This ethnography explores the underground art world in Portland, Oregon by showing how a Portland area artist collective, Oregon Painting Society, navigates their art world. Participant observation, in-depth interviews, and a short latent content analysis triangulate data to show the features and values of the underground art world. Using Becker's concept of art worlds, I show how artists working outside of a traditional art career in a commercial gallery system do their work by exploring how Portland's art world is structured and sustained. I find that group work, cooperation, and resource sharing in a vibrant neighborhood based social network enables artists to substitute resources usually provided by gallery representation and sustain their ability to make artwork without financial support. This is a network that rejects the competitive structure of the commercial system and runs more smoothly the more artists participate in it. I also explore the reasons for Portland's particular ability to support this kind of environment, citing geographic proximity to other art cities, DIY cultural roots, neighborhood structure, affordable city amenities, and a creative class population.