Born and raised in St. Louis. Gregg grew up in St. Louis City's South Side. He attended St. Joan of Arc grade school and Christian Brothers College High School. He earned his Bachelor's of Arts in Political Science at Truman State University and went to work in the Missouri State Capitol in Jefferson City. After working for State Senators and a State Representative he moved back to St. Louis and began working on political campaigns.
In 2008, Gregg started his own political consulting firm, Gladius Communications, and ran for office against a 20 year incumbent Democratic Committeeman. He won the election with 65% of the vote and continues to work in Democratic politics in St. Louis and Missouri. Additionally, He currently acts as the Treasurer of the St. Louis Democratic Central Committee.