Wall Street Can’t Beat Michael Saylor’s Runaway Crypto Engine.
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Wall Street keeps inventing new ways to ride the digital-currency boom — 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.
After huge gains last year, his capital-market machine keeps running — for now. Strategy shares are up about 26% this year, beating Bitcoin’s 16% gain, and currently rank as one of the best-performers in the Nasdaq 100. Traders are still lavishing a hefty premium on Saylor’s stock — well above the value of the firm’s Bitcoin holdings — a dynamic no ETF can match.Saylor was the first, he was the earliest and he’s got the most leverage,” said Matt Maley, chief market strategist at Miller Tabak + Co. “He’s not just playing Bitcoin, but also his own stock and the stock market to his advantage — and using leverage at the right times.

https://www.bloomberg.com/news/articles/2025-05-27/wall-street-can-t-beat-michael-saylor-s-runaway-crypto-engine.