Professionals and entrepreneurs returning to developing countries from developed countries play key roles in the technological ‘catch-up’ of their home countries, but they are rarely well-conceptualized by the theories of globalization. This is especially the case in Asia. The American-trained Chinese engineers who returned to Taiwan were instrumental in creating Taiwan's excellent semiconductor industry during the 1980s and 1990s. In a similar vein, since the late 1990s, Chinese professionals returning to the mainland have also emerged as the most innovative industrial and capital agents in the technological industry. In this article we compare the roles and business strategies of transnational entrepreneurs on the two sides of Taiwan Strait in the information communication industry (ICT). While these Chinese returnees share striking similarities in their educational and personal trajectories, we identify major structural differences underlying their particular resources and commercial strategies. These empirical findings move beyond the assumptions of common behaviour by overseas Chinese, for they highlight the different political economic dynamics between mainland China, Taiwan and the United States in shaping the divergent engagements of these entrepreneurs in the emerging global technology industry.