Airbnb Inc. CEO Brian Chesky hasn’t had an easy 2023. First there was the “Airbnbust” frenzy in March, in which hosts took up arms on Twitter (now X) about shrinking profit margins and a potential short-term rental bubble. Then competitor Vrbo beat Airbnb to a feature that customers have long requested with a loyalty program. And in September, New York City vastly tightened its rules on short-term rentals, nearly squeezing Airbnb out of a market that in the early days represented roughly 80% of its business. Never mind the increasing strictness of return-to-office policies, which has hampered the flexibility that spurred Airbnb’s business in the pandemic years.

By mid-September, when he rolled out a handful of site improvements, it seemed as if Chesky had found himself in a Catch-22, caught between the conflicting demands of guests and hosts. Top of mind among them: Guests want to spend less money and be guaranteed a better product, while hosts are worried about potential declines in bookings and their bottom lines.