Do we like them?

Do we like Brian Chesky?

Our score: 7 out of 10. Decent record on refugees and giving, but little on LGBTQ+ issues and a few rough patches as a boss and platform owner.

Chesky is the co-founder and CEO of Airbnb, and the story he tells about himself turns on a bad week in 2011, when a host's home was trashed. He called it “our moment of truth” in a CNBC interview, said Airbnb apologised to the host, and that it was “really the moment I became a CEO”. The company then introduced a $50,000 Host Guarantee for guest damage.

The rough patch he owns is the 2020 pandemic layoffs, when Airbnb cut about 1,900 people, nearly a quarter of its staff. His letter told people he felt “a deep feeling of love” for them, which landed badly. Looking back he has admitted he fumbled the messaging and said “a company is not a family”. The severance package, with a year of health insurance, was reported as generous.

On the harm check, the record is mostly good. When Trump signed the 2017 travel ban, Chesky tweeted that refusing refugees was not right, emailed staff that he profoundly disagreed with the policy, and offered free housing to those affected. In 2016 he said Airbnb had zero tolerance for discrimination, and the company removed a host after a transgender guest said she was refused a booking. Honestly, we found nothing from him personally on LGBTQ+ rights either way.

The company he keeps is worth a look. Co-founder Joe Gebbia, still on Airbnb's board, joined Elon Musk's DOGE, and Skift reported he had publicly backed Trump and Musk. Airbnb said his views were personal and did not reflect the company, and hosts threatened to leave. Skift's piece did not report Chesky commenting, and there is no suggestion he shares those views, so we're not marking him down for it.

The latest news is mostly business. On 29 April 2026 two House Republican committee chairs opened an inquiry into Airbnb's use of Chinese AI models, citing Chesky's own comments that the company was “relying a lot” on Alibaba's Qwen. In June, Bloomberg reported he is starting an AI lab, funding still early, with Chesky staying on as Airbnb CEO. That's a security and business argument, not a values one.

The good stuff is real. Skift reported that Chesky put $100 million of Airbnb shares into the Airbnb Host Endowment, which supports hosts, and that his giving has also gone to housing Ukrainian refugees. The free-housing offer to people hit by the 2017 ban was fast and practical, rather than just a statement.