“It’s such a fine line between stupid and clever.”

Joel’s foreward to Rich Chapman’s book In Search of Stupidity resonates with me because it’s what I’ve always said about Microsoft: it’s not that we’ve been so much smarter than our rivals over the years, just merely that we’ve been less stupid. Joel says that the worst mistake Microsoft’s made has been the dancing paperclip, but that’s not really true. I can think of a legion of boneheaded, wrongheaded and just plain dumb things that Microsoft has done, large and small, since I first came to work here. Microsoft Bob jumps to mind. Or the first, oh, I don’t know, five years of MSN’s life. Or the Tiger media server – we must have dumped a lot of moolah down that black hole. And for all the public failures that we’ve had, there are plenty of internal screwups that never make it to light.

One thing I think that has made more difference than anything else was the fact that Microsoft tends to be pretty dogged about following the old maxim “if at first you don’t succeed…” Plenty of eventual success stories at Microsoft started off life as fiascos, but we kept plugging away at them until we made them work. Through the years, I’ve been amazed at the way that major competitors who could really give us a fight in some area seem to lose interest once we start to do well against them. (OS/2 springs to mind.) I sometimes wonder if Bill knows the secrets of the Jedi… “This is not the market you are looking for. We can go about our business. Move along.”

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