Dennis Crowley

Dennis Crowley


We sit down with Foursquare Founder and Executive Chairman Dennis Crowley to discuss the interconnectivity of people through technology, the future of Foursquare and splitting his time between NYC and The Hudson Valley.

What’s the biggest misconception about Foursquare?

I think that the biggest misconception is that people still think of it as THAT check-in service that THEY tried five years ago. Meanwhile, we’ve taken all that check-in data and made this awesome local guide that can learn about the places you’ve been to, the places you take your phone, and then actively recommend places you should go to based upon where you’ve been.

With everyone always on their phones, do you think we are too connected?

I think we’re much more connected than we were in the past, obviously. This past weekend, I was with my family and I found myself on my phone more than I wanted to be. Sometimes you hold five different conversations. I think it’s a good thing because I’ve been in touch with a lot more people that I probably would have fallen out of touch with. But in the same time, those interactions happen mostly on a screen than in person.

Where do you see Foursquare in five years?

I think this whole local guides space is really ripe for reinvention and this idea that if everyone in the area right now went on Google and asked Google where we should go to lunch, everyone gets exactly the same lunch results. That system is super broken. Music, movies, and books have all been personalized, but no one has done it for food yet, and I think Foursquare is inventing that trend. Like how to personalize your guide to the city or specialize your local experience.

If you weren’t in tech, what field would you be working in?

I think the one thing I found through working at tech companies is that I really like to make things that people get to use and experience. In grad school, they were all tech things, but rewiring foosball tables to keep score. Trying to build things and help people understand. So, I would find something to build. Now that we’ve got a place upstate, I’ve got other hobbies and I’m going to try to fix these little dirt bikes I have and just go out in the woods and try to learn what goes on in the woods, the birds, and the animals. I want to bring my niece and nephews here and build a campsite with workshops.

You recently purchased a house upstate. What drew you to the Hudson Valley?

For a bunch of years, we’ve done summer shares out in Montauk. I’ve done probably ten years of that. There was just that breaking point where I didn’t want to deal with the train, I don’t really like the crowd out there, it didn’t really seem like our scene anymore. My wife and I were shopping around for wedding venues at the time and we were looking at places upstate and we just fell in love with the area and check out this This idea that we can just invest money up there for this big chunk of land where we have enough room to just ride dirt bikes around, ride bikes in the woods and have a spread where we could just have our friends and hang out.

Do you see yourself ever living upstate full time?

I think about it a lot. It’s impossible to do it right now with this job, but I’d like to be able to spend four days a week up there. This might be years off in the future, but when my wife and I talk about what we’re doing, what it looks like five years from now, we’re thinking about splitting our time up there and here. And actually, we know a lot of people who started doing that up there. We’re two hours outside the city, so it’s pretty easy.

What is your favorite thing about the city?

I can see myself living here for another twenty years and not getting bored of it. There’s always something, whenever you feel like you experienced it all, you just have to walk another five blocks and there’s a whole other universe to explore.

What about least favorite thing about the city?

Traffic! It’s crowded.

What is the best piece of advice you were given when you were starting your first business?

Probably to not to give up when things get really hard because I think these things take a really long time to build. I’ve been doing Foursquare for six years now and we’re just starting to see the pieces come together. Six years is a lot of commitment. A lot of start-ups don’t make it that far because it gets really hard in the middle, and either they can’t find a way to make it work or they decide they don’t want to make it work.

What is something you have dedicated time to everyday at FourSquare?

A lot of it has to do with team management or people management, such as how these people work together. Does everyone know what they’re working on or the big picture, why it’s important and why they’re working on it. A lot of it is culture, organization, and communication.

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