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 way of all of them to search out essentially the most attention-grabbing ones so that you don’t need to.
Greg Isenberga startup podcaster, publication author, and founding father of Late Checkout Studio — a holding firm whose earlier ventures embrace an organization acquired by WeWork — received the dialog began with a narrative a couple of 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 prime 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 saved going,” he shared on X.
VCs sleeping by way of 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 good friend who arrange the assembly and requested if i ought to preserve presenting and he or she mentioned sure. It was ‘weekend at bernies’ meets Silicon Valley,” he wrote.
Curiously, falling asleep didn’t imply the VC wouldn’t make investments. Multiple founders reported receiving time period sheets from companions who’d dozed off throughout the pitch.
“I as soon as pitched a partnership in 2015 for our Sequence A the place one accomplice (well-known Midas lister) fell asleep & one other couldn’t cease scowling. Bought 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 offered HR startup WayUp and is now a accomplice at First Spherical Capital, mentioned her staff didn’t take the cash — and that the VC was shocked.
There have been so many tales about VCs sleeping that former a16z accomplice Arianna Simpson wrote“Are VCs okay?? Narcolepsy seems to be operating rampant.”
There have been, after all, 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 mentioned the VC even wanted a share of the post-acquisition proceeds.
Travis Kalanick, the Uber co-founder famend for his willpower, told a story about discovering {that a} VC was trying to ghost the assembly and go away the constructing. Kalanick mentioned he adopted the VC to his automotive and pitched from the passenger’s seat.
Not everybody had unhealthy experiences to report. Some founders mentioned they’ve by no means had something however great experiences with VCswith just a few even sharing love stories about particular traders. 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 need to be afraid to name out VCs for dumb habits.”
Essentially the most gorgeous tales
Nonetheless, the tales that really shocked had been the ones posted by Cloudflare founder Matthew Prince. “A Sequoia accomplice handed on Cloudflare as a result of he didn’t suppose a lady could lead on a safety infrastructure firm,” Prince wrote. The lady in query is Cloudflare’s co-founder and COO Michelle Zatlyn. Provided 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 accomplice, Shaun Maguire, no stranger to controversy over his remarks himself, replied that he’s at all times admired Zatlyn, and requested Prince to spill the identify of the accomplice who mentioned that. Prince punted, “Perhaps over a drink sooner or later. However I guess you will have a great guess already.”
However wait, Prince dished extra!
He told a narrative about distinguished investor Vinod Khosla, who provided to speculate after which, in keeping with Prince’s recollection, steered 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 unbelievable investor — can’t argue together with his observe report. Simply not the character I’d select to work with.”
It’s value noting that recollections of conversations are inclined to fluctuate, and we don’t know what Khosla truly mentioned, meant, or remembers. However eyes popped at such open speak about 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 today.
Not all of Prince’s tales solid 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 a substitute, Andreessen confirmed up together with his complete funding staff, able to be wowed. The ill-prepared Prince didn’t impress. “I framed the rejection letter they despatched,” he mentioned 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-investorwho acquired a name from a VC affiliate earlier than arriving at a agency’s workplace — warning her a couple of rock formation seen outdoors the window that, apparently unbeknownst to the traders inside, was formed like male genitalia. “The agency will ceaselessly in my thoughts be Dickrock Ventures,” she wrote.
Whereas the Valley’s VCs received roasted most closely, founders shared incidents involving international VCstoo. Some VCs additionally dished about pitching to restricted accomplice traders.
The threads are value studying not only for the laughs, however for what they reveal: the fundraising course of is opaque, the ability dynamic is actual, and the experiences that founders whisper about privately are much more widespread than the business tends to acknowledge publicly.
Maybe Isenberg defined the ethical behind all of those tales greatest. “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 fulfill with you, he means enterprise.
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