Holkins created the webcomic "Penny Arcade" in 1998 with Mike Krahulik, with Holkins writing and Krahulik illustrating. According to an oral history, the two submitted cartoons to a contest run by a magazine in 1998. The magazine did not accept them but the creators sought other places to publish them, and worked with a site called looneygames.com to create what would become Penny Arcade. The strip initially ran once a week. Around a year later, they created their own website for the strip. In addition to the comic, Holkins wrote accompanying blog posts. Initially, this was partly because the format of their website left blank space. Holkins says that while now the posts are a key part of the site, when they first started he would delete each post to make space for the next one so the early posts are lost. These posts are often computer and video game commentary, but also include personal reflections or rants.