Being a prerequisite of intense mutual co-operation, trust between entrepreneurs who are responsible for small and medium sized firms is an important factor of economic development. Against this background a main problem of post-socialist economies was frequently seen in a mismatch between an increased need for entrepreneurial trust on the one hand and a situation which is disadvantageous for the creation of trust on the other hand. The paper discusses the problem of how to conceptualise and study the issue of trust, and, taking the East German ICT-branch as an example, provides some insights into the actual potential of “post-socialist entrepreneurs” to develop relationships of trust. It arrives at the conclusion that in a post-socialist context the emergence of trust among entrepreneurs may be impeded because individual ideas and expectations concerning trustful business relations are sometimes (still) insufficiently adapted to both each other and the “realities” of market economy. However, actual problems of building entrepreneurial trust seem to be resolvable if they are tackled actively, i.e. if the entrepreneurs who are to engage in trusting relationships reflect upon these problems.