As an undergraduate at Harvard University in 2007, Rich received a two-book contract from Random House. Rich's first book, a collection of short humor pieces entitled Ant Farm: And Other Desperate Situations was published in 2007 and was nominated for the Thurber Prize for American Humor.
His second collection, Free Range Chickens, was published in 2008.
Rich's third book and first novel, Elliot Allagash, was released in May 2010. Academy Award-nominated Director Jason Reitman has optioned the movie rights to Elliot Allagash.
In 2012, Rich published his second novel, What in God's Name, which the New York Times Sunday Book Review compared to Douglas Adams' Hitchhiker's Guide to the Galaxy.
Rich released his third collection of stories, The Last Girlfriend on Earth in 2013. Reception was favorable, with The Washington Post praising the book as "hilarious," declaring, "it just might be the best one-night stand you'll ever have."
Rich's fourth story collection, Spoiled Brats, debuted in 2014. The Guardian described it as "simply the funniest book of the year," adding "there are sometimes three laugh-out-loud moments within the same paragraph." The Evening Standard also praised Spoiled Brats, saying Rich is "a Thurber, even a Wodehouse, for today. Who could ask for more? You can give his books to people and just watch them laugh."
