Sub-Saharan Africa in general and Kenya in particular, provide a challenging business environment to any would-be investor. In this contribution the authors first present an overview of the economic, sociocultural and institutional hurdles for small-scale entrepreneurship. These include lack of education and/or experience, gender issues, age of the company, informal economy, access to capital, access to networks, lack of cooperation, lack of equal opportunity and finally the management styles. These challenges notwithstanding, there are some success stories that flourish, in spite of rather than because of the prevailing situation on the ground. Many entrepreneurial initiatives explicitly try to learn from the current policy failures and find spontaneous ways to overcome the sociocultural and institutional hurdles mentioned above. Moreover, some progress is being made by the Kenyan government in terms of policy regulations, which creates a forum for sectoral cooperation, albeit slowly. For this reason, the paper will in particular focus on the impact of management styles. This is the point, according to the conviction of the authors, where a difference can be made. Virtues and values that specifically enhance the productive capacity, such as improved communication, initiative, and more egalitarian management are not inborn and can be learned through training and practice. Two exemplary cases will be put forward, one negative, one positive, which are intended to show that focus on management styles may also be conducive to more effective business policies in general. 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. This should be supported by government policies and regulatory frameworks, which create room for equal access to opportunities and allow for a fair playing ground in an open civil society. This is a continuous and not so simple struggle. In one case that the authors present the management style is an obstacle for growth while in the other one a more promising approach comes to the fore. They conclude that much more attention should be paid to ways in which the management and culture of a company is framed as a success factor for small SMEs.