This type of stubbornness can be mistaken for either genius or recklessness, depending on the result. For the better part of six years, Michael Saylor has built a business around a conviction that quietly unnerves most Wall Street analysts.
Saylor’s company went out and purchased about $330 million more in early April, when the price of bitcoin was significantly lower than the average price Strategy paid for its enormous collection of coins. Not in a quiet manner. Not grudgingly. intentionally.
Key Facts — Michael Saylor & Strategy Inc.
| Full Name | Michael J. Saylor |
| Role | Executive Chairman & Co-founder, Strategy Inc. (formerly MicroStrategy) |
| Company Ticker | MSTR — Nasdaq |
| Total Bitcoin Held | 766,970 BTC (≈3.6% of total supply) |
| Total Cost Basis | ~$58.02 billion at avg. $75,644 per coin |
| Latest Purchase | 4,871 BTC for ~$329.9M (April 1–5, 2026) |
| Avg. Purchase Price (Latest) | $67,718 per bitcoin |
| Q1 2026 Unrealized Loss | $14.46 billion on digital asset holdings |
| Strategy Began (Bitcoin) | August 2020 — first major corporate BTC purchase |
| Q1 Earnings Date | April 30, 2026 |
| Reference | Bitcoin Magazine |
Strategy revealed on Monday that it paid an average of $67,718 per coin to buy 4,871 Bitcoin between April 1 and April 5. The current total is 766,970 bitcoin, which was purchased for about $58 billion at an average cost basis of more than $75,000.
The math is ugly at current prices close to $69,500. By all conventional measures, the company’s overall position is underwater. Nevertheless, the stock increased by about 6% after the filing, and Saylor made no apology-like remarks.
What most people already suspected was revealed in the same Monday disclosure: For the first quarter that concluded on March 31, Strategy reported an unrealized loss of $14.46 billion on its digital asset holdings. For the first time in a while, the firm’s portfolio fell below its cost basis as Bitcoin lost about 20% of its value since the beginning of the year.
The blow was somewhat mitigated by a $2.42 billion deferred tax benefit. Nevertheless, the portfolio’s carrying value of $51.65 billion would frighten any traditional CFO.
“In the past year, some of you purchased MSTR or Bitcoin. This is the first downturn you have experienced. I would advise you to hold on.— Strategy CEO Phong Le, Q4 2025 Earnings Call
Strategy did not use reserves or sell current assets to pay for the purchases in April. Once more, it returned to the capital markets. Sales of the company’s variable-rate Series brought in about $227.3 million. An additional $102.6 million in early April, and a perpetual “Stretch” preferred stock in late March. During the same period, it also made $72 million from the sale of Class A common shares. This financing model, which consistently raises new capital and directs it into the market, has shaped Strategy’s corporate identity just as much as bitcoin.
The “Stretch” preferred shares, or STRC, are intended to pay an adjustable monthly dividend and trade close to a $100 par value. The structure is clever in one particular way: it provides fixed-income investors with indirect exposure to the long-term potential of bitcoin, even though they may never directly touch a cryptocurrency.
At least in theory. In actuality, this means that Strategy can obtain funding from the bond market without issuing more diluted common stock, even though the preferred shares have obligations of their own. Even though this mechanism is rarely discussed as such, it may be one of the more subtly significant financial innovations to emerge from the bitcoin era.
As this has developed over the past few years, it seems as though Saylor has created a living, publicly traded thesis regarding the long-term worth of hard digital money that is both a business and an argument. He has stated time and time again that bitcoin is the greatest treasury reserve asset ever made, without seeming to be ironic. That opinion doesn’t appear to have changed despite the $14.5 billion quarterly loss. If anything, it made it more profound.
Speaking during the fourth quarter earnings call in February, Phong Le, CEO of Strategy, gave newer shareholders who were shaken by the drawdown a sort of pastoral assurance. The message was more straightforward for the veterans, who have held the position since 2020 despite numerous cycles of severe declines: you’ve been here before, and you were rewarded. In the run-up to the Q1 earnings report, which is set for April 30, investors are quietly questioning whether that confidence is earned or just inherited from a long bull run.
Whether Saylor’s anticipated regulatory environment will come to pass on schedule is still up in the air. The House of Representatives approved the Clarity Act, which would establish a federal framework for digital assets, but the Senate has not moved forward with it. Growing bipartisan support on Capitol Hill, according to Saylor, is a boon for both Strategy and cryptocurrency in general.
That tailwind isn’t quite here yet. Citing ETF inflows and growing corporate demand, Bernstein analysts last week reaffirmed their $150,000 year-end price target for bitcoin, citing Strategy’s own accumulation as an indication of institutional conviction. Depending on your point of view, analysts citing your purchases as evidence of a trend are either validating or somewhat circular.
Additionally, Strategy has been strengthening its ties with Wall Street and developing the capital-raising capability required to keep buying bitcoin in large quantities—possibly tens of billions more in stock and preferred share offerings. It appears that Saylor is not thinking in quarters based on the infrastructure being installed. He is considering decades.
The question that will follow Strategy for years is whether that wager pays off or whether the next significant decline in bitcoin finally forces a reckoning. The business is still making purchases as of right now. Saylor continues to speak. Despite its volatility, the market is still keeping an eye on things.