Lenny’s Podcast: The Creator of WordPress Opens Up — Becoming an Internet Villain, Taking a Stand, and the Future of Open Source

Guest: Matt Mullenweg (Founder and CEO, Automattic)
Host: Lenny Rachitsky
Date: March 2, 2025

Episode Overview

In this candid and wide-ranging interview, Matt Mullenweg, the founder of WordPress and CEO of Automattic, sits down with Lenny Rachitsky to address the recent drama and controversy swirling around him and the WordPress community. They cover everything from open source philosophy and the rise of WordPress, to the WP Engine legal conflict, the future of AI and open source, and how Automattic approaches acquisitions. Matt provides unvarnished insights into how he handles intense scrutiny and criticism, reflects on what it truly means to steward open source, and explains why taking a stand — even at personal cost — is sometimes required to defend community principles.

Key Discussion Points & Insights

1. Matt’s Background & Journey into Open Source

• WordPress Origins (05:44–09:28):

  • Co-founded WordPress at 19 as a fork of abandoned project B2, aiming for freedom and extensibility.
  • Dropped out of college, moved to San Francisco, worked at CNET, then started Automattic to offer a SaaS version of WordPress and build adjacent products like Akismet and Jetpack.
  • “That was 19 years ago. So that's now grown to be, you know, over 1,700 people in actually 90 countries. So we've actually been fully distributed and remote and asynchronous from the start, which I think is one of our superpowers.” – Matt, [06:41]

• Automattic Scale & Open Source Focus:

  • Automattic employs 1,700 people across 90 countries, runs WordPress.com, WooCommerce, Day One, Beeper, and more.
  • WordPress powers 43% of all websites, making it the dominant CMS worldwide.

2. Personal Interests and Philanthropy

• Bay Lights Project (11:37–15:32):

  • Matt helped catalyze and fund the iconic Bay Lights project on the Bay Bridge, mortgaging his own condo to ensure completion.
  • He’s on the board of Illuminate, advancing public art in San Francisco.
  • “To me, philanthropy is a barbell: you need to work on the basics, but also the things that lift up the soul, like public art.” – Matt, [14:41]

• Love for Jazz & Community Engagement:

  • Runs a jazz club in San Francisco, integrating arts into his life philosophy (09:28).

3. Open Source Philosophy & Community Building

• What Drives Matt (17:56–21:35):

  • Open source seen as the most important idea of our generation, vital for user freedom in the software age.
  • The GNU GPL license and its Four Freedoms are embedded in WordPress: use, study, modify, and share.
  • “If the founding fathers were around today, I think they would be open source advocates.” – Matt, [18:57]

• Building Movements, Not Just Products (35:48–39:13):

  • Stresses the role of movement-building: “Don’t just build a product, build a movement.”
  • Rituals, art (“Code is poetry”), and a plugin/theme ecosystem act as moats.
  • Open platforms survive when ecosystem participants make more than the core does; WordPress enables this through open source.

4. AI, “Fake Open Source,” and the Future

• AI, Open Source, and Llama (23:52–27:14):

  • Critiques Meta’s Llama as “fake open source” due to user restrictions, violating core open source principles.
  • “If at some point you have to ask for permission, you’re at the whim of this company... There’s just ambiguity there.” – Matt, [24:16]

• AI Models Trained on Open Source (27:42–30:53):

  • Sees value in open source’s impact: AI models are trained on public code, making open source the foundational fabric for the future.
  • Excited for AI agents to eventually contribute most code, automate security scanning, and “hard problems of maintenance” in open source.

5. WordPress, Leadership, and Governance

• Community and Governance (35:20–39:13; 61:52–66:28):
  • Stresses importance of stewardship with “radical delegation,” but ultimately believes in visionary leadership to keep WordPress relevant across decades.
  • Resists putting WordPress’s governance entirely to committee or a nonprofit board: “Great software is never created by committee… it often reflects the vision of a leader.” [62:16]
  • Sees community power in forking as a fail-safe check; humility about eventual succession but preference for a “mayor,” not a committee.

6. The WP Engine Drama — Trademarks, Lawsuits, and Internet Villainy

• Conflict Origin (39:48–52:29):

  • WP Engine, once a WordPress ecosystem ally, was acquired by Silver Lake private equity in 2019, allegedly stopped contributing and began leveraging the WordPress trademark in confusing, brand-damaging ways.
  • Turned off WordPress core features (e.g., revisions/undo) to save costs, diluting user experience.
  • “They're offering something called WordPress. I refer to it as a bastardized, hacked up version. It's diluting our brand.” – Matt, [39:39]

• Negotiations to Lawsuit (48:23–49:46):

  • After failed, allegedly bad-faith negotiations and mounting evidence of user confusion/harm, Matt banned WP Engine from sponsoring community events and went public. WP Engine sued WordPress.org, Automattic, and Matt personally.
  • “Sometimes you have to stand up to bullies and fight to protect your open source ideals.” – Matt, [45:44]
  • Matt acknowledges that every time he takes an unpopular stance it’s met with a wave of outrage, but the core contributors and users mostly stay.

