I’ll just pull quotes from several of his essays.From The Power of the Marginal.

At one end of the scale you have fields like math and physics, where nearly all the teachers are among the best practitioners. In the middle are medicine, law, history, architecture, and computer science, where many are. At the bottom are business, literature, and the visual arts, where there’s almost no overlap between the teachers and the leading practitioners.

…you’re probably better off studying something moderately interesting with someone who’s good at it than something very interesting with someone who isn’t. You often hear people say that you shouldn’t major in business in college, but this is actually an instance of a more general rule: don’t learn things from teachers who are bad at them.

…Where the method of selecting the elite is thoroughly corrupt, most of the good people will be outsiders. In art, for example…

If it’s corrupt enough, a test becomes an anti-test, filtering out the people it should select by making them to do things only the wrong people would do.

…If you’re an outsider, your best chances for beating insiders are obviously in fields where corrupt tests select a lame elite. But there’s a catch: if the tests are corrupt, your victory won’t be recognized, at least in your lifetime. You may feel you don’t need that, but history suggests it’s dangerous to work in fields with corrupt tests. You may beat the insiders, and yet not do as good work, on an absolute scale, as you would in a field that was more honest.

…You’re on the right track when people complain that you’re unqualified, or that you’ve done something inappropriate. If people are complaining, that means you’re doing something rather than sitting around, which is the first step. And if they’re driven to such empty forms of complaint, that means you’ve probably done something good.

I would note that if the test for good essay-writing is that your stuff appears in the New York Times rather than on an obscure web site, then the test is corrupt.

From The 18 Mistakes that Kill Startups:

What’s wrong with having one founder? To start with, it’s a vote of no confidence. It probably means the founder couldn’t talk any of his friends into starting the company with him. That’s pretty alarming, because his friends are the ones who know him best.

I did not have a cofounder when I started homefair.com. But just the fact that my friends didn’t try to talk me out of it probably was a positive indicator. The Internet was novel at that time, and all of my friends had real jobs with health benefits.

From How Art can be Good:

I think with some effort you can make yourself nearly immune to tricks. It’s harder to escape the influence of your own circumstances, but you can at least move in that direction. The way to do it is to travel widely, in both time and space. If you go and see all the different kinds of things people like in other cultures, and learn about all the different things people have liked in the past, you’ll probably find it changes what you like. I doubt you could ever make yourself into a completely universal person, if only because you can only travel in one direction in time. But if you find a work of art that would appeal equally to your friends, to people in Nepal, and to the ancient Greeks, you’re probably onto something.

From Is it Worth Being Wise?:

“Wise” and “smart” are both ways of saying someone knows what to do. The difference is that “wise” means one has a high average outcome across all situations, and “smart” means one does spectacularly well in a few.

…As knowledge gets more specialized…intelligence and wisdom drift apart, [and] we may have to decide which we prefer. We may not be able to optimize for both simultaneously.

…as knowledge has grown more specialized, there are more and more types of work in which people have to make up new things, and in which performance is therefore unbounded. Intelligence has become increasingly important relative to wisdom because there is more room for spikes.

…Wisdom seems to come largely from curing childish qualities, and intelligence largely from cultivating them.

…cultivating intelligence seems to be a matter of identifying some bias in one’s character—some tendency to be interested in certain types of things—and nurturing it. Instead of obliterating your idiosyncrasies in an effort to make yourself a neutral vessel for the truth, you select one and try to grow it from a seedling into a tree.

…perhaps one reason schools work badly is that they’re trying to make intelligence using recipes for wisdom. Most recipes for wisdom have an element of subjection. At the very least, you’re supposed to do what the teacher says. The more extreme recipes aim to break down your individuality the way basic training does. But that’s not the route to intelligence. Whereas wisdom comes through humility, it may actually help, in cultivating intelligence, to have a mistakenly high opinion of your abilities

From Why to Not Not Start a Startup:

This is my excuse for not starting a startup. Startups are stressful. Why do it if you don’t need the money? For every “serial entrepreneur,” there are probably twenty sane ones who think “Start another company? Are you crazy?”

…One reason people who’ve been out in the world for a year or two make better founders than people straight from college is that they know what they’re avoiding. If their startup fails, they’ll have to get a job, and they know how much jobs suck.

…Summer jobs at technology companies are not real jobs. If you get a summer job as a waiter, that’s a real job.

I thought that “serial entrepreneur” was the norm, but evidently Paul thinks that I’m the norm.

Finally, from Microsoft is Dead.

It now seems inevitable that applications will live on the web—not just email, but everything, right up to Photoshop. Even Microsoft sees that now.

Ironically, Microsoft unintentionally helped create Ajax. The x in Ajax is from the XMLHttpRequest object, which lets the browser communicate with the server in the background while displaying a page. (Originally the only way to communicate with the server was to ask for a new page.)

What he means by “Microsoft is Dead” is not that they will suffer in terms of profits. What he means is that you can now develop a new software product without having to worry that Microsoft can create a cheap knock-off, tack it onto the operating system, and drive you out of business. In Graham’s view, the advantage of having something tacked onto the operating system has gone away, or is declining.