The alluring yet nebulous concept of transformative change is increasingly gaining traction in conversations about pathways to more sustainable futures. As such, new conceptual tools are needed to illuminate variety of actors, interests, and capacities at play in potentially radical experiments. This paper draws upon multi-level governance theory, sustainability transitions scholarship, and sustainability entrepreneurship literature, to interrogate the transformative potential of small and medium-sized enterprises (SMEs). We (1) identify characteristics of SMEs that might make them relatively more able to produce radical innovations, (2) explore dimensions of the broader socio-political context that influence the likelihood of this potential to be translated into action in urban spaces, and (3) discuss implications of these dynamics for transformative sustainability governance