In this essay, I investigate the relationship between local political context and entrepreneurship in the arts, specifically entrepreneurship by cultural institutions, which I refer to as “cultural entrepreneurship.” I look at cultural entrepreneurship as a discourse and discuss one locus in particular, the city of Utrecht in The Netherlands. The discourse on cultural entrepreneurship in the Dutch context is influenced by diminishing government responsibility for financial support of the arts. Entrepreneurship is seen in that context as finding new sources of income. Entrepreneurial values such as curiosity and experimentation are dominant in the routine relationship between cultural organizations and their subsidizing administrations but are not incorporated in the understanding of cultural entrepreneurship. After applying these considerations to the observation of the culture-political practice in the city of Utrecht, I suggest a framework that allows us to understand the discourse on the relationship between cultural entrepreneurship and political context along two axes. One axis moves between risk acceptance and aversion, and the other between the private and public interests.