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After graduating with a Bachelor's degree in Business Administration from West Chester University, Tryson began working as a car chief for Kenny Bernstein's Top Fuel drag racing team. After several years the NHRA, he moved to NASCAR, and became Geoff Bodine's crew chief in 1997. After one year, he moved to Geoff's brother Todd's team as crew chief, but was released early into the season. In 1999, he came back as the crew chief for Kevin Lepage's TV Guide team, and won won one pole and had five top-ten finishes over the next two seasons. He joined the Wood Brothers Racing team in 2001, and won his first race with Elliott Sadler that season. In 2004, he teamed with Roush Racing to work on the #6 Viagra Ford for Mark Martin, and served on the team until 2007, when he moved to Greg Biffle's car, also owned by Roush. He spent half of the season with the car before he was fired. He was later picked up by Penske Racing to be crew chief for Kurt Busch, where he has stayed since.