Adoption of E-learning systems to address youth self-reliance entrepreneurship skills knowledge gap in developed countries has been rapidly evolving and reached advanced stages. Nonetheless, in the developing world most especially Sub-Sahara Africa it is still infancy. Of recent, some Non-Governmental Organizations have attempted implementation of Elearning systems as alternative means to traditional elitist spaces to equip the youth with self-reliance job start-up skills. However, despite the usual challenge of ICT infrastructure development, pedagogical usability and accessibility concerns are key undermining barriers to this initiative. This study therefor focuses on design and implementation of a youth entrepreneurship skills E-learning system prototype, ported on mobile technology with an integrated informal lifelong learning model. The proposed infrastructure also accommodates a mobile learning tool that enhances access and usability concerns of out-of-school youth lifelong learners in developing countries like Uganda. System design and development was achieved through a user centred participatory design approach (UCD) in conjunction with Human access point (HAP) design technique. User requirements inform of low-fidelity card paper prototypes were later transformed into working system interfaces. The developed prototype with both web and native mobile tool simplifies the process of self-employment business start-up skills access and development using interactive videos. Similarly, the system guides a youth in selection of appropriate survival skills, and selection of the learning path based on one's previous experience. In addition, the learning environment helps the youth to connect with skilled experts and coaches experienced in vast areas of the business. Conclusively, the platform helps survival skills providers to reach the unreached youth and monitoring of active youth ongoing projects. Evaluation of the developed system prototype was streamlined on the Unified Theory of Technology and Acceptance Model (UTAUT). From here user's feedbacks on the developed prototype were gathered using Survey questionnaires. Study findings revealed that mobile technology can bridge youth survival entrepreneurship skills knowledge gap in developing countries. Similarly, youth survival skills provider's responses on the developed prototype in terms of system access and usability were positive. Briefly, study findings revealed that personalized Smart mobile learning system architecture bridges pedagogical usability and mobility barriers in youth entrepreneurship skills development E-learning systems implementation in developing countries like Uganda.