Michael Saylor Drops Cryptic ‘Working Better’ Hint—Is a Massive Bitcoin Buy Imminent?

Ever wonder if buying the dip is just an eternal dance with bitcoin’s fickle heart? Strategy chairman Michael Saylor seems to think so, teasing fresh BTC buys just as the clock ticks down to a proxy vote that could reshape how dividends flow to STRC perpetual preferred stockholders. With Saylor’s cheeky “Working Better” tweet flaunting a bubble chart of nearly six years of Bitcoin scoops, one can’t help but ask—are these new purchases game changers or just déjà vu dressed in bullish numbers? Considering Strategy’s hefty stash of 843,738 Bitcoins bought at an average $75,701 each, and the crypto slipping just under that lately, timing couldn’t be more… interesting. Meanwhile, retail investors face a “your vote matters” push for a semi-monthly dividend tweak, trying to snag their elusive proxy votes. It’s a whirlwind of strategy, stakes, and serious crypto calculus—because in this game, even the smallest vote can echo loudly. LEARN MORE.

Strategy chairman Michael Saylor on Sunday signaled the Bitcoin treasury company would be announcing fresh purchases of the cryptocurrency in the coming days.

The social media post comes just days ahead of a proxy vote that depends in large part on retailer shareholders to enable semi-monthly dividend payouts on the company’s STRC perpetual preferred stock.

“Working Better” was Saylor’s tweet late Sunday morning to accompany a bubble chart tracking Strategy’s Bitcoin (BTC) purchases over the past nearly six years. That chart, from Iceland-registered StrategyTracker.com, has been consistently posted by Saylor in the days ahead of news of a purchase by the biggest publicly traded Bitcoin holder.

To be sure, any purchases to be announced will likely reflect the company bought at or below the average cost of previous BTC purchases. While, the average cost of Strategy’s 843,738 Bitcoin is $75,701 apiece, the biggest cryptocurrency by market cap has lost 3.65% of its value during May and was trading at about $73,566 at the time of publication, according to CoinMarketCap data.

“Working Better” tweet. Source: Michael Saylor

Blockstream CEO Adam Back highlighted on Sunday that BTC’s 200-week moving average has pushed far above the $61,000 mark. That moving average is seen by some technical investors as a signal of a long-term upward price trend.

Retail investors get pressed to vote on STRC dividend change

Strategy is proposing to pay semi-monthly dividends on STRC, instead of monthly. The company claims that if approved and adopted, it will lead to reduced reinvestment lag, enhanced liquidity, market efficiency and increased price stability.

Just days ahead of the June 7 proxy vote deadline, Saylor and Strategy are making a full press to get retail shareholders to return their proxy votes. On an internal company channel, Strategy’s investor relations team posted a message to all employees concerning the company’s 2026 annual meeting and provided links to the proposals under consideration by shareholders.

Part of message to Strategy employees from internal website. Source: Company filing on Edgar

“The amendment for STRC to pay semi-monthly dividends, needs 50% of all 85M shares outstanding as of April 17, 2026, to pass, which means every single vote counts,” read a May 28 post on Strategy’s verified feed on X.com.

CEO Phong Le posted a video a day earlier thanking STRC shareholders for their trust. “I wanted to personally walk you through the proposed amendment and what it means for you,” he said as an introduction to the minute-and-a-half video.

Retail investors have shown limited interest in casting proxy votes. A November research note from The Harvard Law School Forum on Corporate Governance revealed data that showed retail investors have consistently voted only about 29% of their owned shares during the past five proxy voting seasons. Institutional holders have voted about 77%.

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