Don did not choose the traditional track of going straight to law school, but chose to begin his career as a claims representative at State Farm Insurance. It became immediately apparent that he had an interest in law and was assigned to handle litigation in Broward County for State Farm Insurance. He managed litigation files while working at State Farm Insurance, along with engaging in the special investigative unit.

Towards the end of his time at State Farm Insurance, Don chose to attend Nova Law School in the east coast of Florida. During this time, he transferred over to Progressive Insurance, where he managed and worked with attorneys and representatives throughout the state of Florida, learning the ins and outs of the personal injury and personal injury protection claims business.

Don graduated from Nova Southeastern University Shepard Broad Law Center on 31 May, 2002. He was awarded his Juris Doctor and attained a cum laude designation for his time at law school.

On 9 September, 2002, Don was awarded his license to practice law in the state of Florida by the Florida Supreme Court. He obtained his license to practice law in the Middle District of Florida on 9 September, 2008, which allows him to practice in federal courts. Don has litigated thousands of personal injury and personal injury protection cases, along with handling breach-of-contract matters. He has been a member of the Fort Myers community since 2003 and has owned his own practice since 2008 - Don Mathews & Associates, P.A.

Outside his law practice, Don devotes family time to his wife, Larisse, and two children - Noah and Emily. Both children attend Evangelical Christian School (ECS), with son Noah on the basketball team.