Three of our worst VC stories
Cloudflare CEO Matthew Prince shares negative venture capital experiences, including sexism and miscommunication.
Matthew Prince recounted two negative venture capital encounters. A Sequoia partner rejected Cloudflare because he believed a woman could not lead a security infrastructure company. In a separate incident, Prince met with Marc Andreessen expecting a casual introduction but found himself in a formal pitch meeting with the entire partnership team present. Unprepared for a pitch, Prince was told "You don't seem very prepared" and received a rejection letter he later framed. A commenter shared an anecdote about sleeping through a 30-minute portion of a Series A pitch meeting at a top-three VC firm without acknowledgment from anyone present.
What HN community is saying
The thread shifted from discussing VC horror stories to highlighting positive counterexamples. Multiple commenters noted that positive VC interactions exist but generate less attention than scandals. One detailed account described a VC who convinced fellow board members to sacrifice their own equity to compensate a founder for a lawyer's incorporation error, potentially preventing a $125 million loss. Other commenters praised specific VCs like Casey Aylward, Eric Vishria, and Tony Conrad. The consensus view: most VCs are professional and helpful, but conflict-free transactions lack the narrative appeal of dramatic rejections.
One commenter observed that VC dynamics have shifted from scarcity to abundance of capital, making VCs more eager to maintain founder trust. Use of Stripe Atlas or startup-aware lawyers was recommended to prevent stock plan issues.