As venture capital expands in relevance and influence, investors will begin to face inevitable challenges when deciding where and how to allocate VC funding. Though substantial research has been done to evaluate the myriad financial structures of venture capital, the literature on cross-border VC and its applications are quite limited. This paper will assess the barriers to cross-border VC investments into conflict zones, aiming to understand the feasibility of such investments under the modern VC paradigm. Common barriers will be tested against interviews with a range of venture capital investors to understand the relative importance of these barriers and the extent to which venture capitalists aim to mitigate them. Further, the paper will develop concrete insights into the relevant opportunities and risks present in conflict zone VC investments, along with proposed adjustments to the VC investment model that aim to ameliorate the risks. Ultimately, we aim to understand the calculus of venture capitalists and the ways in which conflict zone opportunities are commonly evaluated, allowing future investors to better examine these opportunities under the framework of a dynamic investment model.