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How I Built ThisAirbnb CEO Brian Chesky: “I Was a Great Founder and a Terrible CEO”
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At a glance
WHAT IT’S REALLY ABOUT
Brian Chesky on loneliness, crisis leadership, and Airbnb’s founder-mode reset
- Brian Chesky describes the day after Airbnb’s Zoom IPO as emotionally empty, prompting a personal reckoning about ambition, validation, and what he wanted beyond success.
- He says he was a “great founder” but a “terrible CEO” early on, citing counterintuitive leadership challenges like hiring for stage, setting direction, and creating culture and alignment.
- He recounts how deference to highly experienced executives, conflict-avoidance, and saying “yes” too often contributed to chaos and sprawl, which he later attributes partly to hubris after early success.
- He says the COVID shock—when Airbnb lost 80% of its business in weeks—forced a shift toward simplified priorities and a more hands-on, detail-driven approach, including skip-level communication.
- He explains how Airbnb.org evolved into a scaled nonprofit effort focused on providing free housing in crises, while he also signals openness to revisiting previously rejected ideas like hotels, advertising, and potentially a loyalty program.
IDEAS WORTH REMEMBERING
5 ideasThe IPO exposed a gap between external success and internal fulfillment.
He describes waking up after the Zoom-based IPO to the same pandemic routine and realizing the achievement didn’t change how he felt, which triggered questions about purpose and identity beyond work.
Being a strong founder doesn’t automatically translate into being a strong CEO.
He says founders may have “decades” of practice building things from childhood, while CEO work is counterintuitive—especially around culture, alignment, and how to lead at scale.
Over-deference to “experienced” executives can steer a young company off course.
He says he often deferred to older, more experienced hires when their guidance conflicted with his intuition, and that deference “was usually a mistake” because outsiders may not understand a company’s specific stage and context.
Loneliness at the top can be driven by isolation and lack of vulnerability, not just workload.
He links his loneliness to being closed off and not being vulnerable with employees, and says President Obama helped him see he needed rooted relationships and real friendships to stay grounded.
Crisis pushed him into a more present, detail-oriented leadership style that he kept afterward.
He says COVID became a “crucible” where survival required him to be intensely hands-on: simplifying, cutting projects, making hard decisions, and staying present—patterns he associated with studying Steve Jobs during crisis.
WORDS WORTH SAVING
5 quotesI think I was pretty much naturally a great founder, and I was naturally a terrible CEO.
— Brian Chesky
I think the inner crisis is when you get to the mountaintop 'cause you spend your whole life trying to climb the mountaintop, and you realize, "This is not gonna change how I feel inside. What do I do now? There's n- what other mountain is there even to climb?"
— Brian Chesky
I think the limit of the company's potential is the limit of me. A company can't grow faster than a CEO's learning curve.
— Brian Chesky
I didn't realize at the time that so much of the emptiness that I felt was just loneliness and that I had to, like, reconnect with myself, my purpose, like why am I even doing this?
— Brian Chesky
I can do anything, therefore, I can do everything, and we miscalculated how hard it would d- be to both grow something and start something new at the same time.
— Brian Chesky
SPEAKERS
Brian Chesky
guestCo-founder and CEO of Airbnb.
Guy Raz
hostJournalist and host of NPR’s How I Built This.
High quality AI-generated summary created from speaker-labeled transcript.
