Michael Saylor, Executive Chairman of Strategy (formerly MicroStrategy), has once again ignited speculation in the crypto community after teasing another possible Bitcoin purchase on social media.
In a post shared on June 29, Saylor displayed Strategy’s Bitcoin portfolio tracker, now showing holdings valued at over $64 billion, with the message: “In 21 years, you’ll wish you’d bought more.” The brief but suggestive tweet aligns with a recurring trend: Strategy’s Bitcoin acquisitions tend to occur on Mondays.
Strategy’s Monday Bitcoin Buying Pattern
Blockchain data and public company disclosures confirm that Strategy has steadily added Bitcoin to its treasury throughout the past two months. These purchases have typically been announced or executed early in the week, with Monday being the most frequent entry point.
Saylor’s latest post included a visual timeline of Strategy’s past Bitcoin buys, marked by orange dots. The recent cluster of purchases suggests that the firm may not be done accumulating yet.
At the time of the tweet, Bitcoin was trading around $108,000, bringing Strategy’s unrealized gain to over $22 billion—a clear validation of Saylor’s long-term bullish stance.
“In 21 Years, You’ll Wish You’d Bought More”
Saylor’s message echoes his long-standing conviction that Bitcoin is the ultimate store of value. Since 2020, Strategy has shifted its corporate treasury policy to prioritize BTC, positioning itself as the largest institutional holder of the cryptocurrency.
The firm currently holds more than 226,000 BTC, according to company filings, reinforcing its role as a market-moving participant.
While Saylor did not officially confirm an upcoming buy, his history of signaling BTC acquisitions via subtle tweets adds credibility to the speculation that another purchase could be announced Monday.
What to Expect Next?
If the Monday pattern holds, market watchers could see another major BTC acquisition by Strategy in the coming days. This would likely further bolster market confidence and potentially spark renewed upward momentum in Bitcoin’s price.
Saylor’s continued commitment also comes at a time when institutional interest in Bitcoin is surging, especially with the growing possibility of a Solana ETF launch and shifting regulatory clarity in the U.S.
Conclusion
With Strategy’s BTC portfolio now worth over $64 billion and Saylor teasing more buys, all eyes are on Monday. Whether the next move is confirmed or hinted, the message remains clear: Michael Saylor is far from done betting on Bitcoin.
Disclaimer
This content is for informational purposes only and does not constitute financial, investment, or legal advice. Cryptocurrency trading involves risk and may result in financial loss.