20VC: Matt Mullenweg on Relationships to Risk, Money and Insecurity as a Leader | Lessons from a Parent’s Passing and the Pre-Grieving Process | What is High Performance in Leadership Today?

Posted on 11th July 2022 by Harry

Matt Mullenweg is the Founder of Automattic, the force behind WordPress, Tumblr, WooCommerce, Jetpack, Longreads, Simplenote, Pocket Casts, and more. What started as a simple open-source blogging platform, Matt has turned into one of the most significant internet properties of our generation, now powering over 43% of sites on the internet. Alongside Automattic, Matt also invests through Audrey Capital and has backed the likes of Stripe, SpaceX, Gitlab, and Sendgrid to name a few.

In Today’s Episode with Matt Mullenweg We Discuss:

1.) The Origins of WordPress:

  • How did Matt start the for-profit, Automattic, as a 19-year-old, having been a lead developer for WordPress?
  • What were the clearest signs to Matt in the early days that WordPress could change the world?
  • What does Matt know now that he wishes he had known at the beginning of WordPress?

2.) Matt Mullenweg: The Essence of Leadership:

  • What does high performance mean to Matt? How has that changed over time?
  • What does truly great listening mean to Matt as a leader today? Where do many get this wrong?
  • How does Matt approach decision-making today? What are the two types of decisions?
  • What are Matt’s biggest insecurities in leadership today? How have they changed over time?

3.) Matt Mullenweg: The Person:

  • Why does Matt have insecurities around his body? How do those insecurities manifest?
  • What did Matt learn about himself in the pre-grieving process before his father’s passing?
  • How does Matt assess his own relationship to risk today?
  • How does Matt think through his relationship to money today? Has it changed?

4.) WordPress: The Company:

  • Why did Matt decide it was the right decision to buy Tumblr? Why did Matt make himself the CEO earlier this year?
  • With many strong cashflow businesses within Automattic, how does Matt think through the balance between growth and profitability?
  • Why does Automattic not have any emails within the company? How do 2,000 people communicate so effectively?

Items Mentioned in Today’s Episode:

Matt’s Favourite Book: Principles by Ray Dalio

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