The starting premise of this paper is that business models can transform social reality—sometimes to an extreme. Then, building on the concept of “grand challenges,” we argue that such transformations can be either positive or negative in nature (or both)—even in the case of business models designed to improve value not only economically but environmentally and socially as well. To further our understanding of the negative aspects, we introduced two conceptual categories of business model: those for oppression or depletion and exclusionary ones. We further argue that bringing the notion of grand challenges center-stage highlights four elements that can contribute to emerging research and inform practice on transformational business models. These elements are: participatory forms of architecture; multivocal inscriptions; scaffolding; and proximity (understood as a caring concern for the “other”). They are central components of what we name transformational business models.