Michael Saylor just crossed 700k BTC but his “circular” Bitcoin funding loop risks a massive high-yield credit disaster

Strategy (formerly MicroStrategy) acquired an additional 22,305 Bitcoin for approximately $2.13 billion between Jan. 12 and Jan. 19, continuing an aggressive accumulation campaign that has absorbed 3.38% of the top crypto's total supply.

That works out to 3.55% of the circulating supply of 19.97 million coins.

The purchases were executed at an average price of $95,284 per bitcoin, according to a Jan. 20 8-K filing with the Securities and Exchange Commission (SEC).

The latest acquisition brings Strategy’s total Bitcoin holdings to 709,715 BTC, a hoard worth roughly $64 billion. The company’s cost basis for the total stack is approximately $53.92 billion, or an average of $75,979 per bitcoin, implying around $10.5 billion in paper gains at current prices.

How Strategy is funding its Bitcoin purchases

While the headline number highlights the company’s relentless buying, the mechanics behind the purchase reveal a significant shift in how Strategy funds its operations.

These latest acquisitions were funded using proceeds from the firm's at-the-market sales of its Class A common stock (MSTR), its perpetual Stretch preferred stock (STRC), and the Series A Perpetual Strike Preferred Stock (STRK).

According to the SEC filing, the Michael Saylor-led Strategy sold 10,399,650 MSTR shares for approximately $1.8 billion last week. It still has about $8.4 billion worth of shares to fund future BTC purchases.

However, the preferred channel is seeing increased activity.

The filing showed Strategy sold 2,945,371 STRC shares for around $294.3 million (with $3.6 billion shares remaining) and 38,796 STRK shares for $3.4 million (with $20.3 billion shares remaining).

This increased bet shows that the company's attempt to turn its bitcoin treasury strategy into a repeatable “yield SKU” that can sit quietly in brokerage accounts and income portfolios is yielding significant interest.

Notably, this financial engineering has produced four distinct exposure tiers that trade on the Nasdaq exchange. This means investors do not need any BTC know-how to invest, as they can simply buy them through a regular brokerage account.

The product lineup is segmented by risk appetite, offering four distinct ways to play the Strategy trade.

The headline act is the Variable Rate Series A Perpetual Stretch Preferred Stock, or STRC. Marketed explicitly as “short duration high yield credit,” this security currently pays an 11.00% annual dividend in monthly cash installments.

Unlike a standard bond where market forces dictate the yield, STRC is an issuer-managed product. Strategy retains the policy power to adjust the dividend rate to ensure the stock trades near its $100 par value.

Data from STRC.live shows that the firm has accumulated 27,000 BTC from the STRC fundraiser.

Below STRC sits a tiered structure of fixed-rate perpetuals.

For the investor who wants a piece of the equity upside, there is STRK (“Strike”). It pays an 8% annual dividend and is non-cumulative (meaning missed payments are lost forever).

However, it functions as a hybrid, offering convertibility to stock that captures about 40% of the gains if Strategy’s common shares rally.

For the risk-averse income seeker, the company offers STRF (“Strife”). This 10% perpetual preferred cannot be converted to stock, but it sits higher in the capital structure.

It is cumulative, meaning the company must make up any missed dividend payments later. With $1.6 billion remaining in capacity, it represents the most conservative tier.

There is also the STRD (“Stride”) instrument, which matches the 10% yield of STRF but removes the safety net. It is non-cumulative and non-convertible.

If Strategy skips a payment, the investor has no recourse, giving STRD the sharpest risk-reward profile among the fixed-rate options. It has $1.4 billion remaining.

Meanwhile, the company has even opened a European front. Last November, Strategy introduced the Series A Perpetual Stream Preferred (STRE), a euro-denominated security that carries a 10% annual dividend paid quarterly.

This instrument carries sharp teeth regarding non-payment. The dividend is cumulative and increases by 100 basis points per missed period, up to a maximum of 18%.

Institutional investors turn to Strategy's preferred

Strategy's financial engineering product list has successfully courted a demographic that typically shuns crypto: the income tourist.

Data from several institutional filings show that high-income and preferred-focused funds are populating the STRC holders list. The roster includes the Fidelity Capital & Income Fund (FAGIX), Fidelity Advisor Floating Rate High Income (FFRAX), and the Virtus InfraCap U.S. Preferred Stock ETF (PFFA).

Meanwhile, the most striking validation comes from BlackRock. The BlackRock iShares Preferred and Income Securities ETF (PFF) is a massive fund that tracks an index usually dominated by sleepy bank and utility preferreds.

As of Jan. 16, the fund held $14.25 billion in net assets. Inside that conservative portfolio, Strategy’s Bitcoin-linked paper has established a beachhead.

The ETF disclosed a position of approximately $210 million in Strategy’s STRC. It holds another ~$260 million across STRF, STRK, and STRD. In total, BlackRock’s ETF exposure to Strategy preferreds sits at roughly $470 million (or 3.3% of the total fund).

Valentin Kosanovic, a deputy director at Capital B, views this as a watershed moment for digital credit.

According to him:

Risks?

The machinery required to sustain these dividends creates a unique set of risks. Strategy is not paying these yields from operating profits in the traditional sense. It is funding them through the capital markets.

The company’s prospectus for STRC states that cash dividends are expected to be funded primarily through additional capital raising, including at-the-market stock offerings.

This creates a circular dependency: Strategy sells securities to buy Bitcoin and then pays dividends on those securities.

Considering this, Michael Fanelli, a partner at RSM US, highlighted several risks associated with this model, including Bitcoin price crashes, the lack of insurance coverage, and the fact that the products are unproven in recessions. He also noted that the perpetual products have no maturity date.

However, Bitcoin analyst Adam Livingston countered that the products are a “mind-bender” for traditional analysts. He argued that “STRC is quietly turning Strategy into a private central bank for the yield-starved world.”

According to him:

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