Liberia was making frantic efforts towards achieving food security through improvements in smallholder farmers’ productivity. However, the 1989-2003 civil conflict destroyed the economic life of the country, and reversed the positive trend towards food security. This situation undermined the growth of smallholder farmers’ entrepreneurship. Hence, this research assesses the extent to which agricultural productivity and climate change influence the entrepreneurship of smallholder farmers. The research was mainly based on primary data, using Statistical Package for Social Sciences (SPSS) to analyze structured questionnaires for 864 smallholder farmers. The production techniques and tools used by smallholder farmers were traditional and this had implications for value added productivity. The entrepreneurship of smallholder farmers was also limited to a few months during and after harvest. The level of entrepreneurship was 47 percent for rice farmers, 67 percent for cassava farmers, and 93 percent for vegetable farmers. The traditional nature of pre-and-post- harvest technologies and facilities affected the productivity and entrepreneurship of smallholder farmers.