Developing countries around the world have implemented Community Health Worker (CHW) programs to improve community health through education, advocacy and direct assistance. CHWs have repeatedly proven their ability to mitigate the growing double disease burden of infectious and chronic illnesses. At the same time, a lack of tangible incentives for CHWs leads to high attrition rates, poor efficiency and lack of coordination and accountability. In the quest for transforming CHWs from volunteers to entrepreneurs, a typology of eight business models where CHWs function as the channels and champions for global health projects has been articulated. In parallel, the literature on the failure modes of telemedicine, eHealth and mHealth ventures is gradually growing and providing new insights and practical design lessons. This article synthesizes the business models and failure modes, i.e. it discusses the primary failure modes for each of the eight business models for sustainable CHW projects and programs. This knowledge is pivotal for innovators and entrepreneurs seeking to engage local entrepreneurs and CHWs to operationalize interventions that tackle last mile health care challenges while creating jobs or providing frameworks for income generation and entrepreneurship.