Leonard began teaching guitar at Jimmy's Music in 1966 part time until his graduation from Sumter Technical College in 1968. Upon graduation he decided to become a full time guitar teacher and sales associate. In 1973, Leonard gave up his full time job and started playing weekend gigs in the local area and continued to teach part time.
In 1975 he received an offer from a local businessman to help start another music store in Sumter. (Standard Music) Again he went back to full time teaching and retail sales at Standard Music. This opportunity was different, it gave him the chance to visit music trade shows and learn about the music industry. He met musical greats; Les Paul, Chet Atkins, George Benson and many others. This inspired Leonard and several of his friends to form the variety band Brandy.
In 1983 with help from a friend, he opened the first Leonard's Music Store, but in 1988 closed the store and got what he called a real job with the State Newspaper. He continued to play music on the weekends..
He still wanted to own his own music store and with help of family and friends reopened Leonard's Music in the old Jimmy's Music building on Broad Street in 1998. This time around things have gone well. In 2010, he and his business partner reorganized and moved to 577 Bultman Drive where they teach over 70 students per week.
Leonard has taught guitar for 45 years and often jokes about teaching grandchildren of former students. He shows no signs of slowing down and continues to provide a valuable service to the Sumter Community.