From $310M Exit to Author to Founder with Andy Dunn, Co-Founder at Bonobos & Founder at Pie
We really, deeply enjoyed today's conversation with Andy Dunn (founder Bonobos and Pie). As the founding CEO of Bonobos, Andy pioneered the digitally native brand model, leading the company to a $310 million sale.
Now, he’s on a mission to defeat social isolation with Pie, a social IRL app designed to make it easier to build real friendships. Pie is currently live in Chicago, the Bay Area, and Austin.
In this candid discussion, Andy shared his journey of building and scaling a successful brand while navigating the complexities of mental health and leadership.
Here’s our notes from this fantastic event with Andy:
Candor vs. Harmony – While harmony is beneficial, candor is often more important in the workplace. Honest conversations now prevent bigger issues later.
Managing the Need to Be Liked – You can’t turn off the desire to be liked, but you can recognize when it’s driving your behavior and adjust accordingly.
Disagreements as Opportunities – Instead of feeling defensive, approach disagreements with curiosity by asking, “How strongly do you feel about this?”
Encouraging Dissent Fuels Innovation – Without cultivating dissent, new ideas won’t emerge.
Taking the Leap – “Go do the thing you want to do. It might not work, but you won’t regret it.”
Unchecked Empathy Can Lead to Burnout – The need to be liked, combined with excessive empathy, can be draining. Authenticity should be balanced with emotional energy.
Team Dynamics Evolve with Growth – When groups reach ~40+ people, tribal instincts emerge, shifting social dynamics and requiring mindful leadership.
Clarity Over Niceness – Being clear is kind; being nice without clarity can lead to misalignment. Leaders set the cultural tone.
Relevance to Today’s Leadership Challenges – The discussion feels especially timely given broader conversations about empathy in leadership.
Business vs. Passion – This resonated deeply in deciding between pursuing an unconventional leadership development idea or opting for a more lucrative path
Resources Shared:
Pattern Breakers: Why Some Start-Ups Change the Future by Mike Maples Jr.
Fortune: Founders – Answer These 2 Questions Before Saying Yes to an Investor.
Thank you to Andy for his time, expertise, and hard-won insights, and to Michael Sippey (Product Advisor, Former CPO @ Medium, VP Product @ Twitter, and Reforge EIR) for moderating!
