> 4. Naughtiness
> 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.
Loopt, BTW, eventually became a shady gay hookup (not even "dating") app--the digital equivalent of the men's rooms in the Port Authority Bus Terminal--before getting acquired for barely more money than it raised in VC funding, and even then, only because one of its VCs was also on the board of the acquirer (Greendot). None of this is mentioned in Loop's sanitized wikipedia entry: https://en.wikipedia.org/wiki/Loopt