This chapter focuses on entrepreneurship and self-employment in an era of competitive product and labor markets. As outlined in further detail in Section 3, researchers suggest that people may be increasingly required to create their own businesses to counter the potential loss of traditional paid jobs due to increasingly competitive global labor markets and the rapid development and deployment of artificial intelligence (AI) and automation (Hamilton, 2016, pp. 95–96; Koebler, 2014). Entrepreneurship has therefore been promoted as a vehicle to support continued economic development, rising living standards, and job creation in this globally competitive environment (Audretsch, Keilbach, & Lehmann, 2006; Hussain, Sultan, & Ilyas, 2011; Parker, 2009; van Praag & Versloot, 2008). Entrepreneurs, for example, have scored highly on employment creation, productivity growth, and high-quality innovations (van Praag & Versloot, 2008, p. 65). This chapter examines how Cloud technologies may facilitate the creation and development of internationally orientated small- and medium-sized enterprise (SME) entrepreneurship. While the exact nature of entrepreneurship has been widely debated (Casson, 2003; Iversen, Jorgensen, & Malchow-Moller, 2008; Parker, 2009; Schumpeter, 1942), Shane and Venkataraman (2000) suggest that entrepreneurs are individuals who exhibit a willingness to take risks, as they actively seek out business opportunities. Entrepreneurship has further been associated with self-employed workers, start-up firms (nascent entrepreneurs), and SMEs (Parker, 2009; Reynolds et al., 2005). More recent research has examined the emergence of “next generation” entrepreneurs, so-called “digital natives,” whose innovation and sales strategies are increasingly built on emerging internet-based technologies (Gagliardi, 2013). The size of this potential market is reflected by the approximately two billion people who are currently connected to the internet, with a further three billion people forecast to be online by 2020 (Wadhwa, 2014).