ohn was born in Kansas City, Missouri and spent his formative years on the Eastern Shore of Virginia. He attended the College of William and Mary in Virginia, where he played football. After graduating college in 1991, he took a year off to pursue one of his passions, snow skiing, and moved to Colorado. He then attended Oklahoma City University School of law and graduated in 1995.
Upon graduation he entered private practice in Arlington, Texas for 4 years. In 2000, John went to work for Farmers Insurance Group defending the company and its insureds from claims. After five years at Farmers, John moved to Progressive Insurance. He was in-house counsel for Progressive from 2005-2015, 4 years of which he was the manager of the Dallas house counsel office.