Greenwood Tulsa, Oklahoma once housed the most thriving black community America has ever witnessed. It was such a powerhouse that it was given the nickname, “Little Africa.” The success of the community was envied to the point that it was burned to ground by white neighborhoods that sat on its outskirts. This time period of the city’s history is also referred to as Black Wall Street - BWS. The actions of the leaders and entrepreneurs who worked together to build such an upbeat atmosphere is something that is praised, but has not been effectively recreated. In today’s black communities around the nation, there are not as many black business owners within the black community and there is no effective support system amongst those who are in the business arena. This article will seek to address this issue by using qualitative data to analysis whether the, success of Black Wall Street can be recreated and sustain in black communities today? The sample group, which consists of a handful of black owned businesses, from Cleveland, Ohio was chosen for this study. These owners will undergo an interview they agree to partake in to inquire about their experiences, hardships and prevention techniques they have deployed to counter any controversy faced along the road of entrepreneurship. Lastly, solutions will be suggested to catapult things into a different direction. There have been barriers put in place to stagnate the progression of African Americans in society from regaining what the past once had, but is now lost. Through unity and activism, it can be sustained for good.