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Set at the intersection of ‘academia’ and ‘entrepreneurship’, this study examines the impact of cultural context upon developing a start-up during the PhD journey. The focus is on ascertaining how contextual factors at a macro level may trigger entrepreneurial activity at a micro level – and how this is managed during the PhD journey. Data is collected using online interviews with 26 international academics (boundary-spanners) who have launched start-ups. Findings show the extent to which context (national/organisational/institutional) influences (i) entrepreneurial activities and (ii) social and professional recognition of entrepreneurship within the PhD journey. We identify the need for boundary-spanning to drive entrepreneurship, and reveal challenges that were not reported in the literature. Our study contributes to management research by providing empirical data in an understudied context, to serve as a benchmark for cultural shift research.