The acoustic singer/songwriter was having a blast during a two year residency at Jimmy Buffett’s restaurant on the Strip in his adopted hometown of Las Vegas, performing tons of his original material amidst the covers during his three hour sets, five nights a week on the outdoor patio. Then he became a true road warrior, logging thousands of miles (and upwards of 150 annual gigs) these past two years as he became the country’s highest booked act on the college circuit.

The multi-talented per...