Rupert grew up in small business with the experiences learned from his Mother & Father's small business drive. As a child, he was raised amongst entrepreneurs who believed in the opportunities America afforded for those who were willing to work hard. Following in his parents footsteps, he purchased income property for low income tenants 1 year after graduating from college. In September 2008, he started an Over-The-Road Logistics company located in Atlanta, Georgia.
In 2012, he joined the modern day gold rush in Williston, ND. He decided to learn how to haul oil before purchasing his 1st truck. After spending a year there and having enough of -30 below weather, he was asked to help transport crude oil in the Wyoming/Colorado region. Currently, the trucks run regionally in the Rocky Mountain area providing Sand Hauling, Dry Van, Flat Bed, Reefer and Power Only services to local customers.