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Social media platforms make trade-offs in their design and policy decisions to attract users and stand out from other platforms. These decisions are influenced by a number of considerations, e.g. what kinds of content moderation to deploy or what kinds of resources a platform has access to. Their choices play into broader political tensions; social media platforms are situated within a social context that frames their impact, and they can have politics through their design that enforce power structures and serve existing authorities. We turn to Pillowfort, a small social media platform, to examine these political tensions as a case study. Using a discourse analysis, we examine public discussion posts between staff and users as they negotiate the site's development over a period of two years. Our findings illustrate the tensions in navigating the politics that users bring with them from previous platforms, the difficulty of building a site's unique identity and encouraging commitment, and examples of how design decisions can both foster and break trust with users. Drawing from these findings, we discuss how the success and failure of new social media platforms are impacted by political influences on design and policy decisions.