Asking enterprise capitalists for funding is a ceremony of passage for tech founders. This has led to one other 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 them all to discover the most fascinating ones so that you don’t have to.
Greg Isenberg, a startup podcaster, e-newsletter 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 few VC falling asleep throughout a pitch assembly. Isenberg has a big following on X, and his submit 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 Collection A. 12 individuals in the assembly. Certainly one of the 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 commonest horror story shared. Not simply drowsing, however full on zonked.
Zynga founder Mark Pincus instructed 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 throughout the pitch.
“I as soon as pitched a partnership in 2015 for our Collection A the place one associate (well-known Midas lister) fell asleep & one other couldn’t cease scowling. Acquired a name 2 hrs after the IC that they have 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 staff 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, quite a lot of 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 trying to ghost the assembly and depart the constructing. Kalanick stated he adopted the VC to his automotive 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 just a few even sharing love stories about particular buyers. Sure, most VCs are hardworking, genuinely strive to be useful, and don’t take naps throughout conferences. However poor experiences are so frequent that Pincus exclaimed, “I f*cking love this second, when founders now not have to be afraid to name out VCs for dumb conduct.”
Essentially the most gorgeous tales
Nonetheless, the tales that really shocked have been the ones posted by Cloudflare founder Matthew Prince. “A Sequoia associate handed on Cloudflare as a result of he didn’t assume 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 nicely.
Sequoia associate 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 title of the associate who stated that. Prince punted, “Possibly over a drink someday. However I wager you have got a great guess already.”
However wait, Prince dished extra!
He told a narrative about distinguished investor Vinod Khosla, who provided to make investments after which, in accordance to Prince’s recollection, instructed that the founder “hearth” 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 good/intelligent. Has been an unimaginable investor — can’t argue together with his observe report. Simply not the persona I’d select to work with.”
It’s value noting that recollections of conversations have a tendency to range, and we don’t know what Khosla really stated, meant, or remembers. However eyes popped at such open discuss certainly one of the Valley’s most profitable, highly effective VCs. Many individuals referred to as Prince’s candor an example of having “FU” money. Prince, of course, is a billionaire today.
Not all of Prince’s tales forged VCs as the villains. Particularly, he thought he had lined up a easy meet-and-greet on a Monday with Marc Andreessen, the co-founder of enterprise agency a16z. As an alternative, Andreessen confirmed up together with his entire funding staff, prepared to be wowed. The ill-prepared Prince did not 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 before arriving at a agency’s workplace — warning her a few rock formation seen outdoors the window that, apparently unbeknownst to the buyers inside, was formed like male genitalia. “The agency will endlessly in my thoughts be Dickrock Ventures,” she wrote.
Whereas the Valley’s VCs received roasted most closely, founders shared incidents involving international VCs, too. Some VCs additionally dished about pitching to restricted associate buyers.
The threads are value studying not only for the laughs, however for what they reveal: The fundraising course of is opaque, the energy dynamic is actual, and the experiences that founders whisper about privately are much more frequent than the business tends to acknowledge publicly.
Maybe Isenberg defined the ethical behind all of those tales finest. “If you happen to’re elevating proper now, simply know: each founder has a narrative like this. The method is bizarre. The ability dynamic is bizarre,” he wrote.
A second lesson could also be: If Andreessen agrees to meet with you, he means enterprise.
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