How Strategy’s $8B Move Shocked Analysts and Bitcoin

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Ah, Strategy-formerly MicroStrategy-has done it again, darling. The Bitcoin corporate treasury pioneer has hit a rather dashing ‘healthy’ milestone in its capital-raising structure. Isn’t that just thrilling?

For the first time, the firm’s preferred stocks ($8.36 billion, but who’s counting?) have surpassed its total convertible debt ($8.21 billion). It’s like watching a high-stakes poker game where everyone’s bluffing except Strategy, who’s quietly raking in the chips.

Now, for those not intimately acquainted with the world of corporate finance, convertible debt is essentially a loan with a maturity date and the delightful added bonus of bankruptcy risk if you default. How charming.

This has been Strategy’s go-to capital-raising tool from 2020 to 2023, but, oh dear, the risk could escalate during major Bitcoin downturns. This debt risk factor has been hanging over Strategy like a dark cloud, especially with the 2028 maturity deadline looming. But fear not, Strategy has a trick up its sleeve.

Enter preferred stocks, darling. Strategy unveiled several of these to complement its common stock, MSTR, to raise capital for its Bitcoin buys. Because why not add a dash of elegance to the whole affair?

Preferred stocks vs. MSTR: A Tale of Two Investments

Preferred stocks, on the other hand, offer a flexible capital-raising option with dividends (not interest) that can be deferred. No maturity date, no repayment-just a lovely reduction in bankruptcy risk even during major Bitcoin downturns. Genius, really. As analyst Pio Vincenzo noted, it’s a bit like switching from a rickety old bicycle to a Rolls-Royce.

“This is a huge milestone for MSTR. It validates the preferred equity strategy and the transition away from convertible debt. The old strategy had an actual bankruptcy risk.”

Chaintany Jain, an official at Strategy, praised the shift as more ‘scalable’ than the old convertible debt. Scalable, darling? How positively modern.

Meanwhile, analyst Rohan Hirani chimed in, noting that the heavy reliance on preferred stocks would help Strategy ‘dismantle’ the bankruptcy-linked vulnerability, allowing the firm to increase its Bitcoin bet. Dismantling vulnerabilities-how very dramatic.

Others viewed the shift as a ‘structural win’ and a ‘bullish path’ for MSTR stock price. Bulls, bears-it’s all rather zoo-like, isn’t it?

Strategy unveiled its first preferred stock, Strike [STRK], in early 2025. Later on, it added four more preferred stocks: Strife [STRF], Stride [STRD], Stretch [STRC], and Euro-denominated Stream [STRE], which was launched in November 2025. A veritable alphabet soup of investments.

Strategy’s Holdings Cross 700K BTC: A Bitcoin Bonanza

With the preferred stocks and MSTR, Strategy has scaled its Bitcoin holdings from 446K BTC in December 2024 to 709K BTC as of early January 2025. That’s a lot of digital gold, darling.

In fact, over the past year, Strategy has made more Bitcoin buys worth over $1 billion each. Spending billions like it’s Monopoly money-how very chic.

However, the MSTR stock price has traded below $200 since Bitcoin lost $100k in November. Even so, MSTR has outperformed Bitcoin on a year-to-date (YTD) basis and traded at $163 at the time of writing. Meanwhile, Bitcoin traded at $89.9k. A bit of a rollercoaster, but isn’t that half the fun?

Final Thoughts: A Toast to Strategy

  • Strategy has reached a milestone in its capital-raising structure by reducing its exposure to debt. Bravo!
  • Analysts believe the shift reduces bankruptcy risk and is ‘bullish’ for the MSTR stock price in the long run. Cheers to that!

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2026-01-23 04:12