Silicon Valley Founders Are Publicly Roasting VCs Online

Over the past few days, some Silicon Valley tech founders have taken to the internet to publicly roast the venture capitalists they once pitched.

The kefuffle began last week when Greg Isenberg, the host of “The Startup Ideas Podcast,” posted to X about his experience raising a $15 million Series A.

“12 people in the meeting. One of the GPs fully fell asleep. Out cold for 30+ minutes. Nobody acknowledged it. Everyone just kept going,” Isenberg wrote, referring to an unnamed general partner.

Isenberg said he continued his presentation, sharing slides with an investor he called an “unconscious man in a Herman Miller chair.”

“That’s venture capital,” he wrote.

Venture capital is the financial engine of the tech industry. Founders with an idea rely on them to kick-start or turbocharge their fledgling companies. Typically, this is not a loan, but an equity exchange. The earlier a VC invests, the riskier the investment. When a company succeeds, however, the returns can be astronomical.

Uber founder Travis Kalanick, responding to Isenberg, said that the venture world has changed over the years. Investors, he said, once took a more casual approach to pitch meetings.

In 2001, Kalanick said he pitched an investor who was sitting in his “parked Lexus.” Kalanick was sitting in the passenger seat.

Kalanick said the investor “grabbed” his laptop, placed it “on his large belly,” pressed it against the steering wheel, and began flipping through the slides himself.

“2001 fundraising hit different,” he said.

The back-and-forth went viral among the niche community of already-successful millionaire and billionaire founders who are terminally online, and the pile-on began.

Cloudflare CEO Matthew Prince said a Sequoia partner passed on Cloudflare because “he didn’t think a woman could lead a security infrastructure company.” Cloudflare was founded in 2009 by Prince, Lee Holloway, and Michelle Zatlyn. The internet services company is now valued at almost $90 billion.

Prince said he also once met with Khosla Ventures about investing in Cloudflare’s Series C.

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 Ventures declined to comment when reached by 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.

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.”