Dennis Crowley, cofounder of the location technology company Foursquare, has publicly shared his deep frustration and sorrow over the financial outcome of the company’s recent acquisition by Infillion. Seventeen years after helping launch the venture in 2009, Crowley revealed in a Substack post that the transaction yielded exactly zero dollars for equity holders, leaving common and preferred stock owners with nothing to show for their years of work.
Addressing the broader human toll of the outcome, Crowley offered an apology to the approximately 1,600 former employees who contributed to the company over nearly two decades. He questioned how a story of collective effort could conclude in a manner that rendered past contributions seemingly valueless.
Crowley served as chief executive officer until 2016 before transitioning to lead Foursquare’s research and development lab through 2021. Following his departure from that operational role, he maintained a seat on the company’s board of directors. A significant turning point in the company’s corporate trajectory occurred in 2019, when private equity firm The Raine Group provided a capital injection. Less than two years later, Gary Little, a managing director at The Raine Group, assumed the role of CEO.
In his retrospective assessment, Crowley placed blame squarely on subsequent leadership decisions. He asserted that leadership failed to preserve the inherent value of the business or generate new value during the subsequent six-year period. According to Crowley, former employees reached out to him to voice their grievances over the direction of the company, a sentiment reflected in Foursquare’s Glassdoor rating of 2.1 stars out of 5.
The zero-dollar equity payout was not prominently communicated to stakeholders, according to Crowley, who noted that the detail was instead tucked away within a 125-page legal document intended for the company’s legal team. He added that no single individual stepped forward to take ownership of or even acknowledge the outcome.
Meanwhile, the acquiring company offered a different perspective on the transaction’s potential. Calynn Krieger, executive vice president of marketing for Infillion, stated via email that Foursquare possessed remarkable technology and a talented team. While declining to comment on Foursquare’s previous leadership, Krieger emphasized that the organization is pleased the business and its underlying value are continuing under new stewardship, with a commitment to fostering future growth.
Reflecting on his own trajectory, Crowley acknowledged his share of responsibility for the events leading up to the acquisition. He noted that strategic choices made during his tenure as CEO ultimately necessitated the private equity investment, and he expressed regret that he was not more vocal while serving on the board. He characterized his prolonged attachment to the firm as a major career misstep, admitting that an excessive loyalty to making the enterprise succeed kept him involved longer than he should have remained, watching the company slowly decay.
In a concluding note directed at other entrepreneurs, Crowley offered counsel regarding founder attachment. He advised that while passion for a startup is natural, founders should recognize when to seek closure and move forward rather than remaining tied to an entity simply because it has not yet reached a formal exit or conclusion.
