Founders share VC horror stories, and some name names

Asking venture capitalists to invest is a rite of passage for technology founders. This has led to another global experience: the venture capital horror story. A Huge conversation Stories like this have been shared all week on X with funny and infuriating comments. We read them all to find the most interesting ones so you don’t have to.

Greg Eisenbergemerging podcaster, newsletter writer, and founder Late checkout studio — a holding company whose previous projects include a company acquired by WeWork — The conversation started with a story about a venture capitalist falling asleep during a pitch meeting. Isenberg has a large following on X, and his post clearly struck a nerve.

“I was once giving a presentation in a board room at a top three venture capital firm for a $15 million Series A. There were 12 people in the meeting. One of the GPs fell asleep completely. He was out in the cold for over 30 minutes. No one acknowledged it. And everyone just kept moving on,” he said. Subscribed to X.

Venture capitalists falling asleep during pitch meetings was the most common horror story shared. Not just sleepy, but full in the zone.

Zynga founder Mark Pincus told his VC-sleep story. “I looked at my friend who was setting up the meeting and asked me if I should still do the show, and she said yes. It was Bernie’s Weekend meets Silicon Valley.” books.

Interestingly, sleep does not mean that venture capital will not invest. Multiple founders Report receiving term sheets from partners who have fallen asleep during play.

“I once pitched a partnership in 2015 for our Series A where one partner (famous Midas listener) fell asleep and the other couldn’t stop sulking. I got a call 2 hours later from IC that they were sending out a term sheet,” he wrote. Liz Wessel. Wessel, who co-founded and sold the HR startup WayUp Now a partner at First Round Capital, she said her team didn’t take the money — and the venture capitalist was blindsided.

There have been a lot of stories about venture capitalists sleeping, that former a16z partner Ariana Simpson books“Is venture capital okay? Narcolepsy seems to be widespread.”

There have, of course, been more than a few stories about VCs signing term sheets and then pulling out at the last minute, or never sending the money at all. The most infuriating part? some It seems that these mutual funds continued the treatment Founders love portfolio companies anyway, wondering To get company updates Or for Serve as a reference. Even VCs, one of the founders said He wanted a share of the post-acquisition proceeds.

Travis Kalanick, the co-founder of Uber famous for his design, Tell a story About discovering that the VC was trying to hide the meeting and leave the building. Kalanick said he followed the VC to his car and got out of the passenger seat.

Not everyone had bad experiences to report. Some founders said they had nothing but… Great experiences with venture capitalwith a few sharing Love stories About specific investors. Yes, most VCs work hard, genuinely try to be helpful, and don’t nap during meetings. But bad experiences are so common that Pincus exclaimed, “I love this moment, when founders are no longer afraid to call out venture capitalists for their stupid behavior.”

The most amazing stories

However, it was the stories that really amazed meThe one posted by Cloudflare founder Matthew Prince. “One Sequoia partner dumped 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. Given that Cloudflare is now a company with a market cap of $87 billion, with projected annual revenues With a value of $2.8 billion In 2026, Judgment has not aged well.

Sequoia’s partner, Sean Maguire, is no stranger Controversial In response to his own statements, he responded that he has always admired Zatlin, and asked Prince to reveal the name of the associate who said that. “Maybe we’ll have a drink someday,” Prince said. “But I bet you have a really good guess.”

But wait, the prince ate more!

he He said A story about prominent investor Vinod Khosla, who offered to invest and then, according to Prince’s recollections, suggested to the founder that he “fire” the co-founders and take their shares. “I think the charity reading was a test of my character. But I was so offended that we never spoke again. We literally blocked his number.”

The prince hastened to do so Add nuance About Khosla: “He’s very smart/intelligent. He was a great investor – I can’t argue with his track record. But not the person I would choose to work with.”

It is worth noting that memories of hadiths tend to vary, and we do not know what Khosla actually said, meant, or remembered. But eyes popped at such an open talk about one of the most successful and powerful venture capital firms in the valley. Many people called Frankly Prince Example of getting paid “FU”. prince, Of course, he is a billionaire these days.

Not all of Prince’s stories portray venture capitalists as the villains. Specifically, he was believed to have arranged a simple meet-and-greet on Monday with Marc Andreessen, co-founder of venture firm a16z. Instead, Andreessen showed up with his entire investment team, ready to impress. The unprepared prince did not impress him. “I drafted the rejection letter they sent,” he said of the outcome. Others He told similar stories From meetings with Andreessen and his company.

Perhaps the funniest story came from Julie Fredrickson, A Founder turned investorwho received a phone call from a venture capital partner before arriving at the firm’s office — warning her of a rock formation visible outside the window that, apparently, unbeknownst to the investors inside, was shaped like male genitalia. “The company will be on my mind forever Decroc Projects“, she wrote.

While Valley venture capital firms have been under intense pressure, the founders shared incidents involving it International venture capital fundsalso. Some venture capital too dish About pitching to limited partner investors.

The topics are worth reading not just for the laughs, but also for what they reveal: the fundraising process is murky, the power dynamics are real, and the experiences founders secretly whisper about are far more common than the industry tends to publicly acknowledge.

Perhaps Eisenberg explained the moral behind all these stories best. “If you’re uploading right now, just know that every founder has a story like this. The process is weird. The power dynamic is weird,” he wrote.

The second lesson might be: If Andreessen agrees to meet you, he means business.