There’s no shortage of founder-VC bonhomie on the internet, but every once in a while a founder spills the beans on what some VC interactions can be like.
Matthew Prince, CEO and co-founder of Cloudflare, recently shared a thread of stories from the company’s early fundraising days — and they are quite something. The stories cover the period between 2010 and 2012, when Cloudflare was a young startup that had just launched at TechCrunch Disrupt.
The Sequoia Pass
Prince’s first story involves a Sequoia partner who passed on Cloudflare for a reason that had nothing to do with the business. “A Sequoia partner passed on Cloudflare because he didn’t think a woman could lead a security infrastructure company,” Prince wrote. “Seriously.”
The woman in question was Michelle Zatlyn, who co-founded Cloudflare alongside Prince and Lee Holloway and today serves as the company’s President. Sequoia’s pass came shortly after Cloudflare’s debut at TechCrunch Disrupt in 2010.
The Unprepared a16z Pitch
The a16z story is a different kind of tale — less about bias and more about a communication breakdown that somehow worked in its own way.
Prince says he got an introduction to Marc Andreessen and scheduled a meeting for a Monday. “I thought it was just a casual meeting,” he wrote. “He thought it was a pitch and brought the whole @a16z partnership team.”
Things did not go smoothly. “At one point one of them said: ‘You don’t seem very prepared,'” Prince recalled. “Which was true because I wasn’t.”
Cloudflare didn’t get the investment. Prince says he framed the rejection letter they sent. The meeting was in March 2012.
The Vinod Khosla Dinner
The most striking story involves Vinod Khosla, founder of Khosla Ventures and a prominent force in Silicon Valley for decades. This one happened during Cloudflare’s Series C round, when Khosla Ventures had already given the company a term sheet.
Vinod took Prince, Zatlyn, and Holloway out to dinner. Near the end of the meal, Zatlyn and Holloway got up to use the restroom — and that’s when things got uncomfortable.
“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?'” Prince wrote.
Prince added that “the charitable read was it was a test of my character” — but says he was so offended that he cut ties with Khosla entirely. “We never spoke again. Literally blocked his number.”
It is worth noting what “them” meant in this context. Zatlyn went on to build Cloudflare into a publicly traded company alongside Prince, and today serves as its President. Holloway, who was the technical architect behind Cloudflare’s platform, had to step down in 2015 due to frontotemporal dementia — a rare neurological disease. When Cloudflare filed for its IPO in 2019, Prince and Zatlyn chose the internal codename “Project Holloway” in his honour, calling him the “genius who architected our platform.”
Khosla, for his part, has never been shy about his opinions on founders and investors. He has previously said that 90% of investors add no value to companies and 70% actively add negative value — a view that reads with some irony given Prince’s account of their dinner. More recently, Khosla criticised the founders of Windsurf for leaving their team behind in a Google acquisition, saying he wouldn’t work with them again.
Where Cloudflare Stands Today
The investors who passed — or were blocked — missed out considerably. Cloudflare went public on the NYSE in 2019 and posted over $2 billion in revenue in 2025, running one of the world’s largest networks across more than 275 cities in over 100 countries. And things might not have gone this way had he taken up Khosla on his offer at the dinner table that night.