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    Home»Money»Foursquare Cofounder ‘Heartbroken’ Over $0 Acquisition Equity Payouts
    Money

    Foursquare Cofounder ‘Heartbroken’ Over $0 Acquisition Equity Payouts

    Press RoomBy Press RoomOctober 21, 2026No Comments3 Mins Read
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    Foursquare’s acquisition left its cofounder sad and angry.

    Dennis Crowley helped launch the location technology company in 2009. Seventeen years later, Foursquare was acquired by Infillion. Crowley wrote on Substack that one point of the acquisition left him “heartbroken.”

    Foursquare’s acquisition earned equity holders exactly $0, Crowley wrote, with no money offered for preferred or common stock.

    “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?” Crowley wrote.

    Crowley left the CEO role in 2016, though he continued to lead Foursquare’s research and development lab through 2021. After that, Crowley kept a seat on the board.

    Foursquare raised capital from The Raine Group, a private equity firm, in 2019. Less than two years later, Gary Little became CEO. Little was one of The Raine Group’s managing directors.

    “Leadership was unable to preserve the value it inherited or create new value during those six years,” Crowley wrote.

    Foursquare employees reached out to Crowley to express their frustrations with leadership, he wrote. He cited the company’s Glassdoor reviews, which rate it 2.1 stars out of 5. The Raine Group did not respond to a request for comment from Business Insider.

    Crowley also wrote that the $0 equity outcome was buried in a 125-page PDF for Foursquare’s legal team. “No single individual stood up to own (or even acknowledge) the outcome,” he wrote.

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    Calynn Krieger, an executive vice president of marketing for Infillion, told Business Insider in an email that Foursquare had “remarkable technology and a talented team.”

    “We have nothing to say about Foursquare’s former leadership, but we’re glad the business and its value continue, and we’re committed to creating even more of it,” Krieger said.

    The lesson Crowley learned

    Crowley took responsibility for his role in the lead-up to Foursquare’s $0 outcome for equity holders. His decisions as CEO led to the need for a private equity investment, Crowley wrote, and he said he wished he were louder on the board.

    His takeaway: “Maybe the biggest mistake I’ve made in my career is falling in love with this company.”

    Crowley was too loyal to “making it work,” he wrote, and stayed longer than he should have. “Watching the company slowly decay has been a grind on my soul,” he wrote.

    In a footnote, Crowley gave founders a piece of advice.

    “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,” he wrote.

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