zlacker

>>mjcl+(OP)
> 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.

"What We Look for in Founders", PG

https://paulgraham.com/founders.html

I think the more powerful you become, the less endearing this trait is.

>>dilap+S1
it seems most of the big companies try to break the rules while in the process become so strong they trade it off for what becomes a marginal fine & cost of doing business. Facebook, Uber come to mind first. This may just be the same.

>>shomba+Q2
Everyone let Uber get away with breaking taxi rules because those rules were only good for the people with the taxi medallion monopoly.

(Which wasn't even the taxi drivers, although they were plenty bad enough on their own.)