It was formed in 1991 when Waltrip resigned from Hendrick Motorsports to start his own team, and was originally named DarWal, Inc.. During the 1970s, Waltrip, like many drivers of the time, formed their own teams for racing, in lower levels, originally DarWal, Inc, was his personal licensing agent and operator for many short-track cars he would race at many circuits on non-Cup weekends or special events, and eventually went to Busch Series racing.

In 1991, the racing team moved up to the Cup level, with Hendrick support, but he divested himself of Busch operations at the end of the 1993 season.

Waltrip has also run part-time with his team, with his final NASCAR Truck Series race coming at Martinsville Speedway, where he finished 12th.

In addition, DWM briefly expanded to two cars, when Rich Bickle finished 34th at that year's Brickyard 400 the No.

26 Kentucky Fried Chicken Chevy also fielded by DWM, as well as Waltrip running special paint schemes to commemorate his 25th year in the sport.

For 1998, Waltrip agreed to terms with concrete company Speedblock to replace Western Auto as his primary sponsor.

However, Speedblock never paid Waltrip and he was not getting enough money from secondary sponsors Builders Square and Hechinger to justify keeping his team open.

After the spring Darlington race, where he ran an unsponsored car with a paint scheme honoring terminally ill NASCAR legend Tim Flock, Waltrip agreed to sell his team to Tim Beverley and became an injury substitute for Steve Park for Dale Earnhardt, Inc.. Beverley would put the team on hiatus after buying it; after he later purchased the assets of ISM Racing's NASCAR operation that same season, he merged his two acquisitions into one and brought Waltrip back to drive for what was now Tyler Jet Motorsports, in what had originally been ISM Racing's #35 Pontiac sponsored by Tabasco.