VC view of how to judge a possible investment, does the entreprenuer have at imagnitive bent
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 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.
