Winer is beyond grumpy. He's pathologically negative about everything. His whole blog is just a series of complaints. He also doesn't seem to program anymore, or know what he is talking about. Why would anyone want to hire him to do anything, regardless of his age? In contrast you have late 40s-early 50s guys like Brandon Eich and Douglas Crockford who are positive and relevant, and do uh, seem to know what makes Javascript different than C. I mean, really...