How WordPress Became a Web Giant | Automattic Founder and CEO Matt Mullenweg
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
This episode features Matt Mullenweg, co-creator of WordPress and founder of Automattic, discussing his remarkable 20-year journey in building one of the world's most influential technology platforms. (04:03) WordPress now powers approximately 43% of all websites globally - 10 times more than its nearest competitor. The conversation explores Matt's evolution from a 19-year-old college student trading websites for saxophone lessons to becoming one of the longest-tenured tech founders still actively running their company. Throughout the discussion, Matt shares candid insights about weathering multiple public controversies, the cyclical nature of entrepreneurship, and maintaining resilience while leading in the public eye.
- Core themes include entrepreneurial resilience through public scrutiny, the philosophy behind open-source technology, balancing work intensity with longevity, and navigating legal battles while maintaining company culture and mission focus.
Speakers
Matt Mullenweg
Co-creator of WordPress and founder/CEO of Automattic, Matt started WordPress at age 19 while studying political science at University of Houston. He has led the growth of WordPress to power 43% of all websites globally, making it the dominant content management system worldwide. Under his leadership, Automattic has expanded from a simple blogging platform to encompass commerce through WooCommerce (processing over $30 billion in GMV annually) and messaging through Beeper, while maintaining its commitment to open-source principles and democratic access to publishing tools.
Ju (Host)
Partner at Kleiner Perkins and host of the GRYT podcast, focusing on exploring the personal and professional challenges faced by founders building history-making companies. Ju brings a venture capital perspective to understanding the entrepreneurial journey beyond the typical highlight reel.
Key Takeaways
Embrace the Hero-Villain Cycle as Natural
Matt reveals that every long-term entrepreneur will experience multiple cycles of being celebrated and then criticized publicly. (10:32) He explains that companies go from magazine covers to being untouchable, but this is simply part of the entrepreneurial journey. Rather than avoiding these cycles, successful founders must develop "psychic armor" to engage with criticism without becoming consumed by it. Matt has personally experienced being "canceled" seven times throughout his career, yet each time taught him valuable lessons about resilience and staying true to core principles during difficult periods.
Measure Output, Not Input When It Comes to Work
While acknowledging the importance of hard work, Matt emphasizes that the crucial metric is results, not hours worked. (59:38) He notes that in any given year, only 15-20 hours of work typically define the entire year's success - the key decisions, partnerships, and pivot points. This perspective helps founders focus on high-impact activities rather than getting caught up in performative busyness. The most successful approach involves working smarter by identifying those critical moments and ensuring you have the context and wisdom to execute when they matter most.
Hard Times Define You More Than Success
Matt argues that struggles and failures provide far more valuable learning opportunities than periods of smooth sailing. (18:30) These difficult experiences reveal who your real friends are, teach you about your own resilience, and often inspire new directions or innovations. He credits his early "hot nacho scandal" with motivating him to create anti-spam technology, turning a mistake into a mission to improve the internet. Rather than avoiding challenges, successful founders learn to extract maximum learning from inevitable setbacks.
Take Strategic Breaks to Maintain Long-term Performance
Automattic has implemented a unique policy requiring employees to take 2-3 month sabbaticals every five years, and Matt personally advocates for strategic disconnection. (40:56) These extended breaks serve dual purposes: they rejuvenate individuals who return with renewed mission and purpose, while forcing organizations to eliminate single points of failure and build resilience. Matt discovered that being away from work was actually worse than enduring attacks while engaged in meaningful work, highlighting the importance of finding purpose-driven rather than just avoiding difficulty.
Engage With Criticism While Staying Grounded in Principles
Rather than ignoring negative feedback, Matt advocates for engaging with critics to strengthen your own understanding and arguments. (20:37) He believes you should be able to argue both sides of any position you truly believe in. However, this engagement must be balanced with staying grounded in core principles and values that don't waver based on public opinion. The key is developing the ability to engage with criticism without becoming defined by it, using feedback to refine your approach while maintaining conviction in your fundamental mission.
Statistics & Facts
- WordPress currently powers approximately 43% of all websites globally, which is 10 times more than the next closest competitor. (04:03) This statistic demonstrates the massive scale and dominance of the platform that Matt built from a simple domain registration at age 19.
- WooCommerce, Automattic's e-commerce platform, processes over $30 billion in gross merchandise value (GMV) annually. (48:57) This figure illustrates how the company successfully expanded beyond content management into commerce, enabling other entrepreneurs to build businesses.
- Matt travels over 200 days per year due to Automattic's distributed nature, with employees in 90 countries around the world. (42:47) This highlights the truly global and remote-first culture of the organization, which predates many modern remote work trends.
