Personality traits and parenting may relate to entrepreneurial competence (EC) and entrepreneurial interests (EI), which both are central elements of Holland's E-type. Three hundred and twenty 10th grade students and 139 small business founders from East Germany were studied using structural equation modeling. Results showed that an entrepreneurial personality (low agreeableness and neuroticism, high extraversion, openness, and conscientiousness), and authoritative parenting were linked to adolescent EC in both samples. EC predicted stronger EI, which in turn related to entrepreneurial career prospects in the students, and to an earlier timing of the first business start-up in the founders. Concerning entrepreneurial success, an early start-up and an entrepreneurial personality of the founder were both found to be beneficial. The discussion concentrates on two implications of the findings: bank professionals dealing with venture capital loans would profit from a more thorough assessment of personality traits and programs to foster entrepreneurship should address adolescents in addition to adults.