Right out of high school Jack began working his way up the ladder into management within the Country Club scene in Nashville. First at Richland, then Hillwood and then onto Nashville City Club as GM, then striking out on his own to start Cawthon’s Caterer, Inc. in 1976. He quickly became one of Nashville’s favorite Society Caterers, often greeting guests in his tuxedo while serving up beluga caviar or to carve the rare beef tenderloin with béarnaise sauce.