- MicroStrategy board member Carl Rickertsen sold his entire $10M stake in MSTR stock.
- No insider purchases were reported in 2025 despite 26 insider sales totaling $864M.
- MSTR stock is down 10% in the past month, raising investor concerns.
- The company holds 582,000 BTC, yet insider actions suggest waning internal confidence.
MicroStrategy, now rebranded as Strategy continues to double down on its Bitcoin-first approach, but behind the scenes, some of its top insiders are quietly heading for the exits. One of the company’s board members has just sold his entire $10 million stake in MSTR stock, raising serious questions about internal confidence in the company’s future.
What’s more surprising? Not a single insider has bought any shares in 2025. This glaring absence of insider buying has amplified concerns that the company’s stock performance, and possibly even the price of Bitcoin, could suffer as a result.
Carl Rickertsen, a board member of MicroStrategy since 2022, recently sold all of his MSTR shares, valued at over $10 million. This exit is especially striking given Rickertsen’s early involvement with the company’s Bitcoin pivot. He originally bought $700,000 worth of MSTR stock when shares were trading below $25. Since then, the stock has surged, making this a highly profitable exit.
According to reports from Protos, Rickertsen didn’t just sell his shares, he exercised stock options and offloaded them all on the same day. Moves like this often suggest a lack of long-term conviction in the company’s direction.
Even more troubling, no other insiders have purchased MSTR shares so far in 2025. Protos reports that there have been 26 insider sales this year, with sell-offs outpacing purchases by over $864 million. This imbalance is raising red flags among retail investors, particularly as MSTR stock has dropped 10% in the past month alone.
MicroStrategy Insiders Sell Amid $63B Bitcoin Bet
The optics are unsettling: while Strategy promotes itself as the ultimate Bitcoin play, its executives appear unwilling to back that vision with their wallets. Retail investors are beginning to question whether insiders are seeing risks that the public hasn’t fully realized.
All of this is happening while Michael Saylor, the company’s founder and executive chairman, continues to champion Bitcoin as the company’s core asset. MicroStrategy now holds an enormous 582,000 BTC, valued at more than $63 billion. Yet, despite these holdings, MSTR shares are down 8% year-to-date, currently trading around $379.
Critics are beginning to speak out. Longtime Bitcoin skeptic and economist Peter Schiff didn’t hold back, branding MicroStrategy’s business model a “complete fraud” and predicting bankruptcy is only a matter of time. While Schiff concedes he regrets missing out on early Bitcoin gains, he remains adamant that gold, not Bitcoin, will ultimately prevail.
As MicroStrategy deepens its commitment to Bitcoin, the widening gap between its public stance and insider behavior is casting a shadow over its strategy and possibly over the broader market as well.
Related | Bitcoin Crashes Below $103K Signaling Intense Bearish Pressure
