I suppose with the explosion of rappers brought on by the advent of the digital age, Skillz would be a regular guy, the middle class of the Hip-Hop realm. Aspirations of full-blown fame have come and gone, he’s settled into a comfortable existence & still managed to make his mark on the world.
In reality all he has to do is look to his left and right to see how many of his peers are still on the scene and have some sort of relevance at this stage of their career. He might play it down a bit, but that fact alone has to put him a few notches above regular. I think he knows that though.