EP 81: Matthew Prince (CEO, Cloudflare): Untold Stories Behind the $20B Business That Runs the Internet

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

🎙 Listen to the show

Apple Podcasts: https://podcasts.apple.com/us/podcast/the-logan-bartlett-show/id1606770839

Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1

Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg

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Follow on Socials

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🐦 Twitter - https://twitter.com/loganbartshow

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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

🎙 Listen to the show

Apple Podcasts: https://podcasts.apple.com/us/podcast/the-logan-bartlett-show/id1606770839

Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1

Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg

🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1

Follow on Socials

📸 Instagram - https://www.instagram.com/theloganbartlettshow

🐦 Twitter - 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, 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.