When it comes to policy issues, a legal scholar would traditionally study sustainable taxation from a “top-down”perspective, thus focusing on the legislator and on rational ways to steer economic life in a more sustainable direction. Here, we start at another end—we think of it as “the bottom-calling-the-top”perspective—in order to highlight (1) a relatively new business model and its merits from a circular economy perspective, namely the so called Product Service Systems; (2) how this model faces initial problems regarding especially foreseeability and that it might therefore have problems making its breakthrough; and (3) thus might need help from the legislator. Business models typically emanate from economic life rather than from political discourse, hence the bottom-up perspective and the bottom-to-the-top expression. Within the “bottom-calling-the-top”perspective, the focus lies on the needs of the economic actors carrying out their business. This text will contribute to the integration of a “bottom-up” perspective into the sustainable taxation discussion, and we will illustrate how a proper dose of bottom-up perspective might contribute to a more viable discussion.