MicroStrategy rides ‘red sweep’ to 477% gain in 2024, topping almost all U.S. stocks

MicroStrategy was already one of the hottest stocks on the planet, but the rally intensified after Donald Trump’s election victory in November.

Of the 439,000 bitcoins the company owns, more than one-third have been purchased since the election.

“With the red sweep, bitcoin is surging up with tail winds,” MicroStrategy founder Michael Saylor told CNBC.

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On the eve of MicroStrategy’s stock market debut in June 1998, founder Michael Saylor stayed in a penthouse suite at the Lotte New York Palace in Midtown Manhattan. Saylor, who was 33 at the time, says it was the most exquisite hotel room he’d ever seen, paid for by lead underwriter Merrill Lynch.

The next morning, Saylor went to the floor of the Nasdaq to watch his company’s stock open. He recalled seeing a note scrolling across the ticker, warning traders: “Please do not confuse MSTR with MSFT.” The latter belonged to Microsoft, the software giant that had gone public 12 years earlier.

MicroStrategy shares popped 76% in their debut, joining the parade of tech companies benefiting from the dot-com boom.

“It was a good day,” Saylor told CNBC.

More than 26 years later, MicroStrategy and Microsoft were again linked together, but for an entirely different reason. In December 2024, Saylor stood before Microsoft’s shareholders to try and convince them that the company, now valued at more than $3 trillion, should put some of its $78.4 billion in cash, equivalents and short-term investment into bitcoin.

“Microsoft can’t afford to miss the next technology wave, and bitcoin is that wave,” Saylor said in a video presentation that he released on X last week. The post has more than 3.6 million views.

Saylor has gone all in on that strategy. MicroStrategy has purchased 439,000 bitcoins since mid-2020, a stockpile that’s now worth about $42 billion and is the basis for the company’s market cap explosion to $82 billion from roughly $1.1 billion when the plan was put in place.

MicroStrategy’s software unit, which specializes in business intelligence, generates just more than $100 million in revenue a quarter. After zooming up in 1998 and 1999, the stock crumbled in the dot-com bust, losing almost all its value. In the decades that followed, it slowly bounced back before rocketing up due to bitcoin.

Four years into its bitcoin buying spree, MicroStrategy is the world’s fourth-largest holder, behind only creator Satoshi Nakamoto, BlackRock’s iShares Bitcoin Trust and crypto exchange Binance.

At Microsoft, the shareholder vote supported by Saylor failed by a wide margin — less than 1% of its investors voted for it.

But the spectacle provided Saylor, now 59, with yet another opportunity to preach the gospel of bitcoin and tout the benefits of converting as much cash as possible into that single digital asset. It’s a story that Wall Street has been gobbling up.

MicroStrategy shares are up 477% this year as of Friday’s close, second to only AppLovin among all U.S. tech companies valued at $5 billion or more, according to FactSet data. That follows a 346% gain in 2023.

While the rally was in full force well before November of this year, Donald Trump’s election victory, funded heavily by the crypto industry, propelled the stock even more. The shares have climbed 60% since the Nov. 5 election, and finally exceeded their dot-com era high from 2000 on Nov. 11.

Saylor has long talked about bitcoin in an evangelical fashion and co-authored a book about it in 2022 titled “What is Money?” But his critics have gotten louder than ever of late, describing Saylor as a cult-like leader and his strategy as a “ponzi loop” that involves issuing debt and equity to buy bitcoin, watching MicroStrategy’s stock price go up, and then doing more of the same.

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