Seeking investment from venture capitalists is a rite of passage for tech founders. This led to another global experience: the VC pitching horror story. A mass chat Sharing of such stories has been happening all week on X, with the comments both funny and infuriating. We read them all to find the most interesting ones so you don’t have to.
Greg Isenberga startup podcaster, newsletter writer and founder Late Checkout Studio — a holding company whose past ventures include a company acquired by WeWork — started the conversation with a story about a VC who fell asleep during a meeting. Isenberg has a big following on X, and his post clearly struck a nerve.
“Once I was pitching in a conference room at a top VC firm 3 for a $15M Series A. 12 people in the meeting. One of the GPs fell completely asleep. Out in the cold for 30+ minutes. No one acknowledged it. Everyone just carried on,” he said. shared with X.
VCs sleeping through field encounters was by far the most common horror story. Not just sleepy, but full on zonked.
Zynga founder Mark Pincus told his VC-sleep story. “I looked at my friend who organized the meeting and asked if I should still pitch and she said yes. It was ‘Bernies Weekend’ with Silicon Valley.” he wrote
Interestingly, the sleep didn’t mean the VC wouldn’t invest. Multiple founders reported receiving term sheets from associates who had fallen asleep during the pitch.
“I once did a collaboration in 2015 for our Series A where one partner (famous Midas lister) fell asleep and another couldn’t stop scribbling. I got a call 2 hours after the IC that they were sending out a deadline sheet,” he wrote Liz Wessel. Wessel, who co-founded and sold HR startup WayUp and is now a partner at First Round Capital, said her team didn’t get the money — and that the VC was shocked.
There were so many stories about sleeping VCs that a16z ex-partner Arianna Simpson he wrote“Are VCs OK? Narcolepsy seems to be rampant.”
There were, of course, more than a few stories about VCs who signed term sheets and then pulled out at the last minute or ghosted, never drawing the money. The even scarier part? Some of these VCs apparently continued to heal anyway founders like holding companies, asking for company updates or to serves as a reference. One founder even said the VC he wanted a share of the proceeds after the takeover.
Travis Kalanick, the co-founder of Uber, known for his determination, told a story about discovering that a VC was trying to derail the meeting and leave the building. Kalanick said he followed the VC into his car and got out of the passenger seat.
Not everyone had bad experiences to report. Some founders said they never had anything but great experiences with VCswith some even sharing love stories for specific investors. Yes, most VCs are hardworking, genuinely try to be helpful, and don’t fall asleep during meetings. But bad experiences are so common that Pincus exclaimed, “I love this moment when founders no longer have to be afraid to call out VCs for stupid behavior.”
The most shocking stories
However, the stories that really surprised were tthose posted by Cloudflare founder Matthew Prince. “A Sequoia partner passed on 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 an $87 billion company with an expected annual revenue of 2.8 billion dollars in 2026, the crisis has not aged well.
Sequoia partner Shaun Maguire is no stranger in the controversy over his remarks himself, he replied that he had always admired Zatlyn and asked Prince to delete the name of the partner who said so. Prince said, “Maybe I’ll have a drink one day. But I bet you already have a good guess.”
But wait, Prince ate more!
He he said a story about prominent investor Vinod Khosla, who offered to invest and then, according to Prince’s recollection, suggested that the founder “fire” his co-founders and take their stock. “I think the charitable reading was that it was a test of my character. But I was so offended that we never spoke again. We literally blocked his number.”
Prince was quick to add shade on Khosla: “He’s extremely smart/intelligent. He’s been an incredible investor — I can’t argue with his track record. Just not the personality I’d choose to work with.”
It’s worth noting that recollections of conversations tend to vary, and we don’t know what Khosla actually said, meant, or remembered. But eyes popped at such an open discussion about one of the Valley’s most successful, powerful VCs. Many people called out Prince’s honesty an example of having ‘FU’ money. Prince, of course, he’s a billionaire these days.
Not all Prince stories cast the VCs as villains. In particular, he thought he had lined up a simple meet-and-greet on Monday with Marc Andreessen, the co-founder of venture firm a16z. Instead, Andreessen showed up with his entire investment team, ready to impress. The ill-prepared Prince was unimpressed. “I framed the rejection letter they sent,” he said of the result. Others told similar stories meetings with Andreessen and his company.
Perhaps the funniest story came from Julie Fredrickson, a founder turned investorwho received a call from a VC partner before arriving at a firm’s office — alerting her to a rock formation visible outside the window that, apparently unbeknownst to the investors inside, was shaped like male genitalia. “The company will forever be in my mind Dickrock Venturesshe wrote.
While the Valley VCs were grilled more, the founders shared incidents that concerned them international VCalso. Some VCs too dish regarding the promotion to investors of limited partners.
The threads are worth reading not just for the laughs, but 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 acknowledge publicly.
Perhaps Isenberg best explained the moral behind all these stories. “If you’re raising right now, just know: every founder has a story like this. The process is weird. The power dynamics are weird,” he wrote.
A second lesson might be: If Andreessen agrees to meet with you, he means business.
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