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Andy Dunn’s Pie App Uses AI to Create Friendships at Crowded Events

Andy Dunn, former CEO of Bonobos, is now leading Pie, a social app designed to help people make real-life connections.
March 5, 2025
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Andy Dunn’s Pie App Uses AI to Create Friendships at Crowded Events


Andy Dunn, the founder of Bonobos, is shifting his focus from fashion to helping people make friends. His new venture, Pie, is a social app designed to bring people together in real-life settings. After raising $11.5 million in a Series A funding round, Pie has grown to over 130,000 active users, despite being limited to San Francisco and Chicago.

As the app gained more users, it faced a new challenge: how to help people connect at crowded events. When hundreds of people show up, how can they know who to talk to or how to make meaningful connections?

Dunn explained the dilemma, saying, “This is the beauty of building a startup. A solution creates a problem.”

Fortunately, a solution was already in the works. Two event organizers on Pie were developing a tool called Sparked Connections, an AI-powered quiz that matches people who are likely to get along at a social gathering. Pie acquired the tool and integrated it into certain events, now branded as “Sparked by Pie.”

At events like Pie’s “Coffee with Strangers,” attendees take a brief personality quiz, answering questions on a scale of 1 to 5 about various topics, such as personal beliefs, passions, and even potential flaws. The app’s AI algorithm then groups attendees into smaller, compatible groups based on their responses. Before the event, these groups are placed in a chat room on Pie, allowing them to interact beforehand.

“We’re starting to power it through [ChatGPT],” Dunn said. “As we gather feedback on who connects with whom, we’ll improve the system to understand why people hit it off.” He believes this approach, powered by AI, could solve a problem that would otherwise be incredibly difficult to tackle.

While it may feel disheartening that algorithms are needed to foster human connections, it’s a reality many are already familiar with through platforms like Instagram or Bumble, where AI already plays a role in social interactions.



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