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This case study chronicles the entrepreneurial journey of Dr Sarah Buchner, founder and CEO of Trunk Tools, as she navigates the strategic and operational inflection points of building a venture-backed technology start-up in the construction sector. While pursuing her MBA at Stanford Graduate School of Business, Dr Buchner applied the research driven ideation (RDI) framework to identify the root causes of labor shortages and high attrition in the construction industry as the core problem to solve. Her original product, TrunkPerform, was designed to set productivity goals and streamline compensation, enabling high-performing workers to earn more based on task completion. With the rise of Artificial Intelligence (AI) and large language models (LLMs), Dr Buchner led her team in developing TrunkText, an AI-powered tool that allowed construction professionals to query large volumes of unstructured construction documentation, and later evolved the offering into a platform with multiple AI agents capable of automating repetitive, data-intensive workflows. With strong signals of product-market fit for both products but limited resources, Dr. Buchner had to prioritize development while managing investor expectations, preserving strategic focus, and maintaining organizational momentum. The case invites students to consider how a founder interprets market signals, reallocates capital across evolving opportunities, and positions a start-up to scale within a complex, conservative industry in the midst of rapid technological transformation.