Following college, Smith taught world history, world geography, and guitar at North Gwinnett High School in Georgia for a time before leaving to pursue music full-time at the age of 28. He began to release his own self-produced albums beginning with 2003’s Undertones, followed a year later by In the Mood. He released three more albums (2005’s The Good Life, 2007’s Hard-Headed Fool, and 2009’s Keeping Up with the Joneses) on his own Undertone imprint before finally breaking into the country charts at number 17 with 2011’s The Broken Record, which came out on the Nashville label Average Joe’s Entertainment. He quickly followed up with Live in Chattanooga (2012) and the acoustic Maysville in the Meantime (2014), gaining new fans and admirers with each release. Working with an outside producer for the first time, he teamed up with Keith Stegall, whose work with the Zac Brown Band comes close to Smith’s feel and approach to country music. He signed with prominent roots label Sugar Hill in early 2015 and delivered While the Gettin’ Is Good a few months later.