|McConnell was born in Athol, Massachusetts to two folk singers who played in local venues in the Boston area. His family moved to Georgia when he was eleven years old, and while there he began playing guitar and writing his own songs. McConnell attended Middle Tennessee State University in Murfreesboro, Tennessee, where he performed regionally and continued songwriting.
McConnell released his debut album on his own label in 2000, when he was 15 years old, and went on to self-issue five more full-lengths and three EPs between 2003 and 2014. Concomitantly with this, McConnell entered into a publishing deal with Warner-Chappell, writing songs for artists such as Meat Loaf, Tim McGraw, Martina McBride, Buddy Miller, David Nail, Rascal Flatts, Jason Castro, Scotty McCreery, Jimmy Wayne, Phil Stacey, Brothers Osborne, Plain White T’s, Eli Young Band, and Brad Paisley, as well as for the television show Nashville.