Masters of Scale Airbnb’s bet on an IRL future, with Brian Chesky
80 snips
Oct 14, 2025 
Brian Chesky, co-founder and CEO of Airbnb, shares insights on real-world connections in a digital age. He emphasizes the importance of belonging, explaining how Airbnb aims to combat loneliness. Chesky discusses the expansion of Airbnb Experiences into local entertainment, and contrasts the human elements of hosting with the rise of AI. With a focus on design as a strategic advantage, he advocates for principled decision-making in business while stressing the need for responsible AI development to create a better future.
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Real World Trumps Screen World
- Brian Chesky argues the internet and social media shrank the world but increased loneliness and isolation.
- He positions Airbnb to get people off screens and rebuild real-world belonging through travel and experiences.
Airbeds To A Global Network
- Chesky tells how Airbnb began with him renting out air mattresses to three guests and socializing with them.
- That origin shaped Airbnb's community-first vision even as the product evolved into full-home listings.
Travel App Becoming Entertainment Platform
- Chesky sees Airbnb evolving from travel app to a new entertainment category for both travelers and locals.
- He believes services lack a dominant marketplace and Airbnb can expand into travel-adjacent offerings.