In short
- Previously a software company, MicroStrategy, under the leadership of its co-founder and chairman Michael Saylor, has transformed into a Bitcoin treasury company by adopting BTC as its primary reserve asset.
- The strategy sold 6,948 BTC between May and August 2026, cashing out approximately $432.5 million, abandoning the stance of "never selling Bitcoin" in favor of "never being a net seller."
- The company resumed buying at the end of August 2026 and set a new position record the following month.
Today, Strategy is one of the most important institutions in the cryptocurrency space, but it wasn't always like this.
The company was originally named MicroStrategy and co-founded by Michael Saylor. Saylor is one of the most influential figures in the Bitcoin world. Initially established as a software business, the company is now renowned for its aggressive purchases of Bitcoin as a corporate reserve asset, making Saylor a representative figure of institutional adoption of this asset.
What is a strategy?
Before incorporating Bitcoin onto its balance sheet, Strategy was best known for its business intelligence software, which helps companies analyze data to make better decisions.
Strategy was founded by Michael Saylor in 1989 and listed on the Nasdaq under the ticker MSTR in 1998. Two years later, Saylor and two other executives reached a settlement with the U.S. Securities and Exchange Commission (SEC), which had accused the company of significantly inflating revenues and profits from software and information services sales.
After a brief rise in 2000, MSTR traded largely within a narrow range for the next two decades, until it began an upward trend at the end of 2020—the year the company announced its first Bitcoin purchase.
As of early 2025, Saylor’s company continued to operate under the name MicroStrategy, but removed “Micro” in February of that year.
The strategy's Bitcoin treasury reserve
In 2020, Strategy adopted Bitcoin as its primary treasury reserve asset. Saylor, concerned that inflation would devalue the U.S. dollar, led the initial purchase of $250 million in Bitcoin to hedge against economic uncertainty.
Saylor was not always bullish on Bitcoin. Seven years before the company adopted the asset, he tweeted: “#Bitcoin days are numbered. It seems like just a matter of time before it suffers the same fate as online gambling.”
After a complete change in attitude, Saylor described Strategy's investment in Bitcoin as believing that this asset "is a reliable store of value and an attractive investment with greater long-term appreciation potential than holding cash."
Thereafter, he pledged to "always buy high" and set a target price of $13 million per bitcoin 21 years from now, based on the expectation that Bitcoin's share of global capital will continue to rise.
The buying strategy has gradually evolved into a machine. The strategy finances itself through short-term debt such as convertible bonds— which investors can eventually convert into shares— and uses the proceeds to purchase Bitcoin. In December 2024, Saylor compared it to Manhattan real estate development in an interview with CNBC, saying, “Every time Manhattan real estate appreciates, they issue more debt to develop more property.” Other publicly traded companies, including MARA, Metaplanet, and Riot Platforms, have adopted the same approach.
In October 2024, Strategy announced plans to raise up to $42 billion, and in January 2025, it increased the number of Class A common shares thirtyfold via shareholder vote. Days later, the company launched Strike (STRK), the first in a series of preferred stock offerings, followed by Stretch (STRC), Stride (STRD), Strife (STRF), and Stream (STRE)—each targeting investors with different risk appetites.
In June 2026, STRC fell below its $100 par value, exposing a "structural crack" in this flywheel: the longer STRC trades below par, the more likely Strategy will be forced to choose between issuing new shares and selling Bitcoin to continue paying dividends. Overall, events have indeed moved in this direction. The decline in STRC has severed one of the company’s financing channels for purchasing Bitcoin.
The mNAV metric for Strategy
The strategy of using debt financing to purchase Bitcoin has long been under scrutiny. In November 2024, Sherwood Media, backed by Robinhood, highlighted the "mathematical issues" involved: MSTR's valuation is three times the value of the Bitcoin it holds, and it may face forced liquidation during market downturns.
This premium is measured by mNAV, the multiple of the company's market capitalization relative to its net asset value. The metric reached 3.89x in November 2024, then fell below 1 during the Bitcoin price decline in 2026, indicating that the market valued the company below the value of its held Bitcoin. Over the six months leading up to February 2026, MSTR's stock price dropped approximately 70%, and the company reported a net loss of $12.4 billion for the fourth quarter of 2025.
