MicroStrategy’s Financial Gambit Hits a Bump With New Stock Deal

MicroStrategy Inc.’s seemingly limitless moves to raise capital for its Bitcoin purchases have run into their first obstacle.

The self-styled Bitcoin treasury company sold preferred stock units — rare, debt-like securities dangling an 8% coupon — last week, but it had to cater to price-sensitive buyers by pricing them at a sizable discount. The shares were sold for $80 apiece, 20% below their marketed price, effectively pushing the yield to 10% for buyers — a steep concession to finalize the deal.

“I can’t remember the last time I saw something priced this low,” said James Dinsmore, a portfolio ...