MSTR Stock in Turmoil: Insider Exodus Sparks Behind-the-Scenes Drama

MicroStrategy''s high-stakes Bitcoin bet faces turbulence as executives head for the exits. Is this a red flag for crypto-backed equities—or just Wall Street''s usual theatrics?

The great MSTR shuffle: Who''s left holding the Bitcoin bag?

Three C-suite departures in 30 days have investors questioning whether Michael Saylor''s crypto crusade is losing its inner circle. No regulatory filings cite ''personal reasons''—but when the CFO, CTO, and general counsel all bail during a bull market, even diamond hands get sweaty.

When the smart money walks, dumb money should run?

Institutional flows into Bitcoin ETFs hit record highs last quarter, yet MSTR''s insiders can''t seem to exit fast enough. The stock''s 45% premium to BTC holdings now looks less like visionary leadership and more like... well, every other overvalued tech stock this cycle.

One thing''s certain: When the corporate treasury holds more digital assets than the IT department holds servers, traditional valuation models go out the window—along with risk-averse executives. Welcome to the new normal where balance sheets moon and common sense gets rekt.

TLDR

• Carl Rickertsen sold all of his MSTR stock worth over $10 million in 2025.
• He originally purchased $700,000 worth of MSTR shares in 2022 when the stock traded below $25.
• MicroStrategy insiders made 26 stock sales in 2025, but no insider purchases were reported.
• Total insider sales for the year have exceeded $864 million, according to reports.
• Despite the selling, MicroStrategy continues to accumulate Bitcoin holdings aggressively.

Board-level activity at MicroStrategy is signalling a strong internal shift as multiple insiders exit positions. Director Carl Rickertsen recently sold all of his MSTR stock, which totalled over $10 million in value. While the company continues to accumulate Bitcoin, the increasing number of sales is beginning to raise serious market concerns.

MSTR Stock Director Fully Cashes Out Holdings

Carl Rickertsen joined the MicroStrategy board in October 2022 and bought $700,000 worth of MSTR stock. At that time, MSTR stock traded below $25, offering a significantly lower entry point. Over time, he reduced his holdings and fully exited his position in 2025.

His final sale reportedly came after exercising stock options and selling the same day. This MOVE was recorded during a period when MSTR stock price had appreciated over sixteenfold. The sale drew attention because of its timing, coinciding with growing scrutiny of insider activity.

Rickertsen’s full divestment follows partial sales made throughout 2023. The Protos report indicated the transactions were strategic and aligned with personal financial decisions. However, the absence of reinvestment could reflect internal sentiment.

Insider Sales Continue Despite Bitcoin Accumulation

Data shows that in 2025, there were 26 insider sales of MSTR stock and no recorded insider purchases. These sales reportedly outpaced purchases by over $864 million year-to-date. Despite this, MicroStrategy continued acquiring Bitcoin aggressively throughout the same period.

Michael Saylor’s firm now holds over 582,000 BTC, reportedly worth $63 billion. While the firm expands its crypto holdings, the MSTR stock has declined by 10% in the past month. The drop in price, despite bullish bitcoin activity, is drawing attention.

Other Bitcoin-related firms like Metaplanet saw different outcomes. Metaplanet’s stock reportedly surged 152% in the past 30 days. The divergence in performance has led to comparisons across market participants.

Critics Question Sustainability of the Business Model

Economist Peter Schiff recently criticized MicroStrategy’s strategy and commented on its long-term viability. Schiff labelled the company model unsustainable and predicted a bankruptcy outcome if current trends persist. He attributed the risk to the firm’s dependency on Bitcoin.

Schiff also stated that Gold remains the more reliable alternative over time. His remarks came after Saylor promoted MicroStrategy’s growing Bitcoin holdings on Bloomberg. The firm’s increasing digital asset exposure continues to invite debate from financial experts.

MSTR stock now sits at the center of this discussion, surrounded by insider exits and external criticism. The pattern of selling and market volatility is bringing added pressure on the stock. Future performance of MSTR stock may hinge on continued confidence in its Bitcoin-led strategy.