What caused Blake's fall from grace?

He's an alcoholic, the big money days are behind him and his material is out of fashion - but he keeps on touring at progressively smaller venues. At least that's the point where we start the story.

He was also divorced several times 3 or 4 and also had a son. I would say the divorces, alimony, and child support cut a lot of the money he did manage to invest well. Other than that he seemed like a guy of simple taste that lived in the moment. Remember he's an artist not a banker. I would say when he was a big deal he lived outside his means and saved very little.