Michael Saylor Hints at More Bitcoin Purchases, Outlines Strategy’s 2.05% Preferred-Stock Math

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, formerly MicroStrategy, has accumulated bitcoin by issuing equity and debt, while paying investors dividends through its floating-rate perpetual preferred stock, STRC. With its annual preferred-dividend obligation closing in on $1.5 billion, the market has questioned whether the company will need to keep selling bitcoin to cover the payments. Its “BTC Breakeven ARR” has therefore become a key gauge of whether the financial model is sustainable.

On July 7, 2026, Executive Chairman Michael Saylor said the company held 843,775 bitcoin worth about $53.8 billion. He said annual bitcoin appreciation of more than 3.3% would generate enough capital gains to fund STRC dividends indefinitely. Even with a 0% return, its $2.55 billion cash buffer would allow it to cover the payments for about 31 years. The company sold 3,588 bitcoin from June 29 to July 5, raising $216 million.

Strategy, formerly MicroStrategy, has treated Bitcoin as its primary treasury asset since 2020 and funded further purchases through common-stock and bond issuance as well as STRC perpetual preferred stock. Its Bitcoin holdings are worth about $52 billion, making MSTR a key proxy for corporate Bitcoin exposure and putting its financing and dividend obligations under close scrutiny.

On March 22, Michael Saylor posted a purchase chart on X captioned “The Orange March Continues,” signaling that Strategy would keep buying. The company bought 17,994 Bitcoin on March 9 and another 22,337 on March 16, investing about $2.9 billion during the month. Bitcoin fell as low as $67,725 that day, below Strategy’s average cost of $75,696 and leaving its holdings with an unrealized loss of more than 10%.

Strategy, formerly MicroStrategy, has long financed Bitcoin purchases through debt and issuances of common and preferred stock, making Bitcoin holdings per share an important measure of shareholder value for investors. The dispute centers on whether issuing additional shares, while expanding the company’s assets, also dilutes existing shareholders by increasing the number of shares outstanding.

Strategy disclosed on June 8, 2026, that it had sold more than 1.4 million MSTR shares and raised about $181 million. It spent $101.3 million to buy 1,550 Bitcoin between June 1 and June 7. BTC Yield fell to 12.8% from 13.0%. Saylor said on June 9 that the transaction remained accretive after accounting for an additional $100 million in cash, which brought reserves to $1 billion.

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 gradually become a publicly traded company that accumulates Bitcoin through debt and share issuance since adding the cryptocurrency to its balance sheet in 2020. Founder Michael Saylor became executive chairman in 2022. Because his wealth is primarily tied to his existing shareholdings, it rises and falls with Strategy's stock price and Bitcoin, underscoring how closely his personal interests are aligned with the company's strategy.

In a proxy statement filed with the U.S. SEC on April 17, 2026, Strategy disclosed that Saylor received a salary of $1 in each year from 2023 through 2025, with no stock awards, options or bonuses. In 2025, he also received $787,031 in security and other compensation, bringing his total compensation to $787,032. By comparison, Chief Executive Phong Le received total compensation of $13,784,204 that year.

MicroStrategy, now known as Strategy, is a leading proponent of corporate Bitcoin reserves, continuously buying the cryptocurrency through debt and equity issuance. The performance of its holdings is seen as a key gauge of whether the digital asset treasury (DAT) model can endure. Earlier weakness in Bitcoin prices had generated paper losses while weighing on the valuations and fundraising capacity of similar companies.

As Bitcoin recovered to about $77,000 in mid-April, Strategy’s shares rose 8% in a single day. Founder Michael Saylor said the company generated $1.3 billion in Bitcoin gains during the first two weeks of April. Strategy currently holds about 780,000 Bitcoin at an average cost of $75,577, putting its position close to break-even and boosting confidence in the DAT market.

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 known as MicroStrategy, is a key bellwether for corporate crypto treasury strategies, raising funds through common and preferred stock offerings to acquire Bitcoin. STRC is a preferred stock that pays monthly dividends. Changes to its dividend affect investor returns and reflect the company’s financing costs and capital needs amid Bitcoin volatility.

Strategy raised STRC’s annualized dividend rate by 25 basis points to 11.5% in March 2026 and has now kept it at that level for a fourth consecutive month. Meanwhile, Bitcoin fell 20% in February, dragging MSTR down 14% for the month and marking its eighth consecutive monthly decline, underscoring the divergence between preferred-stock yields and the risk profile of the common shares.