In this article, we examine whether today’s tech and AI markets are repeating the mistakes of the last valuation bubble. Drawing on firsthand experience from the 2021 funding cycle and its aftermath, we explore how inflated revenue multiples, weak unit economics, and aggressive burn rates have led many companies into distressed M&A and fire-sale exits. We also look at why similar dynamics are beginning to appear in the AI sector, and outline the practical lessons founders should take away now: how to think about valuation, capital strategy, profitability, and building long-term optionality in a market where fundamentals have once again become decisive.