Whilst the extant scholarship offers a detailed exploration of why return migrants enter self-employment or engage in business initiatives in general, we know relatively little about their involvement in transnational economic activities which connect the previous destination coun-try with the origin one and how they compare to other kinds of entrepreneurial venture in this vein. This article aims to understand these motivations by using insights from 50 semi-structured interviews conducted with traders of used cars imported in Romania, a mass phe-nomenon in the Central and Eastern European area and beyond. An important result of this research is that entrepreneurs have to consider a multitude of factors in multiple locations when entering the used-car business. The article also suggests that entrepreneurial motivations among used-car traders are not fixed but, rather, can and do change over time.