Returnee entrepreneurs are often represented in migration and development discourses as agents of development. This assumes that they acquire valuable socio-economic resources abroad which help them to create successful businesses upon return. However, we have scant knowledge of the impact of the geopolitical context on returnee entrepreneurs or their coping strategies. Latin American returnees in particular have received little attention and few studies focus on migrants with ‘South-to-South’ return trajectories. Emphasising the role of territorial conflicts and the agency of individuals, I use a feminist geopolitical perspective to address these gaps. I contribute to migration, mobility, and development studies by studying whether Colombian migrants returning from Venezuela can reintegrate as successful entrepreneurs. Further, I offer the concept of transmobilities to study the cross-border nature of strategies of reintegration. The 30 returnees studied have a trajectory of repeated forced mobilities, ranging from internal displacement in Colombia, subsequent emigration to Venezuela, and final deportation to Colombia by Venezuela’s government. I combine the qualitative methods of multi-sited ethnography, biographical interviews, mental maps, and participatory Minga workshops. The analysis shows that Colombian returnees face intense difficulties in reintegrating despite their strong motivation and entrepreneurial spirit. The geopolitical context of armed struggle, an absent Colombian state, and territorial conflicts between Colombia and Venezuela create an unfavourable environment for returnee entrepreneurs. Consequently, they develop transmobility strategies — including the movement of people, goods, and capital across national borders — at the risk of their own lives. The simplistic discourse of returnees as agents of development needs to be revised.