MicroStrategy rides ‘red sweep’ to 477% gain in 2024, top tech stock

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.

On Monday, MicroStrategy said in a filing that over about the past week it acquired another 5,262 bitcoins for roughly $561 million, at $106,662 per coin. That brings its total holdings to 444,262 bitcoins.

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