Entrepreneurs form and grow businesses in relation to the localised context around them (structure) and also through their own choices and actions (agency). In this way, structure and agency intersect in the lived experiences of entrepreneurs. The purpose of this work is to explore entrepreneurial agency in two ecosystems that, as structures, constrain entrepreneurship within them: Newcastle Upon Tyne (UK) and Perth (Australia). We add to extant analysis that empirically looks at the active agency entrepreneurs participate in, as they attempt to overcome the structural level constraints they encounter. Methodologically, we draw on phenomenological data, arriving at a highly detailed insight, drawing attention to the strong local entrepreneurial communities and distinctive cognitive mindsets that entrepreneurs in the ecosystems we study have agentically developed and cultivated. We suggest how future analysis of entrepreneurial agency may unfold and consider the implications of our insight from a policy implementation perspective.