The SNAAP survey includes questions for alumni to rate both how important the skills they learned in school have been for their careers (perceived importance), and how well their alma maters helped them develop these same skills (perceived preparedness). Survey results and previous SNAAP Data Briefs [see ED612788] suggest a gap between alumni's sense of perceived importance and perceived preparedness (the skill preparation gap). Using three logistic regression models, this study investigates the impact of perceived preparedness and skill preparation gaps on three approaches of arts alumni entrepreneurship: freelancing, founding an arts-related venture, and starting a business of any kind. The study also examines other factors such as family resources, race, and student loans in determining whether someone will start a new venture or work as a freelancer to compare with the influence of university training.