MyGate started its journey in 2016 as a gate management system for gated societies but soon evolved into a multi-sided platform offering solutions to the residents' day-to-day needs via the company's mobile application. Residents could approve entry and exit of visitors, search for local service providers like maids, carpenters, plumbers etc., purchase groceries and a variety of FMCG and consumer durables, engage in group buying, list their properties for sale or rent and engage in peer-to-peer trade. The case highlights the challenges faced by co-founders in balancing the different expectations of stakeholders. As a gate management software, MyGate needed to balance between the security of the residents and the convenience of residents, visitors, and service providers. As a communication medium for brands to reach consumers, MyGate needed to balance the frequency and placement of advertisements so that residents would not be irritated while the platform earned fees for enabling the brands to reach target segments in specific locations. As a gatekeeper, MyGate needed to balance the privacy requirements of residents and the wish of brands to craft more meaningful messages for their target segments. In January 2022, MyGate was yet to turn profitable and needed to balance the objectives of monetisation and expansion of product offerings' geographic footprint. At the core of these dilemmas was the need to balance the current and future profits of a startup which relied on investor funds for survival.