Both Rotterdam’s Kop van Zuid and the Glasgow Harbour waterfront developments are examples of different forms of European urban entrepreneurial megaprojects. They are both situated on formerly vacant land in older industrial cities. In Rotterdam, the municipality has taken the initiative in planning and developing the megaproject, while in Glasgow, this task has been left to the private sector, with the City functioning as a facilitator. While urban entrepreneurialism and megaprojects have been discussed in academic literature for almost three decades, there are too few case studies which delve into the specific visions guiding these projects, the goals which they are meant to achieve and the positions which different actors play. The aim of this article is to analyze the relationship between these visions, goals and positions of actors in megaprojects and whether these relationships can explain how the different outcomes are produced. What we see is that in municipally‐led projects, entrepreneurial goals are more easily formed and implemented than when the public sector acts only as a facilitator to private developers. It will also argue that it is not only structural contexts which are important in determining the types of megaprojects which get built and the success which they achieve, but also the specific values, visions and goals that different stakeholders have.