thank you. Yeah. I’ve finally figured that out. That is what I like to do. I like to build something from nothing and see it turn into something great, and then let’s see what the next thing we can build is. We’ve got a ten year plan with this soccer team, and I think it’s going to keep building, and building, and building, and see how big we can get it.

That’s awesome. Thank you so much for sharing your stories, and perspective, and inspiration for what’s coming up. I’m thrilled with getting to know you better, and just loved hearing all your stories.

Yeah. This is a lot of fun. Thanks for teasing it all out of me, and thanks for talking for a little bit. I really enjoyed it.