Updoot for "gaping anus". That's going to work its way into my everyday parlance.

He is at least thoughtful, a good communicator and helpful.

I listen attentively to pretty much anything Cory Doctorow says about the internet and technology, he's been consistently insightful as hell on the subject. His books are also pretty good.

What book of his would you recommend reading first?

Radicalized is a really good collection of shorter works. https://en.m.wikipedia.org/wiki/Radicalized_(Doctorow_book)

Not only that, but many of his books are freely available epubs with no DRM. You can read them and decide if you like his style before going on to buy the others.

I quite liked Walkaway, but I've got kind of an anarchist bent myself, so.

another vote for walkaway - i got hooked on the idea of "git, but for houses"

I liked Little Brother. Didn't get into Homeland as much though.

This is going to be my goto example of why people need to care about data privacy. This is fucking insane. I'd fire someone for even throwing that out as a suggestion.