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Instead of trying to brainstorm startup ideas, look at your own life for a problem that needs solving.
Chesky says he learned the best ideas often comes from finding a solution for a personal problem.
Know your industry's laws and regulations.
Airbnb has run into problems with local and national hospitality laws. Part of that comes from starting a tech company that must work with laws that don't consider the sharing economy - people as businesses. They didn't know whether to view Airbnb as a person or business. The best solution is knowledge and an open mind.
Chesky says that it's better to have a hundred people that love your company than a million that sort of like it. A hundred people that like you will tell ten people. It is also easier to focus on the needs of a smaller core of customers.
Chesky considers about 20 to 30 entrepreneurs as his mentors. Every time you don't know how to do something, there's someone else who does.