Racing, he posted his best NASCAR finish to date at Homestead-Miami Speedway in the Truck Series, ninth in the No. 06 John Boy and Billy Chevy for MRD Motorsports. 2005–2007 Smith began the 2005 season with Xpress Motorsports's No. 19 team, but lost the ride after sponsorship failed to materialize. He was then hired as the driver of the No. 65 Glynn Motorsports Dodge Ram and in four races in the truck he had a 20th at Texas and a pair of 22nds at Mansfield and Dover, and after that was elevated to Glynn's Busch Series team. Originally unsponsored, the team garnered sponsorships from Who's Your Daddy? and Samson Stone. Despite a streak of six races where he did not qualify worse than twelfth, including three thirteenth-place runs, he was released from the team. He ended the year in the Truck Series MRD for the closing races of the season, finishing 29th, 33rd, and 32nd in three late season starts for that team. At the end of the 2005 season, Smith signed on with Team Rensi Motorsports to run a full Busch season for 2006, with his best finish of tenth coming at Charlotte Speedway. Smith ended the season with one top ten as well as a number of other strong finishes, and ended the season 20th overall in points. Towards the end of the season Smith tested for Ginn Racing at Kentucky, and signed a deal with them to run the full Busch season, and also sixteen cup races which, would come in a car shared with Mark Martin for the 2007 season. 2007–2008 Smith attempted his first career Cup race at the 2007 Daytona 500, in a fourth car, numbered 39, for Ginn Racing. He failed to qualify. Smith made his official Nextel Cup debut at the Food City 500 at Bristol Motor Speedway, finishing 25th in NASCAR's first Car of Tomorrow race. Smith made six starts in the No. 01 sharing ride with Mark Martin. He was removed from the No. 01 on July 17, 2007, and moved to the No. 14 after the release of Sterling Marlin, but before the team could run a race Ginn Racing merged with Dale Earnhardt, Inc. As a result, the No. 14 team's owner points were transferred to DEI's No. 15 team and Smith was out of a ride for the 2007 season, allowing him to keep his rookie status