The paper presents a content analysis of factors influencing whether Venture Capitalists and entrepreneurs seek out and begin cooperating. A considerable amount of public funding in the form of Venture Capital (VC) has been made available in Europe, especially in its least developed parts, to boost economic growth. Studies show that this support for small and medium enterprises only partly attains its goals. Instead of financing the earliest stages of the development Venture Capitalists (VCs) predominantly invest in later stages and instead of equity investment provide mezzanine loans. VCs state that deal flow and quality could be higher, while entrepreneurs complain about problems attracting capital necessary for growth. The analysis suggests that a complex system of interdependent factors influences the willingness and readiness of entrepreneurs to partner with VCs, and the VCs valuation of such partnerships’ potential. It also appears that most important factors affecting the issue under study in Central and Eastern Europe (CEE) are different from those in the countries with a more mature VC industry. The lack of awareness about VC, both in general and in detail, is the main factor preventing entrepreneurs from approaching VCs in CEE. This has not been found to be a factor outside the region.