Michael Saylor Just Bought Another $330 Million in Bitcoin – Does He Know Something We Don’t?

The way Michael Saylor continues to make purchases has an almost stubborn quality. Last Monday, Strategy disclosed that it had acquired an additional 4,871 bitcoins for approximately $329.9 million in a standard 8-K filing nestled among the weekly din of corporate disclosures. The average cost of the purchases, which took place between April 1 and April 5, was close to $67,718 per coin. Bitcoin was trading at about $69,500 at the time of the filing, which was still significantly less than the company’s blended cost basis of over $75,000.

The scene at Strategy’s Tysons Corner headquarters was practically picture-perfect. Silent corridors, analysts going through documents, and somewhere in the building, the choice to proceed. The previous week, the company had halted purchases, ending a 13-week run. For a brief period, people questioned whether the halt had any significance. Apparently, it didn’t. All Saylor was doing was reloading.

The math behind the moment is striking. Strategy has about $58 billion in bitcoin. Additionally, it disclosed an unrealized loss of $14.5 billion for the first quarter. It’s not a rounding error. Most CFOs would have to reconsider everything in light of that figure. However, on the day of the disclosure, MSTR’s stock increased by about 6%, suggesting that investors had already come to terms with the volatility—or perhaps even with Saylor.

Observing this gives the impression that Saylor isn’t actually trading bitcoin. He’s getting married to it. He has previously stated that he has “no doubt” that bitcoin will eventually surpass gold, and he says this so frequently that it has started to sound less like a prediction and more like a creed. He might be correct. It’s also possible that he’s just early, which could take ten years to prove.

The really interesting part comes in the financing section. Strategy raised roughly $227.3 million in late March through its variable-rate Series to finance the most recent acquisition. $72 million in sales of common shares, an additional $102.6 million in early April, and a perpetual Stretch preferred stock. The Stretch shares are essentially a bridge, with fixed-income funds flowing in one direction and bitcoin emerging from the other. They are intended to trade close to a $100 par value with an adjustable monthly dividend. It’s balance-sheet engineering unlike anything Wall Street has ever seen, and it only works if the long-term growth of bitcoin exceeds its cost of capital.

Since the beginning of the year, the value of Bitcoin has decreased by about 20%. That would be reason for retreat for a typical corporate treasury. It seems to be a reason for Saylor to purchase more. CEO Phong Le made a statement during Strategy’s fourth-quarter call in February that many people found memorable: “Some of you bought Bitcoin or MSTR in the last year.” This is the first downturn you’ve experienced. The statement conveyed a subtle caution, akin to a shrug, as if the speaker had previously seen this film.

Does Saylor have any knowledge that we don’t? Most likely not literally. He doesn’t appear to have a secret data point or a private signal. He has developed a thesis over the years that bitcoin will continue to absorb the demand for limited, portable, neutral money while fiat currencies continue to weaken. It is currently impossible to determine whether that thesis is true or if the upcoming earnings report on April 30 shows a flaw in it. However, it’s getting harder to ignore the pattern. Bitcoin declines. Saylor purchases. The cycle is repeated. The rest of the market is still debating whether that is faith, foresight, or something else entirely.