That might be a good idea to try out.
The big problem with this is, he's the guy doing the art, and with the art connections. However, he went to the 2nd best art school in the country, and in order to get the students to keep doing better work, they beat it into the students heads that what they ARE doing is crap, so that's what he thinks his work is.
He doesn't have the confidence to do any of this himself in his work. Everyone else thinks it is good, it's why he got accepted and had a $36,000 scholarship for the school. He just would never think he's good enough to go out and try selling his work unless someone straight out offered to buy it off him.