MicroStrategy Faces 26 Insider Sales Year-to-Date Amid Stock Price Drop

MicroStrategy, a prominent player in the Bitcoin market, has faced significant scrutiny in 2025 due to a surge in insider stock sales. Board member Carl Rickertsen liquidated his entire company shareholding, valued at $10 million, during a period with no insider buying. This move has raised questions about internal trust in the company’s future plans. Rickertsen, who joined MicroStrategy in 2022, initially bought $700,000 worth of shares and gradually sold portions of his holdings before fully exiting this year. The timing of his exit is particularly notable given the stock price surge since his entry.

Data confirms that insider selling at MicroStrategy has reached 26 transactions year-to-date, with no reported purchases by company insiders. The value of these insider sales has exceeded $864 million, suggesting a broader trend of profit-taking or diminished confidence. This wave of insider exits comes as the broader market evaluates the risks and benefits of MicroStrategy’s Bitcoin-centric business model. The company currently holds over 582,000 BTC, with continued purchases despite price swings. However, these internal moves may suggest that top executives are uncertain about the long-term trajectory of their Bitcoin-heavy strategy.

While MicroStrategy continues to invest heavily in Bitcoin, its stock performance has lagged in recent weeks. Over the past month, MSTR has dropped by 10%. In contrast, Metaplanet, another firm involved in Bitcoin holdings, has recorded a 152% increase during the same period. This divergence underscores growing concerns among investors about the effectiveness of MicroStrategy’s current strategy. The absence of insider confidence could further impact retail sentiment. Investors often monitor insider trades as indicators of a company’s internal outlook. When senior leaders sell without any offsetting purchases, it can create doubts about future performance. The simultaneous execution of stock options and immediate share sales further suggests that the motivation may be short-term gains rather than long-term confidence.

Public criticism of MicroStrategy’s approach has intensified. Economist and Bitcoin critic Peter Schiff called the business model a fraud. Schiff’s remarks followed the company’s disclosure of its massive Bitcoin reserves, currently valued at $63 billion. He stated that the firm’s investment in Bitcoin might produce future financial instability. Schiff pointed out Bitcoin’s lagging performance against gold and suggested that the cryptocurrency market could have reached its maximum potential. Despite these critiques, MicroStrategy continues to pursue aggressive crypto investments. Yet, the insider sales trend could add new pressure to the stock. Investors are watching closely to see if the company can maintain market trust amid rising internal exits and external skepticism.