Clover Health Investments Corp. unsettled shareholders in November when the loss-making medical insurer, backed by investor Chamath Palihapitiya, announced a $300 million stock offering. The price of just $5.75 a share was almost two-thirds less than where it traded when joining the stock market at the start of the year.

Clover already had a decent cash pile, but waiting to raise money was risky given "potentially rising interest rates, a potential recession, and a contraction of investor liquidity, leading to a flight from technology-driven growth companies," management later explained. It had a point: Clover's stock has since plunged even further amid a massive rout of cash-bleeding technology firms.