Subsequently, Strategy changed its metrics. In July 2026, the company fully revised its investor metrics, recognizing that after shifting from convertible debt to preferred stock, a “new financial language,” as Saylor called it, was needed. The key metric became “net Bitcoin per share”: instead of dividing its total Bitcoin holdings by the total number of shares outstanding, the company now subtracts its obligations for preferred stock and out-of-the-money convertible debt first, leaving only the portion truly available to common shareholders.
The mNAV has also been redefined as the share price divided by this net asset value. This change is crucial. Under the old calculation, the share price was trading at a discount; under the new calculation, the same share price is nearly at par.
According to the old metrics, the discount has narrowed since summer 2026. Based on SaylorTracker data, Strategy’s underlying mNAV (comparing common equity market value to Bitcoin holdings) fell to a low of 0.58x on June 26, 2026, and rebounded to approximately 0.97x by September 21, when MSTR reached its peak. By October 2026, the metric stood at 0.87x, or 0.93x after dilution. Strategy’s own dashboard, using its revised methodology, shows an mNAV of 1.12x on the same day, indicating that the stock is trading at a premium by the company’s preferred standard.
The strategy's U.S. dollar reserves and U.S. dollar cash accounts
To avoid forced sales of BTC, the Strategy established a cash reserve of $1.44 billion in December 2025. The reserve continued to grow, and in May 2026, 61% of it was used to repurchase $1.5 billion in convertible bonds.
Subsequently, this reserve continued to grow, and Strategy established a second cash pool in August 2026. The two are managed differently: the USD Reserve is used to pay preferred dividends and debt interest, while the newer USD Cash account is not subject to these restrictions. Strategy describes it as dollar liquidity for general treasury purposes, designed to enable management to quickly address “mismatches in the Bitcoin or Strategy securities markets.” Permitted uses include purchasing Bitcoin, paying dividends, repurchasing shares, and redeeming convertible bonds.
Subsequently, USD Cash was primarily used to repurchase STRC. As of October 18, 2026, the USD Reserve held $4.83 billion, while USD Cash held $447.3 million, down from $1.44 billion at the beginning of September 2026.
The constantly changing strategy manual
In May 2026, Strategy revised its long-standing belief of “never sell Bitcoin.” During the Q1 2026 earnings call, CEO Phong Le stated that the company would consider selling Bitcoin if it could increase Bitcoin per share or help manage debt and dividend obligations.
Le said, "We will sell Bitcoin if it benefits the company. We won't just sit there saying, 'We will never sell Bitcoin.'"
Saylor further stated that the strategy might even sell Bitcoin “to inoculate the market—simply to send a signal that we’ve done it,” but later clarified that the company’s goal is “to never be a net seller.” A few days later, the company sold 32 BTC, approximately $2.5 million, marking its first sale since 2022.
In June 2026, Strategy officially launched the "Digital Credit Capital Framework" and the "BTC Cash-Out Program," authorizing the sale of up to $1.25 billion in BTC to strengthen cash reserves, fund dividends for products such as STRC, or repurchase securities. Chief Financial Officer Andrew Kang stated in a statement that this arrangement provides the company with flexibility to act when selling BTC is more advantageous than issuing common stock. Strategy also committed that it will not issue common stock to purchase Bitcoin unless the valuation of its common stock exceeds the value of its underlying assets.
Strategy announces the launch of the Digital Credit Capital Framework, designed to enhance digital credit, improve liquidity, maintain long-term Bitcoin exposure, and support long-term value creation. $MSTR $STRC https://t.co/AUoUCtem53
— Michael Saylor (@saylor) June 29, 2026
The company quickly activated this plan. By mid-August 2026, Strategy had sold 6,948 BTC since May 2026, cashing out approximately $432.5 million at an average price of about $62,250 per BTC to pay preferred dividends and repurchase STRC. Other companies have also been selling: MARA Holdings sold approximately 15,000 BTC in March 2026, and Riot Platforms sold over $250 million worth of Bitcoin.
As the stock price rebounded, selling activity ceased. The Strategy raised $334 million in the week ending August 16, 2026, by selling MSTR shares without touching Bitcoin, and followed up with another $2.01 billion the next week. Today, choosing between selling Bitcoin and issuing stock depends on which option is cheaper at the time.
