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1. Where Strategy stands on October 20
Strategy, the company once known as MicroStrategy and listed as MSTR, held 848,517 bitcoin (BTC) as of October 20, 2026, bought for $64.02 billion at an average of $75,446 per coin. That makes it the largest public-company holder of the asset, controlling roughly 4% of all bitcoin that will ever exist, and a model that dozens of other firms have copied.
The path to that position has not been a straight line. Between May and August 2026 the company sold 6,948 BTC for about $432.5 million, then returned to buying in late August and set a new holdings record in September. This guide walks through how the business began, how its bitcoin strategy works, and what the latest changes mean for the bitcoin treasury strategy it popularized.
2. What is Strategy?
Long before it became a byword for corporate bitcoin buying, Strategy was a business intelligence software company, selling tools that helped organizations analyze their data. Michael Saylor founded it in 1989, and it listed on the Nasdaq in 1998 under the ticker MSTR.
Its early history included a regulatory episode. Two years after the listing, Saylor and two other senior executives settled a case brought by the US Securities and Exchange Commission, which had alleged that the company materially overstated its revenues and earnings from software and information sales. After a brief spike in 2000, the share price then moved in a narrow band for roughly twenty years.
That pattern broke only at the end of 2020, the year the company announced its first bitcoin purchase. In February 2025 it dropped the word "Micro" from its name and became simply Strategy, a signal that the software operation had become secondary to the bitcoin holdings.
3. Why did the company start buying bitcoin?
The shift began in 2020, when Strategy designated bitcoin as its primary treasury reserve asset. Saylor, now co-founder and chair, was worried that inflation would erode the value of the dollars sitting on the corporate balance sheet, and he led an initial purchase of $250 million as a hedge against economic uncertainty.
Saylor had not always been an advocate. Seven years before the adoption, he had publicly predicted that bitcoin's days were numbered and that it would share the fate of online gambling. He later reversed that view completely, describing bitcoin as a dependable store of value with more long-term appreciation potential than cash, and saying he is committed to "buying the top forever." He has also floated a long-range price target of $13 million per bitcoin over a 21-year horizon, premised on a growing share of global capital moving into the asset.
What distinguished the company from an ordinary investor was how it paid for the coins. Rather than relying only on cash flow from software, it issued convertible notes, a form of debt that holders can eventually swap for stock, and used the proceeds to buy more bitcoin. In December 2024, Saylor compared the approach to Manhattan real estate developers, who borrow more as the value of their buildings rises. Other listed companies followed, including MARA, Metaplanet and Riot Platforms.
4. How did Strategy expand its funding?
In October 2024 the company announced plans to raise up to $42 billion to acquire bitcoin. In January 2025, shareholders approved a thirtyfold increase in the number of authorized Class A common shares, and within days Strategy launched Strike (STRK), the first in a family of preferred stock offerings.
Several siblings followed: Stretch (STRC), Stride (STRD), Strife (STRF) and Stream (STRE). Each is pitched to investors with a different appetite for risk, giving the company several ways to raise money without relying solely on common stock or debt.
The structure proved vulnerable in 2026. In June, STRC slipped below its $100 par value, which analysts described as a structural crack. The longer a preferred share trades under par, the harder it becomes for the company to sell more of it, and the more likely management is to face a choice between issuing common shares or selling bitcoin to cover dividends. That is broadly what unfolded, and the decline effectively closed a funding channel the company had used to buy coins.
5. What does mNAV measure, and why did it matter?
Strategy's debt-funded buying drew scrutiny almost from the start. In November 2024, a media outlet backed by Robinhood laid out what it called the math problem: MSTR traded at about three times the value of its bitcoin holdings, meaning that a sharp drawdown in the coin could force painful decisions.
The yardstick for that relationship is mNAV, which compares the company's market value with the net value of its assets. It peaked at 3.89 in November 2024 and then fell below 1 in 2026, which meant the market valued the whole company at less than the bitcoin it owned. MSTR shares dropped about 70% in the six months to February 2026, and the company reported a $12.4 billion loss for the fourth quarter of 2025.
On the older, basic calculation, mNAV touched 0.58 on June 26, 2026, according to SaylorTracker data. It recovered to about 0.97 on September 21, when the shares peaked, and stood at 0.87 in October, or 0.93 on a diluted basis.
6. Why did Strategy change the way it reports its numbers?
In July 2026 the company overhauled its investor metrics. Saylor argued that the move from convertible debt toward preferred equity demanded what he called a new financial language, and the headline measure became net bitcoin per share.
That figure starts with the bitcoin total, subtracts the claims of preferred stockholders and any convertible debt that is out of the money, and then divides by the share count. mNAV was redefined as the share price divided by this net figure. Under the old method the stock traded at a discount to its holdings; under the new one it sits near parity. Strategy's own dashboard, using the new measure, showed 1.12 on October 20, a premium on the company's preferred yardstick.
