Although nobody currently living is responsible for America’s history of slavery, societal inequities established under this race-based system persist today. Enslaved people who were the labor source behind the early U.S. cotton economy received no legal rights as humans and were denied access to education and economic opportunities. The sins of slavery have caused and perpetuated structural barriers that continue to affect descendants of the enslaved. As society is driven by a tech economy that struggles with structural barriers to diversity, is now the time to study and propose reparation models? We will discuss how reparations models grounded in education and entrepreneurship may address barriers to tech and wealth-building opportunities that are out of reach to many African Americans.