Michael Saylor, executive chairman of Strategy (formerly MicroStrategy), has signaled a subtle but significant shift in the company’s long-standing “never sell” Bitcoin narrative. Speaking on The Wolf of All Streets podcast, Saylor said the message needed a reset to avoid making Bitcoin seem like a locked reserve that cannot support the business. Strategy now holds about $65 billion worth of Bitcoin and must demonstrate it can use that liquidity if needed, framing any potential sale as a way to protect the asset that underpins most of the company’s value.
The pivot comes amid mounting financial pressure. Strategy reported a $12.54 billion net loss in its first‑quarter results and disclosed it held 818,334 BTC as of May 3, acquired at an average price of roughly $75,537 per coin. The company has raised $11.68 billion year‑to‑date and continues to accumulate, but Saylor made clear that any sale would not mean stepping away from accumulation. “Even if we were to sell one Bitcoin, we’d be buying 10 to 20 more Bitcoin,” he reiterated, tying the strategy to market conditions, financing access, and investor demand.
The debate intensified after Strategy filed plans to repurchase about $1.50 billion of its 2029 convertible notes at an estimated cash price of $1.38 billion. The filing disclosed that Bitcoin sales could be used alongside cash reserves and ATM equity proceeds to fund the buyback. The transaction is expected to settle around May 19, 2026, after which Strategy would cancel the repurchased notes, leaving roughly $1.50 billion outstanding.
Despite the discussion, Strategy has kept buying. Between May 4 and May 10, the company purchased an additional 535 BTC for about $43 million (average price ~$80,340 per BTC), lifting total holdings to 818,869 BTC. Separate updates showed daily liquidity in the STRC preferred stock reaching $1.53 billion, although no new Bitcoin purchases from that activity had been announced at the time.
