This article identifies ten ways to think different and differently about detailed terms by which investment capital is provided and put to use in furtherance of targeted social/charitable purposes, outcomes, and results. The article has particular, but not exclusive, application for entrepreneurs and investors who provide and facilitate the flow of capital to under-represented, under-served entrepreneurs whether through a fund vehicle or direct investment. Among the topics are those that might be considered mission critical (i.e., structures, scope and priorities, reporting, and remedies), inherently important (i.e., key person provisions, how to deal with debt, and the flow of capital reinvestment and return), and deceptively mundane (i.e., thresholds for approvals, clawbacks and guarantees, and fees). Each has relatively typical approaches and applications in profit-oriented and -prioritized contexts, but they present different challenges for contexts that target social/charitable outcomes. Thus, they also often require different approaches, solutions and thinking. This article asserts that thinking about capitalizing such efforts – their mechanisms and details – should also be different just as thinking about the objects of investment is different. There are at least four tangible benefits for this approach. First, thinking different can help ensure fealty to priority of purpose when focused on other than financial interests. Second, it can help inform internal approaches to decision making about risk taking, allocation of resources, assessment, and other topics. Third and fourth, it can help demonstrated priority of purpose to others while also ascertaining their priorities and alignment (or lack thereof) – in practice as opposed to mere intentions or tolerations – based on how they respond to the proposed approaches to the identified terms and topics
