Tech Founders Share Heart-Stopping VC Horror Stories
Venture capitalists are known for their rigorous due diligence and keen insights. But behind the scenes, founders have shared some jaw-dropping experiences that might make you rethink your pitch meeting.
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Asking venture capitalists for investment is a rite of passage for tech founders. This has led to another universal experience: the VC pitching horror story. A massive conversation sharing such stories has taken place all week on X, with the comments both funny and infuriating.
The Sleeping VCs
Greg Isenberg, a startup podcaster and founder of Late Checkout Studio, got the conversation started with a story about a VC falling asleep during a pitch meeting. “I was once pitching in a board room at a top 3 VC firm for a $15M Series A. 12 people in the meeting. One of the GPs fully fell asleep. Out cold for 30+ minutes. Nobody acknowledged it. Everyone just kept going,” he shared on X.
VCs sleeping through pitch meetings was far and away the most common horror story shared. Not just drowsing, but full on zonked. Zynga founder Mark Pincus told his VC-asleep story: “I looked at my friend who set up the meeting and asked if I should keep presenting and she said yes. It was ‘weekend at bernies’ meets Silicon Valley,” he wrote.
The Ghosting VCs
Multiple founders reported receiving term sheets from partners who’d dozed off during the pitch, only to have them pull out last minute or ghost completely. “I once pitched a partnership in 2015 for our Series A where one partner (famous Midas lister) fell asleep & another couldn’t stop scowling. Got a call 2 hrs after the IC that they were sending a term sheet over,” wrote Liz Wessel, who co-founded and sold HR startup WayUp and is now a partner at First Round Capital.
Wessel said her team didn’t take the money — and that the VC was shocked. “Are VCs ok?? Narcolepsy appears to be running rampant,” former a16z partner Arianna Simpson wrote on X.
The More Galling Part
Some of these VCs apparently went on to treat the founders like portfolio companies anyway, asking for company updates or to serve as a reference. One founder said the VC even wanted a share of the post-acquisition proceeds. Travis Kalanick, the Uber co-founder renowned for his determination, told a story about discovering that a VC was attempting to ghost the meeting and leave the building. Kalanick said he followed the VC to his car and pitched from the passenger’s seat.
Love Stories Among VCs
Not everyone had bad experiences to report. Some founders said they’ve never had anything but great experiences with VCs, with a few even sharing love stories about specific investors. Yes, most VCs are hardworking, genuinely try to be helpful, and don’t take naps during meetings. But poor experiences are so common that Pincus exclaimed, “I f*cking love this moment, when founders no longer have to be afraid to call out VCs for dumb behavior.”
The Most Stunning Stories
Cloudflare founder Matthew Prince shared two stories that truly stunned the community. “A Sequoia partner passed on Cloudflare because he didn’t think a woman could lead a security infrastructure company,” Prince wrote. Given that Cloudflare is now an $87 billion market cap company, with expected annual revenue of $2.8 billion in 2026, the judgment hasn’t aged well.
Prince also told a story about prominent investor Vinod Khosla, who offered to invest and then suggested that the founder “fire” his co-founders and take their stock. “I think the charitable read was it was a test of my character. But I was so offended that we never spoke again. Literally blocked his number,” Prince said.
The Andreessen Experience
Travis Kalanick also shared a story about meeting with Marc Andreessen, co-founder of venture firm a16z. Instead of the simple meet-and-greet Kalanick expected, Andreessen showed up with his whole investment team, ready to be wowed. The ill-prepared Kalanick did not impress.
The Final Thoughts
While the Valley’s VCs got roasted most heavily, founders shared incidents involving international VCs as well. Some VCs also dished about pitching to 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 dynamic is real, and the experiences that founders whisper about privately are a lot more common than the industry tends to acknowledge publicly.
