Question 1

True or false: Brian Chesky was the sole founder of Airbnb, with no co-founders.

Accepted Answer

False. He co-founded Airbnb with Joe Gebbia and Nathan Blecharczyk. The three met at the Rhode Island School of Design.

Question 2

True or false: Chesky’s first Airbnb guests slept on an air mattress in his San Francisco apartment.

Accepted Answer

True. To pay rent in 2007, he and Joe Gebbia rented air mattresses in their living room, giving the company its name.

Question 3

True or false: Chesky wrote Airbnb’s original code for the first website himself.

Accepted Answer

False. Chesky is not a programmer; Nathan Blecharczyk, the technical co-founder, built the initial platform while Chesky focused on design.

Question 4

True or false: Chesky turned down a $10 billion acquisition offer from Google in 2011.

Accepted Answer

True. Airbnb reportedly rejected a buyout from Google around that time, betting on long-term growth—a decision that paid off.

Question 5

True or false: Brian Chesky was a professional hockey player before co-founding Airbnb.

Accepted Answer

False. He studied industrial design and worked as an industrial designer before starting Airbnb. No hockey career.

Question 6

True or false: Brian Chesky once lived in a different Airbnb listing every month for a year.

Accepted Answer

False. He did travel extensively for work but never committed to a full year of living in different Airbnbs—that’s a common myth.

Question 7

True or false: Chesky is a classically trained pianist and considered a career in music.

Accepted Answer

True. He played piano competitively as a child and even contemplated music school before choosing industrial design.

Question 8

True or false: Chesky once slept on a fire escape during a company retreat to save money.

Accepted Answer

False. This story is often confused with early startup frugality, but Chesky never actually slept on a fire escape—it’s an exaggerated tale.

Brian Chesky Trivia Questions