Kyle started his racing career at eight years old, driving go-karts with his dad and his brother, former ARCA driver Clayton Weatherman. In 2014, Kyle raced in select races for Roulo Brothers Racing, a then affiliate of Roush-Fenway Racing. Kyle entered his first Cup Series race at Martinsville in late 2017 with Rick Ware Racing, which is not a winning team but one that is happy to go out and compete.