Increasingly, the role of the instructor is changing from the ‘dispenser of knowledge’ to facilitator of students’ self-learning. In light of this changing reality, instructors across disciplines are being asked, in essence, to develop an entrepreneurial mindset themselves, both in devising their courses and implementing them. At the College of Management (COMAS) in Israel, we have been applying this vision both to the development of course curriculum and to our learning objectives. In this chapter, we reflect on this curriculum-building process. We begin by laying out the rationale for this vision through a brief overview of the much-talked-about gap between higher education and employment and the value of honing entrepreneurship skills in order to increase students’ employability. Then we provide a descriptive analysis of two models of innovative teaching methods that are currently being experimented with and piloted at the college: Experiential Distance-Learning (EDL) and Personalized Project-Based Learning (PPBL). We focus on the innovative nature of these courses and the challenges in their implementation. Finally, we offer a wider perspective of curriculum innovation in an environment in which ‘rocking the boat’ is not always revered and short-sightedness can trump the benefits of experimentation in teaching methods for the long run.