Despite the broad studies by researchers on Diasporan’s diverse support to the continent of Africa, little is known about the perspective and contributions of Diasporan Entrepreneurs. Overall, available findings tend to suggest that diasporan support to Africa mainly comes through financial, cultural, intellectual, social, and political capital. This qualitative multiple case study explores the perspective of 10 successful NYC-based Nigerian American owners about management skills and practices required to overcome transnational barriers and succeed with startup small business initiatives. Interview data were collected through semi-structured interviews, while David McClelland’s Need for achievement theory underpinned the study and served as a theoretical reference. The 4 key findings emerging from the thematic analysis of interviews data included: (a) Resilience/genuine commitment, (b) Financial/Resources management, (c) Human capital/business knowledge, and (d) Organization/Creative Problem-solving skills. Findings may contribute to positive social change as diaspora owners may use the knowledge for improving business skills, and success, which could lead to the creation of jobs and improvement in the standard of living. The Findings may also positively impact relatives, and local communities in Nigeria, as the diaspora flow of investments and remittances may increase. The result may also contribute to improving small business management skills in Africa.