Highlights • This article asks two questions: how can play be used to unravel the discourse of the gendered hero entrepreneur and instead describe mundane entrepreneuring? How can the doing of gendered social orders be problematized when entrepreneuring is equated with play?. • By engaging with the French social theorist Roger Caillois’ conceptualization of play as being at the heart of all higher culture (1961) and with the literature on doing gender the above questions are answered. • Two ethnographic cases act as our vehicle in analysing play as entrepreneuring. • From a rich description of the two cases we find that all four forms of play described by Caillois are present, which illustrates the variation of entrepreneuring and the richness of activities conducted in the ‘doing of entrepreneurship’. • Also, two ways of playing are found. Whilst these two ways are interrelated on a continuum in the theory of play, they have been separated in entrepreneurship discourse, where they underpin the tendency to differentiate between the hero entrepreneur and ordinary people. • Finally, the authors engage in a more interpretive and reflective discussion on entrepreneuring as performative acts through which social orders can be not only reproduced but also transformed.