The dotcom bubble burst in the early 2000s serves as a cautionary tale for investors and tech entrepreneurs. Cisco, a major player in Internet infrastructure, saw its stock peak in March 2000 and has yet to recover. This downturn affected many, including a wave of layoffs and a significant shift in market confidence toward tech investments. Many professionals transitioned into diverse roles as startups collapsed. Discussions around the crisis emphasize the fragility of internet-based business models at the time and draw parallels to today’s tech landscape, particularly in the context of current AI investments. Many lessons can be learned about market ebbs and flows, investor sentiment, and the sustainability of tech-driven ventures.