While Strategy (formerly known as MicroStrategy) continues to double down on Bitcoin, some of its top insiders are quietly heading for a big sell-off. One of the company’s member just sold his entire $10 million stake in MSTR stock.
What’s more surprising? Not a single insider has bought any shares in 2025. This has raised concerns that this could hurt Bitcoin price and MSTR stock performance.
Carl Rickertsen, a board member of MicroStrategy, recently sold all of his MSTR shares, worth over $10 million. This move is raising eyebrows, especially because Rickertsen has been with the company since 2022.
He originally bought $700,000 worth of MSTR stock when the price was under $25. Since then, the stock has skyrocketed, making his exit highly profitable.
Reports from Protos reveal that Rickertsen didn’t just sell, he exercised stock options and dumped the shares on the very same day. This kind of move often signals a lack of long-term confidence in a company.
Carl Rickertsen isn’t the only insider selling MSTR stock. On June 5 and 6, MicroStrategy’s Vice President Jeanine Montgomery also sold 340 shares of Class A stock. The sale price ranged between $370 and $377 per share, bringing her total earnings to about $127,000.
What’s even more worrying is that no insiders have purchased MSTR shares so far in 2025. According to Protos, there have been 26 insider sales this year, with total sell-offs outpacing purchases by over $864 million.
This trend paints a concerning picture for small investors, especially as the stock has dropped 10% in the past month.
That’s a huge red flag for many retail investors, especially when the company’s own executives are not backing the stock they help run.
This comes at a time when Michael Saylor, the face of Strategy, continues to promote the firm’s Bitcoin-first strategy. The company now holds a staggering 582,000 BTC worth over $63 billion.
But despite all that, MSTR shares are down by 8%, currently trading around $379.
Famous economist and long-time Bitcoin critic Peter Schiff didn’t hold back. He called MicroStrategy’s business model a “complete fraud,” and claimed bankruptcy was only a matter of time.
While Schiff admits he regrets not buying Bitcoin earlier, he still believes gold, not Bitcoin, will come out on top.
Heavy insider selling with few or no purchases can signal a lack of confidence in the company’s future, raising red flags for retail investors
Contrary to some reports, at least one insider, director Jarrod M Patten, bought 5,000 shares in June 2025, though the vast majority of insider trades have been sales
As of June 13, 2025, MicroStrategy owns 582,000 Bitcoins. This makes them the largest corporate holder of the digital asset globally.
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