Saylor: I Said You, Not The Company, Should Never Sell Bitcoin

  • The controversy around Michael Saylor is less about whether Strategy still believes in Bitcoin and more about whether investors should now value the company as a conviction trade or a Bitcoin-backed financing structure.

Michael Saylor’s latest defense of Strategy’s Bitcoin sale turns the company’s “never sell” identity into a narrower claim: individual holders should hold forever, but a public company can still use Bitcoin when its financing structure demands cash.

The distinction landed after Strategy sold 32 Bitcoin between May 26 and May 31 for about $2.5 million, a small transaction beside its massive Bitcoin reserve but a meaningful break from the image Saylor has built around permanent accumulation. CoinDesk reported that the proceeds were tied to distributions on STRC, Strategy’s perpetual preferred stock.

READ: Is Strategy Finally Out Of Kidneys? Saylor Suggests MSTR Might Start Selling Bitcoin

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From a circulating clip online, Saylor is shown pushing back on criticism that the sale contradicted his “never sell” message.

“I said to YOU never sell your Bitcoin. I never said that the company wouldn’t sell its Bitcoin,” he said.

Strategy remains the world’s dominant corporate Bitcoin holder. After the 32 Bitcoin sale, the company bought 1,550 Bitcoin for about $101.3 million, raising its total holdings to 845,256 Bitcoin. The Wall Street Journal reported that Strategy also increased its cash reserves to $1 billion to support preferred stock dividend obligations.

However, this deep into the play, Strategy is no longer just a company holding Bitcoin on its balance sheet. It has built a capital structure around the asset, with convertible notes, preferred stock, common equity issuance, cash reserves, and dividend obligations all interacting with its Bitcoin strategy. In May, Strategy disclosed $6.7 billion of convertible notes, $15.5 billion of preferred stock notional outstanding, and an $871 million US dollar reserve.

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For years, the appeal was not “Strategy may sell Bitcoin under limited treasury-management conditions.” The appeal was cleaner: buy Bitcoin, hold Bitcoin, do not sell Bitcoin.

Once preferred distributions enter the picture, “never sell” becomes harder to apply as a corporate rule. An individual can hold through volatility with no payout schedule. A public company with financing costs and investor obligations has to manage liquidity.

The contrast is sharpened by Saylor’s promise before that he himself would never sell Bitcoin earlier this year.

Investor’s Business Daily reported that Strategy’s recent financing choices showed a shift in priorities, with the company raising capital and buying Bitcoin even when the move reduced its Bitcoin-per-share metric from 13% to 12.8%. The report also noted that STRC carries an 11.5% dividend, making financing costs part of the central risk around the model.

The company can still say it is accumulating Bitcoin. The numbers support that: t sold 32 Bitcoin, then bought 1,550.

But the sale established a precedent: Strategy’s Bitcoin can move out of the treasury when management decides the corporate math justifies it.


Information for this story was found via the sources and companies mentioned. The author has no securities or affiliations related to the organizations discussed. Not a recommendation to buy or sell. Always do additional research and consult a professional before purchasing a security. The author holds no licenses.

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