Let me preface this by saying… I want to understand Michael Saylor. I really do. He’s a billionaire, he wears collared shirts with confidence, and he talks about Bitcoin like it’s his first-born child. But every time I try to wrap my head around his strategy (which is basically “buy more Bitcoin at whatever price it's currently trading and never, ever sell”) I feel like I’m trying to explain TikTok to my grandfather. It’s not clicking.

And look, I know the man’s richer than me. He’s richer than my entire extended family and probably owns a yacht with a better internet connection than my house. But just try telling George Washington that a publicly traded software company would one day take out $8 billion in debt to buy a bunch of invisible coins and then just... sit on them like a dragon hoarding gold. He’d ask where the heck the gold went.

Now here’s where things get extra weird… Bitcoin is down roughly 24% from its all-time high, currently trading below the price Saylor paid for his most recent batch… a “just sell your kidney already” $86,969 per coin. That’s the average price he shelled out for 22,048 Bitcoin between March 24 and March 30.

Unfortunately, his timing might’ve been about as solid as buying tech stocks in 1999. Bitcoin dipped down to $79,000, and Strategy (formerly known as MicroStrategy) is now staring at a $5.91 billion unrealized loss for Q1. That’s nearly $6 billion in red ink. But don’t worry… they’re offsetting that with a $1.69 billion tax benefit

Oh and despite being in the hole on his last massive buy and holding 528,185 Bitcoin with an average price of $67,458, Saylor still isn’t selling. At least not yet. But Strategy's latest SEC filing includes the line nobody wants to hear from their neighborhood Bitcoin hoarder: “We may be required to sell bitcoin to satisfy our financial obligations.”

In other words: if they can’t raise more money by selling stock or debt (which they’ve been doing like it’s Girl Scout cookie season), they might be forced to sell at a loss. Which is ironic for a guy who once said, “Bitcoin is hope.” Hope, sure… but hope doesn’t pay $35 million a year in interest or $150 million in dividends.

To make matters worse, MSTR stock has been getting wrecked lately. Shares are down nearly 41% from their peak and down 8% for the year, which is a bummer for anyone who bought in thinking they were getting in early on the next Berkshire Hathaway… but with memes.

And what’s Saylor doing through all this? Posting cryptic tweets about inflation being “just the tip of the iceberg” and waxing poetic about how Bitcoin can withstand taxes, regulation, competition, obsolescence, and “unanticipated events.” You know, like losing $6 billion in a single quarter.

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Stock.News does not have positions in companies mentioned.