Purchase #101 — The Machine That Never Stops
Michael Saylor bought again. On March 2nd, Strategy (formerly MicroStrategy) disclosed the purchase of 3,015 BTC at an average price of $67,700, totaling $201.1 million. This brings their total Bitcoin holdings to 720,737 BTC — approximately 3.4% of all Bitcoin that will ever exist, concentrated in a single company’s treasury.
This was their 101st Bitcoin purchase and their 10th consecutive weekly acquisition. Every Monday, like clockwork, Saylor posts the purchase announcement on X. It’s become such a routine that the crypto market barely reacts anymore. But just because something becomes normalized doesn’t mean it isn’t extraordinary. A publicly traded software company has converted itself into what is essentially a leveraged Bitcoin holding company, and the market has accepted it.
The cumulative numbers are almost absurd. Total acquisition cost: $54.77 billion. Average purchase price across all 101 buys: $75,985 per Bitcoin. Current market value at $69K: approximately $49.7 billion. That puts Strategy about $5 billion underwater on paper. For any normal company, that would be a crisis. For Strategy, it’s Tuesday.
The Stock-for-Bitcoin Machine — How It Actually Works
Understanding where the money comes from is essential to evaluating this strategy. This particular purchase was funded by $230 million from Class A common stock sales and $7 million from “Stretch” preferred stock offerings. In plain terms, Strategy creates new shares of its own stock, sells them on the open market, and uses the proceeds to buy Bitcoin.
This is dilutive to existing shareholders. Each time Strategy issues new shares, every existing share represents a slightly smaller percentage of the company. In traditional corporate finance, this would be considered shareholder-hostile. But Saylor’s argument is that Bitcoin appreciation will more than compensate for dilution — that owning a smaller slice of a much bigger pie is better than owning a larger slice of a stagnant one.
Through 2024 and most of 2025, this thesis held up beautifully. MSTR stock traded at a significant premium to its net asset value (NAV) — meaning the market valued each share at more than the underlying Bitcoin it represented. Investors were essentially paying extra for the “Saylor premium,” betting that his continued accumulation strategy would drive Bitcoin prices higher over time.
But here in early 2026, the math has gotten uncomfortable. With Bitcoin dropping from $100K to the $60K range, MSTR’s NAV premium has compressed and even dipped into discount territory at times. Strategy’s average cost basis of $75,985 is above the current market price. The flywheel that looked unstoppable nine months ago now faces its first genuine stress test.
Why the Bears Think This Ends Badly
Peter Schiff, the gold bug who has been calling for Bitcoin’s demise for over a decade, recently said Strategy’s approach “could become the most catastrophic corporate treasury decision in history.” His argument: if Bitcoin enters a prolonged bear market, Strategy will be unable to issue stock at favorable prices (because MSTR would be trading at a deep NAV discount), cutting off the funding mechanism. Meanwhile, interest payments on their convertible bonds would continue, creating a cash crunch.
Other critics point to concentration risk. Having 3.4% of all Bitcoin supply in one corporate entity creates systemic risk for the broader market. If Strategy were ever forced to sell — through bankruptcy, regulatory action, or shareholder revolt — the market impact would be devastating. It’s the “too big to sell” problem.
I personally think the bear case, while logically sound, overlooks a crucial detail: Strategy’s Bitcoin is held in cold storage with no margin or liquidation price. Unlike leveraged trading positions, there’s no mechanism that forces automatic selling. Bitcoin would have to go to literally zero for Strategy to face insolvency purely from their Bitcoin position. The convertible bonds have defined maturity dates and terms that Strategy can manage through operational revenue from their (still existing, though often forgotten) enterprise software business.
Why Saylor Won’t Stop — The Philosophical Underpinning
Saylor’s worldview is simple: the purchasing power of the US dollar declines every year due to monetary expansion. Bitcoin’s supply is fixed at 21 million and halves every four years. Over any sufficiently long time horizon, Bitcoin’s value in dollar terms approaches infinity, and the dollar’s value in Bitcoin terms approaches zero. Therefore, any Bitcoin purchase at any price will eventually look cheap.
This isn’t financial analysis — it’s a belief system. And like any belief system, it’s unfalsifiable over the short term. If Bitcoin drops, Saylor says “great, we can buy more at lower prices.” If it rises, he says “see, I told you.” The only scenario where he’s definitively wrong is one where Bitcoin goes to zero permanently, which would require the entire global crypto ecosystem to collapse.
What Individual Investors Should Take Away
You should not replicate Saylor’s strategy. He has access to capital markets that retail investors don’t. He can issue stock, sell bonds, and raise billions with a phone call. You can’t. Trying to go all-in on Bitcoin with leverage or borrowed money because “Saylor did it” is a recipe for ruin.
But there are legitimate lessons here. First, consistency matters more than timing. Saylor doesn’t try to time the market — he buys every week regardless of price. Individual investors who DCA consistently tend to outperform those who try to buy dips. Second, spot over leverage. Strategy holds actual Bitcoin, not futures or margin positions. No liquidation risk. Retail investors should follow the same principle. Third, have a thesis and stick to it. Whether you agree with Saylor’s thesis or not, his unwavering commitment to it is what makes the strategy work.
If I had to choose between buying MSTR stock and buying Bitcoin directly, I’d choose Bitcoin every time. Why pay a premium (or accept dilution risk) for indirect exposure when you can own the underlying asset? Automated trading tools can help you maintain Saylor-like consistency without the emotional burden of manually executing every purchase during volatile markets.