Who is Michael Saylor?

Michael Saylor is the Executive Chairman of Strategy, a tech firm he started in 1989. He’s also known for being a strong voice in the Bitcoin world. 

After building a career in software and education, he made headlines by turning his company into one of the biggest BTC holders globally. 

But not everything is clear-cut, some of his Bitcoin-related projects don’t even have accessible whitepapers. So, who is this guy really?

Early Life and Career Background

Growing up and MIT background

Saylor grew up in a military family and later earned dual degrees at MIT in Aerospace Engineering and the History of Science. 

It’s clear he’s both technical and strategic. These early years shaped how he views big systems, whether that’s tech, finance, or even education.

Building Strategy from scratch

In 1989, Saylor co-founded Strategy, which became known for business intelligence software. Big names used their tools to understand data and make better decisions. 

The company did well and went public in 1998. Saylor quickly made a name for himself in the tech world.

Read Also: Michael Saylor's Strategy: How He Beat Tech Giants with His Investments

More Than Just Software: Books and Education

Writing The Mobile Wave

In 2012, Saylor published a book called The Mobile Wave. It talked about how mobile technology was changing the world. It did pretty well and showed that he had a big-picture view of where tech was going.

Founding Saylor Academy

Saylor also started a free online education platform, Saylor Academy. Over 2 million people have taken courses there. 

It’s a lesser-known side of him, but it’s one that shows he’s passionate about access to knowledge.

Read Also: Michael Saylor's Bold Bitcoin Strategy

Bitcoin: The Big Pivot

The first big Bitcoin buy

In 2020, Saylor made a bold move. He shifted Strategy’s cash reserves into BTC, starting with $250 million. He said it was to protect the company from inflation. This decision completely changed the company’s direction.

Going all in on crypto

After that, Strategy kept buying more Bitcoin. They raised money by selling stock and taking on debt. By mid-2025, the company held over 600,000 Bitcoins. 

That’s about 3% of all Bitcoin in the world. Saylor even stepped down as CEO in 2022 to focus fully on Bitcoin strategy.

How Saylor Compares to Other Bitcoin Supporters

Not just another Tesla or Square

Yes, Tesla and Square also bought Bitcoin. But they didn’t reshape their entire company around it. Tesla made one big purchase and stopped. 

Square’s Jack Dorsey supports Bitcoin, but Block (formerly Square) stayed more diversified. Saylor’s company is different, it’s almost fully focused on Bitcoin now.

A model others try to follow

Some companies, like Metaplanet in Japan, copied Saylor’s model. They buy Bitcoin using raised capital and hope their share price follows BTC's gains. 

But it’s risky. Strategy trades at a premium over its actual Bitcoin value, meaning investors are also buying into hype and sentiment.

Read Also: Michael Saylor’s Bold Bitcoin Strategy: $105K Average Buy Revealed

Why This Strategy Isn’t Without Risk

Volatility and debt

The price of Bitcoin moves fast. When it drops, Strategy’s stock suffers too. Plus, they’ve taken on lots of debt to buy Bitcoin. If things go wrong, it could impact investors hard. 

The firm’s core software business still exists, but it’s now a small part of its identity.

A lack of transparency

One major concern is transparency. Some of the whitepapers linked to Saylor’s crypto ventures are hard to access or don’t even load. That makes it tough for investors to know what’s really going on behind the scenes. 

So while Saylor’s bold, there are reasons to be cautious.

Conclusion: Smart Vision or Risky Gamble?

Michael Saylor isn’t your average tech exec. He built a successful software firm, wrote a best-selling book, created a free education platform, and now leads one of the largest Bitcoin holders in the world. 

But his strategy isn’t risk-free. The company is deeply tied to crypto markets, and not everything is clearly explained. 

For now, Saylor’s vision is bold, but investors should look carefully before jumping in.

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FAQ

How many Bitcoins does Strategy hold now?

Strategy currently owns over 600,000 Bitcoins, which is about 3% of the total supply.

Why did Saylor go all-in on Bitcoin?

He believes fiat money loses value over time and sees Bitcoin as a better long-term store of value.

Is Saylor still the CEO of Strategy?

No. He stepped down in 2022 and now serves as Executive Chairman, focusing only on Bitcoin strategy.

How is Strategy different from Tesla or Square?

Unlike those companies, Strategy is almost fully focused on Bitcoin, not just holding it as an asset.

What should I watch out for as an investor?

Strategy’s model is risky. It’s heavily exposed to Bitcoin’s price and lacks transparency in some areas.