Inside Michael Saylor’s Bitcoin Strategy as Firm Moves to Sell $1.25B in BTC

Bitcoin News: Michael Saylor’s Strategy (Nasdaq: MSTR) disclosed in a June 29 filing plans to potentially sell up to $1.25 billion in Bitcoin, describing the move as part of a “Bitcoin Monetization Program” aimed at strengthening liquidity, funding preferred dividend payouts, and meeting interest obligations.

This development represents the clearest shift so far from Saylor’s long-standing accumulation-focused approach, which he has consistently promoted to both institutional and retail audiences.

The immediate catalyst emerged on June 27, when Strategy’s mNAV — the ratio comparing its enterprise value to its Bitcoin holdings — dropped below 1 for the first time. This metric carries more than symbolic weight. The company’s financial model has relied heavily on maintaining a premium to its Bitcoin net asset value, enabling it to issue equity and preferred shares to acquire additional BTC at favorable terms. With mNAV slipping to 0.99, that mechanism has effectively lost momentum.

Strategy currently holds approximately $2.55 billion in cash reserves. The firm noted that any Bitcoin sales would occur “from time to time,” depending on market conditions and funding requirements, leaving timing and scale intentionally flexible.

Additionally, the company approved two separate share buyback programs worth up to $1 billion each—one targeting Class A common stock and the other focused on its Digital Credit Securities, which include preferred instruments such as STRK, STRF, and STRD.

Pressure is most evident within the preferred equity structure. STRK carries an 8% annual dividend on roughly $584 million raised, while STRF offers a 10% yield that can escalate to 18% if payments are deferred, based on $711 million raised. The latest issuance, STRD, generated about $979.7 million at a 10% non-cumulative rate.

In total, annual dividend obligations across these instruments exceed $700 million. When Bitcoin traded near its late-2025 highs around $125,000 and mNAV remained comfortably above 1, covering these costs through new equity issuance was straightforward. At current levels near $60,000 BTC and sub-1 mNAV, that strategy has become far less viable.

This is not Strategy’s first instance of tapping its Bitcoin holdings. On June 1, the company sold 32 BTC for roughly $2.5 million to fund preferred dividend payments. However, the latest filing expands the potential scale of such sales significantly.

Recent Bitcoin price movements have added further strain. BTC fell to around $58,000 last week amid approximately $3 billion in market outflows, coinciding with a sharp drop in MSTR shares and tightening NAV coverage. Although Bitcoin has since rebounded modestly to around $60,175, it remains well below levels where Strategy’s financial model operated efficiently. Options activity around $60,000 has also contributed to volatile, directionless price action.

Longtime Bitcoin critic Peter Schiff weighed in on June 29, labeling Strategy as “now a Bitcoin seller,” highlighting a stark contrast to Saylor’s previous stance that Bitcoin should never be sold. Schiff had earlier remarked, “What Saylor giveth, Saylor taketh away,” suggesting that Strategy’s aggressive accumulation previously supported Bitcoin’s price, a dynamic that could reverse under current conditions. While his comments are pointed, they reflect a broader structural concern.

Strategy, however, has rejected claims of a strategic reversal, reiterating that Bitcoin remains its primary treasury reserve asset and emphasizing that liquidity management does not signal diminished long-term conviction.

The board has also implemented a new policy requiring sufficient reserves to cover at least 12 months of preferred dividends and interest payments, marking a shift toward stricter balance-sheet management and acknowledging tighter access to capital markets.

At the time of writing, MSTR shares were trading at $82.31, down 3.5% on the day and significantly below previous highs reached when Bitcoin approached $125,000. This divergence highlights a key reality: MSTR functioned not just as a Bitcoin proxy, but as a leveraged bet on mNAV staying above 1—a condition that no longer holds.

Bitcoin News: MSTR Outlook — Will $90 Hold or Is Repricing Ongoing?

Currently trading near $92, MSTR is hovering just above a key psychological support level around $90. A decisive break below this threshold, especially on strong volume, could trigger accelerated selling from investors who initially viewed the stock as a premium Bitcoin exposure vehicle. With that premium now eroded, the equity offers neither direct BTC exposure nor the stability of a cash-generating business.

The newly approved $1 billion buyback programs for both common and preferred shares provide management with tools to stabilize prices. If executed assertively, these repurchases could establish a near-term price floor.

However, authorization does not guarantee execution. The company’s priority remains servicing its preferred dividend obligations, which limits its flexibility to return capital to common shareholders.

In the near term, MSTR is likely to trade within a range of $80 to $89, with direction largely dependent on Bitcoin’s ability to reclaim and sustain levels above $63,000. A move above that threshold could restore mNAV above 1, reopening the equity issuance channel. Conversely, a decline toward $55,000 could necessitate Bitcoin sales beyond the currently authorized $1.25 billion and potentially lead to a broader repricing of the preferred securities.

Meanwhile, countries like El Salvador continue accumulating Bitcoin despite external pressures, highlighting that not all large BTC holders face the same structural limitations as Strategy.

The key development to monitor next is whether Strategy initiates a significant Bitcoin sale in the coming weeks and how markets respond, particularly within its preferred equity segment.

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