Founders vent online as VCs face brutal retorts

founders roast – Silicon Valley’s startup crowd has turned the venture pitch process inside out on the internet—trading polished fundraising narratives for raw stories about investors who fell asleep, questioned parents, and made founders feel judged. The pile-on has even pull

Over the past few days, some Silicon Valley tech founders have taken to the internet to publicly roast the venture capitalists they once pitched—trading the usual handshake-and-metrics routine for stories delivered like receipts.

The flare-up began last week when Greg Isenberg. host of “The Startup Ideas Podcast. ” posted to X about raising a $15 million Series A. His account was specific enough to sting: “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. He said he continued his presentation anyway. sharing slides with an investor he called an “unconscious man in a Herman Miller chair.” “That’s venture capital. ” he added.

Venture capital is the financial engine of the tech industry. Founders with an idea often rely on it to kick-start—or turbocharge—their fledgling companies. Typically. it’s not structured like a loan but as an equity exchange. with the earlier a VC invests. the riskier the investment. When companies succeed, returns can be extraordinary.

But Isenberg’s story sparked a wave of replies from founders who said the pitch process felt like something else entirely.

Uber founder Travis Kalanick responded to Isenberg, saying that the venture world has changed over the years. He argued that investors once took a more casual approach to pitch meetings. In 2001, Kalanick said he pitched an investor who was sitting in his “parked Lexus,” with Kalanick 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 a niche community of already-successful millionaire and billionaire founders who are “terminally online,” and the pile-on accelerated.

Cloudflare CEO Matthew Prince said a Sequoia partner passed on Cloudflare because “he didn’t think a woman could lead a security infrastructure company.” Prince founded Cloudflare in 2009 with 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. He wrote that Vinod Khosla—both a longtime investor and the namesake of the firm—took Prince and other founders out to dinner. Prince recalled that. near the end of the conversation. 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 replied to Prince’s account with their own experiences involving Khosla.

Khosla, for his part, spent his Saturday responding to the accusations. He fired 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.” In one post. he wrote: “I am often wrong but always give honest opinions. Some find this harsh, but hypocritical politeness hurts founders,” he wrote. “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.

Not everyone in the community joined the roasting. 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. Cummins wrote: “What did your father do?” the partner asks me in a thick French accent. 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 dominated largely by men, Claire Vo, the founder of ChatPRD, an AI product management platform, shared an episode where an investor interrupted her pitch to say he was glad she wasn’t trying to have kids while building a company.

Vo wrote, “I love an opportunity to tell a nightmare VC story!” She later turned one of Khosla’s posts defending himself into what she called a “pop punk banger.”

For the founders posting online. the common thread isn’t just that deals can fall apart—it’s that the human moments around the pitch can feel dismissive. personal. or outright jarring. The public dispute now leaves the venture industry facing the same uncomfortable question. told in different voices: when founders bring their work and their time. what does it mean for investors to show up—fully awake. fully curious. and fully respectful?.

venture capital startup founders Silicon Valley Greg Isenberg Travis Kalanick Matthew Prince Cloudflare Sequoia Vinod Khosla Khosla Ventures Series A Series C Claire Vo ChatPRD Mark Cummins robotics pitching