Asking a venture capitalist for an investment is a rite of passage for tech startups. This leads to another common experience: a VC pitching horror story. A large conversation sharing these stories has been going on on X all week, and the comments have been both hilarious and angry. We’ve read through them all to find the most interesting ones, so you don’t have to.
Greg Isenberg, startup podcaster, newsletter writer, and founder of Late Checkout Studio, a holding company that includes companies acquired by WeWork, began our conversation with a story about a VC who fell asleep during a pitch meeting. Isenberg has a large following on X, and his posts clearly struck a nerve.
“One time, I was giving a presentation on a $15 million Series A in the boardroom of a top three VC firm. There were 12 people in the meeting. One of the GPs fell asleep completely. I was out in the cold for over 30 minutes. No one acknowledged it. Everyone kept going,” he shared on X.
VCs falling asleep during pitch meetings was by far the most common horror story shared. Full of drowsiness as well as zonked.
Zynga founder Mark Pincus told the story of his VC falling asleep. “I saw a friend who had organized the meeting and asked if I should still present, and she said yes. It was ‘Weekend at Bernice’ meets Silicon Valley,” he wrote.
Interestingly, being asleep didn’t mean VCs weren’t investing. Several founders have reported receiving term sheets from partners who dozed off during the presentation.
“I once pitched a partnership in 2015 for a Series A where one partner (the famous Midas Lister) fell asleep and the other partner couldn’t stop frowning. Two hours after IC, I got a call saying they were sending term sheets,” writes Liz Wessel. Wessel, who co-founded and sold HR startup WayUp and is now a partner at First Round Capital, said his team did not take the money and the VC was shocked.
There has been so much talk about VC’s sleep that a16z’s former partner Arianna Simpson wrote, “Is VC okay? Narcolepsy seems to be rampant.”
Of course, there have been quite a few stories of VCs pulling out at the last minute after signing an end-of-term contract or not sending money and ghosting. What’s even more annoying? Some of these VCs appear to have treated the founders like portfolio companies anyway, requesting company updates or acting as references. One founder said the VC even wanted a share of the proceeds after the acquisition.
Uber co-founder Travis Kalanick, known for his decisiveness, told a story about discovering that a VC had ignored a meeting and attempted to leave the building. Kalanick said he followed VC to his car and pitched in from the passenger seat.
Not everyone has had an experience bad enough to report. Some founders said they had never had a good experience with a VC, and some even shared love stories about specific investors. Yes, most VCs work hard, genuinely try to be helpful, and don’t take naps during meetings. But poor experiences are so common that Pincus exclaims, “I love this moment when founders no longer have to be afraid to call out VCs for stupid behavior.”
the most amazing story
Nonetheless, a truly surprising story was posted by Cloudflare founder Matthew Prince. “Sequoia partners acquired Cloudflare because they didn’t think women could lead a security infrastructure company,” Prince wrote. The woman in question is Michelle Zatlyn, co-founder and COO of Cloudflare. Considering that Cloudflare is currently a $87 billion market cap company with projected annual revenue of $2.8 billion in 2026, that judgment is not outdated.
Sequoia partner Sean Maguire, whose comments sparked controversy, responded that he always respected Zatlin and asked Prince to name the partner who made those comments. “Maybe we’ll have a drink at some point,” Prince said. “But I bet you’ve guessed well already.”
But wait, Prince did more cooking!
He told the story of renowned investor Vinod Khosla. After offering an investment, he suggested that the founder “fire” his co-founders and take their shares. “I think the charity reading was a test of my character, but I was so offended that we never spoke again. I literally blocked his phone number.”
Prince was quick to add nuance about Khosla: “He’s very smart and clever. He’s been an incredible investor. There’s no arguing with his track record, but he’s just not the personality I would choose to work with.”
It’s worth noting that memories of the conversation vary, and we don’t know what Khosla actually said, meant, or remembers. But the public story about one of the Valley’s most successful and powerful VCs made my eyes pop. Many people called Prince’s candor a case of “FU” money. Of course, Prince is a billionaire these days.
Not all of Prince’s stories cast the VC as the villain. Specifically, he thought he had arranged a brief meeting on Monday with Marc Andreessen, co-founder of venture firm a16z. Instead, Andreessen showed up ready to wow along with his entire investment team. The ill-prepared prince failed to impress. “I framed the rejection letter they sent me,” he said of the results. Others told similar stories about their meetings with Andreessen and his company.
Perhaps the most interesting story is that of Julie Fredrickson, an entrepreneur turned investor. He received a call from a VC employee before he arrived at the company’s office. He warned her about a rock visible outside the window, which, unbeknownst to the investors inside, looked like a male genitalia. “In my mind, the company will forever be Dickrock Ventures,” she wrote.
Although Valley VCs received the most criticism, founders also shared incidents involving international VCs. Some VCs also discussed pitching to limited partner investors.
The thread is worth reading not only for the laughs but also for what it reveals. The fundraising process is opaque, the power dynamics are real, and the privately whispered experiences of founders are far more common than the industry admits publicly.
Perhaps Isenberg explained the moral behind this whole story best. “If you’re raising money right now, know this: Every founder has a story like this. The process is strange. The power dynamics are strange,” he wrote.
The second lesson is this: If Andreessen agrees to meet with you, he means business.
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