Skyler was born in Hattiesburg, Mississippi and attended the University of Mississippi. Skyler earned an M.Div. from Reformed Theological Seminary in Orlando, FL, where he served as the Director of Student Ministries at Orlando Grace Church. Skyler currently serves as an assistant pastor at Grace Bible Church in Oxford, Mississippi. His wife, Brianna, is originally from Memphis, TN and teaches 3rd grade at the Regents School of Oxford. Skyler also serves on the Rooted Steering Committee and contributes to the As in Heaven podcast.