It is argued in the article that the peaceful transition to capitalism in communist countries was not possible without the co-action of the nomenklatura, whose interest was to transform their informal access to state-owned capital into an authentic 'grand entrepreneurship'. The necessary acquisition of physical capital was achieved by means of mass privatisation schemes in which the nomenklatura took advantage of their social capital and information asymmetries. In the Czech case, there were three social groups competing for a position among the new entrepreneurial elite. The initially large gains of the nomenklatura gradually eroded when new businesses opened to domestic and international competition, where competitiveness depended on endowments of human (entrepreneurial) and economic capital. In the subsequent wave of ownership restructuring, initiated after 1994, the former nomenklatura was partially squeezed out of the tradable sector, which was occupied by better skilled foreign and domestic entrepreneurs. The exiting entrepreneurs converted their holdings into consumer goods, or defected to sectors less open to competition, where the alignment of social capital and bureaucracy persisted. Their position depends now on the pending reforms of public administration and the search for a more efficient social model.