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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?

10 snips

Jul 11, 2022

Matt Mullenweg, founder of Automattic and a key player in the tech world, shares insights from his journey with WordPress and its global impact. He discusses the evolution of high-performance leadership and the importance of effective listening and decision-making. Mullenweg opens up about personal insecurities and lessons learned during the pre-grieving process following his father's passing. He emphasizes the value of trust and storytelling in leadership and envisions a future that supports individual expression online.

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ANECDOTE

WordPress Origin

Matt Mullenweg's WordPress originated from the open-source project b2/cafelog.
After the original developer left, he and Mike Little forked it, naming it WordPress.

ANECDOTE

Japanese Translation

A Japanese contributor translated WordPress, inspiring Mullenweg with his dedication.
This act showed the potential of WordPress to have a global impact.

ADVICE

Communication is Key

Prioritize clear communication as a leader, focusing on shared understanding and accountability.
Align teams through concise messaging for a solid foundation.

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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