Strategy, where Michael Saylor is the chairman of the board, once stood out as one of the symbol companies of the dot com collapse. After more than 25 years, the company has become one of Wall Street’s most closely watched examples of how it finances and manages the huge Bitcoin accumulation.
New frame and first big sale
Strategy, formerly known as MicroStrategy, holds the largest Bitcoin reserve among publicly traded companies with 843,775 Bitcoins. While the value of these assets held by the company on its balance sheet exceeded 54 billion dollars, the treasury model it developed set an example for many companies listed on the stock exchange.
Strategy announced a new capital framework on June 29. This structure allows the sale of Bitcoin to finance preferred stock dividends, strengthen cash reserves, and conduct securities buybacks. The company then announced that it sold 3,588 Bitcoins, its biggest sale since adopting Bitcoin as its main reserve asset in 2020.
Drew Forman, head of strategy at Talos, emphasizes that the debate is no longer limited to buying Bitcoin alone, but focuses on how these positions are financed, managed and liquidated when necessary.
The company has advocated the approach of accumulating its Bitcoins over the years. For this reason, the new framework that allows sales has raised questions among some investors and analysts. On the other hand, those close to Strategy consider this change as a natural extension of managing a multi-billion dollar digital asset treasure.
The focus of criticism is on the financing structure
Critical analysts, on the other hand, argue that the risk accumulates in the financing architecture built on this asset rather than the Bitcoin asset. New Constructs chief executive David Trainer states that the main factor supporting the company’s valuation is not its software activities, but its Bitcoin position, which has been expanded through debt and preferred shares.
According to the data shared by Trainer, Strategy has $6.7 billion in convertible bonds and $15.5 billion in preferred shares as of the end of May 2026. A significant portion of these resources were used to purchase more Bitcoin.
Mini glossary: A convertible bond is a debt instrument that can be converted into shares under certain conditions. Preferred stock generally offers dividend priority but may impose a regular cash obligation on the company.
David Trainer says that today’s structure uses a different mechanism than in the past, but essentially creates a leveraged equity structure on a volatile asset, which can make valuation fragile.
The collapse of 2000 was remembered again
The discussions regarding Strategy also brought the company’s accounting crisis in 2000 to the agenda again. MicroStrategy announced in March 2000 that it had to adjust its 1998 and 1999 financial results due to accounting errors. The share price dropped from $260 to $86 in a single session, and fell to $33 on April 13, 2000.
The company later settled civil charges with the U.S. Securities and Exchange Commission regarding its accounting practices, but did not admit to the charges. Saylor, on the other hand, returned to the center of the market by turning Bitcoin into the company’s main reserve asset in the summer of 2020.
The real question boils down to durability.
Today, the debate is less about the accuracy of financial reporting and more about whether this increasingly complex Bitcoin strategy can withstand prolonged market pressure. While the Bitcoin price remains well below the peak of over $126,000 seen in October 2025, questions about Strategy’s model have also gained strength.
Some analysts think the model works only as long as Bitcoin gains value and investors continue to provide new capital. Others see the company’s balance sheet management as a more flexible, corporate treasury approach. At the center of the debate is no longer just how much Bitcoin is held, but also how sustainable this position is.
