Generative AI platforms and features are permeating many aspects of work. Entrepreneurs from lean economies in particular are well positioned to outsource tasks to generative AI given limited resources. In this paper, we work to address a growing disparity in use of these technologies by building on a four-year partnership with a local entrepreneurial hub dedicated to equity in tech and entrepreneurship. Together, we co-designed an interactive workshops series aimed to onboard local entrepreneurs to generative AI platforms. Alongside four community-driven and iterative workshops with entrepreneurs across five months, we conducted interviews with 15 local entrepreneurs and community providers. We detail the importance of communal and supportive exposure to generative AI tools for local entrepreneurs, scaffolding actionable use (and supporting non-use), demystifying generative AI technologies by emphasizing entrepreneurial power, while simultaneously deconstructing the veneer of simplicity to address the many operational skills needed for successful application.

Creative entrepreneurs rely on online platforms to build community in order to overcome isolated work conditions. However, because of frequent attempts by larger brands to use their work without permission, creative entrepreneurs constrain their use of social platforms in order to safeguard their intellectual property. In this paper, we describe a multi-year partnership with a feminist makerspace to build a social platform, called Peerdea, that centered creative entrepreneurs’ needs such that online feedback and information exchange, and goal setting and accountability were more readily available to them. Through an iterative, community- collaborative approach with 46 creative entrepreneurs, we report on the kinds of peer support entrepreneurs sought on Peerdea such as feedback on in-progress and unpolished work. We argue that by aligning Peerdea’s design with the makerspace’s community of practice, Peerdea leveraged the relationship and trust building which occurs more readily in person for entrepreneurs. In addition, we highlight the role of a community leader who actively managed the relationships between researchers and entrepreneurs, surfaced failures and championed successes, and provided critical mediation for co-design when participants’ livelihoods were implicated.

The field of human-computer interaction (HCI) has traditionally focused on the design of novel technology artifacts. However, ensuring considerations for artifact maintenance and repair is crucial to sustainably supporting the populations they aim to serve over the long term. Drawing on two multi-year programs for tech capacity building in post-industrial U.S. cities, this article presents a comparative analysis to investigate the challenges and strategies for sustained community-based research in computing. In particular, our work detailed three considerations for academic-community partnerships. First, long-term partnerships prioritized transferring trust across academic and community personnel and continually set expectations that responded to evolving community initiatives (i.e., relational sustainability). Second, partnerships used academic support as a way to kickstart community initiatives, and flexibly reframed interventions to stay aligned with evolving community goals (i.e., economic sustainability). Third, partnerships trained personnel to provide technical support alongside interventions and prioritized advice that resisted short-term trends (i.e., technical sustain- ability). We provide concrete examples of how our two academic-community partnerships carried out such suggestions—such details go unreported in scholarly articles yet are essential for sustainability considerations. We discuss ongoing challenges, such as rethinking when longevity should and should not be the end goal.

Even entrepreneurs whose businesses are not technological (e.g., handmade goods) need to be able to use a wide range of computing technologies in order to achieve their business goals. In this paper, we follow a participatory action research approach and collaborate with various stakeholders at an entrepreneurial co-working space to design “Tech Help Desk”, an on-going technical service for entrepreneurs. Our model for technical assistance is strategic, in how it is designed to fit the context of local entrepreneurs, and responsive, in how it prioritizes emergent needs. From our engagements with 19 entrepreneurs and support personnel, we reflect on the challenges with existing technology support for non-technological entrepreneurs. Our work highlights the importance of ensuring technological support services can adapt based on entrepreneurs’ ever-evolving priorities, preferences and constraints. Furthermore, we find technological support services should maintain broad technical support for entrepreneurs’ long tail of computing challenges.