Using Singer's typology of different types of immigration gateways, this study mainly addresses how metropolitan area conditions impact ethnic labor force entrepreneurial choices across ethnicity and gender, within the contexts of different types of immigration gateways. Employing the 5 percent 2000 Integrated Public Usable Microdata Samples and a multilevel regression strategy, this study demonstrates that different types of immigration gateways have distinctive impacts on ethnic entrepreneurship. After controlling for both personal- and metropolitan-level characteristics, it is found that whites and blacks are more likely to own businesses in newer immigration gateways, while Hispanics and Asians are more likely to do so in the more established gateways. In addition, differences as to the interaction effects of gender and regional labor markets are the most significant for blacks and Asians. Such interaction effects reshape gender differences in business ownership across ethnic groups. Copyright (c) 2010 The Author. Growth and Change (c) 2010 Wiley Periodicals, Inc..