This paper combines the empirical finding of a functional specialization of cities with regional dynamics. We distinguish between cities dominated by headquarters and service firms (urban agglomerations), those with large stand-alone production plants in one sector (industrial agglomerations), and cities with integrated smaller firms (industrial districts). Based on German data, we find differing dynamics across these three city types. Cities that host basic research or integrated incumbents are more conducive to entrepreneurial activity, whereas the opposite is true of industrial agglomerations. Urban agglomerations dominated by headquarters with only administrative functions and the service sector are not very entrepreneur-friendly, either. However, although this type of city provides few externalities for startups in manufacturing, they could very well provide opportunities for service sector startups.