This paper discusses the idea that for Ontario's colleges to meet the intentions and legal requirements of their original mandates, they will need to consider extending the scope of their advancement departments to implement key components of both the Total Resource Development Model (Worth, 2002, ascited by Barrette, 2013) and the Strategic Philanthropy Model (Porter and Kramer, 2002). The first section of this paper will provide a brief history of the purpose and development of the college system in Ontario with particular emphasis on their legal mandate. The next section of this paper then briefly reviews college student demographics and outlines the crucial relationship between the learner and resource needs. A review of the current college funding system is also presented with the author's forecast for future needs, outlining the tense relationship between public and private funding. The final section of the paper explores a model called The Giving Matrix, in which the author attempts to explore the relationship between altruistic philanthropy versus financial contributions and their social/economic impacts. This is an endeavor to provide a deeper understanding of how colleges can organize their advancement departments to better attract Strategic Philanthropy dollars.