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.
Fred WilsonIdeas that most people derided as ridiculous have produced the best outcomes. Don't do the obvious thing.
Fred WilsonMy 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.
Fred WilsonIf you have a native monetization system where the atomic unit of content is the ad unit, that scales down all the way to a small screen experience. That's why Twitter is performing so well on mobile.
Fred WilsonFoursquare's adoption of a game dynamic when it launched is a particularly clever implementation of a social hook.
Fred Wilson