Strategy Plans $1.5 Billion Convertible-Note Buyback With Cash or Bitcoin Sales

Software company Strategy, the world’s largest publicly traded corporate holder of Bitcoin, has long been known for an uncompromising buy-and-never-sell strategy. Executive Chairman Michael Saylor’s proposal to sell Bitcoin to fund dividends breaks with that previous pledge and signals a more flexible approach to capital management. The move shows the company confronting the realities of capital markets and has prompted investors worldwide to reassess the viability of crypto-heavy balance sheets.

Strategy reported a first-quarter net loss of $12.54 billion and still holds 818,334 Bitcoin. To raise funds for dividends, the company sold 3,588 Bitcoin for the first time between June 29 and July 6, 2026, generating about $216 million. The move raised market concerns: JPMorgan warned that the policy would add “two-way risk” to crypto markets, while Fortune warned that Strategy could fall into a death spiral.

Strategy has long raised funds through debt and equity issuance to buy Bitcoin, making BTC a core treasury asset. The company now holds more than 840,000 BTC worth about $64.45 billion, the largest corporate reserve worldwide. Markets therefore often view its financing and Bitcoin purchase cadence as an indicator of institutional demand.

During the week of July 20, 2026, Strategy co-founder Michael Saylor said the company had not added to its Bitcoin holdings that week and had instead bought bonds, although it did not disclose the amount or type of bonds purchased. Describing the situation as the “BitVac,” or Bitcoin vacuum, “charging,” he suggested the move could be building up funds in preparation for the next round of Bitcoin allocation.

Strategy, formerly known as MicroStrategy, has included Bitcoin in its corporate asset allocation since 2020 and has continued to add to its holdings using company funds. Given the size of its position, its trading activity affects not only its balance sheet but is also viewed by the market as an important gauge of corporate Bitcoin adoption.

Strategy bought 535 Bitcoin during the week before July 20, 2026, at an average price of $80,340 per coin, for a total of about $43 million. The purchase came just days after the company signaled that it could sell Bitcoin to secure tax savings. Its overall holdings currently have an average cost of about $75,540 per coin.

MicroStrategy began as a business intelligence software company before adding Bitcoin to its corporate asset allocation in 2020 and gradually transforming into Strategy, a company centered on digital asset reserves. Its model combines cash flow from its core software business with capital-markets financing, making it a key barometer of Bitcoin adoption among publicly traded companies.

As of May 2026, Strategy's Bitcoin holdings were valued at more than $66 billion, firmly establishing it as the world's largest corporate Bitcoin holder among publicly traded companies. The company continues to expand its reserves through innovative financing instruments while using AI to strengthen its software business, creating a dual-track structure built on operating cash flow and its Bitcoin strategy.

Michael Saylor-led Strategy, formerly known as MicroStrategy, has long raised funds through debt and share issuance to buy Bitcoin, making the crypto asset central to its corporate treasury strategy. Its holdings far exceed those of most listed companies, while its financing and purchases have become an important gauge of institutional demand for Bitcoin.

Michael Saylor said Strategy spent about $255 million to buy another 3,273 Bitcoin at an average price of about $77,900 per coin. As of April 26, 2026, the company's total holdings had risen to 818,334 BTC at a cumulative average cost of about $75,537 per coin, bringing it another step closer to its target of 1 million BTC.

MicroStrategy, now known as Strategy, has long used its corporate balance sheet and fundraising proceeds to buy Bitcoin, making it one of the most prominent corporate holders of the cryptocurrency. The accumulation strategy led by founder Michael Saylor has closely tied the company’s share price and financing capacity to Bitcoin’s performance. Its large holdings could also affect market supply and demand and institutional investor sentiment.

In early April, Strategy spent about $1 billion to acquire 13,927 Bitcoin at an average price of roughly $71,900 each, raising its total holdings to 780,897 Bitcoin, or more than 3.7% of the cryptocurrency’s maximum supply of 21 million. The purchase was financed primarily through the issuance of STRC perpetual preferred stock. Saylor said around the same time that Bitcoin may have bottomed near $60,000.

Strategy, formerly known as MicroStrategy, has become the world's largest corporate Bitcoin holder under co-founder Michael Saylor, financing long-term purchases through debt issuance and high-dividend preferred shares. Its financial performance and stock price are therefore closely tied to cryptocurrency markets, while the size of its holdings is large enough to influence market confidence.

Strategy spent about $330 million last week to buy 4,871 Bitcoin at an average price of $67,718 each, lifting its total holdings to 766,970 BTC, or about 3.8% of the circulating supply. The company recorded a first-quarter paper loss of about $14.46 billion and still has about $5 billion in unrealized losses.

Strategy, formerly MicroStrategy (Nasdaq: MSTR), has pursued a Bitcoin treasury strategy led by co-founder Michael Saylor, steadily accumulating BTC through stock issuance and other fundraising. Its vast holdings have closely linked the company's share price to Bitcoin's performance, making it a key gauge of corporate cryptocurrency adoption.

In the week ended July 19, 2026, Strategy spent $76.6 million to buy 1,031 Bitcoin, a notably smaller purchase than in the previous two weeks. The acquisition was funded primarily through common-stock sales. The company's holdings rose to 762,099 BTC, acquired at an average cost of about $75,694 per Bitcoin.

Strategy, formerly known as MicroStrategy, added Bitcoin to its corporate balance sheet in August 2020 and has continued to finance purchases through stock and bond offerings. Its holdings rank among the largest of any publicly traded company, making the pace of its purchases and its funding methods important indicators of corporate Bitcoin adoption.

In a March 16, 2026 filing with the U.S. Securities and Exchange Commission, Strategy said it spent $1.57 billion to acquire 22,337 Bitcoin from March 9 through March 15 at an average price of $70,194. The purchases lifted its total holdings to 761,068 Bitcoin, acquired for about $57.61 billion in aggregate. The funds came primarily from an offering of STRC preferred stock.

MicroStrategy has long accumulated Bitcoin through debt issuance, share sales and other financing methods, treating the cryptocurrency as a core asset allocation. Increasing its holdings to 1 million Bitcoin would further cement its position as the world’s largest corporate holder of the cryptocurrency while making its financial performance even more directly exposed to Bitcoin price swings.

According to the latest figures, MicroStrategy holds about 738,000 Bitcoin. To reach 1 million by the end of December 2026, it would need to buy about 261,000 more. At current prices, the company would need to invest about $523 million a week, requiring approximately $22.2 billion in total fundraising and Bitcoin purchases.