Day 91: Brian Chesky

In the past couple of weeks, I’ve started to read more and more about Airbnb founder Brian Chesky. Airbnb is a company that allows people to offer their homes as a place to stay through an app. It’s like the bed and breakfast establishments that pre-date the huge hotel chains of today.

An art student who came up with the idea when he was broke and unemployed in San Francisco, Chesky has grown his company from a silly idea with a friend to one of the largest startups on the planet. Airbnb recently received a valuation of $24 billion, which is larger than the market value of apparent competitor Marriott. It seems insane to me how a person who wasn’t even really a technology guy before built a company to this size so quickly.

All of this seemed like an impossibility before I read this long piece on him. Besides being a really well-written work of journalism, it sheds light on how Chesky was able to do so much. The key was to get advice from those who had success. However, the way he thought about people’s ability to give advice is the most impressive part. One part of it was that he thought about their successes in ways that directly applied to his company, but more importantly, he went to them for their advice. I think this is an extremely vital thing to do. Although I haven’t met with Sheryl Sandberg and Warren Buffett, I hope that I would be able to work at some important company where the CEO would have a Q&A session with new hires and I’d have some similar opportunities. Even when I have met with people who have done amazing things in the tech industry, my questions have been very vague (“any advice for me?), instead of something that could actually benefit me.

I see Chesky as an inspiration. The story of how he spent hours researching for his Commencement speech and watched the staff set up chairs from the podium to reduce the stress resonates with me in particular. I aspire to follow Chesky’s example in some way or another. I may not lead a powerful company, but I want to learn like the leader of one.


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