Saylor Goes "All In" AGAIN - MicroStrategy Plans Reckless $2B Offering for More Bitcoin Buys...

Just when you thought Michael Saylor couldn’t possibly double down any harder on his Bitcoin obsession, MicroStrategy comes in hot with a plan to raise up to $2 billion through public offerings of perpetual preferred stock. And no, this isn’t some vague “for general corporate purposes” line item. The company straight-up said it: the money’s going to buy more Bitcoin. Because apparently owning 446,400 BTC worth $27.9 billion isn’t enough.

(Source: Giphy) 

In short, MicroStrategy is planning to issue perpetual preferred stock—a glossed up way of saying “stock that doesn’t have a maturity date but pays dividends.” These shares would be senior to the company’s Class A common stock, which means they get dibs in the payout line. Oh, and there’s talk of convertibility to Class A shares, cash dividends, and even redemption options. Basically, they’re throwing in all the bells and whistles to make this offering look as appealing as possible. Translation:“Dilution? Never heard of it…” 

Simply put, MicroStrategy isn’t just a business software company anymore—it’s basically a Bitcoin hedge fund masquerading as a tech firm. Saylor, the company’s founder and executive chairman (and vocal BTC evangelist), has made it his life’s mission to stack sats.

(Source: Barrons) 

Meaning, this  $2 billion raise is part of MicroStrategy’s previously announced 21/21 plan, where they aim to raise $21 billion in equity and debt over three years. The goal? Buy even more Bitcoin, duh. Because again, apparently having 2% of the world’s Bitcoin supply just doesn’t scratch the itch.

But, but, but… even while this move may give someone like Warren Buffet heart palpitations, the numbers don’t lie. As of December 29, MicroStrategy owns 446,400 BTC, with an average purchase price of $97,837 per coin—with their latest spree resulting in  $209 million, snagging 2,138 BTC at the end of 2024. The bigly part? Over the last year, MicroStrategy’s BTC holdings have delivered a 74.1% YTD yield, which is absolutely phenomenal. 

(Source: Microstrategy) 

However, while Microstrategy’s yield may be enough to justify the capital raise to some, you don’t need a CFA to see where this is heading. Raising $2 billion through a preferred stock offering screams dilution for existing shareholders. And while Saylor’s Bitcoin strategy has been a goldmine so far, it’s also turned MicroStrategy into a polarizing stock. Critics, like angel investor Jason Calacanis, have warned that MicroStrategy’s relentless Bitcoin buys could actually hurt BTC’s broader appeal. Meanwhile, skeptics are asking: What happens if Bitcoin’s price crashes? Spoiler: It won’t be pretty. 

Surprisingly though, even with the dilution and the heavy uncertainty of Bitcoin’s continued momentum, this massive announcement hasn’t tanked MSTR shares (yet). Investors seem to be riding the Bitcoin high right alongside Saylor. But make no mistake—this is a high-stakes gamble. MicroStrategy isn’t just betting the farm on Bitcoin; they’re mortgaging the farm, taking out a loan on the tractor, and selling the barn to buy more LOL.

(Source: Giphy) 

This fact alone makes this move one to keep an eye on. Because unlike business dynamics, and unique competitive edges—whether this ends in tears or tendies depends entirely on Bitcoin’s trajectory. Fun times, I tell ya. 

In the end, MicroStrategy is either revolutionizing corporate treasury management or creating the most expensive business school case study of all time. There's no in-between here. And for Microstrategy investors, the ante has just been upped… whether you like it or not. Meaning, do your due diligence and place your bets accordingly. 

As always, stay safe and stay frosty, friends! Until next time…

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Stocks.News does not hold positions in companies mentioned in the article.