Michael Saylor, the ever-persistent Bitcoin bull and co-founder of Strategy, appears to be preparing for yet another BTC buy—the seventh in as many weeks. With Bitcoin cooling off after hitting a new all-time high of $112,000 on May 22, Saylor has taken to social media to drop a familiar yet calculated hint.
“I only buy Bitcoin with money I can’t afford to lose,” Saylor posted to his 4.3 million followers on X, subtly signaling that his company might be eyeing the latest dip as another golden opportunity to stack more sats.
The remark came just days after Strategy’s most recent BTC purchase on May 19, when it added 7,390 Bitcoin to its treasury at an estimated cost of $765 million. That buy pushed the company’s total holdings to a staggering 576,230 BTC—cementing its place as the largest publicly known Bitcoin holder in the world.
According to SaylorTracker, a platform that monitors Strategy’s Bitcoin activity, the firm is sitting on over $21.8 billion in unrealized gains, reflecting a 54% return on its Bitcoin investment to date. And if Saylor follows through on a new acquisition by May 26, it would mark Strategy’s seventh straight week of aggressive accumulation—an unparalleled pace even among Bitcoin-native firms.
The Blueprint for Institutional Adoption
Saylor’s conviction has turned Strategy from a modest business intelligence firm into a Bitcoin titan—an entity whose entire corporate identity is now intertwined with the future of digital gold. This transformation has rippled through the corporate world, nudging other publicly traded companies to reconsider how they manage their treasuries in an inflationary environment.
Instead of spending capital on traditional operational expansions or technological upgrades, Strategy has gone all-in on Bitcoin as a treasury reserve asset. It has consistently raised massive amounts of capital—billions in some cases—in record time. And unlike most firms, which spend those funds on short-term growth, Strategy converts the inflows of depreciating fiat currency into Bitcoin, a move Saylor considers both defensive and strategic in the face of global monetary debasement.
A $10 Trillion Vision?
Market analyst Jeff Walton recently told the Financial Times that Strategy’s Bitcoin-centric model could one day propel it into the stratosphere of corporate valuation.
“Strategy holds more of the best asset, and the most pristine collateral, on the planet than any other company, by far,” Walton said in a documentary. His projection? A future where Strategy could grow into a $10 trillion enterprise—possibly even becoming the most valuable publicly traded company on Earth.
While that might sound audacious, it aligns with Saylor’s own long-term outlook. He has repeatedly forecast that Bitcoin, thanks to its fixed supply and decentralized nature, could be worth millions of dollars per coin over the coming decades. In his view, Bitcoin’s “asymmetric upside” offers an escape hatch from the devaluation spiral that plagues fiat currencies.
Short-Term Hurdles, Long-Term Conviction
Despite this sky-high vision, Bitcoin hasn’t yet been able to decisively break past the $150,000 mark. Saylor attributes the current stall to short-term traders taking profits and a general lack of conviction among newer market participants.
Nonetheless, Saylor remains undeterred. For him, each dip is not a setback but an invitation—a moment to double down. His buying strategy, rooted in deep conviction and macroeconomic analysis, suggests that Strategy is far from done with its Bitcoin shopping spree.
And if the past is any indicator, when Bitcoin takes a breather, Saylor grabs a shopping cart.
