Digital entrepreneurship may result in institutional turbulence and new initiatives are frequently blocked by vested interest groups who posit superior financial and relational resources. In this paper, we explore the role of cities in facilitating digital entrepreneurship and overcoming institutional resistance to innovation. Drawing upon two historical case studies of digital entrepreneurship in the city of Stockholm along with an extensive material on the sharing economy in Sweden, our results suggest that cities offer an environment that is critical for digital entrepreneurship. The economic and technological diversity of a city may provide the field conditions required for institutional change to take place and to avoid regulatory capture.