Once a fading software company struggling to stay relevant, MicroStrategy (MSTR) has outstandingly become the ultimate Bitcoin buying powerhouse, hoarding nearly 2% of the world’s entire BTC supply.

What’s driving this wild transformation? Ambition, audacity, and billions in borrowed cash. In the past month alone, MicroStrategy announced plans to raise a staggering $42 billion through equity and debt. It also spent $10.2 billion snapping up Bitcoin.

But the real spectacle was its fifth convertible bond offering of the year. The terms? ZERO interest and a conversion price set at a ridiculous 55% premium to its current stock price. Investors are essentially giving MicroStrategy free money, banking on Bitcoin’s price (and its stock) continuing to skyrocket. 

It’s no wonder the company’s stock has jumped over 450% this year, pushing its market cap to $90 billion. That’s a jaw-dropping number for a company whose original software business is bleeding cash and shrinking every quarter.

The Bitcoin spiral: A high-stakes loop

MicroStrategy’s entire business model now revolves around Bitcoin. Here’s how it works: they raise money through stock sales and convertible bonds. Then, they take that cash and buy Bitcoin—lots of it. These purchases boost Bitcoin’s value, which in turn raises MSTR’s price.

The company can then raise even more funds at higher valuations. It’s a cycle so audacious that critics don’t know whether to call it genius or madness. Right now, MicroStrategy owns 386,700 bitcoins, worth $37 billion. But the company’s $90 billion market cap far exceeds the value of its Bitcoin reserves.

Unlike companies like Tesla or Block, which dabble in Bitcoin by using surplus cash, MicroStrategy is all in. CEO Phong Le unveiled a plan called “21/21” last month, aiming to raise $42 billion over three years. Half of that will come from stock sales, and the other half from debt.

The plan’s name is a cheeky nod to Bitcoin’s 21 million coin limit and a reference to The Hitchhiker’s Guide to the Galaxy, where “42” is famously the answer to life’s ultimate question. If nothing else, the company’s confidence is almost as colossal as its balance sheet.

Free money and big bets

The $3 billion convertible bond issued this month was an unprecedented move, even by MicroStrategy’s standards. Investors lent the money with zero interest and a conversion price of $672 per share—a 55% premium over the current stock price of $406.

The gamble here is obvious: if Bitcoin’s price continues to rise, MicroStrategy’s stock will follow, making the bonds profitable. If not, those investors are left holding the bag.

But not everyone holding these bonds is just sitting around, waiting for Bitcoin to climb. Many are deploying sophisticated trading strategies. Techniques like gamma trading, delta hedging, and volatility arbitrage allow investors to profit from fluctuations in Bitcoin’s price or MicroStrategy’s stock.

These tactics depend on volatility—a condition Bitcoin has delivered in spades, although its swings have calmed somewhat in recent years.

The bond offering is essentially a massive bet on Bitcoin’s future. If the cryptocurrency’s price crashes or remains stagnant, the house of cards could collapse.

Critics argue that the entire operation feels like a Ponzi scheme, where early investors profit while new ones push up the stock price.

Regulators have kept a close eye on Bitcoin, and for now, it is safe from being labeled a security. The SEC has declared it an exception, much to the relief of Bitcoin enthusiasts and companies like MicroStrategy. But that’s not the only legal challenge.

U.S. regulations discourage company executives from making speculative predictions about stock prices. Michael Saylor, MicroStrategy’s co-founder and Bitcoin evangelist, hasn’t been shy about sharing his opinions.

He’s predicted Bitcoin will hit $13 million by 2045, making the company’s current Bitcoin holdings worth $4.3 trillion. Statements like these could invite scrutiny, especially if the company’s strategy begins to unravel.

The Bitcoin monopoly

MicroStrategy’s dominance over Bitcoin’s supply is raising eyebrows. BTC was designed to be decentralized, but MicroStrategy’s aggressive buying spree has caused concerns about corporate concentration.

Despite these worries, MicroStrategy’s approach has inspired other companies to follow suit. Bitcoin miners like Marathon are now borrowing MicroStrategy’s playbook, issuing zero-interest bonds to fund their operations.

Marathon’s recent bond sale carried a 42.6% premium, proving that MicroStrategy’s bold moves are reshaping how businesses interact with Bitcoin.

But not everyone is impressed by MicroStrategy’s high-stakes strategy. Skeptics argue that it’s reckless, unsustainable, and heavily reliant on Bitcoin’s price continuing to rise.

They point to Bitcoin ETFs as safer alternatives for investors who want exposure to cryptocurrency without the risks of MicroStrategy’s leveraged model.

But supporters see it differently. They highlight the company’s ability to raise money at virtually no cost, thanks to its 0% bonds. They also argue that MicroStrategy offers more than just Bitcoin exposure.

According to Saylor, the company provides flexibility for investors. Its stock can be leveraged, borrowed against, or even traded like an option. For now, Wall Street remains divided.

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