Living Labs aim to engage in user-centered design practices where users are included in their daily life environment as innovative agents. However, empirical insights in end user engagement in Living Lab practices are currently lacking. This article focuses on opening up this black box of user engagement by analyzing the involvement of a group of entrepreneurs in a Living Lab smart city pilot in Amsterdam, the Climate street. The goal of the article is to analyze how and to what extent the Climate street enabled the involved entrepreneurs to engage in bottom up innovation. Theoretically, the article explores this pilot from a Science and Technology Studies perspective, specifically its notion of the socio-technical network. The article concludes that user innovativeness was limited by the pre-configuration of the entrepreneur as lay tester rather than as an active user-innovator. Furthermore, it is suggested that the inherent tension in Living Lab practices between configuring users and actual user practices hampers user innovativeness in general. Granting users more agency and opening up Living Lab practices to daily life dynamics stimulates the transition from tester to innovator in a daily life setting and subsequently makes entrepreneurs more readily smart.