Two of our worst VC stories:

@marketswithmadison

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Why it worked

The video likely resonated with founders and those in the startup ecosystem due to its relatable and often shocking "horror stories" about venture capital. Sharing these experiences, especially those involving dismissive or unprofessional behavior from investors, taps into a common frustration and provides a sense of shared experience and validation.

Summary

The video shares three stories about negative experiences founders have had with venture capitalists. The first two stories highlight dismissive or unprofessional behavior from VCs during pitches, while the third details a condescending and offensive remark made by a VC during a dinner meeting.

Structure

1Introduction to VC horror stories
2Story 1: Sequoia partner dismisses female founder
3Story 2: VC falls asleep during pitch
4Story 3: Khosla Ventures partner makes offensive remark
5Reflection on investor behavior and its impact on founders

Product placement

The video discusses stories about venture capital firms and investors, specifically mentioning Sequoia, Andreessen Horowitz (@a16z), and Khosla Ventures. It also references Cloudflare as a company that received investment.

On-screen text

Matthew Prince @eastdakota X.com Two of our worst VC stories: 1. A Sequoia partner passed on Cloudflare because he didn't think a woman could lead a security infrastructure company. Seriously. 🥺 2. I got introduced to @pmarca. Meeting got scheduled for a Monday, which should have been a clue. I thought it was just a casual meeting. He thought it was a pitch and brought the whole @a16z partnership team. Hilariously, at one point one of them said, "I'm very prepared." Which was true, but I framed the rejection letter. 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. I kept presenting my Series A slides to an unconscious man in a Herman Miller chair and somehow that was considered normal. That's venture capital. You might fly across the country for a firm for people who may or may not be paying attention. It's a dance. And sometimes you follow and sometimes you're unconscious. If you're raising right now, no founder has a story like this. One more I forgot until just reminded: 3. Khosla Ventures wanted to invest in our Series C. Vinod took me, Michelle, and Lee out to dinner after he'd given us a term sheet. Near the end, Michelle and Lee got up to use the restroom. Vinod leaned over and said, "I'm impressed with you, not so much with them, what if you fire them and I'll give you all their stock?" I think the charitable read was it was of my character. But I was so offended that he spoke again. Literally blocked his number. 7:34 AM · 6/5/26 · 4.3M Views Relevant Jack Zhang That's why he's kind of a dick. Matthew Prince I've actually heard this story before. 2.5M Views 212 33K 1.3K Quotes Post your reply

Original caption

Here’s the tea in Silicon Valley 🫖 Founders are airing VC horror stories live on X 👀 #siliconvalley #startups #tea #technews #cloudflare

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Transcript

Two of our worst VC stories: 1. A Sequoia partner passed on Cloudflare because he didn't think a woman could lead a security infrastructure company. Seriously. 🥺 2. I got introduced to @pmarca. Meeting got scheduled for a Monday, which should have been a clue. I thought it was just a casual meeting. He thought it was a pitch and brought the whole @a16z partnership team. Hilariously, at one point one of them said, "I'm very prepared." Which was true, but I framed the rejection letter. 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. I kept presenting my Series A slides to an unconscious man in a Herman Miller chair and somehow that was considered normal. That's venture capital. You might fly across the country for a firm for people who may or may not be paying attention. It's a dance. And sometimes you follow and sometimes you're unconscious. If you're raising right now, no founder has a story like this. One more I forgot until just reminded: 3. Khosla Ventures wanted to invest in our Series C. Vinod took me, Michelle, and Lee out to dinner after he'd given us a term sheet. Near the end, Michelle and Lee got up to use the restroom. Vinod leaned over and said, "I'm impressed with you, not so much with them, what if you fire them and I'll give you all their stock?" I think the charitable read was it was of my character. But I was so offended that he spoke again. Literally blocked his number. That's why he's kind of a dick. Matthew Prince I've actually heard this story before. It seems like almost every founder I know has some version of this story about investors doing ridiculous shit. And some of these investors are getting away with it for far too long. Because the money was the only thing that ever really mattered to them, not the people behind the company that will make them money. And it seems like, on the outset, that might be starting to change.