I'll give out some clues, and you guys guess who I'm describing:

1. His parents were rich Seattle lawyers.
2. He is a Harvard dropout after his sophomore year. (I wonder how he made it in???)
3. His parents set up a company for him to give him something to do.
4. His parents were friends with members of IBM's executive board.
5. Paid $50,000 dollars for a contractor to write an operating system, which his parents managed to land him a deal to sell it before its completion to IBM for millions.
6. He is credited with the Basic programming language, but he actually got most of it from a friend at Harvard.
7. IBM contracted his company to develop OS/2, while at the same time his company contracted DEC (Digital Equipment Corp) to write a Unix like OS, which forms the core of the most popular OS out there today.
8. There's a computing center named for him at a major university in California. What's interesting is that it runs Linux based computers. (I wonder if he knows that...)
This should be an easy one!

Skuzzy, I think you're spot on from a hardware standpoint. Dropping backward compatibility would certainly produce superior hardware IMO. The problem is that nobody would write software for it because their product whould have a very limited market window.
You also bring up an interesting point with Motorola. The 68040 (and in general - the whole 68000 series) were ahead of their time. The problem is (and always has been) that the best marketed product, and not the best product from a technical standpoint, will generally win out. In 1999 Intel spent $1,119,300,000 on advertising, making them number 16 in the US. I'm sure the numbers are even higher than that now.