This article aims at contributing to a more profound understanding of the relationship between the developmental state and private entrepreneurial activity, in particular the internationalization of business ventures. Based on ethnographic fieldwork in Singapore, this article attempts to identify the role of the Singapore developmental state in orchestrating the strategies of domestic firms establishing themselves in foreign markets. From the 1960s, the Singapore government has neglected small domestic firms — its legacy of the colonial past — for diverse economic and political reasons. Initially offsetting the influence of Western culture through the establishment of foreign companies, the government changed its tune, harnessing 'Asian' values and institutional norms to facilitate ventures into China. Altering between different legacies created ambivalence and shifting coalitions with foreign economies. Striking divergence from government directives has been found in the ways in which Singaporean firms go about when venturing across borders and, in particular, when drawing on the city state's legacies to give their ventures legitimacy and meaning. This divergence raises questions about the role of the Singapore state as the paragon of institutional legacy for its domestic businesses.