Saylor hints at larger Bitcoin purchase as Strategy pushes semi-monthly dividends
Michael Saylor is once again signaling that Strategy may be preparing another sizeable Bitcoin acquisition, only days after the firm laid out an ambitious plan to overhaul how often it pays dividends to shareholders.
The company’s co-founder posted the phrase “Think Even ₿igger” on X on Sunday, accompanying it with a chart outlining Strategy’s historical Bitcoin purchases. Saylor has used similar cryptic posts in the past to foreshadow imminent buying announcements, and this latest hint arrives just a week after Strategy disclosed that it had already deployed around $1 billion into Bitcoin in mid‑April.
On April 15, the firm revealed that it had purchased 13,927 BTC between April 6 and April 12 at an average price of $71,902 per coin, committing roughly $1 billion of capital. A day prior to that disclosure, Saylor had stirred speculation with another post – “Think ₿igger” – which many observers now interpret as a precursor to the filing.
The new “Think Even ₿igger” message has therefore sparked expectations that Strategy is preparing to add even more Bitcoin to what is already the largest corporate BTC treasury in the public markets. According to data cited in the filing, the company currently holds 780,897 BTC, valued at about $58.2 billion, making it the most aggressive and consistent institutional Bitcoin accumulator among listed firms.
Saylor’s latest tease coincides with a significant strategic change in how Strategy wants to reward its shareholders. The firm is proposing to move from a monthly dividend to a semi-monthly structure, effectively doubling the number of payouts each year without altering the overall annual yield.
In a video presentation to investors, CEO Phong Le explained that the company aims to distribute dividends twice a month – once on the 15th and again at the end of the month. At the current annual rate of 11.5%, that would translate into 24 payouts per year instead of 12, with the total yearly obligation remaining unchanged.
Le argued that this more frequent payment cadence could smooth out volatility in the stock, improve liquidity, and sustain interest from income-focused investors. The idea is that by narrowing the gap between record dates, fewer extended periods occur in which investors have already secured their upcoming dividend and no longer feel an immediate incentive to hold or buy additional shares.
One of the central issues Le highlighted is the sharp drop in demand for the stock immediately after the ex-dividend date. Once investors are no longer eligible for the next payment, buying enthusiasm tends to dry up, which in turn slows the company’s ability to sell new shares at attractive prices. Moving to a semi-monthly schedule is meant to reduce those “dead zones” in trading activity.
Under the proposal, dividends on Strategy’s preferred shares, trading under the ticker $STRC, would be paid twice a month. The company emphasized that the shift affects only the timing: the annual dividend rate and overall obligation would stay the same. By altering the frequency rather than the cost of capital, Strategy hopes to make the instrument more appealing without increasing its financial burden.
Le also stressed the uniqueness of the plan. If Strategy adopts a semi-monthly schedule, he said, $STRC would fall into what he called “category 1” – effectively, the only preferred instrument globally that pays dividends this frequently. The company believes that such a rarity in the income market could attract new classes of investors looking for more regular cash flows.
Before arriving at this model, Strategy considered a wide range of alternatives. Le noted that the team ran through dozens of potential structures, including weekly and even daily dividend record dates. Those ideas were ultimately abandoned due to practical and regulatory constraints, particularly rules that govern record and payment timing for listed securities.
The NASDAQ exchange, where Strategy’s shares trade, follows industry standards requiring at least a ten-day gap between a dividend record date and the actual payment date. This limitation made ultra-frequent schedules unworkable in practice, pushing the company toward a compromise at two payments per month.
A preliminary proxy statement was filed with the United States Securities and Exchange Commission on Friday. The definitive proxy is expected to be filed on April 28, which will formally kick off the voting period. Shareholders will have until June 8, the date of the annual meeting, to approve or reject the semi-monthly dividend plan. If adopted, the new payment schedule is projected to begin in mid‑July.
The proposed change in dividend policy arrives at a time when Strategy’s stock has been volatile. The shares rose 11.8% on Friday to close at $166.52, yet they are still trading more than 47% below their level a year ago, according to market data. Management is clearly trying to balance its aggressive Bitcoin strategy with measures aimed at making the stock more attractive and more stable for traditional equity investors.
Despite the recent rally, the company continues to hold substantial unrealized losses on its digital asset portfolio. In its first-quarter report earlier this month, Strategy disclosed that its cumulative unrealized losses on digital assets had reached $14.46 billion. The firm nevertheless remains committed to its Bitcoin-first approach, continuing to add coins on a regular basis and signaling that more purchases are likely.
Strategy’s position is unusual even among crypto-exposed public companies. While many corporations hold a modest amount of Bitcoin or other digital assets on their books, Strategy has effectively built its entire long-term thesis around BTC, treating it as both a reserve asset and a core driver of shareholder value. Regular purchases – sometimes weekly – have reinforced this image of the company as a de facto Bitcoin proxy for stock market participants.
For investors, the combination of ultra-active Bitcoin accumulation and a high-yield, semi-monthly dividend proposal presents a complex risk-reward profile. On one hand, the firm offers exposure to BTC’s upside with an income component that is rare in the crypto space. On the other, large unrealized losses and heavy dependence on Bitcoin’s price trajectory introduce significant volatility.
The move toward more frequent dividend payments can also be read as an attempt to broaden Strategy’s investor base. Income-oriented funds, retirees, and institutions with mandates to focus on yield could find a twice-monthly schedule particularly compelling. Regular cash distributions may help offset the psychological impact of sharp price swings in both BTC and the company’s shares.
Meanwhile, Saylor’s new “Think Even ₿igger” message signals that the company is unlikely to step back from its core conviction. If anything, it suggests that Strategy views current market conditions as an opportunity to deepen its BTC holdings, despite – or perhaps because of – the large mark-to-market losses already on its balance sheet.
Market observers will be watching two main milestones over the coming weeks: the April 28 definitive proxy filing that opens voting on the dividend measure, and any subsequent disclosure that confirms a new round of Bitcoin purchases. Together, these developments will indicate how aggressively Strategy intends to pursue its twin goals of maximizing Bitcoin exposure and enhancing the appeal of its equity and preferred instruments.
If shareholders approve the semi-monthly dividend plan and Saylor follows through with another major BTC acquisition, Strategy will further entrench its status as both a high-yield income play and one of the most leveraged corporate bets on Bitcoin’s long-term success. For investors and industry analysts alike, the company remains a bellwether for how far a public firm can go in aligning its capital strategy with a single digital asset.