EP 81: Matthew Prince (CEO, Cloudflare): Untold Stories Behind the $20B Business That Runs the Internet
The Logan Bartlett Show
Fascination with Fireworks and Explosions
This chapter tells a story about their past where they attempted to make fireworks using instructions they found in the library, but ended up with disastrous results.
Matthew Prince is the Co-Founder and CEO of Cloudflare, a public company doing over a billion dollars in revenue. In the episode, Matthew shares fascinating anecdotes from Cloudflare’s early days and how they scaled up customers from obscure markets to major enterprises. He also explores Cloudflare's commitment to maintaining a high talent bar and candidly reflects on his co-founder’s battle with a devastating illness. Overall, an unfiltered conversation about the journey of building Cloudflare into the powerhouse it is today.
Wired article on Lee Holloway: https://www.wired.com/story/lee-holloway-devastating-decline-brilliant-young-coder/
(0:00) Intro
(1:12) The internet was a fad
(3:49) What is Cloudflare?
(6:42) Project Honeypot
(12:53) Meeting Michelle
(19:12) Buying into the vision
(23:04) The internet was built to support the porn industry
(28:48) Borrowing Money
(37:18) Transparency
(43:08) On Lee Holloway
(52:23) Philosophy behind hiring and talent
(1:00:45) Prioritize curiosity and empathy
(1:02:54) The fairness of an initial offer
(1:07:11) Titles are cheap
(1:21:59) How has being an English major manifested itself?
(1:25:14) Building explosives in high school
(1:32:38) Engaging with fans and critics
(1:38:32) Going public
(1:46:39) Conventional Silicon Valley wisdom
Mixed and edited: Justin Hrabovsky
Produced: Rashad Assir
Executive Producer: Josh Machiz
Music: Griff Lawson
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About the Show
Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.
Executive Producer: Rashad Assir
Producer: Leah Clapper
Mixing and editing: Justin Hrabovsky
Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA
🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1
Follow on Socials
📸 Instagram - https://www.instagram.com/theloganbartlettshow
📱 X - https://twitter.com/loganbartshow
🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow
About the Show
Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.
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