Diversity and inclusion is an ongoing challenge for all organizations, but is particularly difficult for resource-constrained startups. Most research on diversity and inclusion has been conducted in large organizations and focuses on a top-down approach to diversity and inclusion. Startups lack the formal structures and resources required for initiating and implementing top-down diversity and inclusion programs. At the same time, startups are uniquely positioned to offer creative ways to act on diversity and inclusion because they are not bound by existing industry norms. In our research, we conducted a longitudinal case study of a technology startup (Tiny Tech). Our findings highlight that Tiny Tech’s diversity and inclusion strategies are markedly different over its startup and scaleup stages. At the startup stage, Tiny Tech’s contextual characteristics and executive action (e.g., flat structure, founder commitment, frequent interpersonal interactions) enabled a bottom-up approach to diversity and inclusion to flourish. As Tiny Tech scaled up and confronted intense operational demands, its focus on diversity and inclusion became diluted, losing the unique advantages it had accrued during the startup stage. Our research highlights an organization’s lifecycle stage as a contingency factor influencing the best approach to diversity and inclusion.