Michael Saylor isn’t backing down. The co-founder of Strategy — officially known as MicroStrategy Inc. — is preparing to sell an additional $4.2 billion worth of preferred stock, roughly over Rp69 trillion, to fuel his latest Bitcoin bet — while trying to reassure investors who fear being left behind.

The plan, announced alongside the company’s second-quarter earnings on Thursday (local time), is Saylor’s latest response to the looming question over his stock: how long can he continue using its high premium to fund larger Bitcoin purchases?

To calm shareholders, Strategy pledged it won’t issue new common shares at less than 2.5 times its net asset value — unless to pay debt interest or preferred stock dividends. Meanwhile, Saylor will continue entering the market opportunistically when the premium is high, turning equity sales into new Bitcoin purchases.

This dual strategy serves two goals: locking in favorable pricing to appease skeptical shareholders, and arming the company with a bigger war chest to keep buying Bitcoin. It's a tactical move that puts Saylor directly at odds with hedge fund managers like Jim Chanos, who have bet the company’s premium will collapse.

“This will ease the concerns of common shareholders worried about potential dilution,” said Brian Dobson, managing director of Disruptive Technology Equity Research at Clear Street. “The market is responding positively to Strategy’s equity product. The demand is evident from the substantial capital raised.”

This marks the latest in a series of financial maneuvers that have transformed an obscure software company into a leveraged proxy for Bitcoin.

This two-pronged approach reflects Saylor’s command of the capital markets during the bullish digital asset phase: using rules of his own design to placate critics while simultaneously reloading the company with financial ammunition to keep acquiring Bitcoin.

This year alone, the company has raised over $10 billion through equity and structured offerings, bolstering a balance sheet that now includes $74 billion worth of Bitcoin. Its shares have soared 3,300% since Saylor’s first crypto purchase, outpacing Bitcoin itself and pushing hedge funds into a high-stakes bet on whether his premium-fueled strategy will hold.

Since Strategy’s first Bitcoin buy in 2020, Saylor has sold equity, issued multiple forms of debt, and stacked preferred stock on top. Along the way, he’s inspired imitator firms and launched a new industry of public companies using a “treasury strategy” dedicated to buying and holding crypto.

A Timely Strategy
Because Strategy trades far above its actual Bitcoin value, it can sell shares at a premium, purchase more Bitcoin, and reinforce its own stock value. This reflexive loop, critics warn, could break if market sentiment shifts.

For now, Saylor’s ability to turn the equity market into a Bitcoin funding engine has made his company both a crypto proxy and a pressure point for skeptics betting the spread will implode.

The company reported unrealized gains of about $14 billion in the second quarter. After deferred taxes, its Bitcoin treasury netted $10 billion in profit, or $32.6 per share, the company said. The impressive profit — first revealed earlier this month — was driven by Bitcoin’s price rebound and recent accounting changes.

Offering demand may fluctuate with Bitcoin’s price. One earlier preferred stock offering this year had to be sweetened with a steep discount to attract price-sensitive investors.

Just last week, the company rolled out a new class of preferred shares, dubbed Stretch, which expanded from an initial $500 million to more than $2 billion. It’s another sign of how skillfully Saylor can engineer financial products into crypto firepower — at least for now.

“The size increase of Strategy’s offering reflects massive market demand for the Stretch Preferred Stock,” said Tyler Evans, co-founder and chief investment officer at UTXO Management. “They’ve done similar upsizes before, but this one is staggering in scale.”