Summary
- Previously known as MicroStrategy, Strategy has shifted to a Bitcoin treasury model, designating BTC as its main reserve asset.
- Co-founder Michael Saylor led the charge in accumulating Bitcoin for the company's treasury.
- In June 2026, Strategy disclosed the sale of 32 BTC, marking a departure from its previous "never sell Bitcoin" policy.
Currently, Strategy stands as a significant player in the cryptocurrency landscape, a transformation from its origins as MicroStrategy, a software firm co-founded by the influential Michael Saylor.
Now recognized for its bold acquisition strategy involving Bitcoin for corporate reserves, Saylor has become a prominent advocate for the institutional adoption of Bitcoin.
Here’s an overview of Strategy and its connection to Bitcoin.
What is Strategy?
Before embracing Bitcoin, Strategy was primarily recognized for its business intelligence software designed to enhance data analysis for better decision-making.
Founded in 1989 by Michael Saylor, the company quickly achieved success, going public in 1998 as MSTR on NASDAQ. However, just two years later, Saylor and two other executives faced an SEC settlement over allegations of significant revenue overstatements from software sales.
Following a brief surge in its stock price in 2000, MSTR traded in a narrow range for two decades, only beginning to rise significantly at the end of 2020 when it made its initial Bitcoin purchase.
Up until early 2025, the company operated under the MicroStrategy name but abbreviated it to Strategy in February, seeking a more impactful and positive brand identity, reminiscent of a scene from The Social Network.
Strategy’s Bitcoin Treasury Reserve
In 2020, Strategy made a pivotal decision by adopting Bitcoin as its primary reserve asset. Concerned about the potential devaluation of the U.S. dollar and inflation, Saylor led the company’s initial purchase of $250 million in Bitcoin as a safeguard against economic instability.
“This investment reflects our belief that Bitcoin, as the world’s most widely-adopted cryptocurrency, is a dependable store of value and an attractive investment asset with more long-term appreciation potential than holding cash,” he remarked at the time.
Over time, the company’s Bitcoin acquisition strategy has evolved, primarily utilizing convertible notes as a means to fund additional Bitcoin purchases. This approach involves raising short-term debt through convertible notes, allowing investors to eventually convert their investments into Strategy stock, with proceeds directed towards Bitcoin acquisitions.
This method has been adopted by other publicly traded firms like MARA, Metaplanet, and Riot Platforms. In December 2024, Saylor compared this strategy to the evolution of Manhattan real estate, stating to CNBC, “Every time Manhattan real estate goes up in value, they issue more debt to develop more real estate.”
In October 2024, the company indicated it had no intention of slowing its Bitcoin acquisitions, announcing plans to raise as much as $42 billion to enhance its cryptocurrency holdings.
Additionally, the company voted in January 2025 to increase its Class A common shares by 30 times, allowing it to acquire even more Bitcoin than originally planned.
Shortly thereafter, the firm announced a new stock offering, Strike (STRK), aiming to raise $584 million for Bitcoin purchases by selling shares at $80 each. They also revealed plans for a $2 billion convertible senior notes sale in February 2025.
Throughout the year, the company introduced additional preferred stock offerings to finance Bitcoin acquisitions, providing various risk-adjusted investment opportunities like Stretch (STRC), Stride (STRD), Strife (STRF), and Stream (STRE) alongside Strike.
This debt-raising approach for Bitcoin acquisitions has also been embraced by other companies like MARA and Riot Platforms. In December, Saylor reiterated this comparison to Manhattan real estate, sharing with CNBC, “Every time Manhattan real estate goes up in value, they issue more debt to develop more real estate.”
As Strategy has grown increasingly linked with Bitcoin, it now describes itself as the “World’s First and Largest Bitcoin Treasury Company” on its investor relations page.
Michael Saylor and His Bitcoin Journey
Although Michael Saylor is now a prominent advocate for Bitcoin, he wasn’t always supportive of the cryptocurrency.
Just seven years prior to adopting Bitcoin as a primary reserve asset, Saylor tweeted that “#Bitcoin days are numbered. It seems like just a matter of time before it suffers the same fate as online gambling.”
#Bitcoin is a swarm of cyber hornets serving the goddess of wisdom, feeding on the fire of truth, exponentially growing ever smarter, faster, and stronger behind a wall of encrypted energy.
— Michael Saylor (@saylor) September 18, 2020
Since that time, Saylor has completely reversed his stance, now asserting that Bitcoin is the premier long-term asset to possess while committing to “buying the top forever,” meaning the company continues to purchase the asset at peak prices.
He envisions potentially buying Bitcoin at $13 million, a price target he has set for the asset over the next 21 years as he anticipates it will increasingly represent a larger share of global capital.
