Note that these are also key characteristics of great teams! All the points are good, but I especially want to quote from the section Naughtiness, since it’s something you don’t see discussed very often:
Though the most successful founders are usually good people, they tend to have a piratical gleam in their eye. They’re not Goody Two-Shoes type good. Morally, they care about getting the big questions right, but not about observing proprieties. That’s why I’d use the word naughty rather than evil. They delight in breaking rules, but not rules that matter. This quality may be redundant though; it may be implied by imagination.
Sam Altman of Loopt is one of the most successful alumni, so we asked him what question we could put on the Y Combinator application that would help us discover more people like him. He said to ask about a time when they’d hacked something to their advantage—hacked in the sense of beating the system, not breaking into computers. It has become one of the questions we pay most attention to when judging applications.
I have written about D.A. Henderson’s Smallpox Eradication Team elsewhere, but want to underscore the naughtiness point here as it relates to teams. In his book Smallpox- the Death of a Disease: The Inside Story of Eradicating a Worldwide Killer Henderson says unequivocally that a willingness to break unhelpful rules was one of the main reasons that his team was able to succeed in its ambitious quest to eliminate the deadly smallpox disease from the Earth.
(Via Hacker News)