Complex sentence: Kipp Buckner started singing barbershop when he was 14 and has won the International Champion Quartet Medal twice, once with the GHG and also in 1987 when he sang with the Interstate Rivals.
Split into simpler sentences: Kipp Buckner started singing barbershop when he was 14. He also has had the honor of winning the International Champion Quartet Medal twice, once with the GHG and also in 1987 when he sang with the Interstate Rivals.