This chapter argues that Thai Yunnanese transnational entrepreneurs have multiple identities in interstitial and relational contexts through everyday practice and performance. Set within a marginalised stigmatised background, these Yunnanese descendants with Thai citizenship have attempted various strategies to reconstruct their identity: business aestheticisation, professionalism, and socialisation; identifying with a Taiwanese identity; accentuating a Thai identity; distinguishing Thai Yunnanese identity; translocalising a People’s Republic of China (PRC) Yunnanese identity; and transnationalising a Chinese identity. Through these aspects, this chapter demonstrates how the Thai Yunnanese transnational entrepreneurs have ingeniously adopted polychotomisation and multi-complementarisation in their assertion of multiple identities to gain diverse positive outcomes. Critically, this chapter, based on qualitative research, has contributed to the understanding of ethnic identities through the lens of an oft-neglected group—Thai Yunnanese—in the nexus of transnationalism, entrepreneurship, and other cultural markers. Finally, this chapter departs from the debilitating nature of assimilation explanation and dualistic perspective in articulating the remaking of a new wave of entrepreneurs that has gone beyond the narrow definition of utilising common background and migrant experience in identity construction.