In this talk, we’ll share our journey at Billy, a startup that embraced modern technologies like serverless architectures, microservices, and even blockchain (Yes we know… Nobody's perfect).. Despite the promise of reduced complexity, we encountered significant friction between our tech stack and business needs during a critical pivot. We’ll explore how architecture options, though designed to defer decisions, introduced excessive complexity, and discuss our strategies for aligning business and technology through bounded contexts, continuous delivery, and targeted refactoring.