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Jeffrey was born in Vernon, CT. His first role was that of a cross-country runner in Once Upon A Mattress. He attended the University of Connecticut, where he received a degree in Actuarial Science. While there he was involved in local theater programs and performed in plays such as Godspell and The Pirates of Penzance. He moved to New York City in May of 2011, where he performed in the world premiere of the productions, Logan's Hollow and In the Bag. He then turned to the screen in roles such as Peter in Skeletons and The Embalmer in Forgotten Kingdom: The Divide. He is a member of the comedy troupe Bedlam and Delirium and studied at HB Studios in Greenwich Village. In 2014 he moved to Los Angeles to pursue a career in television and film.