Michael Saylor finally wants to sell Bitcoin

Strategy Inc. (NASDAQ: MSTR) reported a net loss of $12.54 billion for the first quarter of 2026.

The loss was almost entirely driven by a $14.46 billion unrealized loss, as Bitcoin price crashed to $62,000 during the quarter, thanks to the United States-Israel-Iran war.

However, things might change in how the company handles its existing Bitcoin (BTC) stash.

Related: The only thing better than Bitcoin is...MSTR?

A bigger Bitcoin shopping spree

Strategy continued buying Bitcoin throughout the quarter despite the volatility. 

In fact, the company purchased 89,599 BTC in the first quarter at an average price of $80,900, totaling $7.3 billion. 

As of May 3, it held 818,334 Bitcoin, roughly 3.9% of all Bitcoin that will ever exist, at a total cost basis of $61.81 billion.

This aggressive buying strategy prompted analyst Taiki Maeda to call the next buying window in advance. 

Tracking Strategy's STRC ex-dividend cycles, he projected $2 billion to $3 billion in Bitcoin purchases over the two weeks leading into the May 14 ex-dividend date, consistent with the escalating pattern seen in the March and April cycles, which totaled $1.54 billion and $3.47 billion, respectively.

The earnings blackout compressed that buying window, but with results now public, the machinery is free to restart.

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The Bitcoin sale nobody saw coming

Strategy is now more inclined toward selling some of their Bitcoin instead of just buying.

During the earnings call, Executive Chairman Michael Saylor told analysts the company would likely sell some Bitcoin.

"We will probably sell some Bitcoin to fund a dividend just to inoculate the market — just to send the message that we did it," Saylor said.

President and CEO Phong Le elaborated on the broader shift. Strategy is now actively considering selling Bitcoin to fund dividends, buy back convertible debt, or build its USD reserve, whichever trade is most accretive to Bitcoin per share on any given day.

"We will sell Bitcoin when it is advantageous to the company," Le said. "We are not going to sit back and just say we will never sell the Bitcoin."

Saylor compared it to a real estate developer selling land at a profit, not a retreat from the strategy, but an expression of it. He also noted the company holds an estimated $2.2 billion in unrealized tax benefits tied to high-cost-basis Bitcoin that could be harvested through selective sales.

But this is not the first time they have hinted at selling Bitcoin. 

Back in December 2022, when they were still called MicroStrategy, the company sold approximately 704 BTC for cash proceeds of approximately $11.8 million, at an average price of approximately $16,776 per Bitcoin, net of fees and expenses. 

The company stated it planned to carry back the capital losses from the transaction against previous capital gains to generate a tax benefit. 

Two days after the sale, the company bought 810 BTC for $13.6 million in cash, at an average price of approximately $16,845 per Bitcoin, inclusive of fees and expenses.

At press time, MSTR was trading 1.56% lower at $183.99 during the pre-market hours.

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