Scholarship on race highlights how racism constrains the economic activity of racially marginalized actors, but seldom considers how place matters in these experiences. Alternatively, entrepreneurship scholars are particularly attuned to the role of place in structuring entrepreneurial norms, constraints, and actions, but have been slower to assess how entrepreneurship is inherently a racialized process. I link these literatures together to understand how racially marginalized economic actors navigate through unequal systems to make headway in their professional pursuits. Relying on nearly 100 interviews and a hundred hours of participant observation with Black tech entrepreneurs in Silicon Valley and Atlanta, I find that both groups held similar perceptions as to how racism constrained their entrepreneurial trajectory, but they also took into consideration the available opportunities and constraints within their respective ecosystems. Taking both racial and ecosystem realities into consideration, Black tech entrepreneurs deployed what I call racialized legitimation strategies or specialized tactics aimed at navigating racism and ecosystem norms, to make headway. Yet how they did so varied. Those in Silicon Valley oriented their actions towards making themselves more appealing to a predominantly White class of venture capitalists by gaining elite credentials. Alternatively, those in Atlanta connected with elite Black networks and that provided them with alternative opportunities. Ultimately, by examining Black entrepreneurs in two locations, we gauge to what extent the racialization of entrepreneurship is bounded by place, while also showing us the strategies Black people must adopt to navigate this unequal reality to make their mark.