MicroStrategy Insider Selling: Cashes Out $10M

MicroStrategy Insider Sells Shares During Bitcoin Rally

On June 12, 2025 - Carl Rickertsen, a veteran board member at MicroStrategy (MSTR), sold all of his remaining shares of the company quietly, exiting with approximately $10 million in cash, SEC public filings reveal.

The sale is occurring as MicroStrategy's units price keeps increasing, supported by its huge Bitcoin positions and positive market mood.

Purchased in 2022, Sold All by 2025 

Rickertsen made a brilliant decision in 2022 when he purchased 4,000 shares of MSTR at around $152 per coins, spending approximately $608,000. The tokens has since increased more than 150% since then, resulting in him having a huge profit.

He didn't wait this long to harvest profits. In 2023, he unloaded half of them. This month, he unloaded the remainder — officially closing out his holding in the company.

Source : Twitter

No New Buys This Year 

Up through 2025 so far, Rickertsen has made no MSTR stock purchases that qualified as SEC reportable. All of his recent actions have been sales, indicating a one-way trend in his trading activity.

Sells Shares on Same Day He Receives Them 

Apart from selling he has held before, Rickertsen has also been disposing of his stock option awards — coints that are awarded to him as part of his salary.

But rather than keeping them, he sells them the same day. For instance, on June 2, he received 26,390 assets through options and sold them all on the same day.

Zero Vested Shares Remaining :

Following these recent transactions, Rickertsen reported holding zero vested stocks of MicroStrategy as of June 5. That is, he now has no remaining personal ownership in the company's stock. 

A Broader Pattern of Insider Selling

Rickertsen's departure is part of a broader pattern at MicroStrategy. Over the past five years, insiders have sold significantly more stock than they've bought.

Based on secform4.com data, overall insider sales have outpaced buying by $864 million.

That has raised concerns for investors — particularly since MicroStrategy stock is so closely connected to Bitcoin. The company owns more BTC than nearly any other public company, and its shares frequently track alongside crypto prices.

Why Investors Care

When insiders sell, it isn't necessarily bad news — perhaps they need money or want to diversify. But when no one is buying, something else is going on.

As noted investor Peter Lynch once put it:

"Insiders sell for many reasons, but they buy for only one — they think the stocks will go up."

Because Rickertsen has sold all he owns and has no vested shares, some investors are asking: does he think the stock has topped out?

Only time will know. But for the moment, he's out — and the market is watching.