His main group was Funk's G that played regularly in Burlington opening for national acts like Government Mule, Andy Summers and Groove Collective.
During this time, Smith also played as a sideman in a group called Orange Factory with John Hill on bass.
He made a demo tape with musicians Adam Deitch, Eric Krasno, and Goapele that was engineered by Jeff Bhasker.
This tape helped secure a solid line up of musicians that would perform all over Boston and surrounding areas as Deluxe.
[1] With Ben Rubin and Bob Reynolds as holdovers from Deluxe, Smith added drummer, Marko Djordjevic and guitarist, David Soler to form a new group.
Smith was an early adaptor of the fan-funding method, which he used to finance the making of Lights On after Relix Records ceased operations.
[citation needed] Smith auditioned for the show in Los Angeles and was asked to fly to New York to tape a live performance in front of the judges in April 2014.
He sang his original song Skyscraper Blues and received a standing ovation from judges Howard Stern and Howie Mandel.
[6] The record has guest appearances by Ruthie Foster, David Hidalgo, Lucius, Adam Levy and Bob Reynolds.
The song "Ocala" was featured on The Washington Post's online edition home page on Christmas Day 2016 – months before its release in a story called, Grace, Unwrapped.