Strategy: Restart Buy
Strategy resumed buying in the final week of August 2026, purchasing 4,603 BTC for $369.7 million—the first purchase since June 2026—at an average price of $80,318 per BTC. This price is approximately 29% higher than the average recovery price from the company’s Bitcoin sales during the summer. The funds came from proceeds of MSTR stock sales.
This buying round lasted only one week. By the week of September 7, 2026, the Strategy had stopped purchasing Bitcoin and instead spent $176.3 million to repurchase STRC, doubling the repurchase program's size to $2 billion. After another week of repurchases, the company resumed buying in mid-September 2026, this time using USD cash, and by the end of the month, its holdings increased to 847,666 BTC, setting a new record above the June 2026 peak.
Since then, buying pressure has slowed to $20 million to $30 million per week, while STRC repurchases have remained near $200 million per week. On October 19, 2026, Strategy increased the upper limit of its repurchase program to $3 billion. According to Yahoo Finance data, STRC traded at $99.05 on October 20, 2026, slightly below its $100 par value.
The buying pressure since then has been significantly weaker. The Strategy spent $29 million on Bitcoin during the week it announced $21 billion in third-quarter revenue; over the two weeks ending October 18, 2026, it spent $21.5 million and $22.1 million, respectively. During the same period, the company’s weekly repurchases of STRC ranged between $176 million and $193 million. On October 19, 2026, its board increased the upper limit of the repurchase program to $3 billion. STRC traded at $99.05 on October 20, 2026, still slightly below its $100 par value, according to Yahoo Finance.
The strategy also proposes that dividends for STRF, STRC, STRK, and STRD accrue on a daily calendar basis, including weekends and holidays, increasing the number of record dates for STRC from 24 per year to 365. The company states that this change will help reduce the volatility of its preferred shares. According to company filings, common shareholders may vote on this matter before October 28, 2026.
The Future of Strategy
As of October 20, 2026, Strategy holds 848,517 bitcoins, with an average purchase price of $75,446 per bitcoin, based on a total cost of $64.02 billion disclosed in its latest SEC filing. This makes it the largest bitcoin treasury among publicly traded companies, accounting for approximately 4% of the total bitcoin supply. According to Decrypt data, bitcoin was trading at around $82,500 at the time, giving these holdings a value of approximately $70.3 billion—roughly $6.3 billion above cost, per Decrypt’s calculations.
This position experienced significant volatility. In July 2026, when Bitcoin approached $58,000, MicroStrategy’s unrealized paper loss was approximately $13 billion. As of August 17, 2026, when Bitcoin was trading at $63,553, the company still recorded a $9.9 billion loss. A subsequent five-day rally pushed Bitcoin above the company’s average cost, where it has remained near that level since, despite a brief pullback to around $75,600 in mid-September 2026. MicroStrategy’s stock price also rebounded, rising from $91.67 on July 24, 2026, to $168.50 on September 21, 2026, according to SaylorTracker, before declining slightly; by October 20, 2026, the stock price stood at $144.65, up 6.3% for the day.
The company’s position in the stock market is also under threat. In early September 2026, Saylor and Le urged MSCI to eliminate what they called discriminatory index rules; at the time, funds tracking MSCI indices held 3.1% of Strategy’s underlying shares. On October 15, 2026, MSCI finalized the rule, stipulating that “non-operating companies” whose balance sheets are primarily composed of a single asset will no longer qualify for inclusion in its Global Investable Market Index, effective at the close of trading on November 30, 2026. MSCI will announce the list of affected companies on November 11, 2026; if removed, funds tracking the index will be forced to sell.
Saylor’s ambitions extend far beyond the balance sheet: in October 2024, he outlined a vision to transform Strategy into a $1 trillion “Bitcoin bank,” building capital market instruments around Bitcoin.
He also applied this thinking elsewhere: In December 2024, he told Microsoft’s board that adopting Bitcoin could create $5 trillion in value, but shareholders voted down the proposal.
Editor’s note: This article was originally published on January 8, 2025, and updated on October 20, 2026, with the latest details.
Daily Brief Newsletter
Start each day with the latest headlines, and access original features, podcasts, videos, and more.
Join over 72,000 readers