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Some final words on Foursquare.

From Teendrama Snippets

By Dennis Crowley

October 20, 2026

Some final words on Foursquare.

Some final words on Foursquare.

Almost exactly a month ago, Foursquare was acquired, marking the end of a 17-year story that started around my kitchen table in the East Village in 2009. “The terms of the deal were not disclosed”, but some details have surfaced online. One of our earliest angel investors wrote…

>> Several days after the announcement I got the paperwork about the sale from Foursquare’s legal counsel. [...] around page 50 was the sentence I needed to see, which said that “each share of Preferred Stock was cancelled and extinguished, without any conversion thereof or payment of any cash or other property or consideration therefor, and ceased to exist.”

Translation: The Foursquare acquisition was a $0 outcome for equity holders – $0 for preferred, $0 for common. It’s bittersweet to see these details surface publicly – at least now there’s an opportunity to comment on them.

I was heartbroken by this ending. There are so many people who put so much time and energy and passion and love into building Foursquare – the company, the products, the brand, the culture. If you were part of it (or even close to it), you know exactly what I’m talking about. To our ~1600 former employees over 17 years, I am sorry the Foursquare story ended in such a way that makes it seem like our collective efforts were worth… nothing?

I’m writing this post for three reasons, (1) I want an artifact that that captures FSQ’s ending from my POV to exist on the internet, (2) I want to hold leadership (myself included) accountable for the outcome, and (3) I’ve learned a lot – strategically, emotionally, psychologically – about starting, scaling, and losing a company that I loved, and those learnings feel worthy of sharing with other founders and investors. “Trust” and “transparency” have always been core to Foursquare’s DNA, so if there’s going to be any last word on the company, they should echo these values.

I don’t think anyone was expecting a huge exit these days (there was a big capital stack to pay back before common saw anything, plus many people’s vested options and RSUs had expired), but seeing it go to zero is hard to accept.

Foursquare did struggle as we made the transition from a consumer business to an enterprise business… but we did it! In 2019, 2020 and 2021 we publicly boasted about our $100M+ revenue years. So what happened? In 2019, Foursquare raised additional capital from a private equity firm – the business was starting to work, we had just acquired Placed – and 19 months later the banker who led the capital raise was elevated to the role of Foursquare’s CEO. (Jan 2021)

And six years after that leadership change, we now know how the story ends – as a zero dollar outcome for equity holders. Leadership was unable to preserve the value it inherited or create new value during those six years. Over the past few weeks, dozens of current and former Foursquare employees have reached out to me to express their frustration with the leadership that led the company to this outcome. You can read plenty of the criticism on Glassdoor if you’re interested. There’s 40 pages of it.

I’ll take accountability too. I was the CEO for the first 7 years (and I raised both equity and debt) and was Chair/Co-Chair of the Board for 17 years (as the company raised *more* equity and debt), so I take responsibility in part for how we got here. We raised a lot of capital under my leadership, and my decisions as CEO led us to the point where we needed additional capital, including the private equity round in 2019. (I stepped out of the CEO role in 2016 and stepped away from my day-to-day role running the R&D Lab in 2021). I kept my Board Seat after I left and often thought of myself as a champion for the common shareholder. In hindsight, I could have pushed harder as a board member (though tricky when when holding just one of seven seats).

The CEO job is impossibly hard and often thankless, but even in the darkest of scenarios there’s a way to lead with grace and humility. To many current and former employees, the final chapter of the company felt disrespectful. To provide a single example, current employees told me that, despite an in-person all hands meeting, they learned their shares would be worth nothing via an email from Foursquare’s legal team. Former employees learned these details via an email from Carta, with details buried in a 125-page PDF sent from Foursquare’s legal team. No single individual stood up to own (or even acknowledge) the outcome – the antithesis of the transparency and trust that was so core to our early DNA.From everything I’ve heard, leadership took no accountability and displayed little awareness of the role it played in how we got here. With any other ending (even one that didn’t clear the capital stack) this might have been a different blog post. Instead our final chapters seemed so hastily managed and handled with such little care that I was left to write this makeshift eulogy. You all deserved better.

ADVICE TO FOUNDERS / FINAL WORDS

<deep breath>

Maybe the biggest mistake I’ve made in my career is falling in love with this company**. I put my heart and soul into building it, and tried my best to keep the fire inside of it lit for the better part of 13 years. Looking back, I was far too loyal to the company and the idea of “making it work”. I stayed longer than I should have. I stayed believing that I was helping even though the people in charge didn’t want my help. Watching the company slowly decay has been a grind on my soul. The closure of it “being over” is helpful and welcome and cathartic. I don’t regret any of my time at Foursquare, though I do regret never letting myself “move on” from it (which has certainly held me back from exploring other paths over the years).

It was an ABSOLUTE HONOR to build this company with so many talented people back in the day. My north star for Foursquare’s culture (2010s) was always, “We want people to look back and think, ‘That was the best job I ever had because those were the best people I ever worked with’.” And I hear from ex-Foursquare people over and over again that we absolutely nailed this.

Regardless of this ending, I will always be SO PROUD of the amazing team, company and culture that we created together — one that allowed us to build consumer products that meant so much to millions of people (and inspired features you can now find in everything from Google Maps to Snapchat), and enterprise products that set the bar for how smaller teams could innovate and compete against the biggest of players. Watching hundreds of ex-FSQ people supporting each other in our alumni chat, hiring old teammates as they move from gig to gig, and starting companies (or families!) together never gets old. In my mind, your successes are part of FSQ’s legacy.

I will always be SO THANKFUL for the journey FSQ took me on and how the company got to influence so many people’s careers and stories. Foursquare played a defining role in the grand story that is NYC Tech, and the startup ecosystem that thrives here today will always be a core part of that FSQ legacy. I’m thankful for the investors who took a chance on us, and the army of friends and fans who supported us along the way. I just wish we all got to share a better ending together – an ending worthy of the same energy, passion and conviction that fueled the best parts of Foursquare’s story.

** I imagine I’m gonna get dragged for this “falling in love with the company” thing. If you have never experienced this, I *think* I’d recommend it? Building something you love, with people you love working with, for people who love the things you build for them is one of the BEST things I have ever experienced (and anyone who worked at FSQ in the earlier days will know this feeling) To anyone building, It’s okay to fall in love with the company you’re building, but don’t deny yourself the ability to get closure and move on just because the company itself hasn’t yet experienced an exit or ending.

ps: If you’re looking for a proper eulogy for the company’s achievements and legacy, read this. I wrote it six years ago, but it still holds up. Steven Rosenblatt (FSQ’s OG CRO) also wrote a great post-mortem.

I published this here because LinkedIn felt too… self-congratulatory for this post.I’ll eventually cross-post to Medium for archival purposes.Love and appreciation to anyone who read this far. 👋❤️</end>

Thanks for reading Teendrama Snippets! I try to write something 1-2x/month.

View original article on teendrama.substack.com

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