As the liberal group Democracy for America approached insolvency following the midterm elections, staffers faced a related problem: their CEO, Yvette Simpson, was on vacation at a vineyard in California.

Weeks earlier Simpson had told two members of the development team that $320,000 needed to be raised for DFA to make it through the year, according to two former employees. But as the group’s dire financial state started to become clear to staff, she attended a leadership training...

Continue Reading Wine tasting in Napa and a staff revolt: How a progressive powerhouse went kaput