Michael Saylor lost $6 billion in a day, then bet on Bitcoin.
On March 20, 2000, MicroStrategy, the business software company Saylor founded in 1989, said it would revise its financial results for 1998 and 1999. The SEC, the U.S. securities regulator, later wrote that the stock fell from $260 to $86 that day. Slate put Saylor's one-day paper loss at $6 billion. He settled with the SEC without admitting or denying its allegations.
Twenty years later the company was sitting on cash. Saylor told CoinDesk in 2020: "We just had the awful realization that we were sitting on top of a $500 million ice cube that's melting." On August 11, 2020, MicroStrategy said it had bought 21,454 bitcoins for $250 million.
According to its quarterly results, the company, now called Strategy, held about 848,517 bitcoins on October 25, 2026. They were worth $68.90 billion and had cost $64.02 billion. Its software brought in $125.4 million that quarter.
Every CFO decides what to do with cash the business doesn't need. Saylor made that decision the focus of the company itself.
AI-generated illustration with narration by an AI voice.
Would your board have approved the first $250 million?
What the captions say
- This is the story of how Michael Saylor lost $6 billion in one day, and 20 years later bet his company's cash on Bitcoin.
- In March 2000, Saylor was 35. Shares of his company, MicroStrategy, had just hit $333. It sold software that turns business data into reports.
- Saylor owned more than half of it. On March 20, the company said it would restate its results for 1998 and 1999, lowering the revenue it had reported.
- In one day, the stock fell from $260 to $86. On paper, Saylor lost about $6 billion.
- He kept running the company. In 2013, he even tweeted that Bitcoin's days were numbered.
- Then came 2020 and the pandemic. Saylor began studying Bitcoin. In his words, he went down the rabbit hole.
- He later told the news site CoinDesk, "We just had the awful realization that we were sitting on top of a $500 million ice cube that's melting."
- On August 11, 2020, MicroStrategy announced its purchase. The company had spent $250 million of its cash on over 21,000 bitcoins.
- After that, the company kept buying. By late October 2026, it had a new name, Strategy, and about 848,000 bitcoins, worth about $69 billion.
- The man who once tweeted that Bitcoin's days were numbered had come to call it, in his words, digital gold.
