Gregory first entered the profession in 2008, working for part-time with Monumental Life Insurance Company while working full-time as a contract training for Automotive Manufactures. Gregory noticed the gaps in becoming an agent, not that being an agent is terrible; he could not provide a client with a cohesive approach to Insurance, which is his desire for those he helps. The desire to work cohesively led to the formation of Dunlap Financial Services (DFS).