Reid was born in Logansport, Indiana, where his father Lynn Reid, a former Indy car chief, was the Honda Motorcycle dealer; he later moved his shop to Kokomo, Indiana. Reid is a 2001 Graduate of Taylor High School. Reid began racing at the age of seven before moving on to the World Karting Association two years later. By the time he was twelve years old, he was racing 80cc go-karts and mini-sprint cars under the tutelage of his father.

In 1995, Reid won the Rookie of the Year division in the Mini Sprint 600cc division at Miami County Speedway. He won the track championship at that track over the next two years. In 1999, Reid moved to the Great Lakes Outlaw Sprint Series, a sprint car division based in the MidWest. He drove the George K. Devine Special number 9 to several race wins over the next two years. Reid garnered more awards, the 2002 USAC Sprint Car Rookie of the Year, and the National Sprint Car Hall of Fame Non-Wing Rookie of the Year. He got his first win that year at Eldora Speedway.

He would go on to race in France as part of the Red Bull Racing Formula One program, where he was signed to a sponsorship deal. In 2004, Reid signed a driver development contract with Hendrick Motorsports. He made his Busch Series debut later that year at Richmond International Raceway with NEMCO Motorsports, finishing 37th after a crash. He made two more starts that year. In 2005, he raced seven races for Hendrick in the Busch Series. His best race was at Nashville Superspeedway, where he started and finished seventeenth. Unfortunately, he was released from his contract at Hendrick at the end of the year.

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