Criticism of Strategy’s Bitcoin Reserve
Strategy’s ongoing Bitcoin purchases through debt sales have attracted criticism from industry analysts and media. In November 2024, Sherwood Media, backed by Robinhood, highlighted the “math problem,” indicating that MSTR was valued at three times the amount of Bitcoin it held, raising concerns about potential forced liquidations during market downturns.
This premium, referred to as the mNAV or multiple to net asset value, has historically remained high for Strategy. However, as Bitcoin prices fell in 2026, the mNAV—which peaked at 3.89x in November 2024—dropped below 1, indicating that the company’s market valuation fell below its Bitcoin holdings.
This decline in mNAV coincided with a 70% decrease in MSTR’s share price between August 2025 and February 2026, during which the company reported a $12.4 billion loss in Q4 2025.
Critics have pointed out that if the MSTR share price decreases significantly, the company could be forced to sell Bitcoin to settle its convertible notes, which could disrupt the market further, as noted by Sherwood Media.
Despite the declining share prices and Bitcoin values in February 2026, Saylor dismissed concerns regarding the company's capacity to meet its debt obligations, labeling them as “unfounded.” He stated that the firm would simply “refinance the debt” if Bitcoin prices decline significantly.
To mitigate the risk of forced Bitcoin sales, the company established a cash reserve in December 2025, starting with $1.44 billion. They subsequently increased this reserve, securing over 2.5 years’ worth of debt and dividend obligations as of February 2026. Saylor claims the company can cover its $6 billion debt even if Bitcoin drops to $8,000. In May 2026, the firm used 61% of its cash reserve to repurchase $1.5 billion in convertible notes.
Similar concerns emerged regarding a drop of over 4.5% from the $100 par value of STRC in June 2026, raising doubts about the company’s ability to navigate a prolonged period below par. Analysts pointed to a potential "structural crack" in Strategy's Bitcoin model, suggesting that the longer STRC remains below $100, the more likely the firm would have to choose between issuing new shares or selling Bitcoin to maintain its dividend payments.
Shifting from "never sell" to "never be a net seller"
In May 2026, Strategy modified its longstanding “never sell your Bitcoin” policy, with executives suggesting that selling some Bitcoin holdings could be considered.
During the Q1 2026 earnings call, CEO Phong Le stated the firm might consider selling Bitcoin if it would benefit its “Bitcoin-per-share” position or assist with debt and dividend management.
"We will sell Bitcoin when it's advantageous to the company,” Le stated. “We're not going to sit back and just say, 'We'll never sell the Bitcoin.'"
Saylor elaborated, indicating that they might sell Bitcoin to "inoculate the market—just to send the message that we did it." He later clarified that Strategy aims to “never be a net seller” of Bitcoin, asserting the expectation to acquire substantially more BTC than it might sell to fund dividends or operations. Shortly after this announcement, Strategy resumed its Bitcoin purchases.
However, the firm soon acted on Saylor’s signals, selling 32 BTC, valued at around $2.5 million in the last week of May. This sale coincided with a significant BTC downturn, where prices fell as low as $60,211 in early June, over 52% from its peak of $126,080.
Commenting on the decline during this period, Saylor noted that Bitcoin’s weakness was greatly influenced by the “historic scale” of the artificial intelligence trade, highlighting over $4.3 billion in outflows from Bitcoin ETFs within a month.
Strategy is not the only Bitcoin treasury firm to have sold Bitcoin. In March 2026, MARA Holdings, a Bitcoin mining company, sold 28% of its Bitcoin holdings, approximately 15,000 BTC, raising around $1.1 billion to reduce part of its convertible debt. This move was framed as a strategy to enhance its financial position and shift its focus from Bitcoin mining to becoming an "energy and digital infrastructure company."
A month later, Riot Platforms announced the sale of over $250 million in BTC in the first quarter, part of a "strategic evolution" towards data center development.
Looking Ahead for Strategy
Despite its recent sale, which marked only its second recorded transaction, Strategy is expected to maintain its consistent Bitcoin purchasing.
As of June 2026, it holds nearly 843,706 Bitcoin, valued at approximately $53.53 billion—positioning it as the largest Bitcoin treasury among publicly traded companies. According to SaylorTracker, Strategy is facing significant paper losses exceeding $10 billion due to its average purchase price of $75,701 per Bitcoin.
Saylor’s aspirations for Strategy extend beyond merely increasing Bitcoin reserves. In October 2024, he envisioned transforming Strategy into a “Bitcoin bank” valued at a trillion dollars, introducing capital market instruments linked to Bitcoin for investors.
In addition to expanding its own holdings, Saylor has shared Strategy’s Bitcoin strategy with other major publicly traded companies. In December 2024, he advised the Microsoft board on the potential to generate $5 trillion in value by adopting Bitcoin, although they voted against including it in their balance sheet.
Editor's note: This article was initially published on January 8, 2025, and has been updated with new information as of June 5, 2026.