Mr. Shepherd received his degree from Austin Peay State University in Clarksville, Tennessee, with a major in Art Education and a minor in Psychology and Theology.  Mr. Shepherd moved to Florida in 1996 and joined the Osceola Middle School staff in 2003.  

Mr. Shepherd was nominated for Pinellas County Teacher of the Year in 2006, 2009 and 2012 (Top 10 Finalist) and 2018.  He won the Pinellas County Art Leadership Award in 2012.  Mr. Shepherd won the Art Teacher of the Year for the State of Florida in 2015.

He served as President of the Pinellas Art Education Association from 2006-2012.

Mr. Shepherd's educational goal is to "Inspire the love of learning and the desire to create art, which increases one's self-esteem and self-confidence."

Outside of school, Mr. Shepherd is a professional artist and has sold over 500 paintings; he paints in all media and his favorite style is Impressionism.  He has been a Docent at the Salvador Dalí Museum and Art Teacher of the Junior Docent Art Summer Program for the past 14 years.  He is the Chair of the Artist Enclave Historic Kenwood and also a Youth Minister at King of Peace Church.