A massive conversation on X this week has tech founders swapping their worst venture capital pitch meeting stories — and many are naming names. The thread, started by Greg Isenberg, founder of Late Checkout Studio and a startup podcaster, 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,” Isenberg posted. The response was overwhelming, with hundreds of founders chiming in with their own tales of sleeping VCs, ghosted term sheets, and condescending behavior.
Sleeping partners and weekend-at-Bernies moments
By far the most common story was VCs dozing off mid-pitch. Zynga founder Mark Pincus recounted: “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.” Even more striking, multiple founders reported receiving term sheets from partners who had fallen asleep. Liz Wessel, co-founder of WayUp and now a partner at First Round Capital, said she pitched a top firm in 2015 where one partner (a Midas list member) dozed off and another scowled throughout. “Got a call 2 hrs after the IC that they were sending a term sheet over,” she wrote. Her team declined the offer, and the VC was reportedly shocked.
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Ghosting, last-minute pullouts, and worse
Beyond sleeping, founders shared stories of VCs signing term sheets and then pulling out at the last minute — or simply ghosting, never wiring the money. Some investors even continued to treat the founders as portfolio companies, asking for updates or to serve as references. One founder said a VC demanded a share of post-acquisition proceeds despite never investing. Travis Kalanick, the Uber co-founder, recounted following a VC to his car after the investor tried to slip out of a meeting, pitching from the passenger seat.
Cloudflare’s Matthew Prince names names
The most stunning revelations came from Cloudflare CEO Matthew Prince. He wrote that a Sequoia partner passed on Cloudflare because “he didn’t think a woman could lead a security infrastructure company” — a reference to co-founder and COO Michelle Zatlyn. Cloudflare is now an $87 billion market cap company with projected 2026 revenue of $2.8 billion. Sequoia partner Shaun Maguire asked Prince to name the partner, but Prince declined, saying, “Maybe over a drink one day. But I bet you have a good guess already.”
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Prince also described an interaction with prominent investor Vinod Khosla, who allegedly suggested Prince “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 added nuance, calling Khosla “extremely smart/clever” with an incredible track record, but “not the personality I’d choose to work with.” Prince’s candor — enabled, as many noted, by his billionaire status — has sparked debate about the power dynamics that usually keep such stories private.
Not all bad: Marc Andreessen shows up ready
Not every story painted VCs as villains. Prince recalled a meeting with a16z co-founder Marc Andreessen, who arrived with his entire investment team, expecting a full pitch. Prince was unprepared and didn’t impress. “I framed the rejection letter they sent,” he said. Other founders shared similar experiences with Andreessen, suggesting that when he agrees to a meeting, he means business. Some founders reported only positive experiences, with a few even sharing “love stories” about specific investors who were genuinely helpful.
The bigger picture: power dynamics laid bare
The threads, which include stories from international VCs and limited partners, reveal a fundraising process that is often opaque and fraught with power imbalances. As Isenberg summed it up: “If you’re raising right now, just know: every founder has a story like this. The process is weird. The power dynamic is weird.” Mark Pincus celebrated the moment, writing, “I f*cking love this moment, when founders no longer have to be afraid to call out VCs for dumb behavior.” For founders currently fundraising, the conversation serves as both a cautionary tale and a reminder that they are not alone.
