In 1997, Boles became directly involved in IndyCar racing, serving as spotter for
Roberto Guerrero at Pagan Racing. In August 1997, Pagan Racing was sold and reorganized as Panther Racing. Boles left the office of Mayor Goldsmith and joined the ownership group, which included NFL
quarterback Jim Harbaugh, car dealer Gary Pedigo, motorsports executive John Barnes, and television producer Terry Lingner. In addition to his ownership role, Boles also served as Chief Operating Officier for the team. In 2007, Boles left Panther Racing to join the marketing and advertising agency ignition, Inc. as executive vice-president. He later became partner in the marketing agency i3Worldwide. In addition, he had his own law practice, representing motorsports figures. == Indianapolis Motor Speedway ==