The Baltic people gained notability with their successful use of culture to protest collectively against the common Soviet oppressor in the late 20th century. Rational choice theorists have argued that large rebellious movements are paradoxical because potential revolutionaries face participation and leadership problems. This paper explores Estonia’s “Singing Revolution,” and shows that ethnic Estonians used their cultural beliefs and singing traditions as an informal institutional solution to overcome the collective action problems with organizing and participating in mass singing protests against the Soviet regime. The paper extends the standard rational choice framework to include a dynamic institutional perspective on social change. The success of Estonia’s “Singing Revolution” might be ultimately attributed to the manifestation of entrepreneurship in the form of cultural leadership in pre-Soviet Estonia. Only by adopting and using their ancient cultural legacy facilitated by creative entrepreneurs-leaders were Estonians able to succeed in voicing their true governance preferences in the summer of 1988.