Berkshire Trolls The AI Bubble By Buying Macy's

For the better part of the last year, Wall Street has behaved like a teenager who just discovered Red Bull and leverage at the same time. Anything remotely tied to artificial intelligence has soared into the financial stratosphere.

Startups with no revenue, no profits, and occasionally no actual product are raising millions or billions because their founders can say the words “large language model”. Public company CEOs now jam “AI” into earnings calls with the same shamelessness that “trendy” gastropubs have when being the 4th “new” place on the block to not just offer a good ole’ fashioned cheeseburger, but the breathtaking innovation of a truffle aioli smashburger.

Meanwhile, looming over all of this market hysteria was Berkshire Hathaway and its absurd cash pile. More than $390 billion sitting on the sidelines while markets rocketed higher. The question became an obsession. What were Warren Buffett and his successor Greg Abel waiting for?

Surely this cash hoard was being preserved for some grand masterstroke. Maybe Berkshire would make a massive AI acquisition. Maybe it would take a huge stake in some futuristic robotics company whose product sounds vaguely dystopian. Maybe Buffett would emerge from Omaha wearing a black turtleneck and announce BerkshireGPT.

Nope. None of these. The filing arrived yesterday and Wall Street discovered that the answer was Macy’s: a company most people associate with buying last minute wedding gifts and wandering through perfume fog thick enough to qualify as weather.

In an era when investors are paying breathtaking multiples for companies promising that AI will revolutionize enterprise workflows, Berkshire appears to have strolled calmly into a department store hoping to get harassed by the Vancome lady.

It is notable to write about because it feels so aggressively out of sync with the cultural moment.

Right now entire hedge funds are building investment theses around the possibility that artificial intelligence may someday help your refrigerator compose emails and then there is Berkshire, quietly behaving like an investor that ignores market spectacle and focuses instead on underlying value. While others chase whatever appears most exciting in the moment, Berkshire tends to concentrate on businesses and assets that are durable, understandable, and often overlooked.

Berkshire likely was attracted to Macy’s because it combined several characteristics long associated with Buffett-style investing: a deeply discounted valuation trading near book value and at a low forward earnings multiple, substantial underlying real estate assets including the flagship Herald Square property, strong cash generation and shareholder returns through free cash flow and dividends, and a credible turnaround strategy focused on closing weaker stores while reinvesting in stronger locations.

Berkshire also likely recognized the enduring value of Macy’s higher-performing brands, particularly Bloomingdale’s and Bluemercury, which provide growth and profitability beyond the traditional department store business. In fact, a lot of the reasons Berkshire bought Macy’s remind me of another retail stock that I think is similarly as attractive to own right now.

And this isn’t to say Berkshire is anti-technology. The company increased its stake in Alphabet and clearly understands where the economy is headed. But Berkshire has spent decades avoiding one of the central mistakes in modern investing: confusing a compelling narrative with a compelling investment. A transformative future does not automatically justify any price. Investors learned that during the dot-com bubble, when companies with weak earnings and questionable business models were treated as inevitable paths to wealth. Many eventually discovered that enthusiasm alone is not a substitute for sustainable economics. They will learn this again with the AI bubble.

That is what makes the Macy’s move so interesting. It suggests that Berkshire still sees value in businesses the market has largely dismissed as boring, outdated, or finished. Macy’s possesses valuable real estate, broad brand recognition, and consistent cash generation — qualities that can become easy to overlook in markets dominated by growth narratives. Perhaps most importantly, expectations surrounding the company have become so low that stability itself can exceed investor assumptions.

That may be the broader lesson for investors. Markets often become fixated on whatever appears revolutionary while overlooking companies that quietly generate profits in less glamorous industries. Investors naturally want exposure to the future, but there can also be opportunity in businesses that continue to serve enduring consumer needs and produce reliable cash flow.

Investors should also be careful about dismissing Berkshire Hathaway simply because it appears old-fashioned in an era defined by speed and disruption. Yet Berkshire has continued to compound wealth across market cycles while many trend-driven strategies have struggled to deliver lasting results.

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The lesson is not that investors should rush to buy Macy’s. It is that when disciplined long-term investors begin allocating capital to areas the broader market has written off, it is worth paying attention. Wall Street is often drawn to what is new and exciting. Berkshire has historically succeeded by identifying value where others stopped looking.

Another lesson is that patience remains one of the most underappreciated advantages in investing. Modern markets reward constant activity, rapid reactions, and short-term narratives, but Buffett’s track record has repeatedly demonstrated the power of allowing investments time to mature. Companies facing temporary pessimism or cyclical weakness are often abandoned long before their underlying economics can recover. Berkshire’s approach suggests that long-term value is frequently created not through constant trading, but through disciplined conviction and the willingness to endure periods of unpopularity.

There is also a lesson about temperament. Successful investing is often less about predicting the future perfectly and more about avoiding emotional decision-making when sentiment becomes extreme. During periods of market excitement, investors can feel pressure to chase momentum and follow consensus thinking. Conversely, when industries fall out of favor, fear and pessimism can create opportunities for investors willing to evaluate businesses on fundamentals rather than headlines. Berkshire’s history reflects an investment philosophy grounded in rationality and discipline rather than market emotion.

Finally, Berkshire’s strategy highlights the importance of understanding the difference between a good company and a good stock at a particular price. Even strong businesses can become poor investments when expectations become unrealistic, while unpopular companies can sometimes offer attractive risk-reward profiles if expectations fall too far. The broader lesson is not that every overlooked stock represents hidden value, but that investors benefit from questioning consensus assumptions. Markets are highly efficient much of the time, but periods of excessive optimism and excessive pessimism continue to create opportunities for patient, disciplined capital allocators.

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