Michael Saylor’s machine is running hotter than ever. In just two weeks, his latest vehicle - STRiPS - pulled $2.7 billion worth of Bitcoin from the market, according to Marty Bent on Rabbit Hole Recap. The funding came from a $2.1 billion raise, enough to buy roughly 27,200 BTC at current prices. This isn’t passive holding. It’s a high-velocity flywheel: sell stock, buy Bitcoin, repeat.
The engine is an 11.5% dividend, paid by selling MicroStrategy shares. That yield pulls in yield-hungry retail investors, whose capital funds more Bitcoin purchases. As long as the stock holds, the loop spins faster. Saylor isn’t just accumulating - he’s weaponizing capital markets. The bet? That Bitcoin’s price growth outpaces the dilution from constant equity issuance.
"Saylor is racing toward owning one million Bitcoin by the middle of June."
- Marty Bent, Rabbit Hole Recap
But the structure is fragile. If MicroStrategy’s stock price drops below the issue price of new shares, the company still owes that 11.5% dividend. That forces it to sell more stock into a falling market, which could crater both the share price and the Bitcoin it’s meant to support. Matt Odell calls it a textbook negative feedback loop - sustainable only in a bull market.
Meanwhile, private business owners are copying Saylor’s playbook - just without the public markets. Scott Marmoll, on TFTC, laid out how firms with $2M to $50M in cash flow can shift from dollar treasuries to Bitcoin. Holding cash costs about 10% in purchasing power annually, he argues. Bitcoin isn’t just a store of value - it’s a forcing function for efficiency.
"Holding working capital in cash is a painful necessity that loses 10% of its value every year."
- Scott Marmoll, TFTC
The real arbitrage? Selling to fiat-minded buyers. Private equity still values companies based on dollar yields, creating an artificial bid. Owners can exit at inflated prices, immediately rotate proceeds into Bitcoin, and wait. When BTC appreciates enough, they can buy back their business using only a fraction of their stack. The playbook, now formalized in a PDF by Marmoll and Bent, turns Saylor’s public strategy into a template for private capital.


