Brent Redmond got his start in trucking as a mechanic's helper and tire man at what was for many years Westside Trucking in Gilroy in 1974. With encouragement from his father, Howard "Tooty" Redmond, Brent started "Magic Shop" (detailing and steam cleaning). As an added service to his customers, Brent bought a 1945 Autocar tractor to shuttle trailers to and from the customers’ locations. In the summer months, Brent along with his partner drove the Autocar subhauling for TVT Trucking in Gilroy. After closing the detailing business and selling the Autocar, Brent bought and operated a 1960 Peterbuilt tractor subhauling for Mike Conrotto Trucking of Gilroy. Brent took a job (dispatcher) for Mike Conrotto Trucking in 1978. After rising to the position of Terminal Manager, Brent left Mike Conrotto Trucking to take a position with Argel Produce Brokerage as a produce broker. The job with Argel Produce Brokerage evolved from selling produce to brokering trucks. Brent left Argel Produce Brokerage in September of 1987. After brief employment at a failing local trucking company, Brent then, with the encouragement of his father, formed his own company.