Michael Saylor: ‘We’ll Buy Bitcoin Every Quarter Forever’ — Strategy Deploys Preferred Stock to Defend the Playbook

Strategy Inc. (MSTR) posted a $12.4 billion quarterly loss as Bitcoin tumbled 50% from its peak, yet executive chairman Michael Saylor vows to keep buying “every quarter forever.” To ease shareholder pain, the company is rolling out more perpetual preferred stock—Stretch—offering an 11.25% dividend. We analyze whether Saylor’s infinite Bitcoin loop can survive a prolonged bear market.

Strategy’s 714,000 Bitcoin — and a $12 Billion Accounting Hangover

On February 11, 2026, Strategy Inc. reported its fourth‑quarter earnings. The headline number was stark: a net loss of $12.4 billion. The culprit was not operational failure, but accounting reality. Under fair‑value rules, Strategy must mark its massive Bitcoin hoard to market each quarter, and with BTC down nearly 50% from its October peak, the paper loss cascaded through the income statement.

Yet inside the Tysons Corner headquarters, the mood was defiant. CEO Phong Le and executive chairman Michael Saylor used back‑to‑back television appearances to deliver a coordinated message: we are not selling, we are not stopping, and we have a new tool to keep the machine running.

That tool is perpetual preferred stock—rebranded internally as “Stretch”—which currently pays an 11.25% variable dividend, reset monthly to keep the shares trading near $100 par. To date, the company has sold only $7 million of Stretch, compared with $370 million of common stock issuance over the same period. But Le made clear that Stretch will play a much larger role going forward.

“We’ve engineered something to protect investors who want access to digital capital without that volatility,” Le told Bloomberg Television.

The implication is subtle but significant. Strategy’s common stock has cratered 73% from its November 2024 record high, tracking Bitcoin’s descent. Preferred shares, by contrast, offer income and relative price stability. Le is effectively signaling a pivot: less reliance on equity dilution at depressed prices, more reliance on a hybrid instrument that appeals to yield‑hungry institutions.

‘Stretch’ Preferred Stock: Can 11.25% Yield Tame the Volatility?

Preferred stock is hardly new, but Strategy has tailored the product to its unique position as a Bitcoin treasury vehicle.

Each Stretch share carries a liquidation preference of $100 and pays a dividend that resets every month based on a spread over a benchmark rate—currently set at 11.25%. The reset mechanism is designed to keep the shares trading around par, avoiding the deep discounts that often plague fixed‑rate preferreds when interest rates move.

For investors, the appeal is straightforward: a double‑digit yield secured by a company that holds $48 billion in Bitcoin, with no fixed maturity date. For Strategy, the appeal is equally clear: perpetual preferred counts as equity, not debt, and the dividend is discretionary. Unlike bond interest, missing a preferred dividend does not trigger default.

Yet skeptics note that the preferred dividend, while discretionary, still consumes cash. Strategy’s operating cash flow is modest relative to its size; the company relies almost entirely on capital markets to fund both its Bitcoin purchases and its dividend obligations. Saylor insists this is sustainable.

“We’ve got 50 years worth of dividends and Bitcoin, we’ve got two and a half years worth of dividends just in cash on our balance sheet,” he said on CNBC.

That cash cushion, however, is finite. If Bitcoin remains depressed and capital markets stay closed, the dividend coverage ratio will become a growing concern.

‘We’ll Refinance the Debt’ — Saylor’s Unwavering Credit Thesis

The most striking exchange came Tuesday morning, when Saylor was asked the obvious question: what happens if Bitcoin keeps falling?

His answer was characteristically unflinching.

“If bitcoin falls 90% for the next four years, we’ll refinance the debt,” he said. “We’ll just roll it forward.”

Strategy carries more than $8 billion in total debt, almost all of it in the form of convertible notes issued over the past five years. These convertibles carry low coupons—some as low as 0%—and mature between 2027 and 2032. They are unsecured and contain no maintenance covenants. In other words, Strategy cannot be forced into bankruptcy by a decline in Bitcoin’s price; it can simply keep refinancing as maturities approach, assuming willing lenders exist.

Saylor’s confidence rests on two pillars. First, he believes Bitcoin’s long‑term appreciation will eventually bail out every levered buyer. Second, he argues that Strategy’s credit story is not about Bitcoin’s current price, but about its utility as “digital capital.”

“There isn’t any credit risk in the balance sheet of the company,” he declared.

Not everyone shares this view. Credit analysts point out that Strategy’s convertibles trade at deep discounts, reflecting market skepticism about the company’s ability to repay in cash rather than stock. If the stock price stays depressed, noteholders may demand repayment at maturity—forcing Strategy to either raise expensive equity or sell Bitcoin. Saylor insists neither will happen.

The Broken Premium: Why the Bitcoin Flywheel Stalled

To understand Strategy’s urgency in promoting Stretch preferred, one must revisit the mechanism that powered its three‑year bull run.

From 2020 through late 2024, Strategy’s common stock consistently traded at a substantial premium to its Bitcoin‑per‑share value. That premium allowed the company to issue shares, buy Bitcoin, and immediately increase its Bitcoin‑per‑share metric—a virtuous loop that rewarded both equity holders and Bitcoin maximalists.

At its peak in November 2024, MSTR traded above $500, implying a premium of more than 100% over the net asset value of its Bitcoin holdings. Today, that premium has evaporated. MSTR trades near $130, roughly in line with (and occasionally below) its Bitcoin‑per‑share value.

Without the premium, the equity‑for‑Bitcoin swap becomes value‑neutral at best and dilutive at worst. Hence the pivot to preferred stock: Stretch offers a way to raise capital without further depressing the common equity.

