A native of Wadsworth, Ohio,[1] Hess began racing in 1982; in 1983, he sold a service station that he owned to raise money for his racing career. He moved from competing primarily on dirt tracks to the ARCA series in 1986.[2] He made his first start in the series in 1988; between 1988 and 1996, he competed in 63 races, winning four times.[3] Hess won the ARCA 200-mile (320km) event at Daytona International Speedway, the series' most prestigious race, in 1989 and 1991.[4] In 2001, he made his 64th and final start in the series at Daytona International Speedway, finishing 37th after an accident.[3]
Between 1988 and 1995 Hess made twelve starts in NASCAR's top series, then known as the Winston Cup Series; his first race was at North Carolina Motor Speedway in October 1988, where he finished 20th in a family-owned car; he would run for his family team in ten of the twelve Cup Series races he qualified for.[5] He would also attempt races for owners Henley Gray, Jim Spicuzza, Tom Winkle, and Sadler Brothers Racing,[6] qualifying in a single race for Winkle in 1990.[5] While racing for the Sadler Brothers, Hess was among 86 drivers who attempted to qualify for the 1994 Brickyard 400;[6] after failing to make the top-twenty in first-round qualifying, he was injured in a practice crash while preparing for the second round of time trials and was forced to withdraw from the event.[7] Hess would make his final start in the Winston Cup Series at the 1995 Daytona 500, racing for RaDiUs Motorsports;[8] Hess finished 28th in the race, four laps down.[5]