The emergence in practice of worker cooperative ecosystems, which draws on the entrepreneurial ecosystems (EEs) concept, has been largely ignored in academic research. Contrasting worker cooperative development efforts in Toronto with Montréal, we affirm there are multiple and multiscalar EEs in each region, including both a dominant capitalist and a worker cooperative EE. Productive enterprises like worker cooperatives, operating with a different logic than investor-owned firms, not only construct their own EE, but the relational connectedness of the worker cooperative EE to other EEs also plays a role in outcomes. Worker cooperatives have been less successful in navigating these dynamics in Toronto than in Montréal. Future research might seek to more fully specify the relational and multiscalar configuration of regions’ multiple EEs.