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