This paper investigates the persistence of self-employment in the districts of Kaliningrad, a Russian exclave, between 1925 and 2010. The area experienced a number of disruptive historical shocks during this period. This setting rules out the fact that the persistence of self-employment can be explained by the persistence of institutions and culture. Nevertheless, a high level of persistence of industry-specific self-employment rates is found. It is argued that a historical tradition of entrepreneurship created an awareness about the entrepreneurial potential of regions among the new population that was yielded after the collapse of the Soviet Union. This effect seems to be higher in regions where a specific industry was advanced in terms of technology use.