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Home » “25 Years Ago Today: Michael Saylor Suffers a $6 Billion Loss from the ‘Dot-com Bubble,’ Setting the Record for the Highest Single-Day Loss by an Individual”
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“25 Years Ago Today: Michael Saylor Suffers a $6 Billion Loss from the ‘Dot-com Bubble,’ Setting the Record for the Highest Single-Day Loss by an Individual”

Mar. 22, 20252 Mins Read
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"25 Years Ago Today: Michael Saylor Suffers a $6 Billion Loss from the 'Dot-com Bubble,' Setting the Record for the Highest Single-Day Loss by an Individual"
"25 Years Ago Today: Michael Saylor Suffers a $6 Billion Loss from the 'Dot-com Bubble,' Setting the Record for the Highest Single-Day Loss by an Individual"
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MicroStrategy’s Bitcoin Holdings Surge After Trump’s Election

MicroStrategy, the U.S. publicly listed company dominating Bitcoin holdings, saw its stock price soar after the election of pro-cryptocurrency President Donald Trump, hitting new highs in November last year. However, 25 years ago today, MicroStrategy’s founder Michael Saylor experienced a financial disaster when the dot-com bubble burst, suffering a single-day loss of over $6 billion, setting the record for the highest single-day loss at the time.

Background: MicroStrategy Restarts the “Buy, Buy, Buy” Mode? A Full Analysis of the New Financing Plan

Background Supplement: MicroStrategy’s Bitcoin Leverage Play: Who Bears the Risk and Who Reaps the Rewards?

MicroStrategy, the U.S. publicly listed Bitcoin holder, launched a Bitcoin buying spree after Donald Trump’s election. With 12 consecutive weeks of Bitcoin accumulation, the company has now amassed a total of 499,226 Bitcoin, valued at approximately $42 billion. Trump’s continued support for Bitcoin after his election further fueled MicroStrategy’s stock price, which hit a historic high of $542.99 just before Bitcoin surpassed $100,000, making the company one of the most closely watched in the U.S. market today.

Michael Saylor’s $6 Billion Loss from the Internet Bubble

However, few are aware that before MicroStrategy announced its Bitcoin investment in 2020, the company’s stock had been in a nearly 20-year slump. To find the last high point in the company’s stock price, one would have to go back to the “dot-com bubble” period of 2000.

At that time, MicroStrategy’s stock price surged to $313 amid the speculative boom of the internet bubble. However, following the bubble’s burst and an SEC accounting investigation, MicroStrategy’s stock price plummeted, eventually falling to around $0.5. In this stark contrast, Michael Saylor, as the founder, suffered significant losses.

According to reports at the time, Michael Saylor lost over $6 billion on March 21, 2000, setting the record for the highest single-day personal wealth loss at that time.

Now, 25 years later, reflecting on this major event, will Michael Saylor, who has returned to the peak, lament his past massive losses, or will he continue to learn from that experience, staying cautious as he advances in his career?

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