This study explores the intersection of international business and artificial intelligence (AI), focusing on how new ventures navigate environmental challenges for international expansion within Africa's transportation sector. Despite a wealth of literature on AI in developed countries, a notable gap exists in the understanding of the challenges emerging economies face in implementing AI practices, particularly in the context of Africa‐to‐Africa internationalization. The current study delved into the transformative potential of AI, identifying institutional voids as opportunities for innovation on the continent. Employing the Technology Organization and Environment framework, the study investigated the adoption of AI technology in the African business environment. Qualitative data gathered through interviews with transport tech startup founders across Africa provided insights into technological innovation, institutional dynamics, and market peculiarities. The founders recognized hurdles such as data scarcity, human resource constraints, and regulatory obstacles amid institutional voids. The study underscores the importance of understanding expectations, balancing possibilities and realities, and fostering collaboration. It offers valuable insights into the complexities faced by and opportunities for new ventures leveraging AI in internationalization, with practical implications for strategic AI implementation, policy development, market expansion, technology solutions, and cross‐border transportation within Africa's unique business landscape.