When I was a student, we tried to get him to speak to at our school, but Woz wanted mucho $$$$ to speak. But it seems plenty people will pay what he asks. I guess if my job were to just go around talking about random shit I'm interested in, and I can make $10M doing that, I'd be the happiest person ever too. I don't think it's about naivete.
Edit to clarify: I'm not saying he doesn't deserve to get paid, I'm saying his being "the happiest person ever" is directly correlated to his ability to collect millions just shooting the shit in front of a fawning audience.