--- title: "How Far Can Michael Saylor 'Stretch' It? Strategy's Bitcoin Machine Enters A New Phase" type: "News" locale: "en" url: "https://longbridge.com/en/news/286286842.md" description: "Michael Saylor’s Strategy Inc. (NASDAQ:MSTR) is shifting its Bitcoin acquisition strategy to rely on STRC, moving away from common stock issuance and convertible debt. This change targets yield-focused investors with an 11.5% annual dividend. The success of this strategy hinges on Bitcoin prices rising and maintaining a premium over net asset value. However, risks include potential stagnation in Bitcoin prices and increasing dividend obligations. Traders are monitoring the company's $28.3 billion STRC issuance limit and its $8.2 billion convertible debt obligations due in 2028." datetime: "2026-05-13T15:16:37.000Z" locales: - [zh-CN](https://longbridge.com/zh-CN/news/286286842.md) - [en](https://longbridge.com/en/news/286286842.md) - [zh-HK](https://longbridge.com/zh-HK/news/286286842.md) --- # How Far Can Michael Saylor 'Stretch' It? Strategy's Bitcoin Machine Enters A New Phase **Michael Saylor’s** **Strategy Inc.** (NASDAQ:MSTR) is increasingly relying on STRC to keep buying **Bitcoin** (CRYPTO: BTC), but the math behind the company's accumulation engine is becoming more difficult as dilution pressures build. ## **Strategy's Centerpiece Is Now STRC** Strategy's earlier Bitcoin purchases worked because MSTR traded at a massive premium to its underlying BTC holdings. At roughly 1.24x EV-based mNAV, however, that advantage has narrowed significantly. Research firm Delphi Digital notes that STRC has now become the centerpiece of Strategy's latest BTC acquisition strategy, shifting the company away from relying purely on common stock issuance and convertible debt.   It gives Strategy access to a different investor base. Instead of selling equity upside, the company is now targeting yield-focused investors willing to underwrite an 11.5% annual dividend, paid monthly. That structure allows Strategy to continue funneling capital into Bitcoin purchases without adding another large convertible maturity wall. ## **Bull Case vs. Risk Case** The bull case for Strategy depends on Bitcoin continuing to rise and MSTR maintaining a premium to its net asset value. In that environment, Strategy can keep issuing STRC, buy more BTC and rely on rising Bitcoin prices to offset dilution, creating a self-reinforcing cycle. The risk case emerges if Bitcoin enters a prolonged sideways phase. Dividend obligations would continue growing, common stock issuance would become less effective, BTC-per-share growth could slow and preferred liabilities would keep increasing. Over time, investors may begin questioning whether STRC-funded Bitcoin purchases can continue outpacing the dilution required to sustain the expanding preferred structure. ## **What Are Traders Watching Next** Traders are closely watching Strategy as it approaches its $28.3 billion STRC issuance limit, which currently allows the company to keep buying more Bitcoin while easing dividend-related dilution pressures. The bigger concern lies ahead as Strategy still faces about $8.2 billion in convertible debt obligations, with repayments becoming significant starting in September 2027. While its $2.25 billion cash reserve appears enough to handle the roughly $1 billion put due in 2027, investors remain focused on how the company plans to address the much larger debt maturities arriving in 2028. _Image: Shutterstock_ ### Related Stocks - [BTC.US](https://longbridge.com/en/quote/BTC.US.md) - [MSTR.US](https://longbridge.com/en/quote/MSTR.US.md) - [GLXY.US](https://longbridge.com/en/quote/GLXY.US.md) - [GBTC.US](https://longbridge.com/en/quote/GBTC.US.md) - [RIOT.US](https://longbridge.com/en/quote/RIOT.US.md) - [COIN.US](https://longbridge.com/en/quote/COIN.US.md) - [MSTX.US](https://longbridge.com/en/quote/MSTX.US.md) - [MRAL.US](https://longbridge.com/en/quote/MRAL.US.md) - [BTF.US](https://longbridge.com/en/quote/BTF.US.md) - [MSTP.US](https://longbridge.com/en/quote/MSTP.US.md) - [EZBC.US](https://longbridge.com/en/quote/EZBC.US.md) - [MSTU.US](https://longbridge.com/en/quote/MSTU.US.md) - [MSTW.US](https://longbridge.com/en/quote/MSTW.US.md) - [FBTC.US](https://longbridge.com/en/quote/FBTC.US.md) - [BRRR.US](https://longbridge.com/en/quote/BRRR.US.md) - [BITO.US](https://longbridge.com/en/quote/BITO.US.md) - [LMBO.US](https://longbridge.com/en/quote/LMBO.US.md) - [BLCN.US](https://longbridge.com/en/quote/BLCN.US.md) - [MSOO.US](https://longbridge.com/en/quote/MSOO.US.md) - [IBIT.US](https://longbridge.com/en/quote/IBIT.US.md) - [BTCO.US](https://longbridge.com/en/quote/BTCO.US.md) - [BITB.US](https://longbridge.com/en/quote/BITB.US.md) - [ARKB.US](https://longbridge.com/en/quote/ARKB.US.md) - [COIW.US](https://longbridge.com/en/quote/COIW.US.md) - [CONL.US](https://longbridge.com/en/quote/CONL.US.md) - [BTCC.US](https://longbridge.com/en/quote/BTCC.US.md) - [BLOK.US](https://longbridge.com/en/quote/BLOK.US.md) - [MST.US](https://longbridge.com/en/quote/MST.US.md) - [BTCHKD.VAHK](https://longbridge.com/en/quote/BTCHKD.VAHK.md) - [BTCUSD.VAHK](https://longbridge.com/en/quote/BTCUSD.VAHK.md) - [STRF.US](https://longbridge.com/en/quote/STRF.US.md) - [STRC.US](https://longbridge.com/en/quote/STRC.US.md) - [STRK.US](https://longbridge.com/en/quote/STRK.US.md) - [STRD.US](https://longbridge.com/en/quote/STRD.US.md) ## Related News & Research - [This bitcoin price engine just turned back on](https://longbridge.com/en/news/285977397.md) - [The financial boundaries of Strategies' increased BTC holdings: Can STRC continue to drive growth?](https://longbridge.com/en/news/286196820.md) - [Michael Saylor Says Strategy Could Sell Bitcoin, But 'Buy 10X That Much In The Same Month'](https://longbridge.com/en/news/285981441.md) - [Michael Saylor’s latest tax strategy echoes Strategy’s 2022 bitcoin sale](https://longbridge.com/en/news/285929367.md) - [The Michael Saylor Trade: Sell A Kidney, Keep Bitcoin — With One Caveat](https://longbridge.com/en/news/285404789.md)