The entrepreneurial story of Silvio Berlusconi and the Fininvest group stands as one of the most significant cases of systemic construction in Italy during the second half of the twentieth century. From the real estate venture of Milano 2 to the rise of commercial television, the group managed to integrate real estate, media, advertising, and finance into a single ecosystem, creating an innovative and scalable model. The analysis does not focus on Berlusconi's personal figure, but on the functioning of the Fininvest system as an entrepreneurial machine: vertical integration of the value chain, strategic use of regulatory grey areas, and an advertising-driven television model enabled the group to assert itself and redefine the rules of the sector. What emerges is a laboratory of strategy and organization that shows how an entrepreneurial vision can evolve into a coherent and lasting ecosystem. More than a biographical account, this volume offers a methodological lesson useful to scholars, entrepreneurs, and readers interested in understanding the logics that drive business growth in uncertain and rapidly changing contexts.