Michael Saylor has hinted at another Bitcoin purchase, while the company he leads, Strategy, is pushing shareholders to vote on changes to its STRC dividend. The proxy vote deadline is June 7 — a week from today — and the twin developments have put the firm back in the spotlight.
The latest Saylor tease
Saylor posted a cryptic message on social media this week, widely interpreted as a signal that Strategy is about to add more Bitcoin to its already massive holdings. The company has been the largest corporate holder of the cryptocurrency for years, and each tease from its executive chairman tends to move the market. He didn't offer specifics — no amount, no timeline — but the pattern is familiar. A formal announcement usually follows within days.
Strategy's last disclosed purchase was in May, when it bought 2,100 BTC for roughly $180 million. The company now holds over 220,000 Bitcoin, worth tens of billions at current prices.
Strategy's dividend push
Separately, Strategy is asking shareholders to approve changes to its Series A Perpetual Convertible Preferred Stock — the STRC ticker. The proxy filing, made public last month, seeks to alter dividend terms. The company hasn't detailed exactly what it wants to change, but the vote is binding. If it passes, the dividend structure could shift, affecting how much income preferred holders receive.
The deadline to vote is June 7. That's a tight window for institutional investors who may need to update their positions. Strategy has been urging shareholders to cast ballots early, framing the changes as necessary to maintain flexibility in its capital strategy.
What's at stake
For Saylor, the timing isn't great. He's simultaneously trying to drum up excitement for another Bitcoin buy while asking preferred shareholders to accept potentially less predictable dividends. The two moves aren't contradictory — the dividend tweak could free up cash for more Bitcoin — but they do require shareholder trust.
Strategy's stock has been volatile this year, tracking Bitcoin's own swings. The STRC preferred shares, meanwhile, have traded at a discount to their liquidation preference, suggesting some investors are already skeptical. A yes-vote on June 7 would give Saylor and his team a clearer runway. A no-vote would force them back to the drawing board.
The next concrete thing to watch is Saylor's buy announcement — likely within days — followed by the proxy count on June 7. Both will tell the market how much room Strategy still has to run its playbook.
