The entrepreneurial ecosystem, as a dynamic platform shaped by the interaction of cultural, social, financial, and institutional factors, plays a crucial role in the success or failure of entrepreneurs. In recent years, Georgia has become an attractive destination for Iranian entrepreneurs due to its economic reforms, geopolitical position, and trade relations with Iran. However, operating within a non-native entrepreneurial ecosystem presents multiple challenges. The present study aims to identify the challenges faced by Iranian entrepreneurs in Georgia’s entrepreneurial ecosystem based on Isenenberg’s model. This research is applied in purpose and descriptive–survey in nature, employing a qualitative approach. Data were collected through semi-structured interviews with managers, entrepreneurs with international experience, traders, and members of the Iran–Georgia Joint Chamber of Commerce, and analyzed using thematic analysis. Findings revealed seven major categories of challenges: financing, domestic and foreign policy issues, cultural differences, weak legal and institutional support, limitations in human capital, market barriers, and security risks. These results indicate that although Georgia’s ecosystem offers potential opportunities, it requires joint supportive policies and medium- to long-term programs to facilitate Iranian entrepreneurs’ activities. Accordingly, strengthening bilateral economic cooperation, leveraging cultural commonalities, improving supportive regulations, and addressing financial constraints could enhance entrepreneurial relations between the two countries.