Racing career
Shepherd started in go-karts and moved on to the Thunder Car division at Flamboro Speedway. He progressed from there to Late Model running in the ALSTAR Series and then into Super Late Models with OSCAAR. Shepherd eventually worked his way into Canada's top series, CASCAR, running a season and a half, winning races as well as Rookie of the year. His prowess drew the attention of NASCAR owner Jack Roush, who invited him to Roush Racing: Driver X , the audition that was held in 2005 and televised on the Discovery Channel.
Shepherd turned heads with a surprising performance, ending up as one of six finalists in the competition.
Roush then signed Shepherd to further development, first in the ARCA RE/MAX Series in the No. 39 car for the Daytona season opener, then in several races in the Craftsman Truck Series. Shepherd's series debut was at Memphis Motorsports Park on July 22, 2006, where he finished 23rd. Shepherd made two more starts that year, finishing 31st at Nashville Superspeedway and 18th at Las Vegas Motor Speedway.
In the 2007 season, Shepherd shared the No. 50 ride in the Craftsman Truck Series with T. J. Bell. Shepherd was later released from his development contract due to a lack of sponsorship. He then returned to a part time schedule in the NASCAR Canada Series. He picked up his first win at Kawartha Speedway in September 2010. [1] Shepherd would pick up his second win in 2011, [2] and won three more between 2012 and 2013. He wouldn't return to the series until 2018, where he made six starts. He would run again in 2019 and 2021.
In 2018, Shepherd finally made his NASCAR Xfinity Series debut at Iowa Speedway driving the No. 55 for JP Motorsports. He finished 31st,15 laps down.
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