This chapter traces the complex evolution of entrepreneurship in Ireland, from deep-seated cultural and institutional barriers to the emergence of a dynamic ecosystem fuelled by diaspora engagement and policy reforms in the 2010s. It begins by examining the historical distrust of entrepreneurship in Irish society, rooted in cultural stereotypes and a preference for stable employment. Critics like Michael Casey highlighted the lack of an entrepreneurial spirit and over-reliance on foreign direct investment, exemplified by the departure of the Collison brothers to Silicon Valley. The chapter then explores the turning point of the 2010s, as the Fine Gael administration (2011–2016) embraced entrepreneurship as a national priority, driven by the Irish diaspora—particularly in the United States. Initiatives such as the Global Irish Economic Forum (GIEF), the Global Irish Network (GIN), and the Irish Technology Leadership Group (ITLG) played a pivotal role in fostering innovation, securing venture capital, and building transatlantic bridges. These diaspora-led networks catalysed the rise of Irish tech start-ups, yet their frequent acquisition by foreign multinationals raises questions about the sustainability of indigenous entrepreneurial growth. Ultimately, the chapter assesses whether Ireland is cultivating a self-sustaining entrepreneurial economy or merely serving as a breeding ground for global tech acquisitions. It reveals a nation at a crossroads, balancing cultural legacies, policy shifts, and diaspora-driven opportunities in its quest for economic renewal.