One year after a bipolar episode put him in the hospital, Bonobos cofounder Andy Dunn sold his company to Walmart for $310 million

The Rise and Fall of a Fashion Entrepreneur

For over two decades, Andy Dunn has been a prominent figure in the entrepreneurial world, known for his innovative spirit and his role in shaping men's fashion retail. He co-founded Bonobos, a menswear brand that revolutionized how men shop for clothing online. In 2017, Dunn made headlines when Bonobos was sold to Walmart for a staggering $310 million. However, the success story is more than just financial triumph; it is deeply intertwined with Dunn’s personal struggles, particularly his battle with Bipolar I disorder.

A Crisis Unfolds

Dunn’s journey into the world of entrepreneurship was not merely a linear trajectory of growth and success. It was fraught with challenges, particularly regarding his mental health. Diagnosed with Bipolar I during his college years at Northwestern University, Dunn struggled to manage the condition while navigating the pressures of building a startup. This mental health disorder is characterized by extreme mood fluctuations, including manic episodes filled with intense energy and depressive lows that can leave individuals incapacitated.

For years, Dunn managed to keep his mental health issues under wraps. It was only when a perfect storm of personal and professional pressures collided that he faced a significant crisis. Over time, the strain of running Bonobos, alongside personal life upheavals, led to a manic episode in March 2016 that would change his life forever.

During that fateful night, Dunn experienced delusions, believing he was not only the president of the United States but also Batman. His erratic behavior escalated, resulting in an altercation with his then-girlfriend, Manuela, who later became his wife. The situation spiraled out of control, leading to an intervention by the police and a week-long stay in Bellevue Hospital’s psychiatric ward.

The Turning Point

The aftermath of Dunn’s manic episode marked a pivotal point in his life. With the support of Manuela, family, and a committed healthcare team, he embarked on a rigorous treatment plan that included medication and therapy. Dunn’s experience in the psychiatric ward served as a wake-up call, prompting him to confront his mental health issues head-on.

“I went through some pretty calamitous events that led to good news on the other side of that, which was getting healthier, acknowledging the condition, and being in treatment,” Dunn reflected in a Fortune interview. His experience led him to understand the significant overlap between entrepreneurship and mental health, recognizing that the very traits that fueled his business acumen—drive, confidence, and risk-taking—were also symptoms of his disorder.

Building Bonobos: A Dual Journey

Founded in 2007, Bonobos began as a small e-commerce venture with just $60,000 of Dunn and his co-founder Brian Spaly's money. The idea was radical at the time; selling men’s clothing online was not yet mainstream. However, the duo’s relentless drive led to significant milestones, including a revenue run rate of $2 million within a year and subsequent rounds of funding that propelled the brand to new heights.

Accolades soon followed, with Bonobos securing investments from notable firms like Accel and Lightspeed, ultimately raising over $100 million and attracting major retailers like Nordstrom. By the time Dunn sold Bonobos to Walmart, it was a well-established player in the retail landscape, boasting annual sales of around $120 million.

However, in retrospect, Dunn acknowledges the signs of hypomania—a milder form of mania characterized by elevated moods and increased productivity. He admits that the drive to succeed often masked his underlying mental health struggles. “The characteristics of an entrepreneur are really convergent with the diagnostic criteria for what’s called hypomania,” he noted. This realization not only changed his perspective on his journey with Bonobos but also set the stage for his next venture.

Finding Purpose in Connection: The Birth of Pie

After the sale of Bonobos, Dunn found himself at a crossroads. While he had achieved tremendous success, he was also acutely aware of the isolation that can accompany such a high-stakes lifestyle. Drawing from his own experiences with loneliness, Dunn sought to create a new business focused on fostering connections among people.

In 2020, he founded Pie, a social media platform designed to combat loneliness and create real-world connections. Initially conceived as a dating app for seniors, Dunn quickly pivoted the concept to address the broader issue of platonic relationships, especially in a world increasingly fragmented by digital interactions and social isolation—an issue that had been exacerbated by the COVID-19 pandemic.

“Towards the end of my journey with Bonobos, I was like, ‘You know what? I think I’m done working on making men’s butts look good in their pants,’” Dunn quipped. His vision for Pie was to create a community centered around human connection and mental well-being.

Navigating the Loneliness Epidemic

Launched during a time when the world was grappling with social distancing and isolation, Pie quickly gained traction. Dunn relocated the company from New York City to Chicago, where he discovered a burgeoning market for social connections. The app allows users to discover or host local events, engage in group activities, and connect with others based on shared interests.

Despite initial struggles in the first two years, Dunn’s commitment to enhancing the platform paid off. The app resonated with younger audiences, particularly Gen Z, who were increasingly seeking meaningful connections. “I started to notice that Gen Z was getting good at this, running clubs and art markets and watch parties,” Dunn explained. This insight guided Pie's development, empowering users to create and nurture their communities.

In its six years of operation, Pie has expanded beyond its Chicago roots, reaching users across all 50 states and over 100 cities. With more than 310,000 users, the platform has evolved into a vital resource for those seeking deeper social connections.

The Road Ahead: Challenges and Opportunities

As Dunn continues to grow Pie, he faces both challenges and opportunities inherent in the tech and social media landscape. The platform has secured $24 million in funding, attracting investors such as Ev Williams and Forerunner, who share Dunn’s vision of creating a space for meaningful connections.

The partnership with Nadya Okamoto, a social media influencer with millions of followers, signals a strategic move to leverage her audience in promoting Pie's mission. This collaboration could further enhance the platform’s reach, especially among younger demographics.

However, the journey is not without obstacles. The social media landscape is saturated, and building a unique proposition that stands out requires constant innovation and adaptability. Moreover, as Pie scales, maintaining a sense of community and authenticity becomes paramount.

Conclusion: A Life Transformed

Andy Dunn's narrative exemplifies the intersection of entrepreneurship and mental health—a journey marked by both triumph and adversity. His experience with Bipolar I disorder has not only reshaped his approach to business but also fueled his passion for fostering real connections through Pie.

Reflecting on his past, Dunn acknowledges the profound impact of his crisis on his life trajectory. “A new chapter of my life opened up once this was all in the light,” he stated, emphasizing the importance of vulnerability and openness in both personal and professional realms.

In an age where isolation is increasingly prevalent, Dunn’s story offers hope and inspiration. By transforming his struggles into a platform that champions connection, he is not only redefining his own narrative but also paving the way for others to find community and support in an often disconnected world.