Buy high and never sell: Saylor continues to buy Bitcoin at local peaks despite increased risks

Strategy (formerly MicroStrategy) has gained a reputation in recent weeks for being near the top in the country in weekly Bitcoin acquisitions.

On November 10, CryptoQuant analyst JA Marturn noted that the company’s latest acquisition disclosure by Michael Saylor followed the same scenario.

According to SEC filings, Strategy announced that it acquired 487 BTC between November 3 and November 9 for $49.9 million, at an average price of $102,557 per coin.

The flagship asset has spent most of the past week trading sideways, with Bitcoin reaching a high of more than $106,000 on Nov. 3, before falling more than 9% and trading below $100,000 at one point. The support at $106,400 has turned into resistance and the battle continues against the local floor at $100,000.

But Mr. Thaler’s company could not be bought at the bottom of the market. Instead, the purchase price reached one of the highest prices at which the top asset traded last week.

This is consistent with the company’s previous purchases that coincided with short-term peaks, raising the question of why the company continues to “buy on top.”

The consistency of this visual pattern gives the impression of mistimed execution, but that’s only part of the story.

Why strategies tend to favor BTC strength

Strategy purchases tend to focus on moments of heightened liquidity for reasons unrelated to market enthusiasm.

The company’s treasury department deploys capital at specific points, such as after a stock sale, after a convertible debt issue, or during an internal liquidity event.

These windows rarely match discount market conditions. Instead, they often open during periods when Bitcoin trades with a deeper order book and execution risk is lower.

Market analysts say this structural reality explains why Strategy’s entries often coincide with local highs. A company’s large orders are executed when market depth is strongest. This usually corresponds to an upswing rather than a drawdown period.

As a result, takeover applications can create the illusion of planned purchases at peak times, even though the timing is driven by liquidity availability and internal controls rather than emotion.

For strategies, the marginal price of a particular tranche is secondary.

Saylor has always viewed Bitcoin as a long-term financial product, and the company operates according to that principle. The goal is stable exposure, not precise timing.

Therefore, a firm’s execution window is defined by firm processes, which favor consistency of accumulation over opportunistic entry.

Long-term performance and structural risk

In the longer term, criticisms of strategic timing lose some force.

Since Strategy began purchasing Bitcoin in 2020, its treasury has grown into one of the most profitable corporate asset allocations in modern history.

The company currently holds 641,692 BTC worth approximately $68 billion, purchased at an average price of $106,000, giving it a total value of $67.5 billion. At current prices, this position represents a paper profit of approximately $20.5 billion.

Even more impressively, Strategy has generated more than $12 billion in Bitcoin profits year-to-date in 2025, even though the pace of accumulation has slowed to a few hundred coins in recent weeks.

This is the contradiction at the heart of Thaler’s strategy. Although the entry looks poor, the result is exceptional. This shows a company’s dollar-cost averaging on a structured timeline.

Short-term volatility amplifies the impression that the strategy is buying the top. Multi-cycle reality shows that these “tops” often become entries that bring big profits over time.

A broader comparison drives home that point. Over the past year, Strategy stock (MSTR) has had 87% volatility, significantly higher than Bitcoin’s 44% and more volatile than the company’s other digital asset products.

However, despite this intensity, the cumulative exposure to Bitcoin has turned its volatility into an asymmetric upswing.

However, high profits do not exempt the company from structural weaknesses. The data in the bar chart shows that if you invested $10,000 in MSTR at the dotcom peak, it would be worth $7,207 today, demonstrating volatility over 20 years independent of Bitcoin strategy.

Additionally, some analysts argue that the strategy’s reliance on capital markets poses significant risks if cryptocurrencies enter a multi-year downturn.

Those concerns were exacerbated as the company’s balance sheet evolved.

Chris Milas, an advisor at Melius Bitcoin, Brazil’s first Bitcoin treasury, said the company had no interest-bearing debt during the last bear market and had many years before its earliest bond maturity. Therefore, although stock fluctuations were a pain, the impact on operations was limited.

However, this cycle is different. Strategy currently has interest-bearing debt that must be repaid regardless of market conditions.

Mr. Miras argued that a significant decline in MSTR’s stock price, while historically plausible given the stock’s 70-80% drawdown in previous cycles, would limit the company’s flexibility and increase the likelihood of dilutive capital issuance.

He said that dilution could create a feedback loop that further pressures stock prices and increases downside risk.

In fact, Strategy faces interest payments of approximately $689 million through 2026. Without new capital, the company will not be able to meet its obligations.

Additionally, recent fundraising highlights how funding conditions have changed, with preferred stock issuing yields at around 10.5%, above initial guidance of nearly 10%. Widening spreads indicate that capital is becoming more expensive, complicating the economics of debt-financed Bitcoin accumulation.

For this reason, skeptics point out that the model resembles a leveraged carry trade with limited margin for error. In fact, some have called the process “Ponzi-like” while claiming that the company’s debt is growing faster than its operating profits.

They say this makes the strategy dependent on either rising Bitcoin prices or continued investor appetite for high-yield products.

Signal power and narrative strategy

Despite these risks, the Strategy acquisition continues to have a significant impact on the narrative. The company has frequent and transparent disclosures, and that visibility allows acquisitions to serve as a form of market signal.

Buying the strength of the strategy therefore reinforces the message that Bitcoin is a long-term financial asset, rather than a timing-sensitive trade.

Additionally, some of Strategy’s high-priced filings in recent weeks have coincided with periods of market hesitation, and this filing helps stabilize sentiment by showing steady demand from institutional investors.

This effectively positions Strategy as the most consistent large buyer in the market, and its disclosure serves both operational and symbolic purposes.

This dual role explains why sailors continue to accumulate through short-term peaks.

For Strategy, a given week’s purchase price is secondary to both Bitcoin’s multi-year trajectory and the company’s identity as the largest corporate holder.

Optics can be criticized, especially during times of heightened volatility. Still, the framework that guides purchasing remains consistent. Strategy is not about the next quarter, but about the next decade.