Nestruck began writing for the McGill Daily, one of the student-run newspapers at McGill University in Montreal, while studying drama at the school's English department.
He returned to Toronto in 2008 to take the role of theatre critic for The Globe and Mail.
He is a four-time winner of the Nathan Cohen Award for Excellence in Critical Writing,[3][4][5][6] and in 2013, he was a runner-up for a National Newspaper Award in the Arts and Entertainment category.
[7] He completed a masters at the Centre for Theatre, Drama and Performance Studies at University of Toronto in 2013.
He cited the need to be more present at home for their children, thus making it difficult for him to attend evening theatrical shows, as a reason for his shift to television criticism in 2024.