Founders and venture capitalists have always had a fraught relationship, but a sprawling weeklong conversation on X showed just how often pitch meetings turn into stories of sleep, ghosting, and outright disrespect. The posts were funny, infuriating, and, in some cases, unusually direct about specific investors and firms.
The pitch room horror stories
The thread that helped ignite the conversation came from Greg Isenberg, a startup podcaster, newsletter writer, and founder of Late Checkout Studio, a holding company whose past ventures include a company acquired by WeWork. Isenberg said that while pitching a “$15M Series A” in a board room at a “top 3 VC firm,” one of the general partners “fully fell asleep” for more than 30 minutes while 12 people sat in the room. “Nobody acknowledged it. Everyone just kept going,” he wrote on X.
That story resonated because it was far from unique. Across the discussion, founders repeatedly described investors dozing off during meetings, not merely drifting but apparently conking out completely. Zynga founder Mark Pincus added his own version of the same experience. “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.
Sleepiness, oddly enough, did not always hurt a startup’s chances. Several founders said they still received term sheets from investors who had fallen asleep during the pitch. Liz Wessel, who co-founded and sold the HR startup WayUp and is now a partner at First Round Capital, said she once pitched a partnership in 2015 for her Series A when “one partner (famous Midas lister) fell asleep & another couldn’t stop scowling.” Two hours after the investment committee meeting, she said, “they were sending a term sheet over.” Wessel said her team passed, and that the firm was shocked.
Ghosting, broken promises and awkward follow-ups
Another common complaint was the investor who commits, then disappears. Founders described VCs who signed term sheets and then backed away at the last minute, or who simply stopped responding and never wired the funds. In some cases, the same investors later behaved as if nothing had happened, asking for company updates or references as though they were still involved. One founder said a VC even sought a share of post-acquisition proceeds.
Former a16z partner Arianna Simpson captured the mood with a joke that also doubled as a diagnosis of the industry: “Are VCs ok?? Narcolepsy appears to be running rampant.”
Travis Kalanick, the Uber co-founder known for his aggressive style, offered a different kind of story. He said he realized a VC was trying to ghost the meeting and leave the building, so he followed the investor to his car and kept pitching from the passenger seat.
The names that got attention
Not everyone in the discussion was anonymous. The most striking stories came from Cloudflare founder Matthew Prince, who named investors and recounted conversations that drew immediate attention.
Prince said that “a Sequoia partner passed on Cloudflare because he didn’t think a woman could lead a security infrastructure company.” The woman was Michelle Zatlyn, Cloudflare’s co-founder and COO. The comment landed especially hard because Cloudflare is now an $87 billion market cap company, and the company expects annual revenue of $2.8 billion in 2026.
Sequoia partner Shaun Maguire, who has drawn controversy himself for past remarks, replied that he has always admired Zatlyn and asked Prince to name the partner. Prince declined, saying, “Maybe over a drink one day. But I bet you have a good guess already.”
Prince shared another story, this time about investor Vinod Khosla. According to Prince’s recollection, Khosla offered to invest and then suggested that Prince should “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 wrote.
He also added a qualifier that was notable in a thread full of blunt criticism: “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.”
As with any retelling of a private conversation, the exact wording and intent are impossible to verify from one side of the exchange. Still, the fact that one of the industry’s most visible founders was willing to say so much publicly underscores how much the balance of power has shifted.
Not every story was hostile
For all the roasting, the thread was not a blanket indictment of venture capital. Some founders said they had only positive experiences with investors, and a few shared genuinely warm anecdotes about specific VCs. The point, many implied, was not that every investor behaves badly, but that bad behavior has become common enough to feel normalized.
Pincus framed the moment as a release valve for founders. “I f*cking love this moment, when founders no longer have to be afraid to call out VCs for dumb behavior,” he wrote.
One of the funniest details
Not every memorable post involved billion-dollar companies or famous names. One of the most amusing came from Julie Fredrickson, a founder-turned-investor, who said a VC associate called her before she arrived at a firm’s office to warn her that a rock formation visible from the window apparently resembled male genitalia. “The firm will forever in my mind be Dickrock Ventures,” she wrote.
What the thread says about fundraising
The popularity of these stories says less about one-off bad meetings than about the structure of startup fundraising itself. Founders often enter investor meetings with very little leverage, while VCs decide whether to listen, respond, or disappear. That imbalance makes even small acts of rudeness feel larger, and it helps explain why so many founders remember the worst meetings in vivid detail years later.
Isenberg summed it up in a post that seemed to capture the mood of the entire thread: “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.
And perhaps there was one more lesson buried in the pile of complaints and jokes: if Marc Andreessen agrees to meet, he likely means it. Prince said he once expected a simple Monday meet-and-greet with the a16z co-founder, only for Andreessen to arrive with his full investment team. Prince was not prepared, the meeting went poorly, and he said, “I framed the rejection letter they sent.”
Source: Original report
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Last Modified: July 7, 2026 at 9:30 pm
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