This paper analyzes masculinities and entrepreneurship in Turkey through an in-depth inquiry of the holders of 'new capital', so-called 'Anatolian Tigers', in contemporary Turkey. Based on the findings of a research funded by the Scientific and Technological Research Council of Turkey (TUBITAK), this work questions businessmen’s relations with other men, especially with their masters and/or fathers, and their negotiations of power. The research project, entitled New Capital and Conservatism: Anatolian Tigers from the Perspective of Sociology of Everyday Life, mainly aims to examine the gendered practices of the rising social class of entrepreneurs from different urban centres in Turkey. In line with this research’s focus on the patterns of masculinities, this specific paper concentrates on the hierarchical masculinized relations among businessmen. As masculine identities have been constantly constructed within structured relations of power, masculinist bargains are actively created and fostered through processes of inculcating common values inherited by their masters and/or fathers. Such process also calls for the negotiation of the hegemonic masculine entrepreneurial identity and the boundaries of inclusion and exclusion. In this framework, this research does not only aim to juxtapose the defining characteristics of entrepreneurs’ masculinities but also how they position themselves vis a vis other men is significant. Moreover, while local and national markets have positioned them the assumed identity of ‘Tiger’ as necessarily powerful, aggressive, and assertive; their own positioning within the whole network of practices, meanings and discourses is also important to be discussed. In this line, this work hints an analysis uncovering the patterns of hegemonic masculine entrepreneurial identities in a social and political context marked by increasing conservatism fueled by neoliberal policies .