Cloudflare's Matthew Prince extends Doug Leone feud with a funeral joke
Prince's funeral joke responded to Leone recounting a root canal without Novocain, clarifying who Prince says rejected Cloudflare because co-founder Michelle Zatlyn was a woman.
By Ryan Merket · Published · Updated
Primary source: X
Why it matters
Prince's joke offers a public glimpse of how Cloudflare preserved its founder's access to Doug Kramer while transferring formal legal authority to Alissa Starzak.
Matthew Prince (@eastdakota) pointed to former Sequoia leader Doug Leone as the partner who passed on Cloudflare after doubting that a woman could lead a security infrastructure company.
The identification came through a joke. On August 31st, the Cloudflare co-founder and chief executive said he planned to speak at "Doug's funeral" whether invited or not. Prince posted the line above a video shared on X in which Leone said he had undergone a root canal without Novocain. The exchange was banter, not an announcement of a death.
The context reaches back to a more consequential disclosure Prince made in June 2026. He said that, shortly after Cloudflare launched at TechCrunch Disrupt in 2010, a Sequoia partner declined to invest because the partner did not believe co-founder Michelle Zatlyn could lead a security infrastructure company. Prince said he had waited 16 years to tell the story but did not name the partner at the time.
Prince's August post makes clear that he was referring to Leone. Sequoia never invested in Cloudflare, which raised from other firms and grew into a publicly traded internet infrastructure provider under Prince and Zatlyn.
The episode turns Prince's funeral line from a stray executive joke into a pointed reference to one of Cloudflare's formative fundraising rejections. It also attaches a name to Prince's allegation about the judgment Zatlyn faced as a woman building an infrastructure company.