Michael Saylor just posted on X that Strategy’s 100th Bitcoin buy is days away. The company—formerly known as MicroStrategy—made its first purchase back in August 2020, and now sits on 717,131 BTC bought at an average price of $76,027 per coin. That’s over $54 billion invested.
Right now, with Bitcoin trading around $64,700, the position is underwater by about $12.4 billion. Yet Strategy keeps buying. In fact, they’ve been buying every single month since November 2024, even as Bitcoin ETFs have seen five straight weeks of outflows. While most institutions trim positions when sentiment turns, Strategy treats Bitcoin like a decades-long macro bet. At this point, they’ve locked up roughly 3.4 percent of Bitcoin’s eventual 21 million-coin cap.
- Current holdings: 717,131 BTC (≈ 3.4% of maximum supply)
- Average purchase price: $76,027
- Unrealized loss at $64,700: ≈ –$12.4 billion
How They’re Paying for It All
Strategy isn’t funding these purchases with software revenue. Instead, they’ve turned to the capital markets in a big way. This year alone, the company issued about $7 billion in high-dividend preferred shares. Add that to a pile of convertible notes starting to mature in 2028, and you’ve got a complex financing structure that hinges on one key assumption: bondholders will eventually convert to equity rather than demand cash.
The Dilution Question
Every new share issued means existing shareholders own a slightly smaller piece of each Bitcoin on the balance sheet. Critics call it a “dilution machine.” Saylor’s counter-argument is simple—if Bitcoin goes up ten-fold over the next decade, near-term dilution won’t matter. The entire strategy depends on two things working in tandem: continued access to cheap capital and Bitcoin’s four-year halving cycle driving price appreciation over time.
The Debt Clock
Around $6 billion in debt comes due between now and 2028. Management says they’ll either stack more preferred offerings on top of the existing debt or refinance the converts at lower rates if the market cooperates. It’s a high-wire act, but not unheard of—telecom companies did something similar buying spectrum rights in the early 2000s, and renewable energy firms have used equity-linked debt for long-term infrastructure plays. The difference here is volatility. A single week’s price swing in Bitcoin can erase or create value bigger than Strategy’s annual operating income.
What the 100th Buy Means for Corporate Treasuries
Strategy’s aggressive approach has changed the conversation around Bitcoin as a corporate asset. Smaller companies—game studios, tech startups—have started adding fractional Bitcoin positions, citing both inflation hedging and brand positioning. But none have come close to Strategy’s scale or willingness to lever up the balance sheet this hard.
When the 100th purchase lands in the next few days, it’ll be more than a press release. It’s a symbolic marker for CFOs everywhere trying to decide whether Bitcoin belongs in the same portfolio as Treasury bills and commercial paper. If it works, Bitcoin starts looking like a legitimate reserve asset. If it doesn’t, it becomes a case study in what happens when you marry a public company to a wildly volatile store of value. Either way, the market will be watching when that next SEC filing drops.
