Michael Saylor’s Billion-Dollar Arbitrage: A Blueprint for Strategic Capital Mastery | by Chip Mahoney | The Capital | May, 2025

How MicroStrategy turned balance sheet engineering into a $1B Bitcoin gain — and why SoftBank is paying attention.

Michael Saylor has never been shy about his conviction in Bitcoin. But what he just pulled off isn’t just another headline move; it’s a masterclass in modern financial engineering.

Let’s break it down.

Saylor’s company, MicroStrategy — recently re-branded to “Strategy” — sold $1.5 billion in stock — shares that were already backed, in part, by the company’s $500 million Bitcoin reserve. That new capital wasn’t just left sitting on the books or parked in bonds. Instead, Saylor cycled it directly back into Bitcoin, buying $1.5 billion worth of BTC.

That’s right:

• Sell stock backed by BTC.
• Use proceeds to buy more BTC.
• Lock in the arbitrage between company valuation and underlying assets.

The result? A $1 billion gain, not from market timing or luck, but from pure structural arbitrage.

This is the kind of play that makes even giants like SoftBank take notice.