How I Built This · Nov 2, 2026 · 1h 6m · 58m saved
With Brian Chesky, Co-Founder and CEO of Airbnb
Photo via how I built this / NPR
Airbnb's IPO in December 2020 valued the company at more than $100 billion in a single day, done over Zoom with no bell to ring because of the pandemic. Brian Chesky, co-founder and CEO of Airbnb, told Guy Raz on How I Built This that the day after should have been the best of his life. Instead it was the loneliest.
"I went to bed CEO of a hundred billion dollar public company, never imagining I'd be CEO of a ten-person company. And I woke up the next day and no one's in my house." — Brian Chesky
Brian co-founded Airbnb with Joe Gebbia and Nate Blecharczyk as classmates at the Rhode Island School of Design, took it public at a $100 billion valuation, and pulled the company back from the edge when COVID wiped out roughly 80% of its business within weeks.
The full interview is covered here so you can skip it. 66 minutes of audio, 8 minutes of reading.
Here are the 5 takeaways that matter.
Key Takeaways
Reaching the IPO goal did not change how he felt the next morning
He traces the post-IPO crash to loneliness, not to the pressure of running a public company
President Obama told him directly: "you're really lonely"
Obama said he keeps about 15 old friends he never has to catch up with on his life
Brian was the founder most resistant to Airbnb having a real business model
He wanted the "purity" of a project with no business model until his co-founders talked him out of it
COVID and studying Steve Jobs turned him into a hands-on CEO who skip-levels
He talks two or three layers down the org chart and credits AI with letting him know every detail an audit committee would
Airbnb.org is now committing $500 million a year to free housing nights
The idea traces to a 2008 email, before Airbnb had even launched
1. Lonelier After the IPO
Brian told Guy the rush of hitting the goal wore off almost immediately. He realized the next morning that reaching the thing he had organized his adult life around did not change how he felt inside.
Success did not make Brian any happier, and he noticed it right away
"I had this crisis of realizing, okay, now that I've gone, at my life really isn't any different. I don't feel that much happier than I did the day before." — Brian Chesky
He said the isolation came from becoming CEO, not from the public markets themselves. As a co-founder among friends he had never felt cut off; running the company changed that, because the people around him worked for him.
"The job of a CEO can be so lonely... Your employees have families, so they're not going to hang out with you... and you feel like the walls are caving in." — Brian Chesky
By his own account, he had let his own friendships go dormant on the way to the IPO, leaving him with almost no one outside the company to call.
