The World Economic Forum in Davos suggested that promoting entrepreneurship could be a solution to the problem of youth employment, which is a serious issue with 75 million young people out of work around the world. The entrepreneurial decisions of young people are especially important in regions where economic opportunities are restricted and people choose to move from that region. Two of such regions are East Germany and Northern Cyprus. In this article, the authors are interested in analyzing entrepreneurial tendencies of business and economics students from Northern Cyprus and East Germany in order to provide context-specific knowledge. For this purpose, a survey was conducted at the Technische Universität Dresden and the Near East University with n = 293 participants in 2016. The results were analyzed by using a logistic regression analysis. The study includes with policy implications on the transformation towards entrepreneurial universities to meet the different needs of small and poor cities.