My bro got to reddit frontpage 4 times with his digital art

Whatever you do, please make sure he keeps painting what he loves. You see it getting better, and it's like telling Van Goph he should start illustrating children's books.

Rather than app illustration (he's drawing with his fingers, someone with experience and a copy of Photoshop would do it better) how about an app that makes it simple to paint like that? That guides you through it. Like the simplicity of painting by numbers.
 


The best thing he can do is release a few free "how-to" video tutorials covering small / simple projects, and then put together a comprehensive premium video course. People see shit like that, they want to do the same damn thing (even though they might not be able to and suck at art), so they'll buy it. He can also offer help as an instructor answering questions as well.

Tell him to get a good mic, a decent camera, setup a youtube channel, and then release a premium course either through his own site (you'd have to help likely if he doesn't know shit about websites), or go through a middle man like Udemy.com.
 
have him draw girls pictures on plenty of fish, I mean the guy is talented but I know a lot of graphic artist with similar ability and no one is paying them 50million