Andy Dunn on building Pi, a social app to fix the loneliness epidemic, after his bipolar diagnosis and Bonobos exit

Andy Dunn's next act: a social app built from a psych ward epiphany

Andy Dunn, co-founder of Bonobos, built his new venture, Pi, out of a question his psychiatrist asked him in 2021: when's the last time you had dinner with a friend? Dunn had just moved back to Chicago during the pandemic and realised, despite returning to his hometown, he had no friends nearby. Pi is his answer to that problem — a social app and AI agent platform designed to get people off their phones and into in-person social lives.

What Pi actually is

The core product surfaces events, communities, and people worth meeting in a user's local area. The newer layer is an AI agent called Penelope, which operates inside iMessage and, soon, inside the app itself. Penelope's job is to act as what Dunn calls a "social life instigator" — proactively nudging users toward time with people they've been neglecting. Users can also access Penelope directly through pienelope.com without downloading the app, a deliberate workaround for the friction of asking people to install yet another social platform.

Pi is live in Chicago, Austin, and San Francisco, with New York and LA launches coming. Smaller markets including Columbus, Milwaukee, and Atlanta are also in the pipeline.

“I was talking to my psychiatrist one day, and I told him I was feeling a little bit low... when's the last time you had dinner with a friend?... At one point, the team was 23, and the age of AI is now 12... We've got about 800 community builders on our app right now, and in any given market, once we have 50, it starts to percolate.”

Cold start solution

Dunn's answer to the cold start problem is the Pi Creator Club, which pays community organisers — run club hosts, book club leaders, trivia night organisers — up to $3,500 a month to seed events and plans on the platform. Dunn frames these as Pi's equivalent of Airbnb superhosts or Uber drivers. The app currently has around 800 of these community builders, and Dunn says any given market starts to gain traction once it reaches 50 creators and roughly 1,000 users on the people-discovery tab alongside 50 events.

Team and AI-driven shrinkage

The team has shrunk from 23 to 12 as AI tools compressed the work previously requiring larger product, design, and engineering headcounts. Dunn presents this not as distress but as a feature of the current moment — leaner and faster.

Forerunner Ventures led the Series A. Dunn says he pitched 15 Chicago venture firms and got 15 rejections, then pitched Kirsten Green at Forerunner and received a term sheet within 48 hours. He uses the story as a pointed diagnosis of Chicago's venture ecosystem: roughly 90% of the returns generated by Chicago-based VC firms come from coastal investments, and 90% of capital raised by leading Chicago companies comes from outside the city. There are almost no local angels writing early checks.

The founding backstory

Dunn is candid about the personal thread running through Pi. Nine years into building Bonobos — when the company had over $100M in revenue and 600-plus employees — he was hospitalised at Bellevue's psychiatric ward with untreated, unmedicated bipolar type one. On leaving the hospital, he was arrested and charged with felony and misdemeanor assault, and spent roughly 12 hours in jail. He wrote about the experience in his memoir Burn Rate.

His takeaway, carried directly into how he thinks about building Pi, is that health, freedom, and relationships matter more than startup outcomes. Pi is, in that sense, both a product and a thesis made personal.

The market argument

Dunn believes there's room for the next major American social network, and that it will be AI-native, focused on real-world local friendships rather than engagement metrics, and built against the grain of platforms that profit from keeping users scrolling. The Gen Z-led movement away from passive social media toward in-person community is, in his read, the tailwind. Pi's bet is that the people who hooked users on social media — large-audience creators — are now well positioned to direct those same followers toward offline gatherings.