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Dean was born and raised in Oyster Bay, NY, graduating as the valedictorian from Oyster Bay High School. He went on to study Chemical Engineering at the University of Rochester, where he worked as a tour guide and a teaching assistant in the Chemical Engineering department. While at Rochester, Dean also founded a Stand-Up comedy club and furthered his passion for media studies, earning honors for papers on streaming services and their influence on changing TV show genre boundaries.

Dean has taught and tutored SAT and ACT for A-List since 2018, and was regularly rated as one of their most effective tutors working with students, especially those already starting at a high level of mathematics ability.