I second selling CD's to drunk chicks at shows. My wife buys them all the time... and then never listens to them.
I don't think stealing music songs is what it used to be because it's too much of a hassle - especially with the decline of the PC, CD and USB drives. It's just easier to buy the good songs for $5 on itunes or Amazon MP3, and stream it when I want it on your phone.
He could probably share full versions of the songs on SoundCloud or even YouTube with a reasonable expectation that no one will bother stealing it - of course if he's old and jaded, then forget that argument. I also believe that if he's a small time musician - then the people who care about his music will care about him and buy it instead of steal it.