Career
He currently owns a small business and continues to pursue a racing career. He lives in Wilson County, Tennessee. Montgomery began racing go-karts at the age of 13.
He began rising through the ranks very quickly and by 2000, he was a regular weekly driver at Nashville Speedway United States of America.
Montgomery began his in 2003 with 15 starts in the Busch Series with Brewco Motorsports, posting a top-ten in his series debut at the Koolerz 300.
After that season came to a close, he signed to drive the #8 Dodge for Bobby Hamilton Racing. He finished 21st in points that year, and 23rd in 2005 in the #18.
In 2006, he was to drive part-time for Curry Racing, however, after finishing the season opener at Daytona 19th, the deal fell through and Montgomery left the team