He's been around since 95 - as "an evangelist for Windows 3.0". The issue he's working on the most and trying to "up the level" in is software design. Something he says we're in the Stone Ages with.
He's mentioned Channel 9 quite a bit. They have property in Second Life for evangelism and had a Vista launch there.
Best quote: "I won't argue that we've made your life harder, but we did it for the right reasons."
From Duncan Buell: "Make so Ben's mother can install it" :-) He apparently tells his students to document their code to the point that their mother can understand what it's doing.
One of his contentions is that users will drive technology instead of technology driving users. Based on what I've seen in apps in the PHP community, he is correct. phpBB's success can only be explained by a user driven model. WordPress was not the best blog software (some would still argue that it still isn't) for a long time, but it filled the explicit need people had.
A stat he threw out - 2 million people around the world identify themselves as "professional coders" while over 100 million identify themselves as "non-professional coders".