GoKawiilAsking venture capitalists for investment is a rite of passage for tech founders. This has led to another universal experience: the VC pitching horror story. A massive conversation sharing such stories has taken place all week on X with the comments both funny and infuriating. We read through them all to find the most interesting ones so you don’t have to.
Greg Isenberg, a startup podcaster, newsletter writer, and founder of Late Checkout Studio — a holding company whose previous ventures include a company acquired by WeWork — got the conversation started with a story about a VC falling asleep during a pitch meeting. Isenberg has a large following on X, and his post clearly 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. Everyone just kept going,” he shared on X.
VCs sleeping through pitch meetings was far and away the most common horror story shared. Not just drowsing, but full on zonked.
Zynga founder Mark Pincus told his VC-asleep story. “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.
Interestingly, falling asleep didn’t mean the VC wouldn’t invest. Multiple founders reported receiving term sheets from partners who’d dozed off during the pitch.
“I once pitched a partnership in 2015 for our Series A where one partner (famous Midas lister) fell asleep & another couldn’t stop scowling. Got a call 2 hrs after the IC that they were sending a term sheet over,” wrote Liz Wessel. Wessel, who co-founded and sold HR startup WayUp and is now a partner at First Round Capital, said her team didn’t take the money — and that the VC was shocked.
There were so many stories about VCs sleeping that former a16z partner Arianna Simpson wrote, “Are VCs ok?? Narcolepsy appears to be running rampant.”
There were, of course, more than a few stories about VCs signing term sheets then pulling out last minute, or ghosting, never wiring the money. The even more galling part? Some of these VCs apparently went on to treat the founders like portfolio companies anyway, asking for company updates or to serve as a reference. One founder said the VC even wanted a share of the post-acquisition proceeds.
Travis Kalanick, the Uber co-founder renowned for his determination, told a story about discovering that a VC was attempting to ghost the meeting and leave the building. Kalanick said he followed the VC to his car and pitched from the passenger’s seat.
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