Entrepreneurial philanthropy gives the impression of being a paradox because personal gains and societal benefits are generally seen as opposing forces, which particularly will become clear when philanthropreneurs emerge in the non-profit sector. It is suggested this charitable giving with venture bent might affect an alignment of both worlds. What will happen: a culture clash or a smooth transition? On what issues a partnership is easy to reach, and what are causes for concern? To answer these questions, a literature study has been carried out to construct a preliminary “theoretical framework of entrepreneurial philanthropy alignment”. In this paper a framework has been tested among seven Dutch senior executives of non-profit organisations and five philanthropreneurs. A series of semi-structured interviews were held to explore the variables that could determine the degree of their alignment. These variables were grouped in three domains: 1) Leadership, the linking path; 2) Strategy, the guiding path; and 3) Culture, the driving path. The outcome gave insights to modify and upgrade the theoretical framework, and provided support to study alignment maturity more extensively in a subsequent survey.
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