Jackson was born on the west coast in Seattle Washington, and soon moved to the Kitsap Peninsula. After a college career in Bellingham Washington and being active in the grunge music scene, he moved to Berkeley California. Jackson’s affinity for the outdoors drew him into the equipment company Mountain Hardwear, which was just starting up at the time. Seeking new opportunities led to a stint selling airtime for the Howard Stern show shortly after Mountain Hardwear sold to Columbia Sportswear. Having experienced the lifestyle of the inner city, he was looking for a change. He found a small ad for a contract sales manager in Red Lodge, Montana. Having never been to the state and open to new opportunities, he jumped. Landing sight unseen in the state that would become his future home. Having frequently been a dog owner, one puppy in particular changed his life. Diesel, a Weimaraner, decided he would take himself for a walk one day. On that walk Diesel met Jackson’s future wife. Fast forward a handful of years, Jackson is a father of two boys, and active in the Southwest Montana real estate business.