Michael Saylor’s MSTR Shows Minimal Gains on Bitcoin Investment Amid Overblown Imminent Danger Concerns

Michael Saylor’s company, Strategy (MSTR), is facing increased scrutiny as Bitcoin prices decline. The stock has dropped nearly 70% from last year’s peak, raising concerns about the company’s financial stability and obligations.

Current Financial Position of Strategy

Throughout 2025, Strategy has relied on perpetual preferred stock to finance its Bitcoin acquisitions. The company has primarily issued common shares at market prices to fulfill its preferred dividend obligations. This strategy has become critical as Bitcoin’s recent downturn has refocused attention on the firm’s potential vulnerabilities.

Preferred Share Series Overview

Under the leadership of Michael Saylor, Strategy issued four distinct U.S.-listed preferred series:

• Strike (STRK): Offers an 8% fixed dividend and is convertible into common stock at $1,000 per share.
• Strife (STRF): Features a 10% fixed non-cumulative dividend and holds the most senior position among the preferred shares.
• STRD: Provides a 10% cumulative dividend and is positioned junior to Strife.
• Stretch (STRC): Launched in August at $90 with a 10.5% fixed cumulative dividend; currently trades slightly above the issue price.

Currently, STRK is trading around $73, yielding 11.1%, while STRD has fallen to approximately $66, reflecting a 15.2% yield. STRF stands as the only series above its issue price, trading at about $94 with an approximate 11% gain.

Bitcoin Holdings and Market Conditions

Market participants are now closely monitoring the $74,400 level. This threshold is critical for Strategy, as it signifies when the company would begin to incur losses on its Bitcoin assets accumulated over five years. However, a decline below this level does not instantly trigger a margin call or force asset liquidation.

Future Financial Obligations

The company faces more significant pressures in the coming years. Notably, on September 15, 2027, holders of $1 billion in 0.625% convertible senior notes will have their first put option. These notes were originally priced when MSTR shares were valued at $130.85, with a conversion price set at $183.19.

Currently, as MSTR shares hover around $168, it is unlikely that noteholders will convert them into stock. This could lead to demands for cash repayment, potentially compelling Strategy to liquidate assets or seek new funds unless share prices recover significantly before 2027.

Options for Dividends and Capital Management

Despite recent struggles, Strategy retains various options to manage its obligations. Even if the market value of its Bitcoin holdings declines, the company can maintain its preferred dividend payments through several strategies:

• Issuing additional common shares through at-the-market offerings.
• Selling portions of its Bitcoin treasury.
• Paying dividends in-kind using newly issued stock.

However, employing these methods may negatively impact investor confidence and hinder future capital raises for further Bitcoin investments. As concerns mount, the path forward for Strategy remains uncertain.