In this paper we aim to use the Swedish example of entrepreneurship in education as a springboard to discuss the unexpected alliance between student-centered progressive education and the commercialization of schools. In doing so we wish to highlight the effects of this alliance on the relationship between teaching and learning and, consequently, on the teacher-student relation. In order to do this, we will first examine the conditions for the commercialization of contemporary education, and its impact on the teacher-student relation. Having done so, we will turn to progressive education, examining the curious link between the ideal of student-centeredness and the economization of the role of the student. The paper will conclude with a discussion on some inherent tensions visible in entrepreneurial learning, being at once an effect of the commercialization of schools and a pedagogical project firmly rooted in progressive ideals.