MicroStrategy boss Michael Saylor’s Bitcoin-buying plans paid off big during this year’s boom


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Michael Saylor’s decision back in 2020 to start buying Bitcoin has paid off in spades this year for the co-founder and executive chairman of MicroStrategy Inc. 

Saylor has garnered an estimated $400 million or so from pre-planned daily sales of about 5,000 shares of the enterprise software company from January through last week, based on data compiled by Bloomberg. The share sales follow the exercising of options awarded in 2014 that were set to expire. The stock has doubled this year to around $1,290, surpassing the record-setting gains of the original cryptocurrency during the same period. At the end of 2014, MicroStrategy was trading at around $160.

The outperformance of Tysons Corner, Virginia-based MicroStrategy’s stock appears to be negating investor concern that Saylor, who is the controlling shareholder, may be selling at the peak. During a conference call in November, Saylor noted that for over a decade he has been paid a $1 salary and has not been eligible for any cash bonuses. Exercising the option will allow him to address some obligations as well as to buy more Bitcoin for his own account, he said at the time.  

“I think it’s a bigger story in the media than it has been among investors,” said Lance Vitanza, a managing director at TD Cowen, who has a “buy” recommendation on MicroStrategy. “Investors recognize that Saylor still owns a lot of stock.”

Even so, the premium that MicroStrategy is getting over Bitcoin after the January introduction of US exchange-traded funds that can hold the cryptocurrency is starting to raise eyebrows. In March, Kerrisdale Capital Management LLC said it’s shorting the stock since it was outpacing the surge in the digital asset’s price.

“To me, the biggest question is why you would buy MSTR with a premium over spot when you can now just buy the ETFs?” said Austin Campbell, an adjunct professor at Columbia Business School and a consultant for blockchain firms. MicroStrategy “is a retail magical belief stock, like PLTR, TSLA or GME. They tend to defy fundamentals and trade purely on vibes. That can go on for a while, though not forever.”

In the meantime, MicroStrategy said Monday that it posted a first-quarter loss of $53 million after taking an impairment change against the value of its Bitcoin holdings even though the cryptocurrency surged during the period.  

Under current accounting rules, MicroStrategy can’t recognize any increases in its Bitcoin holding, such as the almost 67% jump in the recent quarter. That’s changing under a recently passed accounting rule that requires valuing the digital asset at market prices. Companies have until 2025 to implement the revision. MicroStrategy didn’t adopt the revision for the first quarter, instead it recorded a $191.6 million digital-asset impairment loss.

The value of MicroStrategy’s Bitcoin holdings has increased to around $13.5 billion since the company started purchasing the digital asset as part of the effort to hedge inflation.

The firm’s Bitcoin cache has increased by 25,250 since the end of the fourth quarter. MicroStrategy is holding 214,400 Bitcoin as of April 26, it said.

“Saylor has a simple strategy for MSTR: sell equity/debt and buy BTC with proceeds,” said Jeff Dorman, chief investment officer at Arca, a digital asset management firm. “As BTC goes up, MSTR stock goes up, so MSTR can sell more stock/bonds and do it again.”


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