James started her training at a professional wrestling school in the Washington, D.C. area. She started her wrestling career on the independent circuit in 1999. Her first work was as a valet for KYDA Pro Wrestling using the ring name Alexis Laree. The name is a combination of her stage name from when she was a dancer and her middle name. As Laree, she managed several male wrestlers. This included managing Tommy Dreamer to win the KYDA Pro Heavyweight Championship. In March, she wrestled in her first match. It was an intergender tag team match with Jake Damian against American Mike Brown and Candie. James trained to get better at wrestling at many places. These places include the Funking Conservatory run by Dory Funk, Jr. and an Extreme Championship Wrestling (ECW) dojo. She also started wrestling for Maryland Championship Wrestling. While there, she was trained by Ricky Morton and Bobby Eaton. Because the independent circuit did not pay enough, James worked as a waitress at an Olive Garden restaurant. Trish Stratus, a former WWE wrestler, was and still is Mickie James' role model