Robert grew up in Castine, Maine. He graduated from high school at George Stevens Academy in Blue Hill and attended the University of Maine where he earned his B.A. in English, summa cum laude. Robert graduated from the Washington & Lee University School of Law, in Lexington, Virginia. While in law school, Robert interned as a clerk for judge of the Circuit Court in Rockbridge County, Virginia, and for the U.S. Attorney's Office in Bangor, Maine.

Robert currently lives in Ellsworth and enjoys hiking in the woods and mountains of Maine with his dogs and daughter.