Just watched season 1 of Silicon Valley. Really looking forward to season 2. I didn't know that it was a mike judge when I started watching, but his comedy is pretty apparent.
As a semi-old-timer, you might like "Halt and Catch Fire". Not a comedy, but it is aimed at nerds and geeks. Roughly tells the story of Compaq and the first IBM PC clones.
I like how they did that whole bit on the most efficient way to masturbate a room of men because that is exactly the kind of dumb bs you have to put up with if you're in the computing industry. It's still funny, but some people don't know how to let an anecdote go.
That scene was absolutely fantastic. I have the sense of humor of an adolescent. In scenes like those I'm never sure if the writer is making fun of people like me for laughing, but I don't care for a second. If there's a deeper joke to be in on, I'm fine being on the outside looking in.
Literally the only reason to watch that show is the final episode. My roommate had to practically tie me to the couch to force me through the first 11 episodes. It was really worth it in the end but I would not and could not watch it again.