His education background is in engineering from Kettering University in Flint, Michigan. During his time there he also served as a contributing member of the Kappa Sigma chapter of the Theta Xi fraternity.
He began racing in a kart at age 15. He moved to a mini-sprint car at Wilmot Speedway in Wilmot, Wisconsin, and was the track rookie of the year and fourth overall.[3] He finished second in mini-sprint points at Wilmot in 1996, and fourth overall in the Wisconsin Mini-sprint Association[3] (which included races at the Calumet County Racing Association). He had five wins on the season, and recorded three wins at Wilmot in 1997.[3] Late in 1997 he raced the one mile dirt track at Springfield, Illinois, in an ARCA series event.
Matthews moved to the Mid-American SuperTruck Series on asphalt in 1998.[3] He had three Top 5 finishes as a rookie, and two features wins and a pole position in 1999 and 2000.[3] He then moved to the Super Late Models at Slinger Super Speedway in 2001, and was the series Rookie of the Year.[3]
In 2003 he quit his job as an engineer at Harley Davidson to race full-time.[3] He competed in the Midwest All-Star Racing Series (MARS), and he won his fiftieth race on a short track that season.[3] He competed in the Slinger Nationals, and finished fifth against nationally known drivers.[3] Another season highlight was finishing third at Madison International Speedway ahead of Kurt Busch and Matt Kenseth.[3] He moved to the American Speed Association National Series in 2004 as well as selected Super Late Model events.[3] In 2005 he competed in six different Super Late Model series from Minnesota to Florida.[3] He earned 34 top-10s, 17 top-5s, and one win during the 2005 season. He also finished top 5 in points in three major touring series that same year. In 2006 he competed in the ARCA series with Eddie Sharp Racing where his best finish was 2nd at Michigan Speedway.[3]