Cheapass Games was founded by game designer James Ernest in 1996. Prior to founding the company, Ernest had worked as a technical writer for Wizards of the Coast, where he wrote rules for games including Magic: The Gathering. This experience inspired him to create Cheapass Games.
Ernest founded Cheapass Games on the philosophy that tabletop games are generally overpriced and are often packaged with dice, counters, play money and other components that the customers already own. Ernest decided his company would package games only in unmarked envelopes, boxes and plastic resealable bags. In 2011, Ernest and his team updated their business model by offering games for free in PDF format.