The paper deals with self-employment of one-(wo)man-firms as the smallest units of entrepreneurial companies and focuses at the blurred boundaries between dependent work and self-employment. We call the overlapping identities hybrid entrepreneurs. Based on the collected data it can be shown that the hybrid self-employed differ significantly from non-hybrid ‘regular’ entrepreneurs with respect to selected socio-demographic characteristics, professional, as well as company-specific factors. The paper takes up several of the findings and tries to discuss them in a framework of (micro) organizations, institutions and self-employment. Taking the case of hybrid employment fosters crucial and provoking questions for an appropriate understanding of the division of enterprises and occupations.