In 2000, Jason won first place in the bluegrass category of MerleFest's Songwriting competition. The following year, he took first place in the North Carolina Songwriters Co-Op contest. Jason was selected as a spotlight performer at the annual Healdsburg Guitar festival in 2009, sponsored by Acoustic Guitar Magazine, and in 2010 he was awarded a fellowship by the International Arts Movement in the prize's inaugural year. In 2012, Jason received a Fulbright grant to teach songwriting to students in Thessaloniki, Greece.
Jason has lived in Boston, Durham, and most recently New York. He tours frequently throughout the US.