Back in late 1999, an ambitious online fashion startup, Boo.com, attempted to revolutionize e-commerce by integrating a virtual shopping assistant into its website. This digital avatar, named Miss Boo, was designed to provide customers with personalized styling advice while enabling them to preview clothing, such as jeans and shirts, on three-dimensional models before making a purchase. While this concept aligns with today’s AI-driven shopping experiences, Boo.com faced significant technical challenges. The website suffered from slow loading times and unreliable performance, ultimately leading to its collapse within months of launch. Now, over two decades later, the tech industry is once again betting on AI-powered autonomous agents, hoping they will achieve greater success than their predecessors.