This paper examines business masculinities and relationalities of empowerment in the everyday life experiences of male entrepreneurs and wives of entrepreneurs in three urban centers in Turkey: Gaziantep, Konya and İzmir. We take gendered power inequalities as structural and relational, and empowerment as a complex, multifaceted process. Based on a relational understanding of gender roles, we scrutinize men’s and women’s decision making areas in an attempt to understand normalized and internalized patriarchal values and assumptions, as well as explicit or implicit challenges against such values. We argue that gendered experiences of entrepreneurs and women married to entrepreneurs offer a complementary analysis of nuanced empowerment strategies in the background of seemingly contradictory currents such as economic globalization, transforming masculinities, rising conservatism and reinforced gender hierarchies.