Silicon Valley founders are publicly roasting VCs online. Here are their wildest stories.

• Founders are publicly airing their “nightmare” interactions with venture capitalists.
• They shared on X what they say have been some of their worst experiences with investors.
• Legendary VC Vinod Khosla joined the fray.

Vinod Khosla, the legendary tech investor and the firm’s namesake, took Prince and his fellow founders out to dinner, Prince wrote. Near the end of the conversation, Prince recalled, Khosla leaned over and said, “I’m impressed with you, not so much with them, what if you fire them and I’ll give you all their stock?”

Prince said he was so offended he never spoke to Khosla again. Other founders responded to Prince, adding their own experiences dealing with Khosla.

It was enough for Khosla to spend his Saturday responding to the accusations, firing off over a dozen X posts. In some, he denied the stories and asked for evidence, but in most, he repeated a single mantra: Honesty is the best policy.

“I am often wrong but always give honest opinions. Some find this harsh, but hypocritical politeness hurts founders,” he wrote in one post. “Brutal honesty gives them a chance to evaluate it and accept or reject the opinion. Great founders elect for honesty. It is not fun to offer brutal honesty.”

Khosla did not immediately respond to a request for comment from Business Insider.

Some industry insiders came to Khosla’s defense. Blake Byers, an early-stage investor and founder, said Khosla founded one of the pioneering companies of the modern computer industry — Sun Microsystems — before becoming one of Silicon Valley’s most influential venture capitalists.

“He is one of the truest VCs to ever do it,” he wrote.

Apologies, I may sometimes be wrong, but I will always give entrepreneurs my best and honest opinion, popular or not. https://t.co/mxtSeepnIT

— Vinod Khosla (@vkhosla) June 7, 2026

Mark Cummins, an angel investor and robotics expert, said he began pitching a partner at a French firm, only for the investor to interrupt with questions about his parents’ careers.

“What did your father do?’ the partner asks me in a thick French accent,” Cummins wrote.

When Cummins said his father had trained as a theoretical physicist before going into business, the partner replied: “Aha! Your father was a failure!” Then, after Cummins said his mother had been a biochemist before becoming a schoolteacher, the investor said, “Also a failure!”

Cummins said he responded, “I have a hundred employees and we need funding. ‘Would you like to hear about my company?'”

In a conversation largely dominated by men, Claire Vo, the founder of ChatPRD, an AI product management platform, said an investor once interrupted her pitch to say he was glad she wasn’t trying to have kids while building a company.

“I love an opportunity to tell a nightmare VC story!” she wrote.

She later turned one of Khosla’s posts defending himself into what she called a “pop punk banger.”

turning the latest vc crashout on the timeline into a pop punk banger https://t.co/KLFZRWY04h pic.twitter.com/tKcaBceQ8q

— claire vo 🖤 (@clairevo) June 7, 2026