A growing literature argues that entrepreneurial ecosystems benefit from intermediary organizations which increase civic capital or connectivity among entrepreneurs, risk capital, knowledge-bearing institutions, sophisticated customers, and complementary service providers. These intermediary organizations, however, are seldom subjected to comparative analysis. Focusing on three regional innovation centres in Waterloo (Communitech), Toronto (MaRS), and Ottawa (OCRI, now Invest Ottawa), we find that all three organizations fostered greater connectivity within their communities, but that they did so in very different ways. Distinguishing among entrepreneur-led “community creators,” institution-led “buzz builders,” and anchor-led “cluster organizers,” we demonstrate how institutional origins and organizational design shape their programming choices and, by extension, the structure of civic capital. While the differences among Communitech, MaRS, and Invest Ottawa have narrowed over time, this analysis suggests that organizations seeking to improve connectivity in immature, entrepreneurial ecosystems face important tradeoffs.