Saylor Leverages Selloff to Bulk Reserves
Michael Saylor’s company, Strategy (MSTR), executed a significant capital raise last week by selling approximately 2.7 million shares of its own stock, generating $335.5 million in proceeds. The move followed a pronounced selloff in the company’s perpetual preferred stock, STRC, which had dipped to a record low of $82.53 before partially recovering to $90.59 during Monday’s premarket session. This aggressive fundraising effort was split between acquiring more Bitcoin and shoring up cash reserves, marking a dual-pronged response to recent volatility in both crypto and equity markets.
Of the total raised, $35 million was allocated to purchase 520 additional bitcoins at an average price of $67,068 each. The remaining $300 million was funneled directly into the company’s US dollar reserve, now totaling $1.4 billion. This cash buffer is intended to support dividend payments for STRC holders—a move that comes as STRC continues to trade below its $100 par value despite offering an annualized yield above 12.9%.
STRC shares briefly touched $82.53 on Thursday before rebounding to $90.59 by Monday morning.
Cash Infusion Shields Preferred Shareholders
The decision to bolster cash reserves is closely tied to obligations on Strategy’s preferred stock, STRC, which launched in July 2025 with the aim of maintaining a stable price near its $100 par value but has since struggled.
As STRC slid below $83 last Thursday and closed at $88.59, the company faced mounting pressure to reassure investors about its ability to meet dividend commitments—currently set at an adjustable rate of 11.5% per year. By raising and allocating $300 million specifically for this purpose, Strategy signaled that it intends to backstop payouts even as market sentiment remains uncertain. On paper, STRC was designed as a stable-yield instrument, but its widening discount has left some investors wary about future performance.
According to coindesk.com, the cash raised from the MSTR share sale is explicitly earmarked for these dividend payments—a concrete step that separates this capital from funds used for further Bitcoin accumulation.
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Bitcoin Holdings Swell Despite Market Jitters
Strategy’s latest Bitcoin acquisition brings its total holdings to an imposing 847,363 BTC, purchased at an aggregate cost of roughly $64.01 billion. This translates into an average acquisition price of $75,651 per coin—a figure notably higher than current spot prices around $65,000 as of Monday morning.
Despite Bitcoin falling nearly 50% since STRC’s launch in July 2025, Saylor’s firm continues buying aggressively.
The most recent purchase—520 BTC for just under $35 million—occurred while combined exchange volumes for May slipped 3.45% month-on-month to $4.41 trillion, their lowest since September 2024. Meanwhile, RWA (real-world asset) perpetual futures volumes rose over 10%, hitting new highs and signaling shifting trader preferences within digital asset markets.
MSTR Rallies as STRC Hits Record Low
While preferred shareholders saw their investments dip below par last week, MSTR common stock moved in the opposite direction—rising 3.5% on Monday as Bitcoin rebounded toward $65,000. This divergence highlights a growing gap between equity and preferred investors: common shareholders benefit directly from Bitcoin exposure and treasury growth, whereas STRC holders face both price discounts and questions about long-term yield sustainability.
Broader tech sector turbulence provided further context: the Nasdaq index fell over 1% on Monday amid sharp drops in Google (down 5%), Amazon (down 3.5%), and Broadcom (down 3.5%). Even so, other digital asset-linked equities like Hive Digital rallied strongly—up 23% for the day—suggesting pockets of optimism remain despite volatility elsewhere.
Strategic Pivot Amid Broader Tech Slide
This latest capital maneuver comes against a backdrop of shifting macroeconomic expectations. Bank of America now anticipates three Federal Reserve rate hikes before year-end 2026—each by 25 basis points—which would lift the federal funds rate target range up to 4.25–4.5%. Rising rates could pressure both risk assets and high-yield instruments like STRC further if inflation persists; core personal consumption expenditures are forecasted at 3.5% for May, up significantly from last year.
It remains uncertain whether Strategy’s dual approach—expanding Bitcoin holdings while boosting dollar reserves—will insulate it from further swings in either crypto or traditional finance markets. For now, however, Saylor appears committed to leveraging both sides of his balance sheet: buying digital assets on weakness while ensuring liquidity for investor payouts.
What to Take Away
- •Strategy (MSTR) sold 2.7 million shares last week, raising $335.5 million in proceeds.
- •$35 million was used to buy 520 bitcoin at an average price of $67,068 each; total holdings now 847,363 BTC.
- •$300 million was added to cash reserves, bringing the total to $1.4 billion to support STRC dividend payments.
Key variables ahead
If STRC’s price remains below its $100 par value after last week’s record low of $82.53 and Monday’s premarket recovery to $90.59, the company’s ability to resume at-the-market STRC share issuance remains unclear, which would immediately limit further capital raises for additional Bitcoin purchases or reserve increases.
