Strategy’s Inner Circle Is Selling—A Storm Warning For Stockholders?

Microstrategy’s (rebranded to Strategy) board shake‑up took a sharp turn this week as insiders moved to cash in. It’s an unusual sight for a company that’s best known for piling up Bitcoin. Yet director Carl Rickertsen sold every last one of his shares, walking away with more than $10 million.

He first bought $700,000 worth of stock in October 2022 when the price was under $25 a share. Since then, the stock has climbed roughly 16× in less than three years.

Insider Sales Hit Record High

According to Protos, Strategy insiders have taken profits in a big way. Rickertsen alone unloaded over $10 million of stock this month. He had sold some shares back in 2023, but this time he cleared out his entire stake.

Protos also notes that he exercised stock options and sold shares on the same day. Some investors see that move as a sign he’s not betting on more gains for MSTR.

“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

— Protos (@Protos) June 12, 2025

No Insider Buys This Year

Based on reports by Protos, there haven’t been any insider purchases in 2025. Meanwhile, there have been 26 insider sales year‑to‑date. Those sales exceed buys by $864 million.

It’s rare to see so much insider selling without a single buy to balance it out. That pattern makes a few retail holders uneasy, especially after a month where the stock slid 10%.

The sell‑off comes even as Strategy keeps adding Bitcoin to its coffers. The firm now holds about 582,000 BTC, worth roughly $63 billion at today’s prices. Yet MSTR shares are down 10% over the past month.

By comparison, Metaplanet—a smaller Bitcoin holdings firm—jumped 150% over the same time. Some traders are asking why Strategy’s stock can’t catch the same kind of lift.

US President Donald Trump’s longtime Bitcoin critic Peter Schiff piled on this week. Schiff called Strategy’s business model “complete fraud” and warned that bankruptcy is only a matter of time.

He made those remarks after Saylor shared a Bloomberg report on the company’s Bitcoin stash. Schiff has pushed gold over Bitcoin for years. Even so, he admitted he regrets not buying Bitcoin back when prices were low.

Investors who back the Bitcoin‑reserve approach say that holding crypto will pay off over the long haul. They argue the stock’s wild ride is part of the deal. Others point to the wave of insider sales as a red flag.

Watchers will be tracking a few things: whether any insiders start buying again, how the share price reacts to the latest Bitcoin purchases, and if critics like Schiff can sway the broader market.

For now, Strategy’s path looks as bold as ever, but a fresh batch of insider sales has put the firm under a brighter spotlight.

Featured image from Getty Images, chart from TradingView