• Trademark Structure and Governance (57:38–61:52):

  • Describes public, complex tripartite trademark/license structure: nonprofit foundation, Automattic (with commercial license), and personal stewardship. Modeled after branches of government for checks and balances.

• Handling Criticism & Outrage (52:17; 71:46–73:29):

  • Matt candidly admits the emotional toll of being cast as a villain, seeing social media amplify negativity, and learning the limits of short-form engagement.
  • “A lie gets around the world seven times before truth has time to get out of bed.” – Matt, [73:31]
  • Finds balance in core community support and metrics (“things are quite healthy”), tries to focus on nuance and long-form dialogue.

• Advanced Custom Fields Controversy (68:55–71:09):

  • Blocked WP Engine’s plugin access during legal dispute, released a fork (“Secure Custom Fields”) to patch vulnerabilities and uphold user security. Court ordered reversal; both plugins now exist side-by-side.

7. Automattic’s (and Matt’s) Acquisition Strategy

• Building a Product Holding Company (76:42–88:52):

  • Automattic acquires promising products and teams to accelerate growth or expand the open-source/open-web “stack.”
  • Bought Tumblr for $3M from Verizon in 2019, currently migrating its backend to WordPress, exploring new monetization models.
  • “It was free like a puppy, not free like beer.” – Matt, [82:03]
  • Most acquisitions (e.g., WooCommerce, Day One) are “take something good and make it better”; turnarounds like Tumblr are rare and challenging.

• Automattic by the Numbers (86:14):

  • Revenue is approximately $500M ARR, with WooCommerce as a major driver.

8. Private Equity and Stewardship — Drawing the Line

• PE Companies vs. Automattic’s Approach (86:38–88:52):
  • Sees difference in intent and impact: “control” vs. minority investments, efficiency vs. dark patterns.
  • “Judge by track record, not just the label. We want to be a good steward of communities and software.” – Matt, [88:32]

9. Life Missions, New Ventures, and Final Thoughts

• Personal Missions (89:02–90:11):

  • Passions: democratize publishing (WordPress), commerce (WooCommerce), and now messaging (Beeper).
  • Early-stage excitement in Beeper, a new messaging aggregator soon to launch broadly.

• On Hiring and Community (93:15):

  • Automattic is hiring globally, uniquely pays the same salaries regardless of geography.

Notable Quotes & Memorable Moments

• On the Power of Open Source:
  “If we don't have fundamental freedoms attached to software, we're not truly free.”
  — Matt Mullenweg, [18:59]

• On AI and Open Source:
  “I do believe the utility of proprietary software eventually approaches zero.”
  — Matt, [27:55]

• On Product Leadership:
  “Don’t just build a product, build a movement.”
  — Matt, [36:02]

• On Facing Criticism:
  “Previously like 1% of the world thought I was terrible, and now I feel like it’s up to like 4 or 5%... as you know, something negative, you feel seven times more than something positive.”
  — Matt, [52:29]

• On Public Outrage:
  “A lie gets around the world seven times before truth has time to get out of bed.”
  — Matt, [73:31]

• On Acquisition Philosophy:
  “It was free like a puppy, not free like beer.”
  — Matt, on buying Tumblr, [82:03]

Timestamps for Key Segments

• Matt’s origins in open source & Automattic’s story: [05:44–09:28]
• Automattic’s global scale & WordPress dominance: [09:42–10:48]
• Bay Lights & philanthropy: [11:37–15:32]
• Open source philosophy: [17:56–21:35]
• AI models, “fake open source,” & Llama: [23:52–27:14]
• Open source’s future and AI code contributions: [30:53–33:43]
• Community and movement-building: [35:20–39:13]
• WP Engine drama & legal conflict: [39:48–52:29]
• Trademark governance & Automattic’s structure: [57:38–61:52]
• Criticism, Internet outrage, and leadership: [52:17–54:35]; [71:46–73:29]
• Advanced Custom Fields plugin controversy: [68:55–71:09]
• Acquisition strategy & Tumblr’s story: [76:42–84:57]
• Private equity vs. Automattic’s approach: [86:38–88:52]
• Closing thoughts, Beeper, and hiring: [89:02–93:15]

Episode Flow for New Listeners

This conversation offers a deep, authentic exploration of modern open source leadership through the lens of WordPress’s most critical moment in years. From origin stories to current controversy, from AI and philosophical principles to hard-nosed business realities, Matt Mullenweg is transparent, reflective, and at times vulnerable about the pressures and paradoxes of being a “hero-turned-villain” — and why, for open source to thrive, uncomfortable stands sometimes need to be taken.

For further details, follow Matt (“photomatt”) on social or visit Automattic’s careers page for open roles.