Strategy: Saylor's bitcoin bet

A Minnesota software company become the largest listed bitcoin holder on the planet: that is the story of Strategy, Michael Saylor’s former MicroStrategy. At the end of June 2026, it owns 847,363 bitcoins, paid around $64 billion. And an event has just happened that its supporters judged impossible: its market capitalisation fell below the market value of its own treasury. The model, brilliant as long as bitcoin rose, faces its first real test. Here is how it works, and where it can break.

A software company become a bitcoin reserve

Renamed Strategy in February 2025, the company led by Michael Saylor, its executive chairman, and Phong Le, its chief executive, has made bitcoin its reason for being. Its historic software activity still exists, but it has become marginal against a treasury of nearly $64 billion. Over some $50 billion raised in five years on the markets, the company has accumulated 847,363 bitcoins at an average cost of about $75,650 per unit, and openly targets a million. To buy a Strategy share is first to buy leveraged exposure to bitcoin.

The engine: the premium to net asset value

The heart of the mechanics comes down to one ratio, mNAV, the market cap relative to the value of the bitcoin held. As long as the stock trades above this net asset value, issuing new shares is accretive: the company raises dollars at a price above the underlying value, buys bitcoin, and the amount of bitcoin per share rises for existing shareholders. This is what Strategy measures through its own metric, “BTC Yield”, at 9.4% since the start of 2026. The paradox is only apparent: as long as the dollars raised buy more bitcoin per share than dilution removes, the operation enriches the incumbent shareholder, what the company calls accretive dilution. The stronger the premium, the faster the machine runs. Two fuels add to this engine: more than $7 billion of convertible bonds, and a stack of five preferred shares issued in 2025, the so-called “Digital Credit” instruments.

The 2026 turn

In June 2026, bitcoin fell back to around $65,000, below Strategy’s average cost of $75,650: the treasury is at an unrealised loss. Above all, mNAV fell below 1.0 for the first time in the company’s history, its market cap now worth less than its bitcoins. The signal is heavy, because no treasury company had ever durably held below its net asset value. Chain consequences: at the end of May, Strategy sold bitcoin for the first time in four years, 32 units, to pay a preferred dividend, and management acknowledged it could sell more if the premium stayed absent and financing closed. It is the explicit abandonment of the “never sell” dogma that had been Saylor’s brand. At the same time, its STRC preferred was trading below its $100 par, a sign that even the preferred channel is seizing.

Cash commitments, with no cash to pay them

Here is the knot of risk. The five preferreds pay cash dividends, from 8% for STRK to 12% for STRC, and the convertible debt bears interest. In all, Strategy faces about $800 million a year of interest and dividends. Yet its software business does not generate such cash. To honour these payments, the company must therefore issue more securities, which the discount makes costly, or sell bitcoin, which it has just started to do. Strategy replies that its treasury covers 71 years of dividends at the current value, when a Grayscale analyst judges it prudent to sell at least $3 billion of bitcoin to secure two years of bonds. Both readings coexist, but one thing is certain: the common shareholder is served last, behind the debt and all the preferreds. To this fragility is added an accounting volatility: since January 2025, a new standard obliges Strategy to value its bitcoin at market price in its income statement, so that a quarter of decline translates into massive displayed losses, unrelated to its real cash.

A reflexive bet

The model is reflexive: the premium feeds bitcoin buying, which feeds the premium, both ways. On the way up, it is a remarkable amplifier. On the way down, it is a trap, as in 2022 when the stock fell nearly 89% while the S&P 500 lost 25%. Three structural pressures aggravate the picture today. Spot bitcoin index funds, launched in 2024, offer the same exposure without the debt or the preferreds, which erodes the premium’s reason for being. The index provider MSCI backed off, in January 2026, from excluding digital-treasury companies, and the stock kept its place in the Nasdaq 100 at the December 2025 review, but MSCI maintained a re-examination, JPMorgan sizing a possible exclusion at several billion of passive outflows. And the dependence on a single man, Saylor, as on a single asset class, concentrates the risk.

At bottom, Strategy is neither a fraud nor a sure thing: it is a leveraged bet, transparent and assumed, on the durable rise of bitcoin. As long as the asset rises and the premium holds, the mechanics enrich the shareholder. When bitcoin ebbs and the premium fades, the debt, the dividends and the discount reassert themselves, and the company finds itself forced to choose between selling its treasury or diluting its holders. The bet stays binary, and 2026 delivers its first real-scale test. For anyone who wants to understand what lies behind such exposure, knowing how to read on-chain data and an issuer’s capital structure has never been so useful.

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Primary sources: Strategy 8-K filings with the SEC (bitcoin holdings, IPOs of the STRK, STRF, STRD, STRE and STRC preferreds, capital-allocation framework, first bitcoin sale of May 2026); CoinDesk (tracking of weekly purchases, mNAV falling below 1, May 2026 sale); strategy.com, Notes section (definition of mNAV, terms of the STRC preferred at 12% and STRK at 8%); first-quarter 2026 earnings call (remarks by Michael Saylor and Phong Le on a possible bitcoin sale); Grayscale, Zach Pandl (bond coverage); JPMorgan (estimate of passive outflows in case of MSCI exclusion); Forbes, Yahoo Finance and BeInCrypto (analysis of the premium compression and performance compared with 2022).