The informal economy consists of economic activity not regulated nor protected by a state entity. It plays a vital role in reducing unemployment and stimulating the economies of many countries in the Global South. In Cameroon, it accounts for 20-30% of the GDP and 90% of employment. Similarly, 47% of Haiti’s population engages in the informal economy. Due to its significance in national economies, those investing in development, including local entrepreneurs, NGOs, and multilateral aid organizations, will often target the informal sector. However, the intentions of investors may or may not align with the goals of the communities in which they are investing. Separate surveys of a fishing community in Cameroon and farming households in Haiti were conducted. To identify factors that contribute to effective community development in the Global South, the two cases were compared to determine how informal economy workers’ perceptions of investors affected their productivity and project success. Fifty Haitian farmers were surveyed to assess the impact that payments for ecosystem services had in establishing and maintaining shade-coffee agroforestry systems. Eighteen semi-structured interviews were conducted to better understand the factors that adversely affect fishers in Cameroon and their strategies to cope with them. The studies suggest that 1) when participants can identify a clear path to self-sufficiency, productivity is higher and 2) sustained support and collaboration between investors and those participating in the informal economy is conducive to higher project success rates.