Entrepreneurship education is currently considered a relevant policy instrument in the promotion of economic competitiveness, and social cohesion. Despite the significant increase in the number of training courses and teaching initiatives, there is still a lack of consensus regarding the most impactful teaching methodologies in entrepreneurship education. In this chapter the role of companies’ in entrepreneurship education is assessed, mainly in the development of students’ enterprising qualities, through a case-study analysis. The ‘Learning to Be’ programme, promoted by the University of Aveiro, is an innovative teaching approach aiming to foster entrepreneurial learning in non-business students, through an experimental learning methodology inspired in the Design Thinking process. In this programme, students were challenged to develop viable solutions to real problems proposed by companies. Overall, students stated that participation in the programme had an impact on them, providing a clear understanding about companies’ reality and possibilities to deal with and solve real problems. This also enabled students to develop their intrapreneurship skills (that is, acting like an entrepreneur within an existing company), which is not addressed in most entrepreneurship educational programmes and initiatives. Regarding the impact on students’ entrepreneurial personality traits, a slight increase in students’ GET Test (General Enterprise Tendency Test) scores was observed when taking the Learning to Be programme, although students maintained medium enterprising qualities both at beginning and at the end of the programme.