I don't know anything about the dude, so I don't know how he gets his money. I'd hazard to guess he draws some income from youtube though.
I'm not saying he's necessarily insincere, but I think he's part of a pretty common pattern, which is some-flavor-of-minority who agrees with 95% of progressivism... but doesn't have any real attachment to the latest excess, or thinks it's a bit silly, so complains about it, which naturally attracts conservative viewership. But the second anyone actually tries to do something, he's terrified that it will go past just cutting back the latest fad, because he actually feels far more in disagreement with and threatened by the right, and he cares a lot more about enshrining 2020 liberalism than he does in fighting 2021 liberalism. So he's always going to be the first to break ranks.