One of the newest faces in the philanthropy world is venture philanthropy and, since its introduction of corporate business rhetoric and venture capitalist techniques to the industry, the actual effectiveness of venture philanthropy has been questioned. This thesis examines where traditional philanthropy is currently failing its beneficiaries, how venture philanthropy presents solutions to those failures, and ultimately, it compares how the venture philanthropy approach affects time of program completion and resulting social returns, as opposed to traditional philanthropy. By developing venture and traditional philanthropy mathematical models based on a venture capital model by Jovanovic and Szentes (2007), I found the optimal stopping point for funding and level of social return are dependent on nonprofit effort and program scope.