One wrong move, and $44B is at risk.
He’s been here before — lost $6B in a single day.
Now he’s betting everything that history won’t repeat
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The world of financial markets is brutal.
Right now, Michael Saylor is leading the charge.
He is the executive chairman and co-founder of MicroStrategy.
A company that raises equity and debt just to buy more Bitcoin.
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Saylor entered MIT in 1983 dreaming of flying jets.
But a medical diagnosis grounded that plan for good.
He shifted gears and joined The Federal Group in 1987,
Where he dove into computer simulations for enterprise software.
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In 1988, Saylor became an internal consultant at DuPont.
He built computer models to predict shifts in core markets.
His simulations showed a recession was coming by 1990.
And that prediction turned out to be accurate.
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In 1989, Saylor used DuPont funding to launch MicroStrategy.
At first, the company focused on data mining software.
By 1992, they landed a $10 million deal with McDonald's.
Their task was to build tools for analyzing promo performance.
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Saylor took MicroStrategy public in June 1998.
They offered 4 million shares at 12 dollars each.
The stock doubled on day one.
By 2000, Saylor’s net worth hit 7 billion and he became the richest man in D.C.
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Saylor’s first major setback came in March 2000.
MicroStrategy announced it would restate its financials.
The stock crashed 62 percent.
Turns out, 1999 revenue was overstated and profits were actually losses.
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On March 20, 2000, Saylor lost 6 billion dollars in a single day.
It was the largest one-day loss ever recorded by one person.
Later that year, the SEC charged MicroStrategy with fraud.
The case was settled, but the damage was done.
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Saylor has always been ahead of the curve in tech.
He understood digital scarcity long before Bitcoin existed.
Back in the 90s, he started buying premium domain names.
Clean, one-word assets with massive future value.
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MicroStrategy spent 2 million dollars on domains like Angel dot com, Alarm dot com, and Wisdom dot com.
Years later, they sold them for over 130 million.
Saylor still owns Michael dot com and Mike dot com today.
Digital assets have always been part of his game.
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In December 2013, Saylor tweeted his first take on Bitcoin.
He warned that without a credible sponsor, it could be regulated out of existence.
A week later, Bitcoin crashed nearly 70 percent from its all-time high.
Saylor tweeted again — but his tone was already shifting.
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Saylor came back to Bitcoin in mid-2020.
He announced that MicroStrategy would adopt it as part of a new capital strategy.
They allocated 250 million dollars.
In just two weeks, they bought 21,454 BTC at around 12,000 each.
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By December 2020, MicroStrategy made its first debt move after entering Bitcoin.
They raised 400 million at 0.75 percent interest to buy more BTC.
Two months later, they raised again.
And did it a third time just four months after that.
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If MicroStrategy is ever forced to sell part of its Bitcoin, the impact could be massive.
Financial pressure, margin calls, or macro stress could trigger it.
That kind of move would shock the market.
It could cause a fast drop and spark panic across all crypto.
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Saylor is not the type to sell unless he has no other choice.
It would take extreme financial pressure to force his hand.
But if Bitcoin adoption keeps rising,
his bet could go down as one of the boldest and most legendary in corporate history.
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