How do entrepreneurs working across multiple countries leverage individual experiences and institutional environments to pursue international markets? This research utilizes Bourdieu's theory of practice as a sensitizing framework to explore transnational entrepreneurs' internationalization strategies. Four case studies reveal the ways in which transnational entrepreneurs rely on diverse sets of resources—economic, social, cultural, and symbolic capital—to navigate multiple institutional environments—cultural repertoires, social networks, legal and regulatory regimes, and power relations—when making strategic decisions about internationalization. Transnational entrepreneurs are uniquely positioned to internationalize directly and, in many cases, as an intermediary for local firms. As such, transnational entrepreneurs pursue a modern middleman role that transcends the multiple institutional environments in which they are embedded.