Regan grew up in New Richmond, WI, with his parents, Pat and Linette Brown. Regan has a little sister, Megan, and an older brother, Ryan. When Regan wasn't out in the barn helping his dad with the horses, he spent a lot of his time playing sports, including baseball, football, and wrestling. He graduated from New Richmond High School in 1997, and spent the following 4 years at the University of Wisconsin – Madison. In 1997, Regan also joined the Air National Guard, where he was a mechanic on F-16s for 6 years. In 2001 Regan started Dental School at the University of Minnesota – Twin Cities. After graduating from dental school, Regan began a 4-year residency in Oral and Maxillofacial Surgery in Memphis, TN. Regan is currently in the 3rd year of his residency and is looking forward to his 4th year when he will be a Chief Resident.