I've tried watching him a few times and got the same feeling. He also goes to great lengths to remind everyone (all the time) of how much money he makes. Is that normal for people in Silicon Valley?
But, more sadly, it just goes to show how desperate his audience is for someone they can look up to and who will, authoritatively, give them some kind of guidance.
He's part of the self-help-vlogger-industrial-complex. There's A LOT WORSE than him out there too.
I like him and I like how he's projecting the life of a regular developer from SV in his videos.