Michael Saylor Signals Strategy Software Will Buy More Bitcoin Ahead of June 8 Proxy Vote

Strategy Software executive chairman Michael Saylor signaled on Sunday that the Bitcoin treasury company intends to buy more BTC in the week ahead, pairing the message with a bubble chart tracking Strategy’s BTC purchases over the past nearly six years.

Saylor’s post came alongside StrategyTracker.com figures showing Strategy’s Bitcoin holdings at 818,869 coins, with a combined market value of about $67.2 billion based on a Bitcoin price near $77,996.91.

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In the same push, Strategy urged Strategy shareholders to vote on a proxy measure that would enable semi-monthly dividend payouts on its STRC perpetual preferred stock.

The dividend campaign is tied to a governance deadline, with the proxy vote set for June 8, and Strategy making a “full press” to get retail shareholders to return their proxy votes.

Strategy also scheduled a live Q&A session with Saylor and STRC CEO Phong Le for May 20 at 5 ET, moderated by Natalie Brunell, with the session livestreamed on YouTube and on X.

Saylor urged retail holders directly in an X post, writing, "If you are a $STRC shareholder and have not already voted, please take a moment to do it now."

Strategy’s official social feed reinforced that framing, saying, "80% of $STRC is held by retail investors. This amendment is for you."

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The proxy measure would permit Strategy to make semi-monthly payouts on STRC instead of monthly, and Strategy said the change would lead to reduced reinvestment lag, enhanced liquidity, market efficiency and increased price stability.

Coverage also pointed to a voting-history contrast, citing a November research note from The Harvard Law School Forum on Corporate Governance that retail investors have voted only about 29% of their owned shares during the past five proxy voting seasons, while institutional holders have voted about 77%.

Despite the limited retail turnout, Strategy rescheduled the May 20 Q&A for retail investors with Saylor and CEO Phong Le, inviting shareholders to submit questions ahead of the session.

While Strategy pushed its BTC accumulation and STRC dividend vote, Stocktwits highlighted on-chain analyst Chain Mind warning that Bitcoin was repeating a technical structure seen before sharp reversals in 2018 and 2021.

Chain Mind wrote, "if history repeats, we will start dumping soon," as it described BTC trading inside a rising wedge formation and marked the setup with yellow dots at prior top points after brief "fake pump" rallies.

The same report said Bitcoin was trading at $78,060, up 0.2% over the past 24 hours, and noted retail sentiment on Stocktwits moved to 'neutral' from the 'bullish' zone.

For Strategy, the immediate consequence is whether retail holders—described as owning around 80% of STRC—will vote in time for the June 8 proxy deadline on the semi-monthly dividend amendment.

The broader stakes are framed around STRC’s payout cadence and liquidity goals, with Strategy arguing the semi-monthly structure would improve liquidity and market efficiency, while the Harvard Law School Forum data cited in coverage underscored that retail voting participation has historically lagged institutional voting.