Amidst the debate about what sort of technology is appropriate for achieving sustainable development, Free and Open Source Software (FOSS) offers some solutions to today’s technology problems for many developing countries. However, there is a paucity of empirical evidence to help us understand the potentials FOSS technologies have for small businesses in Sub-Saharan Africa. This research utilizes nine case studies data from seven African countries to find out how entrepreneurs are leveraging FOSS to help them create sustainable business based on openness. The findings show increasing awareness of the business potential of FOSS, and a business model incorporating both FOSS and proprietary software is needed to run a sustainable IT business in these countries. However, the lack of skilled FOSS developer base, the absence of appropriate policies, and poor payment habits by clients are just some of the factors affecting businesses. Other problems encountered, possible solutions to those problems and lessons to be learnt from each case study are also discussed. The research offers entrepreneurs, ICT practitioners, and policy makers the platform to understand the Why and How FOSS technologies are impacting the traditional way of doing business in Sub-Saharan Africa.