Sub-Saharan Africa in general and Kenya in particular, provide a challenging business environment. In this contribution the authors first present an overview of the economic, sociocultural and institutional hurdles for small-scale entrepreneurship. These challenges notwithstanding, there are some success stories that flourish. Many entrepreneurial initiatives explicitly try to learn from the current policy failures. The paper will in particular focus on the impact of management styles. This is the point where a difference can be made. Two exemplary cases will be put forward as illustration of this point. Management styles and technology policies are required that explicitly defy the compartmentalization of the society by cultivating a community spirit in which differences may flourish, supported by government policies conducive to a fair playing ground in an open civil society. The authors conclude that much more attention should be paid to the management culture as a success factor for small SMEs.