A recapitalization reckoning

If you're an angel who invested in a startup that was meant to go public in 2014, you might be getting a little bit impatient. High-risk, high-reward investing has lost its shine in this environment: the stock market is a mess these days, and you want your cash back.

Enter recapitalization events, where startups restructure their entire cap table to squeeze out old investors, bring on new ones and shift the way equity and debt is managed. For investors, it's a killer way to enter a company on friendlier terms than normal (read: desperation), and a nice way to get liquidity on a startup you're betting on.

For founders, it's rarely good news, as departing investors is not a metric they're going to add to the pitch deck. As one investor said on background, the spur of coronavirus-related recapitalization events shows hella dilution for desperate times."

That's what makes Workhuman's transparency with its recent recapitalization event all the more enticing.

Last year, the human-resources platform brought in $580 million in revenue from customers like LinkedIn, Cisco, J&J and other clients. In April, business grew 40%. Co-founder and CEO Eric Mosley says business has grown five times in size since the company pulled back from its 2014 plans to IPO. Workhuman hasn't raised a single venture round since 2004 (and doesn't plan to any time soon).

Being conservative has paid off; although Workhuman has operated for nearly two decades, Mosley says he thinks the company is still at the tip of the iceberg." The company recently had a recapitalization event to sell the stakes of its earliest investors, who cut a $200,000 check more than 20 years ago.