Be Shameless While Asking Famous People To Be Your Mentors: Airbnb’s Brian Chesky

It can be quite intimidating to approach someone important and ask them to mentor you, but Airbnb founder Brian Chesky says that one doesn’t need to overthink it.

“I’ve been pretty shameless about seeking mentors,” he said at an event. “I’ve been pretty shameless about reaching out to people,” he added. Chesky counts people like finance legend Warren Buffet among his mentors.

Chesky says that being shameless works because famous people might be more willing to become mentors that most people realize. “I remember meeting somebody who’s pretty well known. I asked them, how many people do you mentor? And they said hardly any. And I asked why not? Because no one asked me, they said,” Chesky revealed.

“That’s when I thought wow, that’s a good sign. I should be pretty shameless in asking,” Chesky said.

Chesky said that from then on, he unhesitatingly asked people to be his mentors. “And every step along the way I’ve been shameless. I say shameless because I think people are really proud to ask for help. But my point of view is I don’t want thousands of people paying for my learning curve. That’s like ridiculous. So I should fast track that (by asking for a mentor),” he says.

And Chesky appears to have put all this advice to good use. Airbnb failed to make a splash when it was first launched, so its founders just kept launching until they found some traction. They also used some unconventional means to promote its services, even launching a brand of cereal named Obama-Os to promote its service. And over the years, Airbnb has expanded to nearly all countries in the world, and has largely disrupted the hotel industry. And a chief ingredient to all this happening was the willingness of its founders to simply ask famous people for advice.