>>14656401Sam's an overgrown trust fund kid, look up his history. Grew up in one of the richest Connecticut neighborhoods in all of the US, went to a prestigious art school and has just dicked around making his avant-garde Tim & Eric knock-off "comedy" ever since. He has no real responsibilities, he has never had to worry about money or his future. He's just a spoiled drama student past his prime.
But the worse part (for him) is that he's AWARE of this, and it shakes him to his very core, and despite this he still wants to milk his fans for all they're worth because he feels entitled to money and success. So he's set out to make himself some sort of life guru, like an ironic Jocko Willink. He's appealing to wayward /pol/tard zoomers who can't recognize a loser when they see one, and even if some of his "advice" is technically correct you have to remember he doesn't take any of it himself. He's an unmarried hipster that (I'm pretty sure) lives with other men in a perpetual state of adolescence and will never have to do an actual hard day's work in his entire life.
He may seem like a quirky artist/comedian, but he IS a phony, grifter and sociopath. And he's fully aware of it.