Digital technologies are often seen as a powerful means for poverty reduction. Yet, much of the existing research focuses on macro-level outcomes, leaving gaps in understanding individual-level mechanisms and the processes behind successful digital interventions. This study addresses these gaps by examining how online platforms, developed as social innovation efforts, enable smallholder farmers in Japan to escape poverty. Using a qualitative, case-based approach, we analyze six social enterprises and explore how stakeholder mobilization drives the success or failure of these platforms. We developed a schematic model that captures the nonlinear, collaborative nature of the social innovation process. Our findings reveal a systemic account of why and how only two of the six platforms achieved meaningful impact, offering insights into the factors that shape the effectiveness of digital technologies in reducing poverty. In the end, our model offers practical implications for future digital poverty reduction initiatives.