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In this episode of Nomads 50+, host Chris Kalaboukis speaks with Matteo Cerri, an Italian entrepreneur who has spent the last 30 years in London building businesses in finance, insurtech, media, and hospitality. Over time, his work naturally evolved into a location-independent lifestyle—long before “digital nomad” was a buzzword.
Matteo shares how COVID accelerated remote work for him and many of the companies he’s involved with, making it possible to manage teams across countries and time zones entirely online. We dive into his unique perspective on choosing a home base as a nomad, the challenges Brexit created for European business owners, and why Italy continues to tempt him back.
For those dreaming of Italy, Matteo offers insider recommendations—like Puglia, Lecce, and Cilento—where the lifestyle is rich, the crowds are fewer, and the internet speed is fast enough for any remote worker. He also explains how most Italian towns, even the smaller ones, now have excellent connectivity, easing one of the top concerns for digital nomads.
We explore how locals view nomads in Italy (hint: it’s far more positive than in some countries), the importance of integrating into the community, and how smaller cities can offer a more authentic and affordable experience than tourist hubs.
Whether you’re considering a move to Italy or simply curious about the realities of remote work across borders, Matteo’s insights are full of practical tips and cultural wisdom.