Valuing "Naughtiness"

Paul Graham once again shares his insights about human nature and the requirements for success in an essay. "What We Look for in Founders," is a longer version of a piece he wrote for Forbes about what his investment group looks for when they decide whether to fund tech startups. The whole thing is worth a read, but I found what he said about a quality he calls "naughtiness" most interesting:

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.

It is the view about "rules" I find intriguing here because of a couple of common confusions about the rules we adopt for human interaction that slow many people down for various reasons.

The first confusion is evident in Graham's clarification of what he means by "good." Obviously, he's not going to be interested in helping thugs or pickpockets get ahead, but I suspect that Graham might find the choirboy who meekly does everything he is told to do a less-than-ideal funding candidate.

Since the idea of an objective morality is alien to most people (but morality as a laundry list of arbitrary commandments isn't), the need to make such a distinction clear is understandable, but if morality were commonly understood to have an objective basis, this would be unnecessary.

Interestingly, on "big questions," like violence and theft, almost everyone can see practical reasons for not doing such things, so the common notion of the moral-practical dichotomy is not such a big impediment to people having, in effect, an objective moral code on such "big questions" most of the time.

But on some, less-clear issues, the practical reasons for pursuing one course of action or another are not so clear, and people are more likely to end up defaulting into what everyone else does -- or "rebelling" by doing whatever they feel like doing. These "small questions" include not just what most people regard as moral questions, like whether to give to a charity, but also to things like rules of etiquette and common ways of doing business or solving problems.

Thus, what Graham is looking for seems to me to really be someone who more closely approaches having an objective approach to moral (and practical) questions. Actually having such a code would require one to understand morality in a principled way, so the best one will usually see is someone who gets "big questions" right and is open to exploring anything else. Such an openness requires a high degree of independence of mind from what others say. Indeed, such a refusal to simply "observe [arbitrary] proprieties" reflects at least some rudimentary grasp of a distinction Ayn Rand calls, "the metaphysical versus the man-made."

Man's faculty of volition as such is not a contradiction of nature, but it opens the way for a host of contradictions -- when and if men do not grasp the crucial difference between the metaphysically given and any object, institution, procedure, or rule of conduct made by man.

It is the metaphysically given that must be accepted: it cannot be changed. It is the man-made that must never be accepted uncritically: it must be judged, then accepted or rejected and changed when necessary. Man is not omniscient or infallible: he can make innocent errors through lack of knowledge, or he can lie, cheat and fake. The manmade may be a product of genius, perceptiveness, ingenuity -- or it may be a product of stupidity, deception, malice, evil. One man may be right and everyone else wrong, or vice versa (or any numerical division in between). Nature does not give man any automatic guarantee of the truth of his judgments (and this is a metaphysically given fact, which must be accepted). Who, then, is to judge? Each man, to the best of his ability and honesty. What is his standard of judgment? The metaphysically given.

The metaphysically given cannot be true or false, it simply is -- and man determines the truth or falsehood of his judgments by whether they correspond to or contradict the facts of reality. The metaphysically given cannot be right or wrong -- it is the standard of right or wrong, by which a (rational) man judges his goals, his values, his choices. The metaphysically given is, was, will be, and had to be. Nothing made by man had to be: it was made by choice. ("The Metaphysical Versus the Man-Made," in Philosophy: Who Needs It, p. 27.)

If morality (or any other field) can be approached in an objective manner, and it is a practical science, one must see this distinction at least on some implicit level to blaze trails.

This is not to say that, if the view that the rules of morality were of practical import and could be discovered by reason were more common, everyone would be an innovator, however. There remains the fact that every individual can know only so much, and will simply find some issues much more interesting to think about than others. Back in grad school, for example, I was frustrated at how useless my Windows computer and crippleware at home were, but there was no way I could have (or would have wanted to) come up with the Linux and other software I used to solve that problem. It wasn't that my imagination was limited or that I didn't question -- in the form of rolling my eyes or cursing -- why my computer couldn't do anything: It was that I wasn't interested enough in computing to solve the problem on my own. (Of course, that sets aside the whole matter of whether I would have been a very effective programmer.)

I bring this up because Graham wonders whether "naughtiness" and imagination are redundant items in his list. Even without our common, deficient moral vocabulary getting in the way of understanding what this naughtiness is, I don't think so. As my own stab at this, I think that perhaps naughtiness is an increased drive to apply imagination to certain types of problems that is absent in most other people. Indeed, the drive is increased because it provides such people with enjoyment.

At this point, naughtiness might seem redundant to another list item, determination, but I'm not so sure about that either. How many ace computer programmers (or innovators in other fields) have what it takes to succeed in business? If both of these things are species of determination, I think they are different enough to warrant different metrics.

-- CAV

PS: Don't miss the essay Graham links within the one I discuss above. "How Not to Die" has some useful insights on maintaining focus on major projects that can probably apply beyond starting a business.