The 34-year-old Silicon Valley executive spoke with Cowboy Ventures' Aileen Lee at the 2016 Global Entrepreneurship Summit, where he retold Airbnb's genesis story, recounting the days when he rented out air mattresses in his apartment just to make ends meet and later kept a binder full of credit cards so he could keep his company alive.
"Within a year and a half of doing Airbnb, I remember totally running out of money. I used to have a binder that kids used to put baseball cards in and [Airbnb co-founder Joe Gebbia] and I used to put credit cards in them -- we just literally were funding the company off credit cards," Chesky said. "Many years later, people asked, 'Why did you keep going?' Because I remembered back to that very first weekend, and I remembered how amazing those experiences were. I got to pay rent, but more importantly, we made friends."
Now, nearly nine years later, Airbnb is one of the tech industry's most promising and highly valued companies. Airbnb is not without its problems -- the room-booking service faces discrimination -- but the company is without a doubt one of Silicon Valley's biggest recent successes.regulatory challenges around the world and has had to deal with users' facing
With that in mind, Chesky shared some of his thoughts on the challenges faced by both entrepreneurs and investors and the next generation of entrepreneurs. Here are the highlights, in Chesky's own words.
1. On where the next generation of entrepreneurs will come from.
Investors should remember that the next great entrepreneurs might not look anything like the last great entrepreneurs. They may not look, feel the same at all. They may not sound like that, and that's actually OK, because many of the great entrepreneurs of the last generation were the first of their kind. They may not be men, they may not be from the United States, and I think we need to be very open-minded about that and know that the next generation is mostly not going to be from the United States, because most customers are not from the United States.
2. Entrepreneurs face a long, slow road, but it gets better.
It's important to remember that before somebody was successful, they were probably barely getting by in an apartment, trying to run their company with press that didn't want to talk to them, investors that didn't want to take meetings from them, and customers that weren't interested in what they were selling.
3. Investors should look for creative entrepreneurs with passionate followers.
You should look for two things: a great entrepreneur, and to know somebody's a great entrepreneur doesn't necessarily mean they've started a company before because for a lot of us, it was our first time. But you look in their background and say, 'What've you created in the past? Maybe it wasn't a company, but do you have this creative resilience?' And I think people didn't look past my immediate background.
The second thing is, are people deeply passionate about what you're doing? Do customers love your product? I think it's more important to measure love than growth. If people absolutely love your product, they're going to tell other people, and your product is going to grow.
4. If 100 people love your product, don't give up.
It's not about blind faith, but it's about if you've solved your own problem or seen people be deeply connected to your product. The best piece of advice I ever got was from our first investor, Paul Graham. He said it's better to have 100 people love you than a million people that sort of like you, so if you can find 100 people that love your product -- as long as there are more people like them in the world -- then you have an idea that I believe will spread around the world. But if you can't get 100 people who absolutely love your product, then you do have a problem.
5. Learn how to learn.
There's not one lesson. Unfortunately, there's not even a thousand lessons. There's literally 10,000 or 100,000 decisions that I've had to make -- many of them are very small -- and they're literally every hour for the last eight years. I think learning how to learn is incredibly important.
I think you'll find that if you reach out to people, whether they're in your community or other communities, most people are willing to help, and I think that's what maybe is unique about Silicon Valley. And I think this is happening around the world. Silicon Valley is not necessarily a zero sum game. Most people are willing to take a meeting and help you.