This chapter discusses the concept of entrepreneurship in the artistic field adopting a historical approach. Concepts of the history of entrepreneurship and of cultural and creative entrepreneurship will be used to analyse the figure of the “artpreneur” (artist entrepreneur). The starting point of this analysis is represented by Schumpeter’s comparison between the entrepreneur and artist (1911). After presenting and discussing the similarities between the artist and the entrepreneur in the existing literature, a new conceptual model of cultural entrepreneurship is presented.