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'Wolf of Wall Street' Ackman Sounds Alarm: Current AI Boom Strikingly Similar to 2000 Dot-Com Bubble, Are Microsoft and Amazon Being 'Wrongly Sold'?

TradingKeyJun 4, 2026 8:35 AM

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Bill Ackman warns of a dot-com bubble repeat, citing investor psychology chasing "hot sectors" like chips and energy while neglecting high-quality tech. He believes AI disruption necessitates investor strategy adjustment, focusing on companies with strong moats, cash flow, and AI integration. Ackman sees Microsoft as a key AI beneficiary. He identifies potential IPO opportunities in SpaceX and OpenAI. The tech sector shows historic overbought conditions, with low market fear and a surge in the S&P 500 tech sector, indicating accumulating market risks.

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TradingKey — As Wall Street revels in the AI chip stock frenzy, Bill Ackman has issued a warning. The Pershing Square Capital founder stated bluntly that the current market is repeating the mistakes of the 2000 dot-com bubble, with investors frantically chasing 'the next big thing'—such as chips, semiconductors, and energy—while neglecting high-quality tech stocks with genuine long-term value.

Market Psychology Reverts to 2000: Capital Flocks to "Hot Sectors"

Ackman believes that the similarities between the current market and the dot-com bubble era ultimately stem from the convergence of investor psychology.

"The interesting thing about the market is that people are always looking at the newest things, and right now the 'new things' are chips, semiconductors, and energy; short-term capital is flowing into these sectors," he said. "What typically happens is that truly high-quality assets are cast aside."

He cited the market in 2000 as an example, when investors were in a frenzy over internet stocks, while Warren Buffett's Berkshire Hathaway ( BRK.a) was viewed as a "relic," with its valuation falling to historical lows.

Today, a similar scenario is unfolding—Amazon ( AMZN ), Meta ( META) and Microsoft ( MSFT) and other big tech companies are facing a similar predicament, being labeled "outdated" by the market, which has led to their stock prices becoming severely undervalued.

It is worth noting that these undervalued high-quality tech stocks are precisely Ackman's current core holdings. He revealed last month that he established a new position in Microsoft after its stock price fell following its February earnings report, viewing it as one of the winners of the AI era.

"Investors cannot simply lump all tech stocks into the same category," Ackman emphasized. "Companies that truly possess moats, cash flow, and AI transformation capabilities may be mispriced while the market chases short-term fads."

Investment Logic in the AI Era: Assessing the Risk of Corporate Disruption

Facing the wave of AI, Ackman believes that investor strategies must be adjusted. "In today's investing, you are either participating in AI directly or indirectly, or you are being threatened by it, so you have to understand it." He noted that for long-term investors, the key lies in assessing the risk of a business being disrupted by AI, and "the probability of such risk has increased significantly today."

In his view, Microsoft is a quintessential beneficiary of the AI era. The tech giant not only possesses deep technological accumulation and a massive user base, but more importantly, it is actively integrating AI technology into its products.

Ackman specifically mentioned that the Copilot AI assistant, personally championed by Microsoft CEO Satya Nadella, is becoming a core weapon for Microsoft's product differentiation.

By contrast, companies that have failed to embrace AI in a timely manner face significant risks. Citing the software industry as an example, Ackman believes that companies relying on niche products to charge customers high fees will face severe challenges in the AI era.

"If you're a software company today, you have to be as AI-enabled as possible," he warned. "Some companies that used to have niche software products could charge customers around $30,000 a year; I think those companies are truly at risk now."

Software Industry Divergence Intensifies

Regarding the pullback in the software sector this year, Ackman believes this marks the beginning of industry divergence. He stated that investors need to conduct "very granular analysis" of specific companies and cannot generalize. For companies like Salesforce ( CRM ), one needs to be extra vigilant.

As a giant in the traditional CRM space, Salesforce has made frequent moves toward AI transformation in recent years, but the market remains skeptical about the effectiveness of its transition.

Ackman believes the challenges facing Salesforce are not just technological, but also business-model related. In the AI era, customer demand for software is shifting from functional to intelligent, and whether Salesforce can successfully navigate this transition will directly determine its future prospects.

However, Ackman also emphasized that he is not bearish on the software industry as a whole, but rather believes that market valuations for some companies are too high. "A month ago, I still thought stocks had become exceptionally cheap—unbelievably so—especially for those high-quality companies," he said. "The issue now is that investors need to be patient and discern which companies truly possess long-term value."

Focus on SpaceX and OpenAI IPOs

In addition to current market analysis, Ackman also highlighted potential future investment opportunities, particularly companies approaching an IPO such as SpaceX and OpenAI.

Ackman expressed strong interest in SpaceX, noting its near-monopoly in the low-cost space launch sector. He believes this position will become increasingly vital as space exploration and satellite internet advance. "SpaceX's business model is highly compelling; it is not only transforming the space industry but also reshaping our lifestyle."

As for OpenAI, which is also planning an IPO, Ackman believes it has an intriguing business model but needs to clarify its capital allocation plans to the market.

He stated that while OpenAI's technical prowess is beyond doubt, investors need to understand how it will utilize the capital raised and how it will achieve profitability while maintaining its technological leadership.

Market risks are accumulating.

The U.S. tech sector is currently in a state of historic overbought conditions, with market fear nearly evaporated as investors' sole concern has shifted from a "decline" to "missing out".

BTIG Chief Technical Strategist Jonathan Krinsky pointed out that if this week's close holds current levels, the S&P 500 tech sector will record its strongest 10-week gain since records began in 1990, a cumulative surge of 44.6%.

At the same time, the VIX hit 13 last night, a year-to-date low, as hedging demand against downside risk has plummeted to extreme lows.

This content was translated using AI and reviewed for clarity. It is for informational purposes only.

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Disclaimer: The content of this article solely represents the author's personal opinions and does not reflect the official stance of Tradingkey. It should not be considered as investment advice. The article is intended for reference purposes only, and readers should not base any investment decisions solely on its content. Tradingkey bears no responsibility for any trading outcomes resulting from reliance on this article. Furthermore, Tradingkey cannot guarantee the accuracy of the article's content. Before making any investment decisions, it is advisable to consult an independent financial advisor to fully understand the associated risks.

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