Transnational entrepreneurship is an evolving field of research which occupies an interface between social and regional sciences. The phenomenon of transnational entrepreneurship is driven by entrepreneurs that migrate from one country to another whilst maintaining business-related linkages with their former country of origin and the adopted country. The most critical distinguishing feature of transnational entrepreneurs is bifocality or the ability to function across two different business environments. Most writings on transnational entrepreneurship concentrate on business individuals from the global South operating enterprises in the global North. Absent are empirical studies of the nature and behaviour of transnational migrant entrepreneurs who operate across or between emerging or developing economies. This South-South gap in international research concerning transnational entrepreneurship is addressed in the paper which provides an exploratory analysis of the nature of transnational entrepreneurship occurring in Southern Africa using evidence of Zimbabwean transnational entrepreneurs based in Johannesburg, South Africa.