Flexport's Ryan Petersen and Cloudflare's Matthew Prince share early VC pitch disasters, from sexist rejections to a $6B market estimate

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 to perform for people who may or may not be conscious. It's a dance. And sometimes you lead and sometimes you follow and sometimes your partner is unconscious. If you're raising right now, just know: every founder has a story like this. The process is weird. The power dynamic is weird. You're not crazy for thinking it's weird. No one talks about it because they want to continue raising. But I'm happy to stick my neck out there. It is weird.

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. Hilarity ensued. 🤪 At one point one of them said: “You don’t seem very prepared.” Which was true because I wasn’t. I framed the rejection letter they sent.

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 a test of my character. But I was so offended that we never spoke again. Literally blocked his number.