Pincus-Roth was raised in Chevy Chase, Maryland and attended Richard Montgomery High School in Rockville, Maryland, where he graduated in 1998 and received a Lazarus Leadership Fellowship. At Richard Montgomery he was sports editor, news editor, and editor-in-chief of The Tide and authored an op-ed column entitled "Can I Say One Thing."
He received his Bachelor of Arts degree in philosophy from in 2002. He wrote his senior thesis on Seinfeld and authored a column in the The Daily Princetonian where he opined on the blissful lives of squirrels, unrecognized discrimination, and cultural relativism toward nudity, among other topics.
He wrote and acted for the Princeton Triangle Club musical comedy group.