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The wealth gap between U.S. politicians and their constituents is well documented, but business owners and executives who seek and win elected office have received less scholarly attention. From the graft and corruption of the machine era to the formation of trade associations, government affairs units, and political action committees (PACs), business interests have a long history of involvement in American politics. Business takes a multi-pronged approach to political activities, not only lobbying policymakers but also supporting candidates and mobilizing employees. Over time and across places, large shares of candidates and elected officials at all levels of government have business backgrounds. Why do voters elect business owners and executives? Where—or under what conditions—are business candidates likely to run and win? Using a mix of observational and experimental data, I examine both the supply of and the demand for business executive candidates. With an original dataset that includes gender, race, occupational background, and political experience for nearly 4,000 mayoral candidates from 260 cities over 50 years, I investigate whether and how the electoral fortunes of business executive candidates vary systematically with characteristics of cities, such as geographic region, political institutions, and population. Results of a conjoint survey experiment provide insight on voters’ perceptions of business candidates, their competence, and their policy positions.