Technology advancements, particularly those related to the Internet of Things (IoT), artificial intelligence, open databases, and big data concepts, have resulted in citizens becoming more sophisticated, demanding, and informed. Consequently, they require more sustainable city governance, encompassing not only tangible assets but also intangible assets such as knowledge and intellectual capital. This chapter aims to analyze the problem of monitoring the relationship between regions’ intellectual capital and their sustainable management, sketching the formulation of a dynamical model for that purpose. The basic concept is that it makes sense to assume that each territorial unit (city, region, etc.) has its own intellectual capital and that the sustainability of that unit depends on it. In this chapter, alternatives for modeling and monitoring this relationship are identified and a static (fixed-time) and simple example of this problem, using Portuguese official open data, is used to illustrate the kind of problems involved.