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The increasing popularity in recent years of free transactional legal services to businesses and entrepreneurs has triggered questions about whether that phenomenon is altogether a good thing, given the increasing and competing need for legal services for low-income individuals and families in distress. This Article, prepared for a symposium at Washington University School of Law, offers a beginning and tentative assessment of that topic. The Article reviews the typically short-term benefits that accompany conventional litigation-based legal services and compares that outcome to the more contingent, longer-term benefits that could result from transactional legal services on behalf of emerging businesses. It acknowledges recent research arguing that entrepreneurship has only a weak record of success as a poverty-fighting strategy, while more collectivist transactional projects have seemingly better chances of effecting meaningful change. But it concludes—again, tentatively—that assistance to entrepreneurs, particularly those from underserved communities, at times can serve many of the same purposes as much of the legal work offered by traditional pro bono and legal services providers.