CEO and Co-founder Airbnb
Co-founder and CEO of Airbnb. Notably did not attend Trump's 2025 inauguration, citing that Airbnb's regulations are primarily at city and state level rather than federal.
In May 2022, Brian Chesky pledged $100 million over five years to the Obama Foundation to launch a scholarship program for students pursuing careers in public service. Chesky joined the Giving Pledge in 2016, committing to donate majority of his wealth.
On March 15, 2022, Brian Chesky along with co-founders Joe Gebbia, Nathan Blecharczyk and his wife Elizabeth committed to personally match up to $10 million in donations to Airbnb.org to help house refugees fleeing Ukraine. Chesky had previously stated on CNBC that he personally put in 'millions of dollars' to the initiative. By August 2022, Airbnb.org successfully housed 100,000 Ukrainian refugees.
In May 2020, Chesky laid off 1,900 employees (25% of workforce) during COVID-19. Full-time workers received at least 14 weeks pay, 12 months health insurance via COBRA, equity access, and enrollment in 'alumni talent directory' for job placement. However, in late April, Airbnb laid off 500-600 contingent workers who received only 1 week severance and their laptop—no insurance, restricted equity, or directory access. Amy Silverman, affected contractor, publicly noted contractors were 'not invited to join the directory.' In 2024, Chesky walked back earlier 'family' language, saying 'you don't fire members of your family.'
In 2020, Brian Chesky personally donated $10 million to nonprofit organizations supporting frontline healthcare and essential workers during the coronavirus pandemic.
Multiple academic studies concluded that Airbnb systematically accelerates gentrification and displacement by raising potential rental income without redevelopment, concentrating in tourist-appealing neighborhoods. In New York, 72% of neighborhoods at highest risk of Airbnb-induced gentrification are non-white, making it 'an extractive, unequitable racial gentrification tool.' Critics across dozens of global cities allege Airbnb 'hyper-accelerates affordable housing crises.' In June 2025, Chesky defended against Barcelona criticism, saying 'housing prices rose 60% but Airbnb listings decreased' and 'Airbnb has become a convenient scapegoat.' Company launched $100M affordable housing fund and $200K to housing reform groups, though critics argue this is insufficient given platform's documented displacement impact.
In 2018, Brian Chesky and co-founders Joe Gebbia and Nathan Blecharczyk issued joint statement criticizing Trump's family separation policy at the border: 'Ripping children from the arms of their parents is heartless, cruel, immoral and counter to the American values of belonging'.
A day after Trump issued executive order banning refugees and nationals from Muslim-majority countries in January 2017, Chesky announced Airbnb would provide no-cost housing to refugees and those not allowed into the US. The company's Super Bowl ad that year emphasized message of belonging.
In July 2016, Brian Chesky acknowledged that Airbnb was 'late to this issue' of racial discrimination on the platform, stating 'we took our eye off the ball.' In September 2016, he formally apologized ('I am sorry. I take responsibility for any pain or frustration this has caused') and announced a comprehensive anti-discrimination policy including photo reduction, instant book expansion, and community commitment.
On June 11, 2016, Brian Chesky became one of the youngest signatories of The Giving Pledge, Warren Buffett and Bill Gates' initiative where billionaires commit to giving away at least half their wealth. At 34 years old, Chesky stated he wanted the pledge to be more than 'a bunch of old people.'