Asking venture capitalists for investment is a rite of passage for tech founders. This has led to another universal experience: the VC pitch horror story. TO massive conversation Sharing stories like this has been happening all week on X, with hilarious and infuriating comments. We read them all to find the most interesting ones so you don’t have to.
Greg Isenberga startup podcaster, newsletter writer, and founder of Late departure study (a holding company whose previous ventures include a company acquired by WeWork) kicked off the conversation with a story about a VC who fell asleep during a pitch meeting. Isenberg has a large following on X, and his post clearly struck a chord.
“I was once pitching in a boardroom at one of the top three venture capital firms for a $15 million Series A. There were 12 people in the meeting. One of the GPs fell completely asleep. Knocked out for over 30 minutes. No one noticed. Everyone moved on,” he said. shared on X.
VCs sleeping through pitch meetings was by far the most common horror story shared. Not just numb, but completely drugged.
Zynga founder Mark Pincus told his sleeping VC story. “I looked at my friend who organized the meeting and asked her if I should continue presenting and she said yes. It was ‘Weekend at Bernies’ meets Silicon Valley.” he wrote.
Interestingly, falling asleep didn’t mean the VC wouldn’t invest. Multiple founders reported receiving term sheets from partners who had fallen asleep during the pitch.
“I once pitched a partnership in 2015 for our Series A, where one partner (the famous Midas lister) fell asleep and another couldn’t stop frowning. I got a call 2 hours after the IC that they were sending me a term sheet,” he wrote Liz Wessel. Wessel, who co-founded and sold the human resources startup WayUp and is now a partner at First Round Capital, said her team didn’t accept the money and the VC was surprised.
There were so many stories about VC sleeping that a16z’s former partner Arianna Simpson wrote“Are VCs okay? Narcolepsy seems to be running rampant”.
Of course, there were more than a few stories about VCs signing term sheets and then pulling out at the last minute, or ghosting and never transferring the money. The even more irritating part? Some of these VCs apparently continued trying Founders like portfolio companies anyway, asking for company updates oa serve as a reference. One founder said the VC even wanted a share of the post-acquisition profits.
Travis Kalanick, the co-founder of Uber known for his determination, told a story about discovering that a VC was trying to hide the meeting and leave the building. Kalanick said he followed the VC to his car and jumped from the passenger seat.
Not everyone had bad experiences to tell. Some founders said they had never had anything but Great experiences with VCand some even share love stories on specific investors. Yes, most VCs are hard workers, they really try to be helpful and don’t take naps during meetings. But bad experiences are so common that Pincus exclaimed, “I love this moment, where founders no longer have to be afraid to call out venture capitalists for their foolish behavior.”
The most impressive stories.
Still, the stories that really surprised were notThose published by Cloudflare founder Matthew Prince.. “A Sequoia partner turned down Cloudflare because he didn’t believe a woman could lead a security infrastructure company,” Prince wrote. The woman in question is Cloudflare co-founder and COO Michelle Zatlyn. Since Cloudflare is now a company with a market capitalization of $87 billion, with expected annual revenue of 2.8 billion dollars in 2026, the sentence has not aged well.
Sequoia partner Shaun Maguire is no stranger to the controversy Regarding his comments, he responded that he has always admired Zatlyn and asked Prince to tell him the name of the partner who said that. Prince cleared: “Maybe someday over a drink. But I bet you already have a good guess.”
But wait, Prince served more!
He said a story about prominent investor Vinod Khosla, who offered to invest and then, Prince recalls, suggested that the founder “fire” his co-founders and keep 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 number.”
Prince rushed to add nuances on Khosla: “He’s extremely smart and intelligent. He’s been an incredible investor; I can’t argue with his track record. But he’s not the personality I would choose to work with.”
It’s worth noting that recollections of the conversations tend to vary and we don’t know what Khosla actually said, meant or remembers. But eyes were opened by such an open conversation about one of the Valley’s most successful and powerful venture capitalists. Many people rated Prince’s candor an example of having “FU” money. Prince, of course he is a billionaire these days.
Not all Prince stories feature VCs as villains. Specifically, he thought he had arranged a simple Monday meeting with Marc Andreessen, the co-founder of the venture firm a16z. Instead, Andreessen showed up with his entire investment team, ready to be surprised. The ill-prepared prince did not impress. “I framed the rejection letter they sent,” he said of the result. Others told similar stories of meetings with Andreessen and his firm.
Perhaps the funniest story came from Julie Fredrickson, a founder turned investorwho received a call from a venture capital associate before arriving at a company’s office, warning him about a rock formation visible outside the window that, apparently unbeknownst to the investors inside, was in the shape of male genitalia. “The company will always be in my mind Dickrock Companies“, wrote.
While Valley venture capitalists were the most affected, founders shared incidents related to international venture capitalistsalso. Some venture capitalists too served on how to pitch limited partners to investors.
The threads are worth reading not just for the laughs, but also for what they reveal: The fundraising process is opaque, the power dynamics are real, and the experiences founders whisper about in private are far more common than the industry tends to publicly acknowledge.
Perhaps Isenberg best explained the moral behind all these stories. “If you’re raising the issue now, know: Every founder has a story like this. The process is strange. The power dynamics are strange,” he wrote.
A second lesson may be: if Andreessen agrees to meet with you, he means business.
When you purchase through links in our articles, we may earn a small commission. This does not affect our editorial independence.
