I've been hearing this song, everyday, on RadioNow and I finally tracked it down. Turns out this kid is an Indianapolis boy on the verge of going big.
So here's the video.
Hum.V - Simple Man
Here's another song released on Hum.V's 2007 album "Simple Man". It's called "Patriot".
Here's a link to more information about Hum.V: http://cdbaby.com/cd/humv