Two days ago, my conversation with Brian Chesky went live on my Midlife Chrysalis podcast. It’s blowing up and going viral. Listening to it, I’m reminded how unusual our partnership was — and how much it shaped me.
When I arrived at Airbnb 13 years ago, Brian was a 31-year-old founder navigating hypergrowth. I was in my 50s, fresh off selling my company and wrestling with my own reinvention. On paper, we were an unlikely pair. In practice, it became a powerful intergenerational collaboration.
Brian didn’t hire me to scale operations. He hired me to help scale soul.
During my seven and a half years there (more than half of it working 70 hours a week), I watched him evolve from visionary founder to global CEO under intense scrutiny. What struck me most was not his product genius, but his willingness to be a student — of leadership, of culture, of himself. He asked big questions: What does belonging mean? How do you design a company people love? How do you stay founder-led without becoming founder-controlled?
We had countless conversations about meaning, about elders and mentors, about how success can be both exhilarating and disorienting. I often felt like a modern elder in the room — offering pattern recognition, emotional ballast, and long-term perspective. But the learning flowed both ways. Brian pushed me to think bigger, move faster, and embrace boldness in a digital age. I taught him a little EQ (Emotional Intelligence) and he taught me a little DQ (Digital Intelligence).
Airbnb’s story is often told as a startup fairy tale. For me, it was a masterclass in how different generations can sharpen and steady each other. The young brain (fluid intelligence) and the old brain (crystalized intelligence) can combine to offer the best of both worlds.
This episode isn’t just about business. It’s about growth — his and mine, and especially Brian’s growth as a human dealing with many of the shadows in his life at a time when he was under the microscope as a young, hyper-successful Silicon Valley founder.
This podcast episode is also about what becomes possible when ambition meets wisdom.
Hope you enjoy the episode.
-Chip