he was in Hollywood, writing scripts and screenplays for movies and TV shows, he was still miserable. He asked a small fantasy site (RotoWorld.com) if he could do a column for them. He has been playing fantasy sports ever since he was 14; "it's my passion," he said on the podcast. The site did in fact hire him to do a column, because "Married... with Children is their favorite show." Berry wrote for Rotoworld from 1999 to 2003, when he was let go after the site wanted to lower his pay from $100 a week to $25 a week. Berry then started two fantasy web sites in addition to his Hollywood writing. He started RotoPass.com, a site which aggregates multiple fantasy sports sites that use paywalls, and TalentedMrRoto.com, a fantasy content site. The popularity of these sites led to him dropping his full-time job and focusing on fantasy sports. He also appeared on several media outlets as a fantasy expert. Prior to joining ESPN exclusively, Matthew spent 2005 and 2006 writing the daily fantasy blog for Major League Baseball on MLB.com as well as writing a weekly fantasy column for NBA.com while also serving as editor of the 2005 and 2006 NBA.com Fantasy Basketball Magazine. In addition, he spent those two years making multiple weekly appearances as the official Fantasy Sports Expert for the Fox Sports Radio Network. ESPN and the fantasy explosion Radio host Steve Mason, who was working for FOX at the time, was a fan of the TMR column and asked Berry to do a segment, which ended up lasting over an hour. He eventually was asked to do more guest appearances and was soon hired as their fantasy analyst. Mason then left to go to ESPN Radio, where he introduced Berry to staff in the ESPN base of Bristol, Connecticut. He did a two-hour fantasy show there, which led him to spots on Cold Pizza. That grew into doing segments on ESPNEWS, which led to his getting a column in ESPN The Magazine. That allowed him to start The Fantasy Show. Berry's relationship with ESPN grew to the point that it purchased TalentedMrRoto.com and hired Berry as director of fantasy sports in February 2007. As the popularity and demand for fantasy sports rose, so did Matthew Berry's profile on the network. Berry appeared on the Fantasy Insider on ESPNEWS and First Take once or twice a