Recent increases in the prices of agricultural commodities have spurred a surge of private investment into farming and agribusiness. Given the right types of large-scale investment, this can have a transformative effect in underdeveloped rural areas and have a positive effect on national economic development including the provision of domestic food supply to urban areas that can reduce dependence on food imports. This study analyzes the experience of the Commonwealth Development Corporation (CDC) as an investor in commercial smallholder and estate agriculture and agro-processing in Sub-Saharan Africa and Southeast Asia and the Pacific between 1948 and 2000. A simple analysis of the data was undertaken to determine whether success and failure can be correlated to any critical factors. Seventy-nine (or 49 percent) of the projects were classified as failures or moderate failures in financial terms. This review of CDC agribusiness investments corroborates the view that agribusiness investments are risky, particularly when the investment is in a start-up. While only one fifth of projects were rated complete failures, one third of equity investments generated at least moderately attractive internal rates of return, and overall about 55 percent resulted in financially viable projects. The majority of projects in both Asia and Africa ended up being sustainable businesses that delivered broadly the number of jobs and level of turnover that had initially been anticipated. This raises the question of why, despite this low level of returns on equity, these businesses often survive. The analysis of CDC's agribusiness portfolio demonstrates both historical potential and pitfalls and illustrates the need to continuously adapt and innovate to achieve both political and commercial sustainability.