The term Generation Y describes people born between 1978 and 2000 and is also a much discussed topic recently. As this generation ages it moves into the focus of recruiters and many psychological publications address the workrelated motivation and personality structure of this generation. Despite the huge number of existing studies covering young Generation Y employees the number of publications addressing Generation Y entrepreneurs is very limited. The main goal of this thesis is to analyze the general personality structure of Generation Y entrepreneurs in the so called DACH region, as well as their work-related values and motives. Furthermore this work addresses possible differences between employees and entrepreneurs of this generation. To round up the study it also tries to identify differences between other generations. These goals are achieved through both, a theoretical analysis of existing literature, as well as an empirical study. The empirical part is based on the analysis of personality assessment data of (n = 17.790) Generation Y profiles gathered by the online as-sessment platform mercurypuzzle.com. This platform utilizes two recognized, psychometric instruments Shapes & Views from the assessment company cute in order to create a detailed report of a candidates personality and their workrelated values and motives. Through the comparison of literature addressing general entrepreneurial personality studies and the results of the empirical data analysis it was able to demonstrate the existence of major differences between theoretical described personality structures of entrepreneurs and Generation Y entrepreneurs. Other findings suggest that there are statistical significant differences between those two classes. Corre-spondingly Generation Y entrepreneurs are more directing, persuasive, socially confident, conceptual, imaginative and autonomous. On the other side it appears that they are less agreeable, conscientious, systematic and competitive. As far as the workrelated values and motives are concerned, Generation Y entrepreneurs value financial rewards, flat hierarchies, recognition of performance, fun while working, development opportunities, a high identification with their work and a secure workplace. The high value of security is especially interesting as it is one of the major differences to existing literature. Based on the empirical research of this thesis further research can be done regarding economic implications of these findings.