This paper is an effort to reflect on and document the successes and challenges of a group of ten (10) investment funds, designated as the “Enterprise Funds,” established by USAID following the collapse of the Berlin Wall in 1989 and the break-up of the Former Soviet Union in December, 1991. At the time of this report, nine of the 10 Enterprise Funds have now reached the point in their life cycle where they have ceased making new investments and have either completely exited their investment portfolio or are in the process of doing so. The proceeds of their investments, which in many cases significantly exceeded the amount of the original USAID grant, have been utilized to i) form Legacy Foundations in their host countries which will continue to support private sector development objectives, and ii) return a portion of the original Grant amount to the U.S Treasury.