• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Trendingnow

1

Now worth $200 million, Sarah Jessica Parker credits being ‘one of eight kids that struggled financially’ for her hunger, ambition, and work ethic

2

The Pentagon said Iran War costs $29 billion, but the real cost is closer to $200 billion—and counting

3

Amazon's record Prime Day masks a darker truth: Americans are spending more and getting less

1

Now worth $200 million, Sarah Jessica Parker credits being ‘one of eight kids that struggled financially’ for her hunger, ambition, and work ethic

2

The Pentagon said Iran War costs $29 billion, but the real cost is closer to $200 billion—and counting

3

Amazon's record Prime Day masks a darker truth: Americans are spending more and getting less
Leadership

How a Moment of Doubt Changed Foursquare

By
Polina Marinova
Polina Marinova
Down Arrow Button Icon
By
Polina Marinova
Polina Marinova
Down Arrow Button Icon
July 28, 2017, 1:00 PM ET
Add Fortune on Google for similar content.

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.”

About the Author
By Polina Marinova
See full bioRight Arrow Button Icon
Add Fortune on Google for similar content.

Latest in Leadership

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Leadership

nido
Commentary250 Years of Innovation
As an immigrant turned entrepreneur and college president, here is why I celebrate our nation as it turns 250
By Nido R. QubeinJune 25, 2026
14 minutes ago
A 6 year study shows which CEOs are pushing RTO mandates: The ones with the biggest egos
NewslettersCEO Daily
A 6 year study shows which CEOs are pushing RTO mandates: The ones with the biggest egos
By Claire ZillmanJune 25, 2026
2 hours ago
Jen Wong, chief operating officer at Reddit, speaks during the OMR digital and marketing trade fair
Big TechReddit
Reddit COO targets 1 billion users as internet’s ‘odd duck’ aims for new heights
By Sam BirchallJune 25, 2026
3 hours ago
Ikea’s billionaire founder was so frugal that he bought clothes from flea markets and took free salt and pepper from restaurants
SuccessBillionaires
Ikea’s billionaire founder was so frugal that he bought clothes from flea markets and took free salt and pepper from restaurants
By Orianna Rosa RoyleJune 25, 2026
5 hours ago
Fortune 500 bosses demanding staff return to the office share one trait: narcissism, research finds
C-SuiteLeadership
Fortune 500 bosses demanding staff return to the office share one trait: narcissism, research finds
By Claire ZillmanJune 25, 2026
5 hours ago
MacKenzie Scott alone accounted for one-third of America’s $19.2 billion in megagifts last year
SuccessMacKenzie Scott
MacKenzie Scott alone accounted for one-third of America’s $19.2 billion in megagifts last year
By Sydney LakeJune 25, 2026
5 hours ago

Most Popular

Now worth $200 million, Sarah Jessica Parker credits being ‘one of eight kids that struggled financially’ for her hunger, ambition, and work ethic
Success
Now worth $200 million, Sarah Jessica Parker credits being ‘one of eight kids that struggled financially’ for her hunger, ambition, and work ethic
By Orianna Rosa RoyleJune 24, 2026
1 day ago
The Pentagon said Iran War costs $29 billion, but the real cost is closer to $200 billion—and counting
Economy
The Pentagon said Iran War costs $29 billion, but the real cost is closer to $200 billion—and counting
By Jacqueline MunisJune 24, 2026
1 day ago
Amazon's record Prime Day masks a darker truth: Americans are spending more and getting less
Retail
Amazon's record Prime Day masks a darker truth: Americans are spending more and getting less
By Nick LichtenbergJune 24, 2026
21 hours ago
After forcing workers back to the office, Goldman Sachs and JPMorgan Chase are now letting their staff work remotely—but only for the World Cup
Success
After forcing workers back to the office, Goldman Sachs and JPMorgan Chase are now letting their staff work remotely—but only for the World Cup
By Orianna Rosa RoyleJune 23, 2026
2 days ago
Ray Dalio just finished a 10-day trip to China. He says global leaders know America ‘doesn’t have what it takes to fight to maintain its empire’
Asia
Ray Dalio just finished a 10-day trip to China. He says global leaders know America ‘doesn’t have what it takes to fight to maintain its empire’
By Nick LichtenbergJune 24, 2026
23 hours ago
Trump’s international student crackdown kicked off a domino effect that could shave nearly $500 billion off the economy
Economy
Trump’s international student crackdown kicked off a domino effect that could shave nearly $500 billion off the economy
By Tristan BoveJune 24, 2026
17 hours ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.