Strategy Will Have to Sell Over 50,000 BTC by 2028

Kaleo actually said this could be the company’s best option.

Michael Saylor’s bitcoin-buying intelligence software company has come under scrutiny in recent weeks. The tiny sale of 32 BTC at the end of May was just a drop in the ocean, as the Stretch Preferred Stock (STRC) it uses to buy more BTC by raising capital through an at-the-market continuous share issuance program has fallen well below its par price of $100.

Although the firm and its execs continue to try to reassure the market that they have the funds necessary to cover the dividend payments and that the situation is under control, popular analysts and commentators remain skeptical. And it’s not just Peter Schiff, who has called STRC a ‘Ponzi scheme.’

Markets are closed today.
Volatility is never easy.
Bitcoin keeps working.
So do we.
Thank you for your support.

— Michael Saylor (@saylor) June 19, 2026

Strategy to Sell 50K BTC?

The latest substantial increase in tension on the Strategy front came during the business week, as the company’s STRC experienced a significant sell-off, which, according to Strive CEO Matt Cole, was driven by leveraged investors rather than any deterioration in the issuer’s financial strength.

In a recent interview, Kaleo, an analyst with over 700,000 followers on X, warned that Strategy’s best option now would be to sell 50,000 or more BTC in the next two years.

“They have made it their clear mission that they want to increase net Bitcoin, but what does that necessarily do to create value for MSTR holders?”

He further added that the way MSTR and other assets are being advertised is “reckless right now.” Especially for MSTR, which Strategy has referred to as “amplified bitcoin” for years, but that’s “just a fancy word for saying it’s leveraged,” he explained.

“Leverage works great on the way up. I fully agree with that. You can make a lot of money if you have a lot of leverage and the asset keeps going up. But the issue is that you can also lose a lot more on the way down.”

FTX-Like Crash?

The interviewer and Kaleo compared the recent situation with the 2022 fast-crash of FTX. Although there are some differences, such as SBF using customers’ funds to trade, they concluded that Strategy and Saylor are using investors’ capital to buy more bitcoin (not trade) with the hope that its price will eventually go up.

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Kaleo added that essentially no one expected FTX, once one of the most prominent crypto exchanges, to crash and burn in days. The same way no one expected BTC to tumble toward $16,000. Consequently, he believes that if Strategy is forced to start selling large portions of its BTC holdings to cover expenses and dividends, the cryptocurrency’s price could reach multi-year lows.