
Michael Saylor, Chairman & CEO, MicroStrategy, pauses as he speaks during the Bitcoin 2022 Conference at Miami Beach Convention Center on April 7, 2022 in Miami, Florida.
Marco Bello | Getty Images
MicroStrategy, led by Chairman and CEO Michael Saylor, has again trimmed its Bitcoin holdings, marking the second time the company has divested from the cryptocurrency. This move comes amid persistent geopolitical uncertainty that continues to exert downward pressure on Bitcoin prices and the broader crypto market.
Regulatory filings reveal that between May 26 and May 31, MicroStrategy offloaded 32 Bitcoin for approximately $2.5 million, averaging $77,135 per coin. Concurrently, the company raised $128.3 million by selling 801,994 shares of its common stock during the same period.
The news saw MicroStrategy shares dip over 6% in premarket trading. Bitcoin itself experienced a 2% decline, reaching its lowest point since April 13, reflecting the market’s reaction to the company’s strategic adjustments.
This recent sale follows MicroStrategy’s significant shift away from Saylor’s long-held “never sell” Bitcoin doctrine. The company has embraced a more active balance sheet management strategy, which includes the potential sale of Bitcoin to enhance key financial metrics such as bitcoin-per-share value, facilitate dividend payments, or generally bolster its financial standing.
“Our objective is to become net aggregators of Bitcoin – increasing our total Bitcoin holdings, but more crucially, enhancing our bitcoin per share. We believe this approach will be the most accretive to MicroStrategy’s long-term value,” stated CEO Phong Le during the company’s earnings call in early May.
A cornerstone of this renewed strategy is the introduction of STRC, a yield-bearing security issued by MicroStrategy. STRC allows investors to generate income collateralized by the company’s substantial Bitcoin-backed balance sheet, offering an alternative to direct Bitcoin ownership. The initiative aims to leverage investor demand for income-generating products to accelerate MicroStrategy’s Bitcoin accumulation beyond traditional acquisition methods.

The previous instance of MicroStrategy selling Bitcoin occurred in December 2022. That period was characterized by a pronounced bear market for Bitcoin, exacerbated by rising interest rates, the dramatic collapse of FTX, and widespread contagion effects across the crypto ecosystem, stemming from interconnected lending platforms and hedge funds.
Currently, Bitcoin trades more than 42% below its all-time high of over $126,000. In a notable trend, Bitcoin ETFs experienced their tenth consecutive day of net outflows on Friday, marking the longest such streak on record, underscoring persistent investor caution.
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Bitcoin this year
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