He began playing fantasy sports when he was 14, and began writing for a fantasy sport website as a way to take a break from his Hollywood writing work. This led to his launching two of his own fantasy sports sites, RotoPass.com, and TalentedMrRoto.com. ESPN Radio host, Steve Mason, became a fan of the sites, and invited Matthew Berry to speak on his show. This eventually led to a weekly column for ESPN The Magazine, and an appointment as fantasy director for ESPN in 2007.