This chapter examines how cooperatives emerge, evolve, and respond to changing economic, social, and technological environments. It first explains how cooperative start-ups differ from investor-owned firms. Cooperative formation is a form of collective entrepreneurship, driven by shared social or economic needs rather than private profit. The process involves identifying common needs, organizing committed members, designing an alternative business strategy, building participatory governance structures, and completing legal registration. Because founders receive only “one-over-n” rewards, cooperative entrepreneurship relies heavily on intrinsic motivation, social commitment, and supportive ecosystems such as feasibility studies, mutual funds, and advisory institutions. The chapter then analyzes cooperative evolution after maturity. Cooperatives may face obsolescence, internal rent-seeking, and rigid organizational cultures. Post-maturity paths include demutualization (bankruptcy or conversion into investor-owned firms) or reorganization within the cooperative framework through mergers, alliances, subsidiaries, and organizational innovation. Comparative cases show failure in French consumer cooperatives, which resisted modernization, and success in Italian consumer cooperatives, which adopted pragmatic strategies, strong federations, and large-scale retail innovations. Finally, the chapter highlights the rise of innovative cooperatives—such as Italian social cooperatives, French business and employment cooperatives (CAEs), and citizen-led renewable energy cooperatives—responding to crises in welfare, employment, climate, and community. These models expand membership beyond traditional users or workers, strengthen collaboration with public institutions, and promote citizen participation, social inclusion, and collective responsibility in addressing contemporary social needs.