There is mounting empirical evidence that there is intergenerational transmission of parental preferences for entrepreneurship. However, much of the work on this topic is not explicit about the role of values in this transmission process. Furthermore, nearly all studies neglect potential heterogeneity of values among entrepreneurial parents. This paper contributes to the literature by making use of a natural experiment that allows (1) identifying a group of entrepreneurial parents who have a distinct priority of challenging existing conditions ("mastery") and (2) detecting whether this value orientation is transmitted. Comparing German entrepreneurs two decades after Reunification reveals that the children of self-employed parents who encountered a great deal of resistance in the socialist German Democratic Republic due to their self-employment are much more likely to give mastery as the reason for running their own venture compared to entrepreneurs whose parents did not have to overcome this sort of challenge.