For a productive entrepreneur to succeed, they need to reach a level whereby they grow, scale up, and do actual business in the markets beyond trials. East Africa is flooded with several innovative solutions from the locals, but the region has yet to experience many disruptive innovations. The study aims to address the high failure rate of startups. This research seeks to identify the most significant challenges from idea to commercialization. The study proposed alternative solutions to help reduce the number of startups that are falling into the valley of death. With a qualitative study method, using semi-structured interviews, this paper explored the experiences of technology startups in the emerging technology district of Silicon Dar to highlight the challenges. The results of the study revealed that startups are faced with a number of challenges categorized under the themes of operational environment, funding, and markets.