Wall Street Can’t Beat Michael Saylor’s Runaway Crypto Engine

May 27, 2025, 2:53 PM UTC

Wall Street keeps inventing new ways to ride the digital-currencyboom — from amped-up ETFs and tokenized funds to structured products — and crypto competitors keep circling. But the trade still delivering the biggest rewards belongs to Michael Saylor.

His firm, now branded as Strategy, formerly known as MicroStrategy Inc., pioneered the original capital-markets hack in this era of retail speculation. The playbook? Sell stock and debt. Use the proceeds to buy Bitcoin. Watch the market rip. Then do it all over again.

Michael Saylor
Photographer: Jason C. Andrew/Bloomberg

After huge gains last year, his capital-market machine keeps running — for now. ...

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