This paper develops a first conceptual understanding of motivations and success/survival factors of rich-to-poor Diaspora Entrepreneurship (DE) by focusing on an individuals cultural intelligence and learning ability. Rich-to-poor DE addresses entrepreneurial activities conducted in developing or emerging countries by diasporans originated from developed ones. Despite the growing research interest in the phenomena of DE and its increasing importance for societies and economies, previous researchers have almost solely focused on entrepreneurship by diasporans whose country of origin is an emerging or developing one (poor-to-rich DE). This type of DE has been considered to be driven mainly by necessity, an outcome of the lack of financial and economic alternatives in the home country (Cohen, 1997). Evidence from business practice, however, shows the existence and significance of rich-to-poor DE, which is assumped to be more opportunity-driven. The aim of this paper is to clarify the difference between rich-to-poor DE and poor-to-rich DE, and to develop research propositions regarding motivations and success/survival factors of the rich-to-poor type employing cultural intelligence theory (Earley, 2002) and learning theory.