“We’re not going to be selling, we’re going to be buying Bitcoin,” Saylor reiterated. “I expect we’ll be buying Bitcoin every quarter forever.”

But buying requires capital. With the equity window partially closed, Strategy must convince investors that Stretch preferred is a compelling alternative.

What Is Strategy’s ‘Stretch’ Preferred Stock?

Issuer: Strategy Inc. (MSTR)** **

Type: Perpetual non‑cumulative preferred stock** **

Par Value: $100 per share** **

Current Dividend Rate: 11.25% (variable, resets monthly)** **

Dividend Payment: Quarterly, discretionary** **

Use of Proceeds: General corporate purposes, including Bitcoin acquisition** **

Trading Symbol: MSTR‑PRA (expected)** **

Outstanding as of Feb 2026: ~$7 million (initial phase); company plans to increase issuance significantly

The “Stretch” name reflects the product’s hybrid nature: it stretches the definition of preferred equity, stretches the yield curve, and, if successful, stretches Strategy’s runway to continue accumulating Bitcoin without diluting common shareholders.

‘Digital Capital’ and the Volatility Paradox

Saylor has long argued that Bitcoin’s notorious price swings are not a bug, but a feature.

“It’s going to be two to four times as volatile as traditional capital like gold or equity or real estate,” he explained. “It’s got two to four times the performance this decade of traditional capital. So the volatility is the bug, but the volatility is the feature.”

This framing serves a dual purpose. Externally, it conditions investors to accept wild drawdowns as normal. Internally, it steels the organization against the temptation to capitulate. By repeatedly describing Bitcoin as “digital capital”—a new asset class distinct from both commodities and currencies—Saylor creates conceptual air cover for the company’s single‑asset concentration.

Yet even digital capital must eventually demonstrate utility beyond price appreciation. Strategy generates virtually no revenue from its Bitcoin holdings; it does not lend them out, stake them, or use them in any productive application. The coins sit in custody, inert, awaiting a higher price.

Saylor believes this is sufficient. “It’s the most useful global capital asset in the world,” he said. “You can put more leverage on it. You can trade it in more ways than any other kind of capital assets.”

For now, the market remains unconvinced. Strategy’s stock has fallen 60% year‑over‑year and 17% year‑to‑date, roughly matching Bitcoin’s drawdown.

Market Reaction: Saylor’s Words, Le’s Execution

Following the earnings release and the dual television interviews, Strategy’s stock initially fell 5%, then stabilized. The preferred Stretch product, still in its infancy, saw modest trading volume. Analysts remain split.

Bullish commentators point to Saylor’s unbreakable resolve and the lack of forced‑sale triggers. They note that Strategy has survived previous 70%+ Bitcoin drawdowns—notably in 2022—and emerged with its holdings intact.

Bearish voices highlight the deteriorating financial metrics. The company’s average Bitcoin acquisition cost now stands at $76,056, more than $7,000 above the current spot price. Every daily close below that level adds to the unrealized loss. While unrealized losses are non‑cash, they impair the company’s ability to raise additional debt or equity on favorable terms.

Phong Le, the relatively low‑profile CEO, is now tasked with executing the Stretch rollout. His background is operations, not capital markets; whether he can sell the preferred product to institutional income funds remains an open question.

What Comes Next for Strategy and the Bitcoin Treasury Model

Strategy is no longer just a software company with a Bitcoin hobby. It is a $48 billion (mark‑to‑market) Bitcoin fund that happens to retain a legacy business intelligence operation. The transformation is complete, and with it, the company’s fate is inextricably linked to Bitcoin’s price cycle.

The next 12 months will test whether the Saylor playbook is infinitely repeatable or whether it contains a hidden terminal clause.

If Bitcoin recovers—if it returns to $100,000 or beyond—the current preferred stock issuance will be remembered as a shrewd counter‑cyclical move. The 11.25% dividend will look cheap relative to the appreciation of the underlying collateral.

If Bitcoin stagnates or falls further, Strategy will face growing pressure to explain how it can keep paying an 11.25% yield on billions of dollars of preferred equity while its primary asset languishes.

Saylor’s answer is consistent: wait. Wait four years, eight years, a decade. He has spent five years convincing the market that time arbitrage is a legitimate investment strategy.

The next few quarters will reveal whether that conviction is contagious—or whether it has reached its limit.

The Bigger Picture: Strategy as a Bellwether for Corporate Bitcoin Adoption

Strategy’s journey has always been viewed through two lenses: as a standalone corporate story and as a proxy for institutional Bitcoin adoption.

When Strategy bought its first Bitcoin in August 2020, the idea of a public company holding cryptocurrency on its balance sheet was radical. Today, dozens of public companies have followed, though none at Strategy’s scale.

The Stretch preferred offering, if successful, could provide a template for other Bitcoin‑treasury firms to raise capital without diluting equity. It also signals a maturation of the financing ecosystem around digital assets—yield‑seeking capital is now willing to take corporate credit risk tied to Bitcoin volatility.

Yet the converse is also true. If Strategy stumbles—if it is forced to sell Bitcoin, or if the preferred dividend is suspended—the reputational damage would extend far beyond a single stock. Every corporate treasurer watching from the sidelines would conclude that the Bitcoin treasury model carries unacceptable tail risk.

Michael Saylor understands this. He has staked his legacy, and his company’s future, on the proposition that Bitcoin is not just an investment but a fundamental reordering of global capital.

“I don’t really make predictions over 12 months,” he said. “I think that bitcoin is going to double or triple the performance of the S&P over the next four to eight years. And I think that’s the only thing we need to know.”

For now, that is enough. The preferred shares are being printed. The debt is being rolled. The Bitcoin is being held.

The next chapter will be written not in press releases, but in the price charts of the asset Saylor calls digital capital.