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.

In June 2010, I moved out of my apartment and I have been mostly homeless ever since, off and on. I just live in Airbnb apartments and I check in every week in different homes in San Francisco.

The stronger the culture, the less corporate process a company needs. When the culture is strong, you can trust everyone to do the right thing. People can be independent and autonomous. They can be entrepreneurial.

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

In organizations (or even in a society) where culture is weak, you need an abundance of heavy, precise rules and processes.

The office is the laboratory and meeting your users is like going into the field. You can't just stay in the lab. And it's not just asking users what they want, it's about seeing what they're doing.

Do things that won't scale; it will teach you.