Michael Saylor’s Bitcoin Crusade: How a CEO Became Crypto’s Most Relentless Evangelist

MicroStrategy's ex-CEO didn't just buy Bitcoin—he bet his company on it. Now, he's reshaping corporate finance one satoshi at a time.

From skeptic to maximalist: Saylor's $5 billion dollar gamble

While Wall Street hedged, Saylor went all-in—turning MicroStrategy into a Bitcoin proxy that outperformed gold, bonds, and most tech stocks. His playbook? Convert cash reserves into BTC, issue debt to buy more, then repeat until the SEC starts asking questions.

The institutional domino effect

After MicroStrategy's first billion-dollar purchase, Fortune 500 CFOs suddenly discovered FOMO. Pension funds quietly allocated. Family offices diversified. All while Saylor kept preaching his 'digital gold' sermon on CNBC—with the zeal of a convert and the spreadsheets of an accountant.

When true believers outperform hedge funds

MicroStrategy's BTC holdings now dwarf its original software business. Critics call it a leveraged bet; shareholders call it visionary. Meanwhile, traditional asset managers still can't decide if crypto is a scam or their next fee generator.

The ultimate irony? A legacy tech CEO became crypto's most effective missionary—while Silicon Valley's disruptors were busy minting dog token memes.