The Real Story Behind Why Foursquare's Dennis Crowley Stepped Down as CEO

Here's how one moment of anxiety changed the entire trajectory of Crowley's career.

In December 2013, Foursquare founder and CEO Dennis Crowley was absorbed in reading Nick Bilton's new book Hatching Twitter. Over the weekend, he had just gotten to the section when the board decides to suddenly replace Ev Williams as the CEO of Twitter.

And then Crowley saw a meeting pop up on his calendar: "Meeting with Foursquare board members Ben Horowitz and Albert Wenger on Friday, Dec. 13."

Crowley immediately emailed his assistant to ask what the meeting was about, but she didn’t know. That’s when the panic set in. He was almost certain he was getting fired.

When Crowley entered the boardroom, Horowitz and Wenger started making small talk and asking him about his holiday plans.

“Gentlemen, if you have something to say to me, just say it. Just break the news,” Crowley told them. They looked confused and asked what “news” he was talking about. “You guys aren’t here to fire me right now?” he said. To which they responded, “What’s wrong with you? We just wanted to check in before the holidays.”

It led to a serious conversation about Crowley's self-doubts, the challenges of his role, and the difficulties of transitioning from a consumer-focused company. And finally, he said what had been on his mind for a long time: He wasn't sure if he was the right person to lead Foursquare.

"Sometimes, it's hard to have those hard conversations," Crowley says. "So you need a moment like this one that forces the hard conversation to happen.”

That moment of anxiety changed the entire course of Foursquare's trajectory and Crowley's career. Over the next two years, he would find his own successor, step down as CEO, and move to an executive chairman role.

In this conversation, Crowley gives an honest account of what happened when he realized that he was no longer the right person to lead the company he founded.

Below is an excerpt of the interview, but I encourage you to watch the full interview here:

(Photo Credit: Sebastian Alvarado / Coffee & Football)

In the time between the meeting and when you stepped down as CEO, you never once changed your mind and said, “No, no just kidding, I can be the operator after all"?

CROWLEY: I didn't have the "just kidding" moment, but I did have a lot of sleepless nights where I thought, ‘Am I doing the right thing? Is this the right thing for the company? Is it the right thing for me?’ It was a really stressful time in my life.

My brother worked at Foursquare at the time, and he was one of the first people I told. He was angry at me because he didn't think it was the right move while I was like, "I think it is." That was a hard conversation to have with him because this was someone who knew me better than anyone else. It was a really stressful time in my life.

Looking back, I don't have regrets. It enabled the company to do things it wouldn't have been able to do otherwise, and it enabled me to do things I wouldn't have otherwise done.

Just how important is self-awareness in a founder or CEO and how often should they be evaluating their current state of satisfaction?

It's a constant thing. The company meetings were always my primary tool to get a read on if we were doing well or not. I was always able to do a good job reading the audience of 200 people. There were moments where I had to talk about what we were doing from an advertising and enterprise data analytics perspective, but it wasn't the thing I was most passionate about. I felt almost as if I was acting in the role of the CEO as opposed to being the CEO. There were certainly parts of the company where I knew the space so well, and that wasn't the enterprise side of the business for me.

I'm sure I could've gone down the road of, "I'm going to be a scholar of this and learn it really well," but I know myself well enough to know if I'm not truly passionate about something, I'm not going to give it the attention that it deserves. I knew that wasn't fair to the people who were busting their ass trying to make the company work. The best thing to do is to get them someone who is passionate about understanding it and taking the company where it needs to go.

How do you know if something is just a temporary moment of doubt or if it's truly an existential unhappiness?

It's the amount of time you spend noodling on the same problem without being able to come up with a solution.

Saying I was losing sleep over this means I was literally not being able to sleep and waking up in the middle of the night super stressed over it: "Is this the right decision or not?" One of the harder things I had to do in my career at Foursquare is let go of the role.

In hindsight, I can say it was the right decision, but I can tell you I was feeling physically sick in the conference room rehearsing my notes. Twenty minutes before I had to get on stage and communicate it to the staff, I had doubts.

But it was the day after when I walked to work, not as CEO but as executive chairman, that I had this moment of levity and release where I was like, "I did it. I don't carry this weight on my shoulders." I remember exactly where I was — I was on the corner of Bleecker Street and Bowery — where I had the emotional release of laughing and tearing up at the same time.

It was 24 hours after I communicated it to the company that I realized it was the right thing to do. Sometimes you don't know the next day, and sometimes you don't know until 4 years later. It's hard. There are no easy answers.

What advice do you have for founders who find themselves feeling exactly how you felt in 2013? What kinds of questions should they be asking themselves?

"Are you the right person for the job?" You can ask that in your head all day long, and I think one of the transformative moments for me was being able to ask that question out loud. It's important to note that it didn't come up at a board meeting; it came up at an ad-hoc meeting where two investors just happened to be in town. It could've very easily been at a coffee shop. And that was a chance for me to ask that question out loud.

The other one is: "Is this what you personally want to be doing?" Is this core to what I feel I'm best at, and is it the thing that energizes me? One of the best pieces of advice I've ever been given is that there are two types of relationships — there are ones that energize you and there are ones that drain energy from you.

For a long time, Foursquare energized me because I was doing the things that I loved, and we went through a period where Foursquare was draining energy from me because I was not working on the things that I loved. If you have to say as a CEO, "The things I'm working on I'm not passionate about," then maybe you're not the right person for the job. If you're not dreaming and fantasizing and frantically sketching about all the things you can do with the business, then that's the time you realize it's not for you.

Are you being energized by your job? Are you being energized by the company? Would you want this job right now? Is there something else you'd rather be doing, and if so, how do you do that?

What does the word success mean to you?

I think about this a lot. Someone said, "Foursquare is so successful." And I was like, "Are we? What's the measure of success?" We employ 350 people. We have the capability to be profitable in a given quarter. Our tools and technology can help in really great ways. So I look at this place, and I think this company is on its path to being successful.

Personally? I don't think [my first company] Dodgeball was successful. Did I make some money off of it by selling it to Google? Yes. Was that the thing that made me super happy? No. What makes me happy is building things that change the way people use public space. That's success for me.

This is a good lesson: Find the thing that you want to work on. Find the thing that brings you joy and energizes you, and then keep working on that thing until you feel successful at it.

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