Is Strategy Ready for Another Bitcoin Purchase? Saylor Drops Hint

For his latest X post, Strategy chief Michael Saylor got all dressed up in a tuxedo, with a touch of AI as always, posting “Make the Winning Bet” as his firm’s Bitcoin (BTC) campaign hits the five-year mark. This is a bit of stagecraft that is often delivered by Saylor on Sundays and comes right before an update to the software company’s holdings.

What started Aug. 11, 2020, looks like a running list of convictions now. The balance shows 628,946 BTC accumulated at an average entry of $73,288 per coin. At current marks, that’s about $74.45 billion in value and a stated gain of 61.52%.

The summer tape shows methodical additions in size: 10,100 BTC on June 16, 4,980 on June 30, 4,225 on July 14, 6,220 on July 21 and a larger 21,021 on July 29, followed by a 155 BTC uptick recorded Aug. 11. The related cost basis is currently at $46,094,194,448, with the latest snapshot showing a market price of $119,309.

Make the Winning ₿et pic.twitter.com/5dM5LqOQ4G

— Michael Saylor (@saylor) August 17, 2025

Those numbers are now the foundation for the MSTR equity.

Numbers

Strategy trades under MSTR at $366 per share with a market capitalization of $104 billion and an enterprise value of $115 billion. The firm’s dashboard shows that Bitcoin makes up 71.7% of the market cap, and the NAV multiple is at 1.395.

This shows that the stock usually sells for more than the market value of its Bitcoin stack. Each time there’s a purchase wave, that spread can change a bit because the equity supply is fixed while the treasury grows.

The new post doesn’t promise a filing, but it is still a challenge. You have to pick the side of the table Saylor’s been on for the last five years, expect the spreadsheet to do the talking and assume the policy hasn’t changed: Accumulate on schedule, let the disclosures confirm it and treat the anniversary as a cue rather than a curtain call.

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