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.