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Online technologies are increasingly hailed as enablers of entrepreneurship and income generation. Recent evidence suggests, however, that even the best such tools disproportionately favor those with pre-existing entrepreneurial advantages. Despite intentions, the technology on its own seems far from addressing socio-economic inequalities. Using participatory action research, we investigated why this might be, in an intimate, close-up context. Over a 1-year period, we—a collaborative team of university researchers and residents of Detroit’s East Side—worked to establish a neighborhood tour whose initial goal was to raise supplementary income and fundraise for community block clubs. We found that in addition to technical requirements, such as communication tools, a range of non-technological efforts is needed to manage projects, build self-efficacy, and otherwise support community participants. Our findings widen Ackerman’s “socio-technical gap” for some contexts and offer a counterpoint to overgeneralized claims about well-designed technologies being able to address certain classes of social challenges.