MSTR's Michael Saylor Says Selling Bitcoin May Be Necessary To Maximize BTC-Per-Share Over Seven Years

Michael Saylor said in a recent interview that Strategy may sell some Bitcoin because models relying solely on equity, credit or Bitcoin holdings fail to maximize BTC-per-share over a seven-year period.
Michael Saylor speaks at the Bitcoin Conference 2026, held in Las Vegas, Nevada, United States on April 27, 2026.(Photo by Tayfun Coskun/Anadolu via Getty Images)
Michael Saylor speaks at the Bitcoin Conference 2026, held in Las Vegas, Nevada, United States on April 27, 2026.(Photo by Tayfun Coskun/Anadolu via Getty Images)
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Prabhjote Gill·Stocktwits
Published May 22, 2026   |   11:22 AM EDT
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  • Michael Saylor said Strategy’s long-term goal is not simply buying more Bitcoin, but increasing Bitcoin exposure on a per-share basis for shareholders with a target to accomplish that in seven years.
  • Strategy CEO Phong Le said selling Bitcoin near the company’s cost basis could avoid meaningful tax consequences for STRC investors.
  • Strategy currently holds nearly 850,000 Bitcoin worth more than $65 billion, making it the world’s largest corporate Bitcoin holder.

Strategy (MSTR) executive chairman Michael Saylor said in a recent interview that the reason he hinted the company may sell some of its Bitcoin (BTC) is because every model that avoids doing so ultimately fails to maximize BTC-per-share over the next seven years.

“Any model that we put together that's limited only to equity or only to credit or only to Bitcoin always underperforms,” Saylor said in an interview with Natalie Brunell, explaining the seven-year “maxed out Bitcoin” deadline. “I think it's not unlikely that we'll sell some bitcoin between now and the end of the year.”

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Saylor’s comments follow his earlier hints to the same during the company's first quarter (Q1) earnings call. "Our ability to sell Bitcoin either to buy U.S. dollars or sell Bitcoin to buy debt if it's accretive to Bitcoin per share is something that we would consider doing going forward,” he stated at the time.

MSTR’s stock fell 2.75% in morning trade on Friday, while Bitcoin’s price edged 0.3% lower – below the $77,000 mark. Retail sentiment on Stocktwits around both assets trended in ‘bearish’ territory over the past day. Chatter around MSTR remained at ‘low’ levels and message volume around Bitcoin stayed at ‘normal’ levels. 

Selling Bitcoin Will Remain Tax Efficient, Says MSTR CEO

Strategy currently holds nearly 850,000 Bitcoin on its balance sheet, valued at over $65 billion. It is the largest corporate holder of the apex cryptocurrency. 

The company has historically funded purchases through a combination of common stock issuance, convertible debt and preferred equity products tied to Bitcoin exposure. It has only ever sold Bitcoin once, in December 2022, when it sold 704 BTC for around $11.8 million to harvest tax loss.

This time, investors are worried if selling will lead to a tax hit. Strategy CEO Phong Le stated it should not materially change the tax treatment of Strategy’s STRC preferred stock product. “Won’t change anything in terms of tax of STRC,” Le said. “Sell Bitcoin at cost basis, break even, no tax.”

Strategy Eyes More Frequent STRC Dividend Payments

Saylor and Le also showered praise for Vivek Ramaswamy-backed Strive (ASST) deciding to offer daily dividends on the company’s preferred stock (SATA). “We don’t need to steal their thunder,” Saylor said. “Would like to see ASST get 10x bigger.”

Strategy is also looking to increase the frequency of STRC dividends with a proposal of semi-monthly payoffs currently open for a vote. Saylor said that if MSTR shareholders ask for daily dividends, the company may make that shift. For now, he’s looking forward to seeing how the demand for STRC and SATA plays in the coming year with two different dividend schedules. 

Read also: Mark Cuban Claims Bitcoin Failed As War Hedge – But Data Shows BTC Outperforming Gold

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