Olive AI

Olive AI raised $856M to automate healthcare administration using AI. Valued at $4B at its peak, the company promised to eliminate repetitive tasks in hospitals and insurance companies. But the product struggled with the complexity of healthcare workflows—each hospital had unique systems, regulations, and processes. Olive expanded too fast, hiring over 800 employees and acquiring companies before achieving reliable product-market fit. In 2023, the company sold off its business units piecemeal and effectively shut down. The lesson: healthcare is one of the hardest industries for AI disruption due to regulatory requirements, integration complexity, and the critical nature of accuracy in medical contexts.