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How Strategy Is Turning Bitcoin Into Digital Credit

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In a retail-focused Q&A, Strategy executives clarify their approach to digital credit, potential Bitcoin sales, and the metrics that matter for long-term holders.

May 20, 2026StrategyYouTube
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The Multivariate Model: Why Selling Bitcoin Could Be Optimal

Strategy's digital credit model treats Bitcoin as one component of a broader capital-allocation system that also includes equity, credit and cash. Michael Saylor says the company continuously models those instruments with the goal of maximizing Bitcoin per share over a seven-year horizon, rather than following a rule that Bitcoin can never be sold. In that framework, even a Bitcoin sale can be considered if management believes another financing action produces a better long-term result.

Market Odds84%

Polymarket odds that Strategy sells Bitcoin by year-end, up from 30% after the May earnings call.

Saylor emphasized that the goal is not to hoard Bitcoin but to increase Bitcoin per share. Selling Bitcoin at a high cost basis could even generate tax losses that don't affect dividends. The market's 84% odds may overstate near-term risk, but the company is prepared to use all four levers (equity, credit, cash, and Bitcoin) to optimize long-term results.

How Stretch's $100 Peg and Anti-Fragile Design Work

  • Peg Is a Business ObjectiveSTRC's $100 target is the company's 'number one business objective,' but the instrument is designed to trade within a range. Saylor likens it to a ship's stability: selling pressure creates countervailing demand from hedge funds who profit from the spread.
  • Hedge Funds Provide Natural SupportWhen STRC trades 75-100 basis points below par, about $1-2 billion of institutional capital steps in. Below $99, support increases exponentially; below $97, even more. This servo mechanism requires no company intervention.
  • Dividend Rate Likely Stable for YearsSaylor expects the 11-12% dividend to persist, calling it 'low volatility, stable, enthusiastically embraced.' Phong Le added that the product is only 10 months old and true maturity may take 20 years.
  • Semi-Monthly Dividends Come FirstThe proposed June 8 vote discussed in the Q&A concerned a shift from monthly to semi-monthly dividends, intended to improve liquidity and reduce volatility. Daily dividends, as pioneered by Strive, may be considered later if shareholder demand justifies it.

Semi-Monthly Dividends and the Strive Rivalry

At the time of the Q&A, Strategy was seeking shareholder approval at a June 8 vote to shift Stretch dividends from monthly to semi-monthly, a step Saylor called 'bold and progressive.' He praised Strive Asset Management for launching a daily-dividend digital credit instrument, but noted that Strategy is 100x larger and operates under different governance. 'I wouldn't mind seeing them get 10x bigger,' he said, viewing the coexistence as healthy for the market.

Phong Le added that the company considered changing all preferreds but focused on Stretch first because it is the flagship. The other preferreds (Stride, Strife, and Strike) may eventually receive similar treatment, but only after Stretch matures. 'We want to get Stretch working as well as possible and then turn to the other ones, ' he said.

Anti-Fragile by Design: Why DeFi Unwinds Won't Break Stretch

When asked about the risk of a large levered DeFi position unwinding and crashing the $100 peg, Saylor compared Stretch to a skyscraper that must flex. 'If you try to take the flex out of the building, it'll be rigid and then it will snap,' he said. Stretch is designed so that selling pressure attracts countervailing demand from hedge funds, not from the company itself.

The support mechanism is exponential. A $2 billion dump in an hour would push the price down perhaps 150 basis points, but below $99 support increases sharply, and below $97 'even more.' Saylor said hedge funds with hundreds of billions in capital stand ready to buy because they earn a quick 150 basis points when the instrument bounces back to par. The system is designed to self-stabilize.

From 1.22x Break-Even to 3-4x MNAV: The Bitcoin Yield Engine

Saylor walked through the math behind the 1.22x MNAV break-even for accretive MSTR issuance, explaining that the complication comes from convertible debt dilution. The cleaner metric is BTC yield, the rate at which Bitcoin per share grows. With 20% BTC yield last year and 12% so far this year, the company can double Bitcoin per share in roughly three to seven years, which warrants a premium to net asset value.

The plan to reach 3-4x MNAV has three pillars: first, demonstrate the business can produce consistent BTC yield; second, build a durable machine that can run for a decade; third, communicate the story to equity markets. Saylor invoked the Lindy effect, noting that each year of consistent performance makes the business model seem more durable, expanding the multiple.

'When the market embraces the business model, the P/E expands,' he said, comparing it to Apple's iPhone era.

Saylor on Market Valuation“When the market embraces the business model, the P/E expands.”— Michael Saylor

Comparing Strategy's potential to Apple's P/E expansion from 8 to 30 when the iPhone was seen as durable.

