Matters started out playing at small bars and was then signed by Third Side Records. He released his debut album A Whisper and a Sign before forming the four piece band Syd Matters, who played on his second album Someday We Will Foresee Obstacles. The band released the album Brotherocean in 2011. Their songs “To All of You” and “Obstacles” were featured in the 2015 video game Life Is Strange.