20VC: The Two Biggest Mistakes Every Founder Makes, Why Founders Are Not Ambitious Enough Today, Why Having a Narrow Target Customer is Dangerous & The Three Possible Outcomes in Company Building with Matthew Prince, Co-Founder @ Cloudflare

Posted on 16th October 2023 by Harry

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.

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?

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