Interview with Dennis Crowley of Foursquare

May 21, 2010

10:05 am


In this episode, Tim Jahn is chatting with Dennis Crowley, CEO of foursquare, a New York based startup that builds mobile products that help make cities easier to use and the world more interesting to explore.

I caught up with Dennis at the Big Omaha conference, which happened May 13-15, 2010 in Omaha, Nebraska. This episode is part of a series of special edition interviews I shot while at Big Omaha which we highlight previously. If you can’t see the video, please click here.

The good stuff (aka, the transcript)

My name is Dennis Crowley. I am the co-founder of foursquare, a New York based startup that builds mobile products that help make cities easier to use and the world more interesting to explore.

I’ve been working in the startup space for awhile. I’ve worked for a couple of other startups that did mobile stuff that overlapped and tried to make cities easier to navigate. I also used to run a project called Dodgeball which was one of the very early mobile social services. We brought that to Google in 2005 and worked on it for a couple of years.

The project just kind of went away and Google ended up turning it off. After Google turned it off, we decided that we would build something different, maybe a little smarter, something that would work better on iPhones and Android devices.

I think some of the motivations behind foursquare are kind of selfish. We build things primarily that make it easier for us to meet up with our friends. How do you take a Wednesday when you don’t have any plans and suddenly you have something to do? How do you take a lousy party on Saturday night and create software that surfaces up the next best thing to do?

We’re taking baby steps to solve some of those problems. Like social coordination and what to do, what’s interesting in Omaha. This is my first time here in Omaha. I’m a little disappointed that foursquare should be better at telling me the things to do. We don’t do that yet but we’re working on it. So I’m hoping the next time I come to visit Chicago or San Francisco, foursquare is actively prescribing experiences for me to seek out.

What one piece of advice would you give to someone, like yourself, who has that drive to create and make change? What one piece of advice would you give to succeed in that?

I have to give this talk tomorrow and I’m kind of struggling with what the talk should be about because everyone here is a fantastic speaker. I think the whole theme of the talk will be about the past 10 years and how I’ve been having people telling me the things I’m working on are bad ideas and not interesting and no one’s going to use them. If you believe it enough yourself, you just keep going for it.

It’s really productive to get feedback from people, except when the feedback is “this is a stupid idea.” If you’re really passionate about it and you feel like there’s a place in the world for the stuff you’re thinking about, you should just try it and see what comes out of it.

That’s really the way I think about it. I was building stuff in 2000 and people thought it was dumb. I kept adding to it, we brought it to Google, they shut it down. We thought maybe that means it’s a bad idea but we still wanted to do it…we’re just constantly hammering away at things we personally find interesting. We find that when we do that, other people usually find the same stuff interesting.

Someone was asking the panel “have you experienced any failure in your career?” My whole career has been one failure after the next. The failure is when you pivot and you start working on something else. When the Dodgeball stuff didn’t work out at Google, I personally took it as a failure. But now, with two or three years hindsight, I’m thinking we learned a lot from that experience, we learned what was wrong with Dodgeball and tried to fix it. We’re still passionate about the same ideas and we’re just going at it and just taking a second take at it.

It’s like when you write a paper in college and the first draft sucks, the second draft is better, and the third draft is the one you end up turning. Instead of doing that over the course of a weekend, I spent ten years writing the same paper.

Is foursquare the one you’re turning in, is it another draft, or are you just playing it by ear?

I don’t know, I’m pretty happy with the way this one’s going. But there’s so much more that we want to do with it. It’s hard to get to all the things we’re really excited about. There’s just two many of them. Ask me again in a year or so. I want to take everything that I’ve ever dreamed of building, ten years of dreams and product ideas, and cram them into foursquare.

There are lots of problems to be solved. You have all these people, places, things to do, and I’m constantly thinking of ways to make cities more efficient. When you think about all the data feeds and maps and things we can do on mobile phones now, there’s this huge opportunity to make things that really change the way that people explore and experience the world.

The music featured during the intro and credits of this episode is a song called “Dye Your Hair Red” from local Chicago band REGO.

Editor’s Note: This video episode was created by Tim Jahn, a longtime Chicago TECH cocktailer and storyteller who produces the online video series, Beyond The Pedway focused on better telling the local business stories in Chicago. You can follow Tim on Twitter: @timjahn.

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Tim has conducted over 150 interviews on, a website he founded for creative entrepreneurs to learn from the successes, failures, and journeys of fellow creators. Follow Tim on Twitter @timjahn.

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