Rich is an alumnus of The Dalton School, a former president of The Harvard Lampoon, and the son of The New York Times editorialist Frank Rich. He received a two book contract from Random House prior to his graduation from Harvard University in 2007.

Rich's first book, Ant Farm: And Other Desperate Situations, has been described as a collection of "giddy what-if scenarios". Excerpts of the book were printed in The New Yorker's "Shouts and Murmurs" column. His second book, Free Range Chickens, was published in 2008. His first novel, Elliot Allagash, was released on May 25, 2010.

In 2009, Rich co-created the collector's edition trading cards New York Superheroes.

Rich is currently a writer for Saturday Night Live.