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Michael Saylor’s Strategy names the ‘last resort’ condition it will sell Bitcoin

Michael Saylor’s Strategy names the ‘last resort’ condition it will sell Bitcoin
Paul L.

Michael Saylor’s Strategy (NASDAQ: MSTR) formerly MicroStrategy has outlined the conditions under which it would part with its Bitcoin (BTC) holdings, framing the move as an extreme response to market stress. 

According to CEO Phong Le, the firm would consider selling Bitcoin only if its stock fell below its net asset value and it simultaneously lost access to new capital, he said in an interview with What Bitcoin Did published on November 28.

Under those conditions, the executive noted that selling a portion of its holdings would become a defensive step aimed at preserving what the company views as its core metric of Bitcoin yield per share.

“That would be a last resort. There’s the mathematical side of me that says that would be absolutely the right thing to do. There is the emotional side of me, the market side that says, we don’t want to really be the company that’s selling Bitcoin,” Le said. 

The discussion around a potential sale comes as Strategy’s massive Bitcoin treasury continues to post gains. The company now holds 649,870 BTC valued at roughly $59.33 billion. Its average acquisition cost stands at $74,430 per coin, giving it a profit margin of about 22.66% based on current valuations.

Despite the appreciation, Strategy’s equity metrics show the stock still trades below the value of its underlying Bitcoin. The company’s basic market capitalization is listed at $51 billion, rising to $57 billion on a diluted basis, while enterprise value sits at $66 billion. 

Strategy Treasury Metrics. Source: Bitcoin Treasuries

Strategy’s business model 

Notably, the company’s model relies on keeping its stock trading at a premium to net asset value. When that premium exists, Strategy raises equity and converts the proceeds into more Bitcoin, steadily increasing BTC per share. 

If the premium disappears and new equity becomes too dilutive, Le said selling Bitcoin to meet obligations becomes the logical fallback, even if it contradicts the firm’s long-standing accumulation strategy.

Notably, amid the recent Bitcoin price drop, the firm has come under pressure, with some on Wall Street warning that its strategy could falter and calling for it to offload part of its BTC holdings.

The pressure stems from rising fixed payouts tied to preferred shares issued in 2025, which carry escalating annual obligations of roughly $750 million to $800 million as different series mature. 

To this end, the company aims to fund these commitments mainly through equity issuance while the stock trades at a premium, a cycle Strategy believes strengthens investor confidence. 

Featured image via Lex Fridman YouTube

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