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The political agenda of transition from a command to a market economy in Estonia also marks the development trajectory of ICT and entrepreneurship. The efforts of the Estonian government in the development of ICT infrastructure, education and e-government from the 1990s, and entrepreneurship promotion in the 21st century, manifest as political entrepreneurship. Political entrepreneurship is seen on three levels: (1) as the investment or re-allocation of resources into a desired object; (2) a change of broader economic (freedom) policy and institutions, incl. the public sector; (3) the change of societal order and transformation of the political system and its institutions.Societal changes in Estonia in the 1990s were characterised by a lack of resources; against this backdrop, some political entrepreneurs played a triggering role in launching ICT infrastructure projects. The Estonian Parliament was also quite enterprising at this time. The competence and motivation of decision-makers in the Parliament have changed significantly since the 1990s and early 2000s, which has influenced political decisions in subsequent periods. By using the case of the academic data network EENet, and its chronology, we analyse the development of political entrepreneurship in Estonia. The question is whether today’s decisions facilitate a continuation of the success story that began in the 1990s.