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

Trendingnow

1

Jeff Bezos wants the bottom half of earners to pay zero income tax—he says nurses making just $75K should save $12K a year

2

Despite a $500 million net worth, Shaq just finished his fourth degree. He warns graduates: 'Your character will take you further than your resume'

3

Bolt CEO says he let go of his entire HR team for creating problems that didn’t exist: ‘Those problems disappeared when I let them go’ 

1

Jeff Bezos wants the bottom half of earners to pay zero income tax—he says nurses making just $75K should save $12K a year

2

Despite a $500 million net worth, Shaq just finished his fourth degree. He warns graduates: 'Your character will take you further than your resume'

3

Bolt CEO says he let go of his entire HR team for creating problems that didn’t exist: ‘Those problems disappeared when I let them go’ 
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

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

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

Beyond the diploma: Skills that actually get graduates hired
Future of WorkWorkplace Innovation Summit
Beyond the diploma: Skills that actually get graduates hired
By Ashley LutzMay 22, 2026
8 hours ago
satya nadella
AITech
Microsoft reports are exposing AI’s real cost problem: Using the tech is more expensive than paying human employees
By Jake AngeloMay 22, 2026
9 hours ago
She grew Salesforce’s team by 600% in South Asia. Meet one of India’s most powerful women
NewslettersMPW Daily
She grew Salesforce’s team by 600% in South Asia. Meet one of India’s most powerful women
By Angelica AngMay 22, 2026
10 hours ago
Svenja Gudell, chief economist at Indeed
SuccessWorkplace Innovation Summit
Indeed chief economist says we’re entering an era of ‘great mismatch’ thanks to a generational imbalance of workers
By Emma BurleighMay 22, 2026
10 hours ago
Steve Wozniak
SuccessCareers
Apple’s Steve Wozniak says he cofounded the tech giant after 5 rejections from HP—not to ‘make money.’ For years, his paycheck was just $50
By Preston ForeMay 22, 2026
10 hours ago
A year in the life at HP: What matters to its sustainability lead in May 2026? 
EuropeHP
A year in the life at HP: What matters to its sustainability lead in May 2026? 
By Francesca CassidyMay 22, 2026
14 hours ago

Most Popular

Jeff Bezos wants the bottom half of earners to pay zero income tax—he says nurses making just $75K should save $12K a year
Success
Jeff Bezos wants the bottom half of earners to pay zero income tax—he says nurses making just $75K should save $12K a year
By Preston ForeMay 21, 2026
1 day ago
Despite a $500 million net worth, Shaq just finished his fourth degree. He warns graduates: 'Your character will take you further than your resume'
Success
Despite a $500 million net worth, Shaq just finished his fourth degree. He warns graduates: 'Your character will take you further than your resume'
By Preston ForeMay 20, 2026
2 days ago
Bolt CEO says he let go of his entire HR team for creating problems that didn’t exist: ‘Those problems disappeared when I let them go’ 
Workplace Culture
Bolt CEO says he let go of his entire HR team for creating problems that didn’t exist: ‘Those problems disappeared when I let them go’ 
By Preston ForeMay 19, 2026
3 days ago
Pay transparency is exposing a bigger problem: Most companies can't explain why they pay what they pay
Workplace Culture
Pay transparency is exposing a bigger problem: Most companies can't explain why they pay what they pay
By Sydney LakeMay 20, 2026
2 days ago
McKinsey partner says up to 50% of work hours could be transformed within the next 5 years
AI
McKinsey partner says up to 50% of work hours could be transformed within the next 5 years
By Emma BurleighMay 21, 2026
1 day ago
Indeed chief economist says we’re entering an era of ‘great mismatch’ thanks to a generational imbalance of workers
Success
Indeed chief economist says we’re entering an era of ‘great mismatch’ thanks to a generational imbalance of workers
By Emma BurleighMay 22, 2026
10 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.