On Sunday, Michael Saylor, the chairman and co-founder of Bitcoin treasury giant Strategy (formerly MicroStrategy), shared the infamous “Orange Dot” to signal that the company is preparing to make its 99th BTC purchase, expected to be bigger than the previous $90 million buy.
Few figures in the financial world are as polarizing or consistent as Saylor, and the development comes despite the broader crypto market grappling with its most severe downturn in years.
Michael Saylor Teases 99th Bitcoin Buy for Strategy
The timing of his post is significant, as Bitcoin, which touched a new all-time high above $126,000 in October 2025, is currently undergoing a four-month-long bear market. The latest flash crash has dragged prices under $70,000. For Strategy, this is not just a market correction, but a test of its merit.
Following a series of aggressive acquisitions since August 2020, the business intelligence software provider-turned-Bitcoin treasury firm now holds 714,644 BTC, valued at $49.07 billion. However, the recent drop has pushed bitcoin’s price below Strategy’s average cost basis of $76,056 per BTC.
For a tense period in early February, the world’s largest corporate bitcoin holder was considered technically “underwater,” facing billions of dollars in unrealized paper losses on its assets. Saylor’s tweet suggests that Strategy’s 99th bitcoin buy could serve as a psychological anchor for investors, reinforcing the company’s position as an aggressor rather than a victim of the market.
However, the performance of Strategy’s stock, MSTR, has mirrored bitcoin’s volatility – an asset it tracks. Since October’s flash crash, MSTR has been faced with a grueling retreat, falling over 70% from its July 2025 peak of $457. The stock hit an 18-month low earlier this month after Strategy reported a staggering $12.4 billion net loss for Q4 2025. This was primarily driven by the new FASB accounting rules that require companies to mark digital asset holdings to their subsequent market value.
MSTR Rebounds 10% After CEO Reassures Investors
However, the tide turned slightly this week. MSTR shares jumped 10% in a relief rally after Saylor’s recent CNBC appearance and social media posts. Furthermore, investors were relieved by CEO Phong Le’s comments, in which he reassured them that the company has sufficient cash reserves to cover its dividend and debt obligations for the next 30 months. Crucially, he noted that Strategy’s balance sheet would face true structural stress if bitcoin’s price fell to $8,000 and remained there for several years – a scenario Saylor has dismissed as nearly impossible.
Despite the rebound, concerns remain for MSTR. Analysts are keeping a close watch on the stock’s Multiple on Net Asset Value (mNAV) – a key metric used to evaluate digital asset treasury companies based on how much the market values their equity relative to the value of their crypto holdings. Historically, MSTR traded at a significant premium to the bitcoin it holds, allowing Strategy to sell its expensive stock to buy BTC at cheaper rates – a cycle that Saylor refers to as “BTC Yield”.
Since the market rout began, that premium has largely evaporated. In September 2025, Strategy’s mNAV fell toward the 1.0 mark, which meant the market was pricing the company almost exactly at the value of its coins, with zero premium for the underlying software business. When the metric stays near or below 1.0, a DAT’s ability to raise capital via equity sales is severely hampered.
Strategy introduced the 42/42 Capital Plan to counter such a scenario, which is a three-year strategy aiming to raise $42 billion in equity and $42 billion in debt to continue its bitcoin accumulation. To maintain liquidity, the company also introduced a stack of preferred shares, such as STRK, STRF, STRD, and STRC. These instruments have allowed Strategy to buy more bitcoins than ever without being forced to count on the lending market, with its latest purchase of 1,142 BTC for approximately $90 million coming last week.
At the time of writing, Bitcoin (BTC) is trading at $68,856 – down 2.46% in 24 hours. Strategy (MSTR) closed Friday’s trading session at $133.88 – up 4.39% for the day.
