[Mz]

From pg's own remarks on the topic http://www.paulgraham.com/founders.html:

They delight in breaking rules, but not rules that matter.

I get the feeling these folks can't tell the difference between the two. And I am thinking "naughty" is not necessarily the best word for this quality and is bound to be misinterpreted by some folks.

[onan_barbarian]

The assumption that these 'naughty' people automatically have a good intuition for the rules that matter is interesting. It's a bit like all those people who think that they drive perfectly well when yakking on a cell phone, drunk driving, or going 20 over the limit, or perhaps both. Everyone's an expert on highway safety, apparently ("my intuition tells me I'm not distracted here, I don't care what those statisticians say").

Interestingly, I have known a surprisingly large number of dangerous drivers (alcohol, speeding or both) in the tech scene and many have fit whole YC 'naughtiness ethos' pretty well.

Playing by the rules without necessarily understanding all of them might have helped these guys at the moment when they outed a bunch of people as applying to YC using Twitter.

[Mz]

The assumption that these 'naughty' people automatically have a good intuition for the rules that matter is interesting.

Language has its limits in attempting to convey what the author really means. I assume pg was trying to convey that, in his experience, those folks who make good entrepreneurs do, in fact, have good intuition for when it is appropriate to break the rules. But I'm not really comfortable speaking for him. He's perfectly capable of speaking for himself. I just don't feel that I heard it the same way you did. (Though perhaps neither of us heard what he really meant. <shrug>)

[tesseract]

I think "naughty" is a great word for that quality. The undesirable quality would be maybe something more like "reckless".

[Mz]

I can't think of a better word, I just know that 80% of what most kids hear is "no" or some variation thereof, so most people have a very negative spin on a lot of language. This fact gets me in enormous trouble because it seems to incline many people towards an assumption of guilt. The things I say and do are usually rooted in very innocent motives, though I fail to conform and such. I think it's a complicated topic and the value of 'breaking the rules' comes in having a different understanding of "the rules", kind of like Einstein's Theory of Relativity technically makes Newton's theory of gravity obsolete -- yet we use the formula for gravity anyway for many things because if you stay on earth, there is no real advantage in doing the more complex calculations. Gravity is close enough. (Or so I gather. I'm not much of a physics person.)

I'm sure this one trait and trying to explain exactly what pg and YC are looking for in that regard could be a paper by itself, but no doubt all that complexity really didn't have a place in the piece he wrote at the time. Still, "naughty" strikes me as kind of a blunt instrument for explaining it. I have two "naughty" kids -- two ASD kids who just are baffled by why most folks do what they do and I spent their lives explaining it to them in terms that made sense. And I couldn't be imprecise in explaining it or it simply wasn't useful information to them. I think "naughty" is imprecise in this instance. It's a perfectly good word for those folks who get what pg means but for those who don't, it's a time-bomb waiting to go off. This may be just the first such explosion given how recent events have ramped up the number of applicants.

But that's just my opinion.

Peace.