MicroStrategy Exec Cashes Out $10M in Shares as Bitcoin Bet Raises Eyebrows

Another day, another crypto whale making moves—but this time, it''s not retail investors sweating the dip. MicroStrategy''s Bitcoin-heavy strategy faces scrutiny as a top insider offloads $10 million in shares. Guess even true believers need exit liquidity sometimes.

Wall Street''s favorite ''HODL'' play looks shaky. The enterprise software-turned-Bitcoin-ETF company keeps doubling down on its crypto gamble—while insiders quietly cash chips. Classic ''do as I say, not as I do'' energy from the C-suite.

Meanwhile, Bitcoin maximalists shrug. Price dips are just buying opportunities... until they''re not. The real question? Whether MicroStrategy''s balance sheet can handle the next crypto winter without becoming a forced seller. Tick tock, Michael Saylor.

• 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.

🚨 MICROSTRATEGY DIRECTOR DUMPS ENTIRE STAKE

Carl Rickertsen just cashed out ALL his $MSTR shares for $10M+ while the company keeps buying $BTC.

When directors quietly exit, investors should pay attention.

What does he know that Saylor fans don’t? 🧵

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.

“Insiders might sell for many reasons, but they buy for only one: they think the price will rise” – Peter Lynch.

😶‍🌫️ Well, ZERO insiders have bought $MSTR in 2025. Instead, there have been 26 insider sales this year alone.

5 year score: Insider sales exceed purchases by $864M. pic.twitter.com/nZSzqFcWZe

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.

I don''t regret the posts. But sure I regret not buying it when I first learned about it.

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