Saylor’s New $4.2 Billion Bitcoin Plan Aims to Reassure Skeptics

Michael Saylor isn’t backing down. The Strategy co-founder is preparing to sell $4.2 billion more in preferred stock to fuel his latest Bitcoin bet — while throwing a lifeline to investors worried he’s diluting them into oblivion.

The plan, unveiled with second-quarter earnings on Thursday, is Saylor’s latest answer to the big question hanging over his stock: how long can he keep using a lofty premium to fund ever-larger Bitcoin buys?

To reassure shareholders, Strategy pledged it won’t issue new common shares at less than 2.5 times its net asset value, except to cover debt interest or preferred dividends. At ...