A prominent value investor has expressed caution regarding the high valuation anticipated for the upcoming initial public offering (IPO) of Anthropic, an artificial intelligence company. The investor, speaking in an illustrative conversation with a potential buyer, highlighted the risks associated with paying a premium multiple for growth stocks in the AI sector.

Anthropic is expected to debut on the market with an estimated valuation of approximately US$2 trillion, a figure based on an annualized revenue run rate near US$65 billion. This places the IPO’s price-to-revenue multiple at around 30 times, a level that the investor characterized as steep, even when factoring in projections of rapid revenue growth. Anthropic’s revenue is forecasted to double within the year and potentially double again by 2028, but the investor warned that such top-line expansion alone may not justify the lofty valuation.

The investor emphasized that for such an investment to prove profitable, several conditions must align beyond revenue growth. These include the company’s ability to maintain or improve profit margins, manage share dilution, and sustain market sentiment toward high valuation multiples over time. The investor cautioned that if the market later revalues Anthropic at a lower multiple—as seen in historical examples—investors could face disappointing returns despite the company’s growth.

As a case in point, the investor recalled Cisco Systems, which experienced a more than twofold increase in revenue from 2000 to 2010 yet saw its stock price decline by over two-thirds during that period. This example served to illustrate how market sentiment and valuation multiples can dramatically influence investment outcomes separate from business performance.

In contrast to the growth-focused approach exemplified by Anthropic’s IPO, the investor outlined a more conservative strategy favoring established companies trading at discounted valuations. The illustrative portfolio choice cited was Diageo, a multinational alcoholic beverage company facing headwinds such as softening volumes, dividend cuts, and changing consumer habits. Despite these challenges, Diageo benefits from scale, significant free cash flow generation, and a recent leadership change aimed at cost efficiencies. The investor described this approach as buying “ugly ducklings”—companies that may not be favored by the market but whose underlying value provides a margin of safety.

Ultimately, the investor acknowledged the inherent uncertainty in predicting future outcomes and the divergent risk tolerances among investors. While some may choose to invest based on high-growth potential, others prefer to emphasize valuations that offer protection against unforeseen setbacks. Both approaches acknowledge the unpredictable nature of markets, differing primarily in how risk is managed and tolerated.