Many initiatives have been taken to promote the private sector, which is now considered the engine for growth in all economies. A common approach to private sector development is the building of capacities for identification of innovative ideas and transforming these into bankable business plans. Unfortunately, little effort has been done to systematically learn from such experiences and hence inform improvements and replication for impact. This paper analyses the experience of organising an online internet based business plan competition by the University of Dar es Salaam Entrepreneurship Centre in collaboration with Business in Development Network Foundation based in Netherlands in 2007. The aim is to explore and share challenges, lessons and critical success factors for such and related initiatives.