In a wide-ranging conversation that underscored Strategy’s evolution from an enterprise software company into one of the world’s most influential corporate bitcoin accumulators, CEO Phong Le said the firm now has “more flexibility than ever” to continue expanding its bitcoin position across future market cycles. Appearing on the latest episode of the What Bitcoin Did podcast with host Danny Knowles, Le detailed how the Washington, D.C.–area company — rebranded from MicroStrategy to Strategy in February 2025 — has engineered a capital structure explicitly designed to support perpetual bitcoin acquisition.
Le’s message was unambiguous:
Strategy has no near-term refinancing pressure, no liquidity stress, and a deliberate balance-sheet architecture that allows it to opportunistically raise capital through both equity and long-dated convertible debt. This dual-path financing approach, he argued, forms the core “magic” behind Strategy’s ability to accumulate bitcoin year after year while weathering the volatility of crypto and broader macro markets.
Built for Flexibility Long-Dated Debt + Opportunistic Equity
During the interview, Le emphasized that Strategy’s capital-markets strategy has become just as central to the company’s identity as either its enterprise analytics business or its bitcoin treasury. The company’s long-dated convertible note tranches — which do not begin maturing until December 2025 — give the firm breathing room and optionality that few public companies enjoy.
“We deliberately engineered our balance sheet to avoid liquidity stress,” Le said. “Our capital stack is very strong. The first debt maturity doesn’t hit until December 2025. It gives us a lot of flexibility to be opportunistic.”
That optionality is multi-layered:
Equity Access Through At-the-Market Programs
Strategy can issue shares incrementally when equity markets are strong, taking advantage of favorable pricing without committing to large blocks. Le noted that the company’s shareholder base, by now, fully understands the firm’s bitcoin-forward mission and accepts dilution as a strategic tool rather than a last resort.
Long-Duration, Zero- or Low-Coupon Convertible Notes
Strategy has repeatedly demonstrated that it can issue convertible debt at attractive terms — including zero-coupon offerings — even in uncertain macro environments. These convertibles, Le said, carry minimal near-term dilution risk and provide extremely cheap financing relative to traditional debt.
The Ability to Choose Timing and Capital Type
“We’ve shown we can do both. We can choose the timing of both,” Le said of equity versus debt issuance. “We can raise during strong equity markets, or lean on convertibles when rates and market conditions favor long-duration issuance.”
The overarching theme: Strategy decides when to raise capital — the market doesn’t force it.
From Software Vendor to Public-Market Bitcoin Access Vehicle
Strategy now holds more than 158,000 BTC on its balance sheet, placing it among the largest corporate bitcoin holders in the world. The firm’s rebranding from MicroStrategy to Strategy earlier in 2025 was more than cosmetic; it formalized a transformation years in the making.
“Our shareholder base understands who we are,” Le said during the podcast. “We’re the only access point to this strategy in public markets.”
In other words, investors aren’t buying Strategy stock as a pure enterprise software play. They are buying into a dual-business model:
— A steady-cash-flow software firm that generates operational income
— A long-term bitcoin operating strategy powered by the capital markets
This combination has given Strategy a unique position among public companies, functioning almost like a hybrid between a bitcoin ETF, a tech firm, and a capital-markets-driven treasury vehicle.
Addressing Valuation Skepticism: Why Strategy Believes the Model Works
Le acknowledged during the interview that some investors and analysts continue to question how Strategy should be valued. Should its stock track bitcoin directly? Should its software division be valued separately? Should the convertibles be treated as leverage or as future equity?
These debates intensify during bitcoin downturns, when Strategy’s shares — ticker MSTR — often amplify bitcoin’s downward volatility.
“It’s natural for investors to wonder about valuation when bitcoin is volatile or trading below recent highs,” Le said. “But we’ve proven this approach through multiple cycles.”
He argued that the company’s ability to repeatedly raise capital at favorable terms, even during challenging macro periods, serves as validation of Strategy’s long-term model. If the market doubted the sustainability of the firm’s bitcoin strategy, he noted, the company wouldn’t enjoy the demand it consistently sees for its convertibles and equity offerings.
The Road Ahead: More Bitcoin, More Optionality, More Capital-Market Mastery
With bitcoin holdings already exceeding 158,000 BTC, Strategy plans to continue deploying excess cash flow from its analytics business into bitcoin. But operational cash flow is only one input into the model.
The real engine, Le suggested, remains the company’s ability to raise capital on demand — and at scale.
“As long as we’re executing — on software, on bitcoin, and in capital markets — we think the story will remain compelling,” he said.
This three-pillar execution framework appears to be Strategy’s internal compass:
Software Execution
Provide steady cash flow, maintain customer relationships, and ensure the traditional business remains strong enough to backstop corporate operations.
Bitcoin Execution
Maintain the long-term accumulation thesis: buy over time, through volatility, and across cycles.
Capital-Markets Execution
Issue equity or debt when conditions are ideal, not when liquidity pressures force reactive moves.
Le said Strategy’s deliberate balance-sheet architecture gives it near-unprecedented resilience among public-market companies. With no short-term refinancing risk, the firm can focus on strategic timing rather than survival.
The Market’s View: Pressure, Pain, and Potential Upside
Strategy’s Class A shares (MSTR) closed Friday at $17.18, up 0.88% on the day but down 41% year-to-date. By comparison, bitcoin itself has fallen only 3.14% during the same period — suggesting that MSTR has once again acted as a high-beta proxy for bitcoin, amplifying both optimism and fear.
CoinDesk market analyst James Van Straten noted that the market may still “test Strategy’s enterprise valuation” — or even drive the stock below the firm’s aggregate bitcoin cost basis. Such a move could represent a “max pain” scenario before a recovery.
Even so, Van Straten believes the bottom is likely already in for both bitcoin and MSTR. He argued on X that once Strategy successfully navigates the remainder of its current convertible note structure, investor sentiment could shift sharply.
“Once they ride out this cycle of convertibles,” he wrote, “both bitcoin and MSTR will rally hard.”
A Corporate Bitcoin Engine Built for Decades, Not Quarters
The message across the interview and wider market commentary is clear:
Strategy is playing a long game measured not in quarters or even years, but in decades.
Phong Le’s leadership, and the firm’s capital-market innovations, have turned the company into:
- a predictable bitcoin accumulator,
- a high-leverage bitcoin exposure vehicle for public investors,
- a software firm whose cash flow fuels alternative asset expansion, and
- a masterclass case study in using debt and equity markets to reshape a corporate treasury model.
With no near-term debt cliffs, strong demand for its long-dated convertibles, and a shareholder base aligned with its bitcoin mission, Strategy believes it can continue accumulating BTC indefinitely.
“We’ve shown we know how to use the capital markets well,” Le said. “And that’s what makes this strategy work.”
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