Italy’s aging population and shrinking villages pose significant challenges to its stagnant economy despite the pivotal role of Italian SMEs. To address this issue, this project aims to (1) understand the relationship between digital activity, internet connectivity, and small business development in the Lombardy and Sicily regions, specifically Sondrio and Enna province; (2) understand problems currently faced by small business owners and how digitalization can help them strive; (3) develop accessible digital toolkit for small businesses in Italy to scale, increase their sales, and create a greater sense of place. The engagement process with small business owners in Sondrio, Vizzini, and Centuripe highlighted the gap in SMEs digital adoption and the practice of the territorial capital (Perucca, Eur Plan Stud 22(3):537–562, 2014), in which SMEs see themselves as a part of a larger ecosystem built on local connections. Therefore, the project proposes a web platform incorporating digital storytelling and localized e-commerce marketplace to facilitate SMEs expansion and growth by focusing on the unique stories and characteristics of Italian SMEs. This project provides a targeted intervention to promote economic growth in Italy’s shrinking villages and aging population, recognizing the vital role of SMEs in the country’s overall added value.