Bitcoin News: Michael Saylor’s Strategy (Nasdaq: MSTR) said in a June 29 filing that it could sell up to $1.25 billion in Bitcoin under what it calls a “Bitcoin Monetization Program,” a move aimed at strengthening liquidity, funding preferred dividends, and meeting interest payments.
The disclosure marks a clear pivot from Saylor’s long-promoted strategy of continuous Bitcoin accumulation. For years, the company leaned on that narrative to attract both institutional and retail investors.
The shift follows a key inflection point on June 27, when Strategy’s mNAV — the ratio of enterprise value to its Bitcoin holdings — dropped below 1 for the first time. That level is critical because the company’s capital strategy relied on trading at a premium to its Bitcoin net asset value, enabling it to issue equity and preferred shares to acquire more BTC efficiently. With mNAV at 0.99, that engine has effectively stalled.
Strategy holds roughly $2.55 billion in cash and said any Bitcoin sales would occur “from time to time,” depending on market conditions and capital needs, without committing to a fixed timeline.
Alongside this, the company approved two share buyback programs worth up to $1 billion each—one for Class A stock and another for its Digital Credit Securities, which include preferred series STRK, STRF, and STRD.
The strain is most visible in the preferred stack. STRK carries an 8% dividend on about $584 million raised, while STRF offers a 10% yield that can climb to 18% if payments are deferred, based on $711 million raised. The latest series, STRD, generated roughly $979.7 million at a 10% non-cumulative rate.
Combined, these obligations exceed $700 million annually. When Bitcoin was trading near $125,000 and mNAV remained above 1, covering those costs through fresh equity issuance was straightforward. With BTC now around $60,000 and mNAV below 1, that approach has become far more difficult.
Strategy has already taken small steps in this direction. On June 1, it sold 32 BTC for about $2.5 million to fund preferred dividends. The latest filing significantly increases the potential scale of such sales.
Market conditions have added pressure. Bitcoin recently fell to around $58,000 amid roughly $3 billion in outflows, while MSTR shares declined sharply, compressing the company’s NAV buffer. Although BTC has since rebounded modestly to about $60,000, it remains below levels that previously supported the model, with options positioning around that range contributing to choppy price action.
Critics were quick to respond. Peter Schiff described Strategy as “now a Bitcoin seller,” highlighting the contrast with Saylor’s earlier stance that BTC should never be sold. While the comment is pointed, it reflects a broader structural reality: Strategy’s aggressive buying acted as a form of price support, which can reverse if selling accelerates.
The company has pushed back on suggestions of a strategic shift, reiterating that Bitcoin remains its primary treasury reserve asset and framing the move as liquidity management rather than a change in long-term conviction.
The board has also adopted a policy requiring at least 12 months of reserve coverage for preferred dividends and interest payments, signaling a more disciplined approach to balance-sheet management and acknowledging tighter access to capital markets.
MSTR shares were trading at $82.31 at the time of writing, down 3.5% on the day and well below prior highs seen when Bitcoin approached $125,000. The divergence underscores a key point: MSTR has functioned not just as a Bitcoin proxy, but as a leveraged bet on mNAV staying above 1—an assumption that no longer holds.
Bitcoin News: MSTR Outlook — Key Support in Focus
At around $92, MSTR is hovering just above a psychological support level near $90. A break below that level could trigger further selling, particularly from investors who once viewed the stock as a premium Bitcoin vehicle. With that premium now gone, the equity offers neither direct BTC exposure nor strong operating cash flow support.
The $1 billion buyback programs for both common and preferred shares could provide some support if used aggressively. However, the company’s priority remains meeting preferred dividend obligations, limiting flexibility for capital returns.
In the near term, MSTR is likely to trade between $80 and $89, with direction closely tied to Bitcoin’s performance. A move above $63,000 could push mNAV back above 1 and reopen the equity issuance channel. A drop toward $55,000, however, could force larger Bitcoin sales beyond the current $1.25 billion authorization and potentially lead to further repricing across its preferred securities.
Meanwhile, El Salvador continues accumulating Bitcoin despite external pressures, highlighting that not all large BTC holders face the same structural constraints as Strategy.
The next key signal will be whether Strategy executes a meaningful Bitcoin sale in the coming weeks and how markets respond, particularly within its preferred securities.
