Michael Saylor is at it again. The Strategy chairman signaled another Bitcoin purchase on Monday and simultaneously called on retail investors to vote on a proxy measure that would allow the company to pay STRC dividends twice a month. The dual move underscores Saylor's relentless bet on Bitcoin and a push to reshape how Strategy returns value to its shareholders.
Another Bitcoin buy on deck
Saylor didn't give a dollar figure or a timeline, but the signal alone was enough to get the crypto corner of Twitter buzzing. Strategy has been the most aggressive corporate buyer of Bitcoin, holding well over 200,000 BTC. Another purchase would extend that lead and reinforce the playbook Saylor has stuck to for years: borrow cheap, buy Bitcoin, watch the market do its thing.
The timing matters. Bitcoin has been trading in a relatively tight range this month, and a fresh buy from the largest corporate holder could nudge sentiment. Saylor has never been shy about telegraphing his buys — he tends to announce them before they're even executed.
The proxy measure for semi-monthly STRC dividends
Alongside the Bitcoin teaser, Saylor urged retail investors to vote on a company proxy measure that would enable semi-monthly STRC dividend payouts. That's an unusual cadence. Most companies pay dividends quarterly or annually. Twice a month would be a shift toward regular, frequent income for holders of Strategy's preferred stock or token — likely the STRK or STRC security.
The pitch is straightforward: give retail investors a steady stream of payouts, and maybe keep them loyal even when Bitcoin's price gets choppy. But the measure needs shareholder approval, and Saylor is directly asking his retail base to show up at the ballot box.
If the measure passes, Strategy would be committing to a much tighter payout schedule. That puts pressure on cash flow, but Saylor has repeatedly argued that Bitcoin is the best treasury asset and that the company can generate returns through capital markets activity, not just operating income.
The proxy vote is a concrete test of retail investor enthusiasm. Saylor has built a fervent following among Bitcoin maximalists. Whether they'll actually vote — and vote yes — is an open question. Most retail shareholders don't bother with proxy ballots.
Next steps
The vote deadline hasn't been disclosed yet, but Saylor's public push suggests it's coming soon. Meanwhile, the market will watch for the Bitcoin buy announcement — usually followed by a Form 8-K filing within days. If history is any guide, the purchase will be sizable and the dividend measure will pass. But nothing in crypto is guaranteed.
