Patrick T. Fallon | Bloomberg | Getty Images
Bill Gurley, general partner of Benchmark Capital Holdings Co.
The situation had been weighing him down for months. Fellow venture capitalist Chamath Palihapitiya, who hosts a poker game on Mondays that often includes Gurley, angel investor Jason Calacanis and Yammer founder David Sacks, said it was evident as far back as late 2016.
At a Christmas party in Palo Alto, while a group of close friends enjoyed the holiday festivities indoors, Gurley was outside on the porch on his phone with a "pained look on his face," said Palihapitiya, founder of venture firm Social Capital.
"He felt obliged to everyone around him -- his partners, employees and even the CEO -- to do the right thing," Palihapitiya said.
Nirav Tolia, the CEO of Nextdoor and a business partner of Gurley's for 19 years, wasn't at the party but he echoed that sentiment.
"Bill suffers when his companies are suffering," said Tolia, whose social network for neighborhoods counts Gurley as its first investor. "The magnitude of Uber is larger than anything any venture capitalist has ever dealt with."
At the June LP meeting, one investor said, it was as if Gurley "knew a storm was going to take place" and the rest of the world had no idea what was coming.
To a large degree, he was right. Soon after the meeting, the Holder report was released. It contained a scathing rebuke of Uber's culture and made 47 recommendations to the company. They included creating a board oversight committee, rewriting Uber's cultural values, reducing alcohol use at work events and prohibiting intimate relationships between employees and their bosses.