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What city will be the next Silicon Valley? It has turned into a tired narrative. The world is a multi – centered and complex place. It is likelier for many successors of the Bay area model to emerge, as the global ICT market comprises of many innovation hubs, venture capital attractors and assets of these unique ecosystems. It would be preferable to develop a realistic business plan, tailored after the specific needs of each locale. Regarding the ICT ecosystem of Thessaloniki: One that showcases highly educated human capital, that is hard to retain. Greek macro-economic flaws like bureaucracy, heavy taxation, chaotic and unstable policies, and constant law reforms, to a persistent record - high software piracy and a low entrepreneurship mentality keep strong till today and hinder development. The driving force behind Greek ICT has been stately or EU funded software, services, and infrastructure – far from a viable economic model, that is being put under further pressure in the aftermath of a decade long economic recession and the unfolding COVID-19 crisis. The scope of the dissertation is to study the ICT ecosystem of Thessaloniki, considering its properties and assess quantifiable and qualitative data of the financial landscape, compare them to similar cities, showcase strengths and weaknesses, classify Thessaloniki in a global scale and highlight realistic proposals and suggestions.