Asking enterprise capitalists for funding is a ceremony of passage for tech founders. This has led to a different common expertise: the VC pitching horror story. A massive conversation sharing such tales has taken place all week on X with the feedback each humorous and infuriating. We learn by all of them to seek out probably the most attention-grabbing ones so that you don’t must.
Greg Isenberg, a startup podcaster, publication author, and founding father of Late Checkout Studio — a holding firm whose earlier ventures embody an organization acquired by WeWork — obtained the dialog began with a narrative a few VC falling asleep throughout a pitch assembly. Isenberg has a big following on X, and his put up clearly struck a nerve.
“I used to be as soon as pitching in a board room at a high 3 VC agency for a $15M Sequence A. 12 folks within the assembly. One of many GPs absolutely fell asleep. Out chilly for 30+ minutes. No person acknowledged it. Everybody simply stored going,” he shared on X.
VCs sleeping by pitch conferences was far and away the most typical horror story shared. Not simply drowsing, however full on zonked.
Zynga founder Mark Pincus advised his VC-asleep story. “I checked out my pal who arrange the assembly and requested if i ought to preserve presenting and he or she stated sure. It was ‘weekend at bernies’ meets Silicon Valley,” he wrote.
Apparently, falling asleep didn’t imply the VC wouldn’t make investments. Multiple founders reported receiving time period sheets from companions who’d dozed off through the pitch.
“I as soon as pitched a partnership in 2015 for our Sequence A the place one associate (well-known Midas lister) fell asleep & one other couldn’t cease scowling. Received a name 2 hrs after the IC that they had been sending a time period sheet over,” wrote Liz Wessel. Wessel, who co-founded and bought HR startup WayUp and is now a associate at First Spherical Capital, stated her group didn’t take the cash — and that the VC was shocked.
There have been so many tales about VCs sleeping that former a16z associate Arianna Simpson wrote, “Are VCs okay?? Narcolepsy seems to be working rampant.”
There have been, in fact, various tales about VCs signing time period sheets then pulling out final minute, or ghosting, by no means wiring the cash. The much more galling half? A few of these VCs apparently went on to treat the founders like portfolio corporations anyway, asking for company updates or to serve as a reference. One founder stated the VC even wanted a share of the post-acquisition proceeds.
Travis Kalanick, the Uber co-founder famend for his dedication, told a story about discovering {that a} VC was making an attempt to ghost the assembly and go away the constructing. Kalanick stated he adopted the VC to his automobile and pitched from the passenger’s seat.
Not everybody had unhealthy experiences to report. Some founders stated they’ve by no means had something however great experiences with VCs, with a number of even sharing love stories about particular buyers. Sure, most VCs are hardworking, genuinely attempt to be useful, and don’t take naps throughout conferences. However poor experiences are so widespread that Pincus exclaimed, “I f*cking love this second, when founders now not must be afraid to name out VCs for dumb conduct.”
Essentially the most gorgeous tales
Nonetheless, the tales that actually shocked had been the ones posted by Cloudflare founder Matthew Prince. “A Sequoia associate handed on Cloudflare as a result of he didn’t assume a girl may lead a safety infrastructure firm,” Prince wrote. The girl in query is Cloudflare’s co-founder and COO Michelle Zatlyn. On condition that Cloudflare is now an $87 billion market cap firm, with anticipated annual income of $2.8 billion in 2026, the judgment hasn’t aged effectively.
Sequoia associate, Shaun Maguire, no stranger to controversy over his remarks himself, replied that he’s all the time admired Zatlyn, and requested Prince to spill the title of the associate who stated that. Prince punted, “Perhaps over a drink at some point. However I wager you might have a very good guess already.”
However wait, Prince dished extra!
He told a narrative about distinguished investor Vinod Khosla, who provided to speculate after which, in accordance with Prince’s recollection, urged that the founder “fireplace” his co-founders and take their inventory. “I believe the charitable learn was it was a take a look at of my character. However I used to be so offended that we by no means spoke once more. Actually blocked his quantity.”
Prince was fast to add nuance about Khosla: “He’s extraordinarily sensible/intelligent. Has been an unimaginable investor — can’t argue along with his monitor document. Simply not the persona I’d select to work with.”
It’s price noting that recollections of conversations are likely to range, and we don’t know what Khosla really stated, meant, or remembers. However eyes popped at such open discuss one of many Valley’s most profitable, highly effective VCs. Many individuals known as Prince’s candor an example of having “FU” money. Prince, of course, is a billionaire nowadays.
Not all of Prince’s tales forged VCs because the villains. Particularly, he thought he had lined up a easy meet-and-greet on a Monday with Marc Andreessen, the cofounder of enterprise agency a16z. As an alternative, Andreessen confirmed up along with his complete funding group, able to be wowed. The ill-prepared Prince didn’t impress. “I framed the rejection letter they despatched,” he stated of the consequence. Others told similar stories of conferences with Andreessen and his agency.
Maybe the funniest story got here from Julie Fredrickson, a founder-turned-investor, who acquired a name from a VC affiliate earlier than arriving at a agency’s workplace — warning her a few rock formation seen exterior the window that, apparently unbeknownst to the buyers inside, was formed like male genitalia. “The agency will eternally in my thoughts be Dickrock Ventures,” she wrote.
Whereas the Valley’s VCs obtained roasted most closely, founders shared incidents involving international VCs, too. Some VCs additionally dished about pitching to restricted associate buyers.
The threads are price studying not only for the laughs, however for what they reveal: the fundraising course of is opaque, the facility dynamic is actual, and the experiences that founders whisper about privately are much more widespread than the trade tends to acknowledge publicly.
Maybe Isenberg defined the ethical behind all of those tales finest. “In case you’re elevating proper now, simply know: each founder has a narrative like this. The method is bizarre. The facility dynamic is bizarre,” he wrote.
A second lesson could also be: if Andreessen agrees to satisfy with you, he means enterprise.
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