MicroStrategy Could Be Forced to Dump Bitcoin — Saylor Reacts Boldly

The largest public corporate holder of Bitcoin, MicroStrategy, is under financial pressure and may have to consider liquidating some of its huge crypto holdings. Recently led by bitcoin evangelist Michael Saylor, the company filed Form 8-K with the U.S. Securities and Exchange Commission (SEC), disclosing worrisome weaknesses in its financial structure. These worries, combined with a volatile crypto market, have brought its MicroStrategy Bitcoin strategy into question concerning sustainability.

The Core of the Problem: Debt, Cash Flow, and Crypto Dependency

MicroStrategy currently holds approximately 528,185 Bitcoins, which were bought at an average price of $67,458 per coin. This investment is just about $35.63 billion, thereby leaving the company as the clear kingpin of institutional Bitcoin accumulation. The MicroStrategy Bitcoin strategy has come under scrutiny as the most recent SEC filing lays bare some cracks in the foundation of this very high-risk approach.

What MicroStrategy should consider, however, is that irrespective of the extraordinary value of its Bitcoin treasury, the firm’s core enterprise software business does not provide positive operational cash flow. With an enormous debt load that includes $8.22 billion in outstanding obligations and annual interest payments of $35.1 million, it also holds more than $1.6 billion in preferred stock, against which it owes $146.2 million in dividends annually—interest to which it now is unable to entertain.

Rather than use its income to repay these liabilities, MicroStrategy acknowledges that it expects to fund or refinance with additional debt or equity. This raises concerns, as any price drop in Bitcoin would negatively affect its ability to do so. Thus, should Bitcoin’s market value sink below the company’s average purchase price, MicroStrategy would likely find itself forced to liquidate a portion of its holdings, and possibly at a loss, to earn the most desperately needed cash.

How the Bitcoin Price Drop Fuels Pressure

Bitcoin was trading only 13% higher than MicroStrategy’s average cost basis at the time of the SEC filing. That narrow window indicated probable trouble: below $67,000, the company might come under increasing pressure to sell. That could be troubling news, as since then, Bitcoin has risen—trading at around $81,900 on April 11, 2025, after a 6% gain that day—but the storm clouds of volatility still loom. 

In Affordability, since Bitcoin is mostly what MicroStrategy holds, it means that the finances of that corporation live and die by the performance of Bitcoin. The MicroStrategy Bitcoin strategy exposes the firm heavily to price fluctuations. Steep declines in crypto could easily bring MicroStrategy’s balance sheet down under maintenance and inhibit investors’ enthusiasm, ultimately creating massive sales pressure not just from MicroStrategy but across the board. This would indicate direct mosaic risk from the holdings of such megacorporate cryptos.

Michael Saylor’s Response: “HODL” Philosophy Stays Intact

Despite the financial cautions, Michael Saylor, the co-founder and executive chairman of MicroStrategy, continues to stand his ground in his belief in Bitcoin. By the same token, he responded to the hype over the SEC filing by taking to X (formerly Twitter) and simply posting the word: “HODL.” It is an acronym that is used widely in the crypto community to mean Hold On for Dear Life, indicating a long-term belief in Bitcoin’s value regardless of the volatility in the short term.

That would go viral to register more than 1.4 million views and many more retorts by other crypto believers in the comments. In a follow-up tweet, Saylor doubled down with, “Bitcoin is the Best Idea. There is no Second Best.” It reflects a strong belief in line with the ideological core of the MicroStrategy Bitcoin strategy, which sees the cryptocurrency not just as an asset of finance but as technology for revolutionary money.

MicroStrategy’s History of Bitcoin Commitment

MicroStrategy has aggressively pursued this Bitcoin acquisition strategy since August 2020, when it first announced a $250 million purchase made within the company. Thereafter, it has never failed to supplement its purchases with indebtedness, equity offerings, or convertible notes.

In December 2022, MicroStrategy sold a total of 704 BTC for an estimated value of $11.8 million, being among the few occasions that the company has liquidated parts of its holdings. The transaction at the time was said to be a strategic tax move. Still, it proved that the MicroStrategy Bitcoin strategy would be open to selling on occasion but under certain conditions, especially for necessity.

As of the end of 2024, MicroStrategy was reportedly still issuing equity to raise funds for more Bitcoin purchases, with potentially no sign of reducing that strategy. However, the SEC filing and the ensuing pressure as dividends and interest payments mount suggest that it might be getting to a critical point without any increase in Bitcoin’s price.

Market Impact: A Domino Effect?

Wider implications come with the potential for direct MBS to be reasonably be forced on into selling Bitcoin if it has such high amounts of it; thus, selling and putting pressure on the market could create a domino effect that could trigger further sales by other holders.

Also, directly or indirectly, investment sentiment on MicroStrategy itself may be affected. The MicroStrategy Bitcoin strategy company shares are often correlated with Bitcoin prices; hence, a potential fall in cryptocurrency value could also translate into a fall in MicroStrategy stock price, increasing financial difficulty.

Crypto analysts have warned that this kind of corporate leverage to Bitcoin constitutes a systemic risk in its market structure. If a Bitcoin maximalist corporation finds itself under pressure to sell like MicroStrategy, it can set off a loss of confidence followed by much wider price correction.

A High-Risk, High-Conviction Strategy

Cold calls so long at MicroStrategy, with institutional adoption for Bitcoin turning its pages on behalf of those like ‘Michael Saylor,’ who would not waver in faith for such asset classes and would rationalize for other firms and investors making brought-out crypto viable cash reserves. Recent financial disclosures made by the company further illustrate the perils of making foreign investments.

Over $35 billion is already at stake in Bitcoin with growing debts and software revenues returning frustratingly low revenues. The MicroStrategy Bitcoin strategy heat is on. Saylor and MicroStrategy also appear to be willing to liquidate – at least in terms of what they say publicly.

The next few months will remain critical to judging whether the company’s high-stakes gamble on Bitcoin will pay off or whether it will have to back down from its positions, thereby setting off a chain reaction within the entire ecosystem of crypto. As always with Bitcoin, volatility remains the only certainty.