I could see him driving uber for the enjoyment. He seems like a real people person and to have the opportunity to interact with random people is part of the fun of being out in the streets whether you're driving people around or filming your friends playing on skateboards.
I think that's why he's always able to point his camera at interesting characters around him innately. It's a gift and not just dumb luck.
Also, he has a great memory of his archive of footage and organized his catalog well.
I've never watched one his videos and gotten bummed out. He's one of my favorite videographers. As a photographer, I prefer the guys who may not have the most technical knowledge or the best camera, but instead, they just have the "eye" that no amount of money or study will give you.