Doctor Profit compared Saylor’s approach to the 2000 dot-com bubble, and added that buying blindly without strategic selling is a “reckless” trading approach.

Strategy has spent years aggressively buying Bitcoin, pitching the move as a long-term, high-conviction bet, but critics say that the approach has crossed from bold into reckless.

Popular analyst Doctor Profit, for one, drew parallels to the dot-com bubble, while warning that the firm risks repeating history amid today’s AI-fueled frenzy.

Blind Faith vs Market Timing

In a recent post on X, Doctor Profit stated that he repeatedly expressed his concerns with Strategy’s co-founder, Michael Saylor, that nonstop Bitcoin accumulation, financed and backed by issuing company shares, was “playing with fire.” According to the analyst, those warnings were dismissed and even mocked.

He pointed out that since then, Strategy’s share price has fallen by roughly 75% from its highs, while Bitcoin itself is down 50% from its peak. With Saylor’s reported average BTC entry around $76,000 and the asset trading near $63,000, the position sits roughly 17% below cost.

Doctor Profit also argued that, despite accumulating since 2020, the company has never realized meaningful profits or executed serious strategic selling. Meanwhile, its stock has suffered a substantial drawdown, exposing shareholders to extreme volatility with little relief.

Looking back at past cycles, Doctor Profit said Saylor’s experience during the 2000 dot-com collapse offers a warning. He explained that intense excitement surrounding AI today may be creating a similar late-cycle setup, increasing the chance of history repeating itself by 2026.

Rather than de-risking as these signals emerged, Doctor Profit claimed that the executive chairman doubled down, increasing exposure while ignoring red flags.

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“I truly wish MSTR and Saylor the best, but I cannot understand how reckless this trading approach is in such a late-cycle environment. Markets reward discipline, not blind belief in Bitcoin. There is always time to buy and time to sell. I hope he will listen next time instead of mocking my warnings.”

The fresh concerns come against the backdrop of Strategy’s latest Bitcoin purchase, which is smaller than its past billion-dollar buys but consistent with its long-standing accumulation plan. The firm spent just under $40 million to acquire 592 BTC at an average price of $67,286, which pushed its total holdings to 717,722 BTC.

The purchase was funded through equity sales. Nearly 298,000 Class A shares were sold via the firm’s at-the-market program over the past week, according to an update cited by Walter Bloomberg. Strategy still has substantial capacity to raise more capital through future ATM sales, as $37.4 billion in securities remain available, including MSTR and STRK stock.

Billions at Risk

As Bitcoin’s price decline deepened, earlier warnings from Michael Burry and Zac Prince drew fresh attention to the fragility of BTC treasury business models. For instance, Burry recently said BTC’s drop increases the risk of broader stress across crypto and related financial markets. “The Big Short” investor had said that further downside could severely impact companies that accumulated Bitcoin at higher prices, potentially leaving firms like Strategy billions underwater and cut off from capital markets.

Former BlockFi CEO, Prince, also questioned the sustainability of BTC treasury models, saying they rely on financial engineering rather than core business fundamentals and may struggle to justify valuations without real operating revenue.