Entrepreneurship promotion continues to be an important domain for economic policy and growth. Closely related to entrepreneurship promotion are the very individuals engaging with entrepreneurship, whose belief and efforts to succeed are highly correlated with their view that they ‘have what it takes”, measured as entrepreneurial self-efficacy (ESE). ESE has thus become a critical factor toward understanding entrepreneurship support. However, most extant scholarship focuses on formal and university education, while little is said about incorporating entrepreneurship and ESE with technical vocational education and training (TVET) to develop entrepreneurs. This is surprising because so many micro and small businesses, particularly trades, are heavily anchored in TVET. This study compares academic and TVET post-secondary students in Trinidad and Tobago to determine the factors that enhance their ESE. Data emerged from three (3) regression models explaining how academic and TVET students’ ESE are correlated with several factors. Parents with a university degree, friends who are entrepreneurs and an extracurricular focus on entrepreneurship were vital factors that saw a positive correlation with ESE among the TVET population. In contrast, academic students are driven primarily by experiences. Full-time work experience and entrepreneurial experiences were significantly correlated with the ESE of academic students. Our work highlights that academic and TVET students’ ESE have different world views that impact education. This study demonstrates the importance of tailoring entrepreneurial learning for TVET students by linking ESE with cultural capital theory. We found that when teaching academic students entrepreneurship, more emphasis should be placed on experiential learning. Our research provides empirical findings we believe to be both unique and highly relevant to the literature of entrepreneurship education.