The United Nations declared 2025 the international year of the co-op. In an economy strife with wealth accumulation, and asset ownership concentrated within the top income bracket, cooperatives present a democratically governed and collectively owned alternative to the norm. Community Investment Cooperatives (CICs) are an example of such a mechanism, where people from a certain area can invest in local businesses, in exchange for a small financial and/or social and environmental return. Although this model is nascent in the wider, national community economic development landscape, it holds a lot of potential for significant change through collective action and ownership, especially in Ontario, where capital flight has been a persistent issue. This paper investigates potential barriers and enablers in the uptake of CICs among individuals in Ontario. To explore this more deeply, it looks closely at existing community-based, financial capital-building organizations both, at the national and the provincial level and what conditions have enabled their growth. Additionally, it explores barriers and enablers for existing CIC owners and potential leverage points across the province. Grassroots organizations like CICs do not have the adequate resources required to achieve scale because of deeply entrenched structural, cultural and legal barriers. They are subject to more scrutiny from all institutions and individuals because of the risks associated with allocating people’s money for stable returns. Despite these challenges, several possibilities exist for CICs in the form of community connections and partnerships within the system. Isolated efforts by individual actors in the system would be inadequate to truly empower and strengthen CICs or any community-based effort for that matter. The responsibility to create enabling conditions for these organizations lies with actors across a wide spectrum, ranging from individuals to policymakers, but those with more power need to be more proactive and supportive of these initiatives for them to scale up effectively.