Technically, his first illustration for Magic: The Gathering was the oversized Vanguard card for Maraxus, but the first real card set he did work for was Tempest. He was actually hired as the art director, and in doing so, was allowed and expected to contribute artwork to the set. Unfortunately, art direction wasn’t something Matt enjoyed. He wanted to do more art and less management, so he took an offer with FASA Corporation to be a staff illustrator. Once things at that company started to look bad, Matt was given another opportunity to work for Wizards -- this time, as the lead concept illustrator.
Matt founded his tabletop game company, Privateer Press, Inc., in 2000 as an avenue to tell stories and create expressions of his own original property concepts.