This comparative analysis examines the neighboring entrepreneurial ecosystems in Bulgaria and Romania. In transitioning from past planned economies, these countries maintain similar approaches to entrepreneurship, yet they also exhibit distinct differences. Secondary data analysis revealed that both countries maintain a highly educated workforce with high start‐up skills and similar levels of global competitiveness in growing economies, while still facing low‐risk acceptance and low opportunity perception. On the other hand, Bulgaria excels in networking, building joint venture deals, attracting investment, maintaining a stronger focus on R&D, and the ability to nurture collaboration between industries and universities, while Romania displays stronger political stability, greater ease in starting a business, a more advanced infrastructure, and easier access to credit. As these countries capture the strengths of their respective economies, both Bulgaria and Romania may one day represent powerful hubs of innovation. Organizational leaders may use this study as a comparative springboard to learn new, yet workable policies that may support entrepreneurship within their respective ecosystems.