You simply can't be tentative in a startup. You have to go for it at every chance you get. And if the leader of the organization is anxious, his or her fear pervades the organization. Everything comes from the top in a company. So if you are starting a company or building one, face your fears and move past them. It's critically important to your company.

Money is information, like bits.

The fact is that the amount of money startups raise in their seed and Series A rounds is inversely correlated with success

When my dad was in Vietnam, we lost a parent for a year. Thank God we didn't lose a parent for good.

I get everything that satisfies my soul from bringing together objects that are in the world, manipulating them, working with spatial arrangements, and having things presented in the way I want to see them.

Certainly anything that is news or opinion needs to be free on the Web, because the Web is this very fluid medium that is very much driven by links and the flow of visitors through a discussion via links.

My venture investing career has three phases, all roughly 6-8 years long. The first, at Euclid, was software to Internet. The second, at Flatiron, was Internet to bubble. And the third, at USV, has been web 2 to mobile. I have always used a new firm to denote a new investment phase for me. Throw away the old. Start with the new.