Michael Saylor Faces Backlash Over Private Jet Purchase Amid MicroStrategy Slide

Michael Saylor is once again at the center of Crypto Twitter’s scrutiny after new regulatory filings revealed that Strategy (formerly MicroStrategy) recently spent $27 million on a deposit for a corporate aircraft.

The disclosure has fueled a wave of criticism from users who argue that the purchase reflects misplaced priorities during a period of sharp volatility for both Bitcoin and Strategy’s stock.

Shareholders Question Strategy’s Spending Priorities

According to MicroStrategy’s Form 10Q filed on November 3, the company’s net cash used in investing activities rose sharply year-over-year. 

The filing revealed that for the nine months ending on September 30, Strategy made a $27 million deposit on a new corporate aircraft.

It also disclosed $19.38 billion in Bitcoin purchases funded through convertible notes, stock offerings across its STR series, and ongoing ATM programs.

Although companies often use corporate funds for executive travel, critics argued that the context is especially important for Strategy. 

The firm no longer resembles a traditional product-driven software company. Instead, it functions as a vehicle tied to Bitcoin’s volatile price movements. 

With MSTR down about 30% over the past month, some investors questioned whether a multimillion-dollar aircraft aligns with its stated Bitcoin-first strategy.

Investor Confidence Tested

Crypto Twitter reacted sharply, arguing that shareholder capital should focus on increasing the firm’s Bitcoin position rather than expanding executive privileges. 

Users expressed frustration that the jet deposit came alongside billions in financing tied directly to new equity issuances. Others suggested the timing of the purchase undermined confidence in the company’s alignment with its retail investor base.

Strategy supporters countered that corporate aircraft are common for firms with global operations and high-volume executive travel requirements. They also noted that the $27 million deposit represents a small fraction of the capital committed to Bitcoin accumulation during the same nine-month period. 

Still, the dispute reflects a broader disagreement over how a Bitcoin-focused public company should balance its operational needs with public optics.

As Bitcoin continues to fluctuate, the episode highlighted how closely Saylor’s decisions are tied to market sentiment, especially during periods of heightened volatility. 

The debate also revealed how investor expectations shift when a company positions itself almost entirely around a single macro-sensitive asset.