Knowing he needs cash is a
big step toward buckling down to get it.
The next step is to accept when he has cash, he'd best work on getting more before what he has runs out. Sounds simple and logical, but the people I've known that just couldn't seem to get along in society, all had that problem. When they had some cash, they didn't worry about how they would get more, until the needed it. Then they needed it right now, which led to dicey and dangerous stunts for quick cash.