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?
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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