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Abstract One of the challenges of designing, building, and sustaining an entrepreneurial ecosystem (EE) is how to do this in a way that is not so rigid and inflexible that it impedes the creativity and innovation it is meant to foster, yet not so loose and ill-defined that it is ultimately ineffective and short-lived. In this chapter, it is posited that this situation can be remedied by treating the ultimate market of an EE—its entrepreneurs—as one that is segmented by entrepreneurship skill level. This is made possible by a clinical assessment tool that permits the measurement of skill strengths and weaknesses and the categorization of entrepreneurs by level of skill. This, in turn, facilitates the creation of cohorts of entrepreneurs at the same skill level who can work with a coach to develop their skills. As the entrepreneurs carry out their skill development plans, the coach prepares them to take full advantage of the resources provided by the entrepreneurship support organizations (ESOs) in the EE support subsystem. In this way, entrepreneurs are connected to each other by skill level and across skill levels. Entrepreneurship support organizations are connected to each other as a team, each of which has a role to play that appropriately matches its capabilities and capacity to the skill level of the entrepreneurs it serves, which strategically links the entrepreneurs to the ESOs. The ecosystem becomes a cohesive and powerful infrastructure for developing entrepreneurs who are capable of successfully building their businesses.
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