Strategy, the bitcoin-hoarding firm founded by Michael Saylor, sold 32 bitcoin for roughly $2.5 million last week, marking its first sale since the depths of the crypto winter in late 2022. The company said in a regulatory filing that it expected to use the proceeds to fund distributions on its preferred stock.
The sale represents a notable shift for a company that built its identity around accumulating and holding bitcoin. Saylor began transforming his software-intelligence company, formerly known as MicroStrategy, into a bitcoin hoarder in August 2020. He initially used the corporate treasury to fund bitcoin acquisitions, then tapped equity markets through at-the-market share offerings, and later became one of the largest global convertible-bond issuers, raising more than $6.2 billion in 2024 alone to fund purchases.
Bitcoin fell 3% to about $71,467 on Monday afternoon. The cryptocurrency has fallen 18% this year but has traded in a fairly narrow range recently, even as tech stocks hit new records. Shares of Strategy dropped 4% in mid-day trading.
Some investors have grown skeptical about Strategy’s ability to sustain its preferred-stock dividends over the long term. Late last year, the company set up a $1.44 billion cash reserve to fund dividend obligations, but that coffer has decreased to $900 million, according to the filing.
Over the past year, Strategy has launched a suite of high-yield preferred stocks on the Nasdaq, including Strike, Stretch, Strife, and Stride, along with the euro-denominated Stream. Individual investors have flocked to the products for their yields; Stretch, which has become a favorite among individual investors, offers a variable dividend that recently stood at 11.5%.
Saylor and Strategy CEO Phong Le first floated the idea of selling bitcoin to cover dividend obligations last year, as prices crashed from an October peak above $126,000. The comments sparked backlash because Saylor had spent years urging his social-media followers to never sell bitcoin.
In an interview in early May, Saylor told The Wall Street Journal that Strategy was open to selling some bitcoin to fund preferred dividends but only as part of a broader approach in which the company remains a net buyer over time.
“If you sold one bitcoin to buy 10 bitcoin more, technically you sold a bitcoin, but economically you bought nine more bitcoin,” Saylor said. “And so we are really just running the engine rationally so that we can acquire more bitcoin and hold it longer to the benefit of all of the investors.”
At the time, Saylor said the company would sell bitcoin to monetize capital gains and prove that the asset was easily tradable — a response to short sellers betting against the company’s stock. “If we say we never sell, then the short narrative would be, since they can’t sell it, it must not be worth anything,” he said.
The bitcoin-buying strategy Saylor pioneered has faded as individual traders, who once fueled the hype, have shifted their interest toward artificial-intelligence stocks. Institutional players remain, but their appetite has turned toward tokenization — the process of turning traditional assets into tradable tokens on the blockchain — according to the Journal.
Strategy still holds around 843,706 bitcoin, worth more than $60 billion at current prices, dwarfing the $2.5 million in proceeds from last week’s sale.