Despite widespread recognition of the importance of place in entrepreneurship research, much less attention has been paid to the methodological challenges that inquiries into place presents. Understanding the relationship between place and entrepreneurship is becoming increasingly important as focus turns to sustainable entrepreneurship and as policy makers turn to ‘place-based’ approaches to regional sustainability challenges. This chapter provides insight one researcher’s experiences engaging stakeholders in discussions about the relationship between a place-based university programme for sustainability and local sustainability agendas. The chapter reveals the struggles experienced by both researcher and participants in articulating what places and the local region means to both individuals and to the programme. The findings provide an important insight into how researchers studying place need to be cognisant of the limitations and flexibility of language when engaging research participants in discussing the relationship between place, sustainability, and entrepreneurship.