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  1. With the rise of social media, entrepreneurs are feeling the pressure to adopt digital tools for their work. However, the upfront effort and resources needed to participate on these platforms is ever more complex, particularly in underresourced contexts. Through participatory action research over two years in Detroit's Eastside, we found that local entrepreneurs preferred to become engaged digitally through a community collective, which involved (a) resource-connecting organizations, (b) regular in-person meetings, (c) paper planning tools, and (d) practice and validation. Together, these elements combined to provide (1) awareness and willingness to use digital tools, (2) regular opportunities to build internet self-efficacy, and (3) ways to collectively overcome digital obstacles. We discuss our findings in the context of digital engagement and entrepreneurship, and outline recommendations for digital platforms seeking to better support economic mobility more broadly. 
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  2. 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. 
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