Around 1915, Smith formed a string band and began performing at minstrel shows and medicine shows, and over subsequent years performed at venues around western Virginia, especially in the Abingdon area and at Emory & Henry College. In 1936, Smith and his sister, Texas Gladden, delivered a memorable performance at the White Top Folk Festival in southwestern Virginia. The performance impressed Eleanor Roosevelt, who was in attendance, and two years later she invited Smith and Gladden to perform at the White House. These early appearances brought them to the attention of various folklorists and musicologists, including Alan Lomax, who at the time was working for the U.S. Library of Congress.