Back in February 2016, Conrad had resigned under pressure from Zenefits, while the former unicorn retrenched and slashed its valuation by more than half under new leadership. But by April that year–after spending time at home, depressed and binge-watchingmovies while the Securities and Exchange Commission and state insurance commissioners opened investigations into his former startup–he was back with a new HR software startup, Rippling.
While Conrad declined to be interviewed for this story , in a video interview in May from his home in San Francisco, he said that Rippling still had cash on hand from previous financings and hadn’t needed to raise new funds. “For me, the rationale was wanting to insulate the company from any potential future macro shock,” he said then. “I’m terrible at predicting these things.”
With tech’s recent downturn, Parker Conrad’s decision to load up cash at Rippling with a $250 million fundraise in May looks smart. Rippling today is worth two and a-half times the $4.5 billion that Zenefits was worth at its peak. Conrad, a stocky man with reddish blond hair who grew up in a wealthy family and attended Harvard, has crossed the billionaire mark for the first time.