After receiving his BFA in Drama and English from Randolph-Macon College, Jamie moved from Virginia to Chicago in 2001. For the first few years, he did a lot of improv and sketch comedy. Jamie studied at Second City's Conservatory and performed on several teams at Improv Olympic. Of his many great experiences, his favorites were Boomtown, an improv team born out of the Playground Theatre's Incubator program, and True Pilsner, a sketch comedy troupe that would perform at any theatre or bar that would have them.
Eventually, Jamie landed with a great talent agency, Big Mouth Talent. Since then, he has been fortunate enough to make a living as an actor doing commercials, including the Coors Light campaign with the NFL coaches. At one point, a casting agent at TPR Casting hooked him up with a theatre audition for Author Miller's Incident at Vichy at Steep Theatre. Loving the people and work, he hung around until they made him a member.