Anderson learned to play bass guitar at age 7, and later began playing acoustic guitar in a trio that included his father and father's cousin. By 17, Anderson had signed his first songwriting deal. He then signed with Sea Gayle, a division of Arista Nashville owned by Brad Paisley.
In late 2011, he released his debut single "Amy's Song". The song samples Pure Prairie League's 1973 hit "Amie" and includes backing vocals from Vince Gill and Pure Prairie League founder Craig Fuller. Taste of Country reviewer Billy Dukes gave the song four stars out of five, praising Anderson's "smoky" voice and the lyrics.