How a Moment of Doubt Changed Foursquare

July 28, 2017, 5:00 PM UTC

Foursquare’s Dennis Crowley recounts the moment he realized he was no longer the right person to lead the company he cofounded. This is Crowley’s story as told to Polina Marinova.

When Nick Bilton’s book Hatching Twitter came out, I couldn’t put it down. It was early December of 2013, and I had reached the part where Twitter’s board replaces cofounder Evan Williams as CEO.

A few days later, I checked my email to see a meeting on my calendar. It read: “Dennis meets with Ben and Albert.” In other words, Foursquare board members Ben Horowitz and Albert Wenger wanted to meet with me, the cofounder and CEO of Foursquare. “Oh, my God! I’m going to be fired, like in the book,” I thought.

That Thursday, I walked into Foursquare’s New York office to find Ben and Albert already sitting at the table in the boardroom. They were on the far side, so I sat directly across from them on the near side. I remember thinking, “I might not have a job after I walk out of here.” They started making small talk about the company and asking me about my holiday plans.

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

And then I had to explain that I was reading the Twitter book when this meeting showed up on my calendar. After we laughed about it, there came this very serious moment of, “Well, what’s going on? Why did you think we were going to fire you?”

I wasn’t quite sure how to respond. The company was doing well, but I wasn’t. I began telling them all of my self-doubts. I told them about the challenges of the job and the difficulties of transitioning from a consumer-focused company to an enterprise one. But then I dropped this bombshell: “I don’t know if I’m the right person to lead Foursquare anymore.” I was the right person to get it to this point, but I needed help.

That moment of anxiety was the catalyst for us to have a frank conversation about how I envisioned my role at Foursquare.

For the next two years, I executed a plan that involved hiring an operator, expanding the management team, selecting my successor, and transitioning into an executive chairman role. In January of 2016, I stepped down as the CEO of Foursquare.

I hadn’t thought of switching my role until I got out of that meeting. Before that, all I thought was, “This is a hard job, and being an operator doesn’t come naturally to me.” That Thursday morning was the first time I had considered the company would be better off with a more experienced leader. I was self-aware enough to know that I’m good at a lot of things, like building products, but this was not one of them. 

A version of this article appears in the Aug. 1, 2017 issue of Fortune with the headline “Learning Not to Lead.”

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