Gregg attended Penn State University where he played football and co-captained the 1972 team. In 1972 he received a Bachelor of Arts in Economics and a Bachelor of Arts in Political Science. Before enrolling in law school Coach Paterno asked him to join the Penn State Football staff. For the next 4 years, he was the defensive secondary coach.

He then received his MBA from Penn State in 1979. He joined the investment firm of Goldman Sachs & Co in their Philadelphia office where he worked for 8 years in the Private Client Group.  Finally, he moved to Florida to join Raymond James & Associates in 1993. In 2003 he moved to Carr Capital Management in the Raymond James ICD division.