A native to Chapel Hill, North Carolina, Simon grew up immersed in bluegrass music playing with people like, Andrew Marlin, Emily Frantz, Jon Stickley, Bobby Britt and Hank Smith. Looking to try something new, Simon auditioned and was the first mandolin major to be admitted into Interlochen Arts Academy where he studied classical mandolin repertoire and techniques. During this time, Simon discovered a great love and passion for jazz music and following his graduation Simon came to Boston to attend New England Conservatory as the first mandolin player admitted into their Jazz department.
Simon is also a part of numerous musical projects including a progressive duo project Paper Waiter, which explores original music derived from genres such as jazz, western swing and indie rock. Simon exercises his compositional voice in more traditional jazz settings playing original music with his quartet and trio.