Cloudflare's Worst VC Stories: The Sequoia Pass and the Andreessen Ambush

Matthew Prince @eastdakota · Cloudflare Founder Posted June 5, 2026
“A Sequoia partner passed on Cloudflare because he didn't think a woman could lead a security infrastructure company. Seriously.”
Matthew Prince (@eastdakota), June 5, 2026. Short excerpt; the full thread belongs to its author.

What this teaches

Cloudflare's CEO shares two of the company's worst fundraising stories: a Sequoia partner who passed because he didn't think a woman (co-founder Michelle Zatlyn) could lead a security infrastructure company, and an unprepared meet-and-greet with Marc Andreessen that turned out to be a full pitch. Posted during the June 2026 viral VC horror-story wave.

Why it matters

A founder of an ~$87B company naming a top firm's bias-driven pass, with the co-founder in question now COO. Widely covered by TechCrunch and Newcomer.

Key lessons

  • Passes are often about investor bias, not the business
  • Great companies get rejected by the best firms for bad reasons
  • Treat every investor meeting as a pitch

This is an editorial summary. The full thread, and the credit, belongs to Matthew Prince.

View the thread on X →
Sequoia Capital on VCMatch Sequoia Capital appears in this story. See the firm's stage, check size, and thesis on VCMatch. View investor →