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. We read through them all to find the most interesting ones so you don’t have to.
Greg Isenberg, a startup podcaster, newsletter writer, and founder of Late Checkout Studio — a holding company whose previous ventures include a company acquired by WeWork — got the conversation started with a story about a VC falling asleep during a pitch meeting. Isenberg has a large following on X, and his post clearly struck a nerve.
“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.
Interestingly, falling asleep didn’t mean the VC wouldn’t invest. Multiple founders reported receiving term sheets from partners who’d dozed off during the pitch.
“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. Wessel, who co-founded and sold HR startup WayUp and is now a partner at First Round Capital, said her team didn’t take the money — and that the VC was shocked.
There were so many stories about VCs sleeping that former a16z partner Arianna Simpson wrote, “Are VCs ok?? Narcolepsy appears to be running rampant.”
There were, of course, more than a few stories about VCs signing term sheets then pulling out last minute, or ghosting, never wiring the money. The even 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.
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
Still, the stories that truly stunned were the ones posted by Cloudflare founder Matthew Prince. “A Sequoia partner passed on Cloudflare because he didn’t think a woman could lead a security infrastructure company,” Prince wrote. The woman in question is Cloudflare’s co-founder and COO Michelle Zatlyn. 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.
Sequoia partner Shaun Maguire, no stranger to controversy over his remarks himself, replied that he’s always admired Zatlyn, and asked Prince to spill the name of the partner who said that. Prince punted, “Maybe over a drink one day. But I bet you have a good guess already.”
But wait, Prince dished more!
He told 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 read was it was a test of my character. But I was so offended that we never spoke again. Literally blocked his number.”
Prince was quick to add nuance about Khosla: “He’s extremely smart/clever. Has been an incredible investor — 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 remembers. But eyes popped at such open talk about one of the Valley’s most successful, powerful VCs. Many people called Prince’s candor an example of having “FU” money. Prince, of course, is a billionaire these days.
Not all of Prince’s stories cast VCs as the villains. Specifically, he thought he had lined up a simple meet-and-greet on a Monday with Marc Andreessen, the co-founder of venture firm a16z. Instead, Andreessen showed up with his whole investment team, ready to be wowed. 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-investor, who received a call from a VC associate before arriving at a firm’s office — warning her about a rock formation visible outside the window that, apparently unbeknownst to the investors inside, was shaped like male genitalia. “The firm will forever in my mind be Dickrock Ventures,” she wrote.
While the Valley’s VCs got roasted most heavily, founders shared incidents involving international VCs, too. 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.
Perhaps Isenberg explained the moral behind all of these stories best. “If you’re raising right now, just know: every founder has a story like this. The process is weird. The power dynamic is weird,” he wrote.
A second lesson may be: If Andreessen agrees to meet with you, he means business.