'You’ll Wish You Bought More' – Saylor’s Weekly Bitcoin Tease Signals Another Buy

With 592,345 BTC now worth a staggering $64 billion, Strategy founder Michael Saylor teased yet another bitcoin buy early Sunday. As usual, Saylor followed his weekly ritual—posting a chart from a tracker that maps out Strategy’s growing stash.

On the Brink of the S&P 500 – Strategy’s Bitcoin Bet Might Seal the Deal

It looks like the biggest corporate holder of bitcoin (BTC), the business intelligence outfit Strategy—formerly known as Microstrategy—is back on a buying streak. A subtle hint came from Saylor’s cryptic post, which showed a fresh orange dot lighting up the firm’s portfolio tracker. On Sunday morning, Saylor declared:

In 21 years, you’ll wish you’d bought more.

As of today, the company’s cache has climbed to 592,345 BTC after scooping up 245 BTC last week, with the buy made public on Monday, June 23. The Sunday before, Saylor had already dropped a subtle clue about the purchase. Strategy’s trove—now worth just over $64 billion at bitcoin’s price of $108,136 per coin—was secured at an average cost of $70,681 per BTC, totaling $41.87 billion.

Strategy’s bitcoin bet is up 52.86%. Had the company opted for ethereum ( ETH) instead, applying the same dollar-cost averaging (DCA) strategy since 2020 and matching the exact purchase dates, it would be sitting on just over 17.12 million ETH—but the value would be 1% lower in dollar terms. If Saylor and crew had gone the ETH route, they’d be staring at a $292 million loss today. Instead, the firm is sitting on a tidy $22.13 billion gain.

Additionally, Strategy (MSTR) is on the brink of securing a spot in the S&P 500 index. The last box to check is posting positive cumulative GAAP net income across the past four quarters—a feat that now rests almost entirely on where bitcoin lands at the close of Q2 2025. Bitcoin dipped 11.82% in Q1, but Q2 has brought a 30.85% climb so far. Historically, BTC’s Q3 performance has been a coin toss, with equal odds of gains or losses.