The difference between the two readings is a reminder that the metric is a matter of definition. Investors comparing the stock with its bitcoin should check which version of mNAV they are looking at.
7. How large are the cash reserves?
In December 2025 Strategy set up a dedicated cash reserve, starting at $1.44 billion and later enlarged. In May 2026 it used 61% of that buffer to repurchase $1.5 billion of its convertible notes.
In August 2026 the company created a second pool called USD Cash. The original USD Reserve is restricted to paying preferred dividends and interest on debt. USD Cash carries no such restriction and works as general liquidity, allowing management to respond quickly to dislocations in bitcoin or in the company's own securities. Permitted uses include buying bitcoin, paying dividends, buying back stock and repaying convertible notes.
In practice, USD Cash has mostly gone toward buying back STRC. As of October 18, 2026, the USD Reserve held $4.83 billion and USD Cash held $447.3 million.
8. Did Strategy really stop being a buy-and-never-sell company?
Yes, in part. In May 2026, on the first-quarter earnings call, chief executive Phong Le said the company would consider selling bitcoin if doing so improved bitcoin per share or helped manage debt and dividends, and that it would not simply promise never to sell. Saylor suggested a sale might inoculate the market, then clarified that the aim was to never be a net seller.
Days later the company sold 32 BTC for about $2.5 million, its first sale since 2022. In June it introduced a Digital Credit Capital Framework and a BTC Monetization Program, authorizing up to $1.25 billion of bitcoin sales to build cash reserves, support payouts on STRC-style securities or repurchase company securities. Chief financial officer Andrew Kang said the framework allows the firm to monetize bitcoin when that is more advantageous than issuing common equity. The company also committed not to issue common shares to buy bitcoin unless they trade at a premium to its holdings.
By mid-August 2026 Strategy had sold 6,948 BTC since May, raising about $432.5 million at roughly $62,250 per coin, to fund preferred dividends and STRC buybacks. It was not alone among holders: MARA reportedly sold about 15,000 BTC in March 2026, and Riot Platforms sold more than $250 million worth.
The sales stopped once the share price recovered. Strategy raised $334 million by selling MSTR stock in the week to August 16 without touching its bitcoin, then $2.01 billion the following week. The choice between selling coins and issuing equity now comes down to which source of cash is cheaper at the time.
9. When did Strategy resume buying bitcoin?
In the last week of August 2026, Strategy bought 4,603 BTC for $369.7 million, an average of $80,318 per coin. It was the first purchase since June and was financed with proceeds from MSTR stock sales. The price per coin was about 29% above what the company received for the bitcoin it sold over the summer.
The burst lasted a week. In the week to September 7 the company bought no bitcoin and instead spent $176.3 million on STRC buybacks, doubling its repurchase program to $2 billion. After a second week of buybacks it resumed purchases in mid-September using USD Cash, and by the end of that month its holdings reached a record 847,666 BTC, above the June peak.
Since then the pace of buying has slowed to between $20 million and $30 million a week, while STRC buybacks have run near $200 million weekly. In the two weeks to October 18, Strategy bought $21.5 million and $22.1 million of bitcoin while spending $192 million and $193 million on STRC repurchases. On October 19 the repurchase cap was raised to $3 billion.
STRC traded at $99.05 on October 20, just under par. Strategy has also proposed that dividends on STRF, STRC, STRK and STRD accrue every calendar day, including weekends and holidays. For STRC that would replace 24 record dates a year with 365, a change the company says will reduce price volatility in the preferred shares. Common shareholders can vote until October 28, according to a regulatory filing.
10. What is next for Strategy and MSTR?
At roughly $82,500 per bitcoin, the holdings are worth about $70.3 billion, around $6.3 billion above cost, by a calculation based on the figures above. The position has swung widely. In July, with bitcoin near $58,000, Strategy was about $13 billion underwater, and on August 17, at $63,553, the shortfall was $9.9 billion. A five-day rally then lifted the price above the company's average cost, where it has largely stayed, though narrowly in mid-September when bitcoin dipped to about $75,600.
MSTR rose from $91.67 on July 24 to $168.50 on September 21 and then eased, trading at $144.65 on October 20 after a 6.3% gain that day, according to SaylorTracker.
The most pressing near-term risk is an index decision. In early September, Saylor and Le urged the index provider MSCI to abandon a rule they called discriminatory, noting that funds tracking its indexes held 3.1% of Strategy's basic shares. On October 15, MSCI finalized the rule: non-operating companies dominated by a single asset will be excluded from its Global Investable Market Indexes, effective after the close on November 30. MSCI will publish the list of affected companies on November 11, and removal would force index-tracking funds to sell.
Beyond that, Saylor has long described a larger ambition. In October 2024 he outlined a vision of Strategy as a bitcoin bank worth a trillion dollars, built on capital market instruments tied to the asset. In December 2024 he told Microsoft's board that adopting bitcoin could create $5 trillion in value, a proposal Microsoft shareholders rejected.