|| What role if any do educators have to play in developing entrepreneurship? The recent report from the EU (2006) on entrepreneurship in Higher Education highlights the importance of education in the promotion of more entrepreneurial attitudes and behaviours and refers to the challenge of stimulating entrepreneurial mindsets in young people. In particular it notes that at third level the primary purpose of entrepreneurship education should be to develop entrepreneurial capacities and mindsets and advocates an action learning approach. The report (2006) emphasises the need to use experience based teaching methods in order develop entrepreneurial thinking and states explicitly that traditional educational methods (like lectures) do not correlate well with the development of entrepreneurial thinking. It follows then that traditional modes of assessment (like exams) do not facilitate the development of entrepreneurial attitudes and behaviours. Similarly Gibb (2002) expounds a view that questions traditional educational methods in the context of developing entrepreneurship. He argues that 'entrepreneurship can play a significant role in a range of very different environments in societies across the world, within and between countries and cultures'. However, he suggests that the traditional paradigm of entrepreneurship education would need to change in order to facilitate that. He implies that entrepreneurship that exists solely in the dimension of business schools is too narrow, and hinders its ability to address major issues in society. This paper seeks to explore the fundamental challenges involved in entrepreneurial learning and teaching. The main question this paper seeks to explore is whether the use of a portfolio led assessment model for teaching key transferable skills associated with entrepreneurship education is appropriate for the achievement of the stated learning objectives and the development of key transferable skills. This paper presents some preliminary results of a pilot study involving first year level 7 and level 8 Business enterprise students at IADT, Dunlaoghaire. The findings reveal some insights into the value of portfolio assessment for first year students.