The Financial Story Most People Miss

On March 20, 2000, Michael Saylor lost $6 billion in a single day—in just hours. The SEC confirmed it, and The Washington Post called it the largest one-day personal loss ever recorded at the time.

Today, Saylor controls 672,497 Bitcoin, about 3.2% of BTC’s total supply, with a cost basis of $50.44 billion.

What Wall Street overlooked is the psychology behind this shift. The mindset that allows someone to endure a $6B loss without collapsing is the same mindset that enables extreme, concentrated conviction in a volatile asset. This isn’t recklessness—it’s learned resilience.

The 2000 crash taught Saylor that accounting profits can be erased overnight. The 2020 Fed response taught him that fiat currency can be debased just as quickly. Bitcoin, by contrast, has no earnings to restate and no central bank to manipulate—making it the opposite of what once destroyed him.

The outcome is binary. By 2026, Saylor will either be worth $50B+ or experience another career-defining collapse. There’s no middle ground.

Ironically, the same man who once said Bitcoin’s “days were numbered” now owns more BTC than any corporation or institution—second only to Satoshi.

Genius or repetition of past trauma?

The answer arrives before 2030.