After playing for Coach Ed Bayne and the Billings Royals in 1989 and 1990, Bryan played a year of baseball at Jamestown College in North Dakota. From 1997-2005, he volunteered as a Little League coach, leading the 10-year-old Billings Heights All-Stars and 12-year-old Billings Heights All-Stars to All-Star state championships in 2003 and 2005. respectively. Bryan next signed on to coach the Billings Regulators, a position he held from 2005-07 and 2010-13. With the Regulators, he took four teams to the Triple Crown World Series in Steamboat Springs, Colorado, placing fifth in 2006, sixth in 2007, and seventh in 2012. Bryan was named head coach of the Blue Jays in 2014, guiding the team to a second place finish in district.