Ten years ago, he moved back home to Kentucky with his wife and high school sweetheart, Rhonda, to raise their four children on a farm. He began battling big government as a concerned citizen in 2007, and stopped or lowered four separate tax initiatives in his county.

In 2010, Massie won the race for Lewis County Judge Executive. In the first nine months of his administration, he eliminated enough wasteful government spending to pay his first three years salary as Judge Executive.