Robert was born in Stamford, Connecticut, where he was one of three brothers. He attended Stamford Catholic High School, graduating in 1984. Following his high school education, Robert received a baseball scholarship to attend Eckerd College in St. Petersburg, Florida. However, an injury forced him to transfer to the University of Connecticut, where he earned a Bachelor of Arts degree in Political Science in 1988.
After completing his undergraduate degree, Robert pursued a career in law. He graduated from Pace University School of Law in 1991 and passed the bar exams in Connecticut, New York, and Pennsylvania on his first attempt. Robert was subsequently admitted to the Connecticut Bar in 1991.
In addition to his legal career, Robert is also an accomplished actor and voice over artist. He has hosted several radio programs, including "The Law Show" in the mid-1990s and "Ask the Lawyer" in recent years. Robert's first foray into acting was the PBS-TV documentary series "American Experience: Hijacked!", which he narrated alongside Campbell Scott.
Since then, Robert has appeared in numerous national projects, working alongside many well-known stars in both acting and voice over roles.