why do people listen to him? He is just some random guy who doesn’t seem to be involved in bitcoin dev at all

Yeah...he makes a lot of noise.

No idea. A few years ago I went to one of his meetups Because it was only a couple hours away and I wanted to see what the deal was and he is not technical at all. Thankfully Portland has a slew of actual technical Bitcoiners that we're fun to talk to.