I went to his talk when he was in Vancouver, and it was… interesting. It came across as very tone-deaf, the tech equivalent of the man standing on the side of the street screaming about how our sinful behaviour will invite the lord's wrath.
He's described, in recent history, the method in which he accesses the internet; namely, to queue up a list of URLs, batch-fetch them, and then read them offline at a later date. That the person arguing about how our software is taking our control from us doesn't use it in any manner remotely recognizable to us is odd, but for him to argue against web apps which he has, apparently, never used and presumably does not fully understand (beyond his experiences with mainframes and virtual terminals, which are conceptually similar) seems impractical and somewhat tone-deaf.
The man is opposed to the way technology is going, and good on him for sticking to his principles, but he's basically staying ignorant of the last 15 years of technology development. He refuses to use any technology which isn't free software from the top to the bottom, which means he basically can't use sufficiently modern technology, and yet he wants to lecture us about what it does and how it works.
Yet, his position is still somewhat inconsistent. He'll use other people's cell phones, he doesn't refuse to use servers which are entirely free software, and there's no way that the networking gear between him and other servers (e.g. his mail server) is 100% free software. He seems to draw the line at paying for it, but not at using or benefitting from it indirectly.