Roger was born in Berwyn, Illinois and was raised in Chicago's western suburbs. He earned a Bachelor of Science in accounting from the University of Illinois in Champaign-Urbana in 1983, passed the CPA exam in May 1983, and earned his law degree (Juris Doctor) at IIT-Chicago Kent College of Law (with high honors) in 1986. He is also a licensed Illinois real estate broker.

Roger's legal career has included stints with large, medium and small law firms. His practice is concentrated in income tax, real estate, estate planning, corporate law and general representation of medium and small business entities and their principals. He also is on the board of several not-for-profit entities.