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Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072

Every single 20VC episode is recorded with Riverside.FM. It is the one product that I could not live without. Try it today here (https://creators.riverside.fm/20VC) and use the code 20VC for 15% off. ----------------------------------------------- Matthew Prince is the co-founder and CEO of Cloudflare, on a mission is to help build a better Internet. Matthew has scaled Cloudflare to over $1BN in revenue, $20BN in market cap, and over 3,200 employees. Today the company runs one of the world’s largest networks, which spans more than 200 cities in over 100 countries. Matthew is a World Economic Forum Technology Pioneer, a member of the Council on Foreign Relations, winner of the 2011 Tech Fellow Award, and serves on the Board of Advisors for the Center for Information Technology and Privacy Law. ----------------------------------------------- Timestamps: (0:00) Intro (00:43)Personal Origins and Experiences (02:31) Professional Insights and Company Milestones (23:35) Entrepreneurial Challenges and Lessons (46:00) Reflections on Startups and Investment (01:02:49) Quick-fire Round ----------------------------------------------- In Today’s Episode with Matthew Prince We Discuss: 1. From Selling Fireworks to Public Company CEO: How did Matthew first make money selling fireworks as a kid? Does Mathew believe in the trope “you have to love what you do”? What does Matthew know now that he wishes he had known when he started Cloudflare? 2. Money, Identity and Happiness: Why does Matthew feel many of the most successful founders lose their way when they leave their companies? How does he assess Gates, Bezos and others? Does Matthew tie his own identity to Cloudflare and the success of the company? How does Matthew evaluate his own relationship to money today? How has it changed over time? How does Matthew keep score today on how he is doing? What is success to Matthew? 3. The Three Outcomes for Companies Today: What are the three outcomes available to companies today? What is the worst and why? What are the two biggest mistakes Matthew sees founders make today? Why does Matthew know that diverse teams are more successful? What is the proof? What is Matthew’s single biggest advice to founders when it comes to selecting a co-founder? 4. Focus is BS: You Have to Have Mega Ambition: Why does Matthew believe it is BS to have a very specific target customer from the offset? What does Matthew believe are the benefits of not having an ICP in the early days? What are the biggest pieces of VC advice to founders that Matthew knows to be wrong? ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Matthew Prince on Twitter: https://twitter.com/eastdakota Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ------------------------------------------- #MatthewPrince #Cloudflare #20vc #HarryStebbings

Matthew PrinceguestHarry Stebbingshost
Oct 15, 20231h 7mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Cloudflare’s Matthew Prince On Vision, Co‑Founders, And Avoiding Slogs

  1. Matthew Prince, co-founder and CEO of Cloudflare, discusses his entrepreneurial upbringing, the origin story of Cloudflare, and how his co-founder dynamics shaped the company’s culture and success.
  2. He and host Harry Stebbings debate whether early-stage startups should focus narrowly on niche customer segments versus leading with a grand, expansive vision, especially on the venture-backed path.
  3. Prince reflects on identity, happiness, money, and the often-troubled lives of founders after exiting their companies, emphasizing the importance of purpose and mission over wealth.
  4. He also shares hard-earned lessons on co-founder selection, handling difficult conversations, the impact of Cloudflare on global events like the Ukraine war and Iranian protests, and why he prefers public market investors’ alignment and accountability.

IDEAS WORTH REMEMBERING

5 ideas

For venture-backed startups, think huge from day one, then execute narrowly.

Prince argues that in the venture path you must articulate an ambitious, world-scale vision (e.g., “run the internet”) to attract top talent and capital, even while your early product work and customer engagement may be focused on concrete, smaller steps.

The worst outcome isn’t failure; it’s the multi-year “slog.”

He frames startup outcomes as wild success, quick failure, or a long, low-growth grind where founders stagnate and investors disengage; he sees rapid failure as far preferable to a decade lost in a marginal business.

Pick co-founders who are complementary, not clones—or you’ll fight over control.

Prince contrasts a failed prior startup with three near-identical co-founders to Cloudflare, where he, Michelle, and Lee had sharply differentiated skills and clear “lanes,” reducing conflict and increasing coverage of the problem space.

Co-founder alignment comes from clear decision rights and mutual respect, not constant harmony.

At Cloudflare, each founder owns specific domains (e.g., product vs. go-to-market), and disagreements are resolved by deferring to the domain owner’s decision and then committing, which minimizes drama and re-litigation.

Diversity is a competitive advantage, not a PR exercise.

Prince emphasizes that diverse teams—across perspectives and backgrounds—see different risks and opportunities, just like a diversified portfolio, and that Cloudflare’s varied founding DNA helped it reimagine its market.

WORDS WORTH SAVING

5 quotes

Our vision is to run the internet.

— Matthew Prince

The second-best outcome is quick failure. The worst outcome by far is the slog.

— Matthew Prince

Don’t pick the people who you had lockers next to in junior high school.

— Matthew Prince

More diverse teams win. The reason you do diversity is because more diverse teams win.

— Matthew Prince

Not having money sucks… but cars are cars and houses are houses. After a point, it’s not what motivates you.

— Matthew Prince

Matthew Prince’s entrepreneurial background and the genesis of Cloudflare from Project HoneypotFounder identity, purpose, and the psychological toll of success and exitHow to choose and work with co-founders, including division of responsibilitiesDebate on niche focus versus bold, expansive vision for venture-backed startupsCloudflare’s role in global geopolitics and digital civil society (Ukraine, Iran, sanctions)The realities of money, happiness, and definitions of success for foundersVCs vs. public market investors and the “slog” as the worst startup outcome

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