Watching nonprogrammers trying to run software companies is like watching someone who doesn’t know how to surf trying to surf. Even if he has great advisers standing on the shore telling him what to do, he still falls off the board again and again.

Never put yourself in a position that will put yourself at risk if you make the wrong decision. We spent cash on everything. It's fashionable to make 'bet the company' decisions, but don't do it.

Software development takes immense intellectual effort. Even the best programmers can rarely sustain that level of effort for more than a few hours a day. Beyond that, they need to rest their brains a bit, which is why they always seem to be surfing the Internet or playing games when you barge in on them.

All non-trivial abstractions, to some degree, are leaky.

If you are a programmer working in 2006 and you don’t know the basics of characters, character sets, encodings, and Unicode, and I catch you, I’m going to punish you by making you peel onions for six months in a submarine.

Not having a schedule is OK if it's your PhD and you plan to spend 14 years on the thing, or if you're a programmer working on the next Duke Nukem and we'll ship when we're good and ready. But for almost any kind of real business, you just have to know how long things are going to take, because developing a product costs money.

A user interface is well-designed when the program behaves exactly how the user thought it would.