
This piece examines the current AI investment landscape through the lens of the dot-com bubble of 2000, drawing parallels between the two periods of technological revolution and market exuberance. The author recalls sitting in a classroom during the spring of 2000, confused by a market that valued companies on clicks and eyeballs rather than revenues and cash flow. Shortly after, the dot-com valuation bubble burst, yet the internet-powered economy continued to grow, proving that both enthusiasts and skeptics were partially right. Today, AI occupies a similar position as the next revolutionary technology and the centerpiece of every investment conversation. The AI supply chain is experiencing unprecedented adoption, revenue growth, and capital expenditure, with fundamentals across frontier models, compute infrastructure, and energy demand off the charts. However, valuations of both public and private companies imply these trends will continue indefinitely. Two podcast guests capture the debate: Gavin Baker views AI as one of the most extraordinary moments in capitalism, while Rajiv Jain avoids hyperscalers due to downside risk from massive capex without free cash flow follow-through. Both may be correct, as AI may transform businesses while markets have already priced in a decade or two of progress. The allocator dilemma has shifted from how to gain AI exposure to how to position portfolios when access is no longer an obstacle, especially as mega-cap private winners prepare to go public. The power law in venture capital is more pronounced than ever, creating allocation imbalances across public and private markets. The hard part comes after being right: deciding what AI is worth today and how much exposure to own.