I have a lot of respect for the man despite his personality problems. He knew what he wanted at a young age and pursued it with determination and persistence and achieved it. Mathematica and the business he built to support it are both great accomplishments. I'm sometimes surprised he's not more popular on HN than he is.

I mention all that so it won't seem too mean-spirited when I repeat this:

I've heard a joke, "Which will achieve self-awareness first, Wolfram or Wolfram Alpha?"

He's a great man, but flawed by too-great appreciation of his own greatness.