[2] Prior to founding Cheapass Games, Ernest worked as a juggler at various venues,[3] including Camlann Medieval Village,[4] and as a freelancer with Wizards of the Coast.
[6] In 2005, Paizo Publishing created Titanic Games with Ernest and Mike Selinker.
He has had success with Kickstarter, successfully crowdfunding games like a new version of Unexploded Cow and Get Lucky (which takes the concept and core mechanics of Kill Doctor Lucky and adapts it as a card game), among others.
In April 2016 they launched a Kickstarter campaign to bring the game to actual publication.
[10] In 2018 The Brothers Chaps, creators of Homestar Runner, collaborated with James to create the cooperative game Trogdor!!