The entrepreneurship teacher is a key factor in the promotion of entrepreneurship education, and hence should practice what he/she teaches by, at minimum, exhibiting a positive attitude towards the practice of entrepreneurship, or where possible by setting up a business. This paper investigates whether there are significant differences between secondary school teachers of entrepreneurship education who have set up a business and those who have not, in terms of personal attributes, skills, innovativeness and locus of control. Further, based on the theory of planned behavior, the study examines the extent to which contextual factors (institutions and culture) influence the entrepreneurial intentions of the teachers who have not yet set up a business. The study utilizes a survey research design to collect data from a sample of secondary school teachers (N=270) who were attending a refresher course from the four regions of the country. Likert scale questionnaire items for the various dimensions were obtained from published studies. Independent sample t tests and regression analysis were used to analyze the data. Findings indicate that teachers who have set up a business score higher in terms of creativity and enthusiasm to set up new projects. Further, institutions and cultural dimensions (uncertainity avoidance) have a negative moderating effect on perceived behavioral control for teachers who have not yet set up a business.