Mike Arrington, founder of Techcrunch, wrote a great article "Are you a pirate?" which captures the essence of the startup mind set. I have been on both sides; the pirate life with 5 startups (Forte, AltaVista, Napster, Bowstreet, Groove Networks), and corporate life with two big companies (Microsoft, Google). The pirate analogy works for me. In fact, at Napster, we were actually called pirates. Literally.
Another analogy that I often use is startups play poker, big companies play chess. Entrepreneurs are "all in" every day. Jason Calacanis is an awesome entrepreneur, and I think it is not surprising that he is also a great poker player. The skills required to play both at a high level are very much the same.
Startups play poker, big companies play chess – There are huge differences between startups and big companies. Success is not easy in either case, but the approaches are radically different.
Using a game analogy, startups are more like poker players. They take big risks, they bluff, they make quick decisions, change direction constantly, and they keep their competitors off balance. In poker you never have all the information, but you must make fast decisions. You never know if what you are seeing is a real threat, a bluff, or something that will soon disappear under the stress of the game.