The development of an entrepreneurial strategic orientation is of growing concern for global corporations. Through a human capital lens, we probe how and when firms can develop and cultivate managerial entrepreneurial resources; by explicitly encouraging cross-cultural experiences that stimulate systematic shifts in mindset and behavior. Drawing on paradox theory and intercultural psychology, we put forth a model positing that cross-cultural experience (an endowment firms can either hire for or facilitate themselves) develops managerial entrepreneurialism—consisting of (a) venture ideation, (b) opportunity recognition, and (c) entrepreneurial behavior—through the intervening mechanism of a paradox mindset. As a boundary condition we uncover that paradox mindset formation partially hinges on home cultural tightness-looseness. We employ three distinct experiments on multinational samples of individual professionals (n = 506), active entrepreneurs (n = 370), and current managers in global firms (n = 288) to test our theorizing. Finding general support for our model, with analyses yielding important theoretical and practical implications from non-findings too, we conclude that a paradox mindset is a necessary, but not de facto, mediating step between cross-cultural experience and the cultivation of entrepreneurial managers. We also find that paradox mindset formation is conditional and related to home cultural tightness-looseness.