This study used the multiple case study research approach and presents a comparative analysis of the similarities and differences in entrepreneurship styles among second, third and fourth generation overseas Chinese and Filipinos in the Philippines. Specifically, it aimed to compare the entrepreneurs' entrepreneurial characteristics, leadership styles, and value orientation. The results indicate that the two groups are heterogeneous even though they operate business in the same country. However, slowly, the influence of Filipino culture is seen in the fourth generation overseas Chinese. The study hopes to provide new generation of entrepreneurs insights on entrepreneurial styles that need to change to cope with the fast-paced economy brought about by globalization, and traditional styles they can still adopt to capitalize on their rich cultural and ethnic background.