Widely known for his work directing his friend Lin-Manuel Miranda's works In the Heights and Hamilton. He won the 2016 Tony award for Best Direction of a Musical for his work on Hamilton's original Broadway run.
He graduated from Wesleyan University alongside Lin-Manuel Miranda in 1999. He co-founded the freestyle hip-hop group Freestyle Love Supreme with him while the two were underclassmen.
He served as the director for Fox's Grease: Live! 2016 TV event. He was nominated for two Emmy Awards for his work.
He married theater actress Angela Christian.
He directed John Krasinski in the play Dry Powder, which premiered off-Broadway at the Public Theater in New York City, in 2016.