Why Strategy Won't Retire Its Older Preferreds

Despite the success of Stretch, Strategy remains committed to its four other preferred stocks: Strife, Stride, Stream, and Strike. Saylor called them 'undervalued' and said the company is not selling them under their shelf registrations. 'Probably the single most important thing I could say on this call if you were an STRF holder or STRD or STRK or STRE is we think they're undervalued,' he stated.

Instead of retiring the preferreds, the company is retiring its six convertible bonds, which are senior liabilities. By removing senior debt, Strategy improves the credit quality of the perpetual preferreds. The bonds are 'liabilities, ' while the preferreds are 'opportunities', institutional products with more duration and delta that serve a different investor base.

Metrics for Long-Term Holders

  • Bitcoin Per Share Is the True NorthSaylor advises equity holders to focus on BTC yield, the rate at which Bitcoin per share compounds. The company grew from 50, 000 satoshis per share five years ago to over 200, 000 now.
  • MNAV Premium Depends on DurabilityIf the business can sustain 20% BTC yield for 10 years, an MNAV of 3x is warranted. Each additional year of consistent performance increases the Lindy multiple.
  • Tax-Loss Harvesting Is a FeatureSelling Bitcoin at a high cost basis can generate tax losses that improve after-tax returns without affecting dividends.
  • Stability Over Basis PointsThe company prioritizes low volatility over saving a few basis points, keeping the dividend at 11.5% to avoid uncertainty.

Improving by Subtraction: The Via Negativa Strategy

When asked how Stretch could be made even better, Saylor invoked Nassim Taleb's concept of via negativa: making something better by taking away rather than adding. The best way to improve Stretch is to eliminate the senior bonds, increase its credit rating, and let it season. 'If it had been operating consistently for three years, it would be a 100x better product,' he said.

Phong Le added that the next leap forward will come from third-party innovation on top of Stretch as a platform. Examples include D5 protocols like Apex, which grew to $500 million in three months, and potential ETF wrappers or bank distribution. 'I don't sit here and think to myself what is the next product,' he said. 'The focus right now is making Stretch the best product possible for the next three to five years.'

Digital Credit for Everyone: Stretch as a Mainstream Asset

Saylor envisions Stretch becoming a staple for everyday savers, offering 11-12% yield when traditional banks pay near zero. But broad adoption requires product maturity, regulatory clarity (such as the Clarity Act), and integration with wealth management platforms. 'I think there's a huge opportunity with a product like Stretch to provide yield generation to people regardless of income level,' he said.

The company also sees education as a core responsibility, especially for the next generation who will inherit these holdings. 'When you talk to people about Bitcoin, you open their eyes to macroeconomics, security, sovereignty, and investing, ' said Saylor. Phong Le noted that 80% of Stretch holders are retail, a humbling reminder that real people are putting their savings into the company's securities.

The Integration of All Capital Markets

In his closing remarks, Saylor declared this 'the most exciting year in the history of the industry,' as traditional finance, DeFi, equity markets, and credit markets converge. He urged viewers to focus on digital credit, especially STRC, as a genuinely new asset class. 'People's knee-jerk reaction is to say it's like something else that didn't work,' he warned. 'But it really is a new thing with new implications.'

He encouraged using AI to explore ideas and noted that ideas can go from zero to billions in a year. 'If you have epiphanies and new ideas, you're doing it right. If you think this is just like every other year, you're missing the opportunity.' The company plans to continue this direct engagement with retail shareholders, who submitted the questions that shaped the entire webinar.

▶YoutubePublic
SpeakerStrategy
ChannelStrategy
PublishedMay 20, 2026
Duration1h 14m
Analysed by KnowledgePilot

Full 1h 14m source analysed with timestamp references throughout this article.

Watch original on YouTube ↗

TLDR

  • Strategy considers selling Bitcoin as part of a multivariate capital allocation model.
  • The $100 peg for STRC is the company's primary business objective, not a legal obligation.
  • BTC yield (Bitcoin per share growth) is the key metric for equity holders.
  • Stretch dividends at 11-12% are expected to remain stable for years.
  • Strategy views Stride, Strife, and Strike as undervalued and will not retire them.
  • Selling high-cost-basis Bitcoin can generate tax losses without affecting dividends.
  • Digital credit is a new asset class; Stretch is designed to be anti-fragile against large sales.

In this article

  • The Multivariate Model: Why Selling Bitcoin Could Be Optimal
  • Semi-Monthly Dividends and the Strive Rivalry
  • Anti-Fragile by Design: Why DeFi Unwinds Won't Break Stretch
  • From 1.22x Break-Even to 3-4x MNAV: The Bitcoin Yield Engine
  • Why Strategy Won't Retire Its Older Preferreds
  • Improving by Subtraction: The Via Negativa Strategy
  • Digital Credit for Everyone: Stretch as a Mainstream Asset
  • The Integration of All Capital Markets
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