In the tech startup world, a rite of passage is seeking venture capital. The horror stories are a universal experience – and they’re not just scary, but often hilarious. Greg Isenberg, founder of Late Checkout Studio and a podcaster, kicked off a conversation on X with tales of VCs falling asleep during pitch meetings.

One VC reportedly dozed off for 30 minutes in a top-tier firm’s boardroom while pitching for $15 million, with everyone else just ignoring it. The infamous ‘weekend at Bernies’ meeting where Mark Pincus pitched and the partner fell asleep is legendary. However, VCs who fell asleep still sometimes sent term sheets.

Not all horror stories revolve around sleep. Travis Kalanick recounts a VC attempting to ghost out mid-meeting, leading him to follow the VC to his car for an impromptu pitch from the passenger seat. But not everyone had bad experiences; some founders reported only positive interactions with VCs.

The real shock came from Matthew Prince of Cloudflare who revealed that Sequoia Capital passed on their company because a partner thought women couldn’t lead security infrastructure companies – despite Cloudflare’s success and $87 billion valuation. Vinod Khosla, a16z’s cofounder, was reportedly rude in another pitch, suggesting firing co-founders. Prince described these experiences with dry wit, calling it ‘having FU money’.

The stories underscore the often fraught relationship between startups and VCs, but also highlight the importance of transparency and mutual respect in the investment world.