I believe the scope of than answer is greater than a HN thread, but I might just be wussing out. Hopefully others will engage you. If not, happy to take it offline.

I will say this: be careful of selection bias! Looking back, sure, if I show you a thousand examples that ended poorly your response will be something like "But they weren't really smart. Look how poorly it all turned out!" This is, at best, circular reasoning. The important thing is that, at the time, these folks were the best and brightest and put in charge for that very reason.

Good starting point: http://www.amazon.com/Logic-Failure-Recognizing-Avoiding-Sit...