Soliciting investment from venture capitalists is a rite of passage for tech founders. This led to another universal experience: the VC pitching horror story. A mass conversation sharing of these kinds of stories has been happening on X all week, with comments both funny and infuriating. We read them all to find the most interesting ones so you don’t have to.
Greg Isenbergstartup podcaster, newsletter author and founder Delayed Checkout Studio – a holding company whose previous venture was a company acquired by WeWork – the conversation started with a story about a VC falling asleep during a meeting. Isenberg has a huge following on X, and his post clearly struck a nerve.
“Once I was pitching in a boardroom of a top 3 VC firm for a $15 million Series A. 12 people in a meeting. One of the doctors fell asleep. It was cold for 30+ minutes. No one acknowledged it. Everyone moved on.” Shared on X.
VCs sleeping with pitch meetings was the most common horror story shared. Not just a sleeper, but a full throbbing one.
Zynga founder Mark Pincus told his VC-dream story. “I looked at my friend who organized the meeting and asked if I should go ahead with the presentation and he said yes. Meet Silicon Valley ‘weekend at bernies'” he wrote.
Interestingly, falling asleep didn’t mean the VC wouldn’t invest. Multiple founders reported receiving term sheets from partners who fell asleep during the pitch.
“I once pitched a partnership for our Series A in 2015 where one partner (the famous Midas list) fell asleep and the other couldn’t help but scowl. 2 hours later I got a call from IC saying they were sending the term sheet.” Liz Wessel. Wessel, who co-founded and sold HR startup WayUp and is now a partner at First Round Capital, said his team didn’t get the money and the VC was shocked.
There were so many stories about former a16z partner Arianna Simpson sleeping with VCs he wrote“Are VCs good? Narcolepsy is rampant.”
Of course, there were several stories of VCs signing term sheets, then pulling out at the last minute, or never pulling the money. The even more outrageous part? Some of them these VCs were probably continuing treatment founders like portfolio companies anyway, they ask for company updates or for serves as a reference. One founding VC even said he wanted a share of the profit after the sale.
Uber co-founder Travis Kalanick, known for his determination, told a story About discovering that a VC is trying to dream up a meeting and leave the building. Kalanick said he followed VC to his car and got out of the passenger seat.
Not everyone had bad experiences to report. Some founders said they never owned anything else Great experiences with VCwith a few even shares love stories about private investors. Yes, most VCs are hardworking, genuinely try to help, and don’t fall asleep during meetings. But bad practices are so common that Pincus said, “I love this moment where founders aren’t afraid to call out VCs for dumb behavior.”
The most amazing stories
Still, the truly astonishing stories were tit was posted by Matthew Prince, founder of Cloudflare. “The Sequoia partner switched from Cloudflare because he didn’t think a woman could lead a security infrastructure company,” Prince wrote. The woman in question is Cloudflare co-founder and COO Michelle Zatlin. Considering that Cloudflare is now a company with a market cap of $87 billion with expected annual revenue $2.8 billion In 2026, the decision has not aged well.
Sequoia partner Shaun Maguire is no stranger to the dispute According to him, he always admired Zatlyn and asked Shahzade to reveal the name of the partner who said this. The prince said, “Maybe one day we can drink. But I’m sure you already have a good idea.”
But wait, Prince did more!
He he said a story about prominent investor Vinod Khosla, who offered to invest and then, according to Prince’s memoir, “fire” his founding co-founders and buy their shares. “I think it was a test of my character when I read it for charity. But I was so hurt that we never spoke again. We literally blocked his number.”
The prince left quickly add nuance On Khosla: “He’s extremely smart/intelligent. He’s been an incredible investor – he can’t argue with his experience. He’s just not the type of person I’d choose to work with.”
It should be noted that memories of conversations vary and we do not know what Khosla actually said, meant or remembered. But eyes fell on such an open conversation about one of the Valley’s most successful, powerful VCs. Many people called Prince’s sincerity An example of having “FU” money. prince, of course he is a billionaire these days.
Not all of Prince’s stories portray VCs as villains. In particular, he thought he had arranged a simple meeting with Marc Andreessen, co-founder of the venture firm a16z, on Monday. Instead, Andreessen showed up with an entire investment team ready to impress. The unprepared Prince was not impressed. “I drafted the rejection letter they sent,” he said. Others told similar stories Meetings with Andreessen and his firm.
Perhaps the funniest story is Julie Fredrickson, a became a founding investorbefore arriving at the firm’s office, he received a call from a VC associate alerting him to a rock formation that looked like a male genitalia, apparently unknown to the investors inside, just outside the window. “The firm will always be in my mind Dickrock Ventures“, he wrote.
While the Valley’s VCs were mostly roasted, the founders shared stories about it international VCsalso. Some VCs too edible on offers for limited partner investors.
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 practices founders whisper about privately are more common than the industry admits publicly.
Perhaps Isenberg best explained the moral behind all these stories. “If you’re currently breeding, just know: every founder has a story. The process is weird. The power dynamics are weird,” he said.
A second lesson might be: If Andreessen agrees to meet with you, he means business.
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