This Essay, which is a lightly edited version of the keynote address delivered at the Drexel Law Review Symposium on “Inheritance and Inequality” at the Drexel University Thomas R. Kline School of Law on September 27, 2024, examines the intersection of race, wealth, and social enterprise policy. It challenges prevailing myths about entrepreneurship and upward mobility in the United States. The Essay also critiques the cultural hegemony and political rhetoric surrounding the “American Dream,” particularly the promise of business ownership as a pathway to economic success, which often obscures structural inequalities. Using family history as a lens, the Essay highlights the limitations of generational wealth transfer and exposes the systemic barriers faced by marginalized communities. It introduces the concept of the “entrepreneurial industrial complex” to explain how dominant narratives perpetuate inequality and examines the shortcomings of current policies supporting small and minority-owned businesses. The Essay concludes by proposing structural reforms to prioritize measurable social impacts, innovative business models, and equitable resource allocation to foster a more inclusive and sustainable entrepreneurial ecosystem.