Will Strategy Sell Bitcoin? Saylor Says ‘Never Sell’ Needed a Reset

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Michael Saylor said Strategy may sell some of its Bitcoin when necessary, signaling a more flexible approach compared to his long-standing “never sell” stance.

Speaking on The Wolf of All Streets hosted by Scott Melker, Saylor explained that Strategy wants to show Bitcoin can function as a usable corporate asset rather than a reserve that can never be touched.

He said the company currently holds around $65 billion worth of Bitcoin and needs to demonstrate that the asset can provide liquidity and support business operations when needed.

Saylor stressed that selling some Bitcoin would not mean the company is abandoning its long-term accumulation strategy. He previously stated that even if Strategy sold one Bitcoin, it could still buy 10 to 20 more later depending on market conditions, financing access, and investor demand.

The discussion comes after Strategy reported a $12.54 billion net loss in its first-quarter results. The company said it held 818,334 BTC as of May 3, with an average purchase price of roughly $75,537 per Bitcoin. Strategy also reported raising $11.68 billion so far this year.

Attention around potential Bitcoin sales increased further after the company filed plans to repurchase around $1.5 billion of its 2029 convertible notes.

According to the filing, the estimated cash repurchase cost is around $1.38 billion. Strategy said the transaction could be funded through cash reserves, equity proceeds, or proceeds from potential Bitcoin sales.

The expected settlement date for the repurchase is around May 19, 2026, pending standard closing conditions. After completion, the repurchased notes are expected to be canceled, while around $1.5 billion in remaining 2029 notes would stay outstanding.

Despite the debate over possible sales, Strategy has continued buying Bitcoin. Between May 4 and May 10, the company purchased an additional 535 BTC worth about $43 million at an average price of roughly $80,340 per coin.

That latest purchase increased Strategy’s total holdings to 818,869 BTC as of May 10.

Separate market updates also showed growing activity around Strategy’s STRC preferred stock products, which reportedly reached $1.53 billion in daily trading liquidity. Investors continue watching how the company uses those financial products to support future Bitcoin purchases.