Every day I would wake up and think, 'Today is another missed opportunity to do something important.' After enough days like this, you start feeling like you are getting old, even when you are relatively young. We are all natural entrepreneurs, and being manacled to a desk job is not for us.

The stuff that matters in life is no longer stuff. It's other people. It's relationships. It's experience.

I had to learn to get comfortable in a role of ambiguity where I had to seek out advisers and learn quickly.

In June, 2010, I moved out of my apartment and I have been mostly homeless ever since.

What I've been surprised by is not how different people are, but how similar they are. There are certain types of Airbnb people, and they are in every city in the world - it's just that in some cultures, there is more of a generational divide.

It's better to have 100 people love you than to have 1,000,000 people like you.

Build something 100 people love, not something 1 million people kind of like.