Studies of alumni from arts-focused degree programs in American higher education have revealed the need for arts entrepreneurship training for self-reliant careers, resulting in the creation of at least 168 programs and course offerings for students in a range of arts disciplines. Using factor analysis of datasets from the 2015–2017 administrations of the Strategic National Arts Alumni Project, a multi-institution online alumni survey, this paper divides the skills most relevant to arts entrepreneurship training into four latent categories: critical thinking, leadership, business management, and artistic specialty. A logistic regression revealed statistically significant associations between the latent variables with alumni’s propensity for freelancing and new venture creation. We also identified that race interacts with both student loan amount and family social and cultural capital. Arts-focused higher education programs should consider how they can offer training in these skill groups and complementary opportunities for financially challenged college students and those with fewer familial connections to the arts without creating additional barriers to careers in the arts.