Saylor’s MicroStrategy Buys Bitcoin Dip as 40% of Holdings Turn Red

As Bitcoin experienced one of its sharpest weekly declines in recent memory, falling below both the $100,000 and $95,000 psychological barriers, MicroStrategy executed what has become its signature strategy: buying the dip. According to company disclosures and Michael Saylor’s social media posts, the business intelligence firm acquired 8,178 BTC for $835.6 million at an average price of $102,171 per coin during the market downturn. This purchase brings MicroStrategy’s total November acquisitions to 9,062 BTC worth $931.1 million, demonstrating the company’s unwavering commitment to accumulating Bitcoin despite volatile market conditions.

The timing of these purchases has proven challenging in the short term. With Bitcoin currently trading around $90,300, the newest 8,178 BTC acquisition is already down approximately 10.5%, representing a paper loss of roughly $88 million in just days. Similarly, all of MicroStrategy’s November purchases, totaling $931.1 million, are now worth about $827 million at current market levels—a decline of just over 11% since acquisition. This immediate depreciation highlights the risks inherent in timing cryptocurrency markets, even for sophisticated corporate investors with substantial resources.

CryptoQuant’s detailed breakdown reveals the complex reality of MicroStrategy’s Bitcoin position. While the company maintains an overall paper gain of 22%—equivalent to approximately $11 billion on its total holdings—roughly 40% of its 649,870 BTC stash is now showing unrealized losses. This situation results directly from the company’s recent buying activity, which pushed newer acquisition lots above today’s market price. The analysis shows that only 60% of MicroStrategy’s Bitcoin holdings remain profitable at current price levels, a significant shift from early last month when the company enjoyed a peak profit ratio near 68% with gains calculated at about $32 billion.

The company’s current position stands in stark contrast to the deep losses it faced from mid-2022 into early 2023, when as much as 75% of its holdings were underwater and the portfolio was down about 33%, representing roughly $1.32 billion in paper losses at that time. MicroStrategy’s overall holdings now total 649,870 BTC, equivalent to roughly 3.2% of Bitcoin’s circulating supply, acquired for approximately $48.37 billion at an average cost of $74,433 per Bitcoin. At current prices, the holding’s market value sits near $59.38 billion, maintaining that substantial overall gain despite recent market turbulence.

Not all market participants view MicroStrategy’s aggressive Bitcoin accumulation strategy favorably. Peter Schiff, the well-known gold investor and longtime cryptocurrency skeptic, has intensified his criticism of the company’s approach. Schiff specifically targeted MicroStrategy’s rising average cost basis—now approximately $74,433 per BTC—which he argues has been moving closer to current market values and could limit upside potential if prices fail to rebound significantly. In comments made on Sunday, Schiff went so far as to label MicroStrategy Inc.’s singular focus on Bitcoin as ‘a fraud.’

The gold advocate has challenged Michael Saylor to a live debate at Binance Blockchain Week in Dubai this December, setting the stage for a potential showdown between two prominent but diametrically opposed investment philosophies. Schiff argues that the company’s recent gains primarily stem from Bitcoin’s overall price appreciation rather than strategic business acumen, warning that if investor confidence in Bitcoin erodes, MicroStrategy’s financial stability could face significant challenges. This criticism comes as the company continues to report strong performance metrics, including a BTC yield of 27.8% year-to-date for 2025.

For outside observers and retail investors, MicroStrategy’s current situation provides several important lessons about cryptocurrency investing. Even the market’s largest and most committed corporate holders can see substantial portions of their inventory fall into loss positions during market downturns. The company’s newer purchases have undoubtedly reduced its headline returns, transforming what was a 68% profit ratio in early October to the current 22% overall gain. However, these acquisitions have not wiped out the company’s substantial paper profit, demonstrating the importance of cost averaging and long-term perspective in volatile asset classes.

The short-term results for MicroStrategy’s November Bitcoin purchases appear poor, with immediate double-digit percentage losses. Yet the company’s filings indicate that Saylor and his team treat price dips as opportunities to add coins at discounted rates, maintaining their conviction in Bitcoin’s long-term value proposition. The ultimate success or failure of these recent acquisitions will depend entirely on future price movements, highlighting the speculative nature of timing cryptocurrency markets. As the debate between cryptocurrency proponents like Saylor and traditional asset advocates like Schiff continues, investors are reminded that even well-capitalized corporate strategies face significant volatility in the emerging digital asset space.