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?

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