This article uses census data from the 2006–08 American Community Survey to illustrate the range of Asian American entrepreneurial activities in the Los Angeles and the New York City areas and finds that Los Angeles self-employment is characterized by emerging high-skill “professional service” industries while New York continues to be dominated by low-skill traditional “enclave-associated” niches. Within these patterns, there are also notable interethnic and generational differences. I discuss their socioeconomic implications and policy recommendations to facilitate a gradual shift of Asian American entrepreneurship toward more professional service activities that reflect the demographic evolution of the Asian American community and the ongoing dynamics of globalization.