“Transformational philanthropy” may be a new term to some of you. Here is an easy way to understand the concept: imagine a gift that has as profound an impact on the donor who makes it (and often their family) as it does on the organization receiving the gift. That is the essence of transformational philanthropy. In this paper, we will examine the "natural" benefits that accrue to professionals and charitable organizations that help the families with whom they work remain together. In short, we will look at how to create multi-generational, transformational philanthropy, which results in multi-generational philanthropists and donors.