Seeking investment from venture capitalists is a rite of passage for technology founders. This led to another universal experience: the VC pitch horror story. A large conversation sharing stories like this took place on X over the week, and the comments were both funny and infuriating. We read everything to find the most interesting, so you don't have to.
Greg Eisenberg, startup podcaster, newsletter writer, and founder of Late Checkout Studio, is a holding company whose holding company includes companies acquired by WeWork. The conversation started with a story about a VC who fell asleep during a pitch meeting. Mr. Eisenberg has many fans of X, and his post clearly struck a nerve.
“I was once pitching in the boardroom of a top-three venture capital firm for $15 million in Series A. There were 12 people in the meeting. One of the GPs fell asleep completely. He was out in the cold for over 30 minutes. No one acknowledged it. Everyone just kept going,” he shared on X.
VCs falling asleep during pitch meetings were the most commonly shared fear story. It's not just sleeping, it's completely zonked.
Mark Pincus, founder of Zynga, talked about his sleep at VC. “I looked at the friend who had set up the meeting and asked if I should continue presenting, and she said yes. It was 'Weekend at Bernie's' meets Silicon Valley,” he wrote.
Interestingly, snoozing didn't mean VCs wouldn't invest. Multiple founders have reported receiving term sheets from partners who fell asleep during the pitch.
“I once pitched a Series A partnership in 2015 when one partner (the famous Midas Lister) fell asleep and the other one couldn't stop grimacing. Two hours after the IC, I got a call saying they were sending me a term sheet,” writes Liz Wessel. Wessel, who co-founded and sold HR startup WayUp and is now a partner at First Round Capital, said her team did not receive the funding and the VC was shocked.
There have been so many stories about VC's sleep, with former a16z partner Arianna Simpson writing, “Is VC okay? Looks like there's an epidemic of narcolepsy.”
Of course, there were many stories of VCs signing term sheets and then pulling out at the last minute or ghosting and not transferring funds. What's the trickier part? Some of these venture capital firms appear to have continued to treat founders like portfolio companies, asking for company updates and providing references. One founder said the VC even wanted a share of the proceeds after the acquisition.
Uber co-founder Travis Kalanick, known for his determination, told a story about the time he discovered a venture capitalist was trying to cancel a meeting and leave the building. Kalanick said he followed VC to his car and pitched from the passenger seat.
Not everyone had a bad experience to report. Some founders said they had nothing but great experiences with VCs, and others told love stories with particular investors. Yes, most VCs are hardworking, genuinely try to be helpful, and don't take naps during meetings. But as bad experiences are common, Mr. Pincus exclaimed: “I fucking love this moment when founders don’t have to be afraid to call out VCs for stupid actions.”
the most amazing story
However, what really surprised me was an article posted by Cloudflare founder Matthew Prince. “Sequoia's partners passed on Cloudflare because they didn't think a woman could lead a security infrastructure company,” Prince wrote. The woman in question is Michelle Zatlin, Cloudflare's co-founder and chief operating officer (COO). Considering that Cloudflare is currently a $87 billion company with a projected annual revenue of $2.8 billion in 2026, this judgment hasn't gotten old yet.
Sequoia's partner Sean Maguire, who is no stranger to controversy with his own comments, said he has always respected Zatlin and asked Prince to reveal the name of his partner who made the comment. Prince joked, “Maybe sometime over drinks. But you've already guessed a good thing.”
But wait, Prince cooked more!
He told a story about prominent investor Vinod Khosla, who, Prince recalls, offered to invest and then suggested that the founder “fire” his co-founder and take the stake. “I think the charity reading was a test of my character. But I was so angry that we never spoke again. I literally blocked his number.”
Prince was quick to add nuance about Khosla: “He's very smart. He's a great investor and I can't argue with his track record. He's just not the type of person I would want to work with.”
Note that memories of conversations tend to vary, and we don't know what Khosla actually said, meant, or even remembers. But it was eye-opening to hear such an open story about one of the Valley's most successful and powerful venture capital firms. Many called Prince's candor an example of having “FU” money. Of course, Prince is now a billionaire.
Not all of Prince's stories cast VC as the bad guy. Specifically, he thought he had scheduled a quick dinner with Marc Andreessen, co-founder of venture firm a16z, on Monday. Instead, Andreessen showed up with his entire investment team and was ready to be surprised. The unprepared prince was not impressed. “I put together the rejection letter they sent me,” he said of the results. Others told similar stories about meetings with Andreessen and his company.
Perhaps the most interesting story came from founder-turned-investor Julie Fredrickson. Before arriving at the company's offices, he said, he received a call from a venture capital official who warned investors inside that a rock visible outside the window was clearly shaped like a penis. “In my heart, this company will forever be Dicklock Ventures,” she wrote.
While Valley VCs were most heavily criticized, founders also shared incidents involving international VCs. Some VCs expressed displeasure about limited partners pitching to investors.
This thread is worth reading not only for the laughs it brings, but also for what it reveals. The funding process is opaque, the power dynamics are real, and the experiences that founders privately whisper to each other are far more common than what the industry tends to admit publicly.
Perhaps Eisenberg best explains the lesson behind all these stories. “If you're raising money right now, know this: Every founder has a story like this. The process is strange. The power relationships are strange,” he wrote.
The second lesson is: If Andreessen agrees to meet with you, he means business.
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