Jan 26, 2024 · 29m · saastr
What's New at WordPress with Matt Mullenweg, CEO of Automattic and Co-Founder of WordPress
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this in-depth interview, Automattic CEO and WordPress co-founder Matt Mullenweg discusses 20 years of open-source stewardship, product diversification across commerce and messaging, navigating AI content proliferation, and best practices for leading distributed teams.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Jason holds 31.5% of the talking time here. How this is scored →
Jason as informed peer 3.7 Guest teaching 4.0 Guest disagreement 1.4 Jason pushing back 1.6
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 24:17 Rejection of the mandatory IPO playbook
Matt pushes back against the conventional venture narrative that companies must IPO, arguing that rigid solutions ignore specific shareholder liquidity needs.
Hardest push from Jason ▶ 11:30 Jason challenges Automattic's revenue captureJason pushes on Automattic's monetization strategy, arguing that holding a 43% web market share should theoretically generate tens of billions in direct ARR.
Biggest teaching moment ▶ 11:48 Ecosystem revenue vs. corporate revenueMatt clarifies that the $10B WordPress revenue pool is intentionally spread across hundreds of independent companies rather than captured by a single Fortune 500 balance sheet.
Jason holds their own ▶ 22:05 Jason details tech IPO dry spell benchmarksJason cites macroeconomic B2B IPO data, referencing HashiCorp, Klaviyo, and the $200M revenue scale requirement to ground the liquidity conversation in market realities.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Web Market Share and the Evolution of Blogging | 3 | 3 | 1 | 1 | Jason draws on his long personal history of daily blogging to ask about market share and the perceived decline of blogging. Matt explains that market share is an outcome rather than a goal and outlines the root causes behind blogging's historical decline. | |
| Navigating AI Content Floods and Value of Authenticity | 4 | 4 | 2 | 2 | Jason raises concerns regarding AI-generated spam devaluing human content using Quora and ChatGPT as examples. Matt reframes human intelligence as inherently sacred and argues AI will serve as a filtering tool for discernment. | |
| Automattic's Business Model and Multi-Product Portfolio | 2 | 4 | 1 | 1 | Jason asks for clarification on the relationship between WordPress and Automattic. Matt breaks down the commercial entity's multi-product portfolio and open-source foundation. | |
| Monetization, Platform Ecosystem, and Internal Reorganization | 5 | 5 | 2 | 3 | Jason challenges Matt on whether Automattic is under-monetizing its 42% web market share and asks about ecosystem coopetition. Matt explains the decentralized $10B economy and the internal taxonomy separating hosting from ecosystem tools. | |
| WordPress Updates and Scaling WooCommerce | 4 | 4 | 1 | 1 | Jason highlights WooCommerce's dominant position in e-commerce from an investor perspective. Matt reveals that Automattic acquired WooCommerce despite poor initial code quality because user demand was unmistakable. | |
| Public Market Strategy and Shareholder Liquidity | 5 | 4 | 2 | 2 | Jason inquires about public market timing and liquidity pressures. Matt demurs on financial market expertise, detailing his founder fiduciary model of personally matching secondary buyers rather than rushing an IPO. | |
| Upcoming Innovations and Best Practices for Distributed Teams | 3 | 4 | 1 | 1 | Jason asks about managing distributed teams in a post-pandemic environment. Matt debunks the assumption that remote work succeeded seamlessly during COVID, emphasizing that regular in-person meetups are mandatory for cultural health. |
Statements from this episode (17)
Mullenweg: Broad Missions Enable Decades-Long Founder Motivation
“I think you just gotta pick a big mission. We started in In 2003 to democratize publishing. And so that was broad enough that we've been able to stay at that and it's banded and it's evolved over time, of course, like what it means to publish has evolved over …”
Mullenweg: Tech Markets Are Mostly Driven by Compounding, Not Fads
“They can sometimes still technology is the funnest marketplace to work in the world. Like people can switch very quickly, but mostly there's compounding.”
Mullenweg: WordPress powers around 42% of websites
“I think we're right now around like 42% of websites.”
Mullenweg: WordPress had 0.8% market share when tracking began
“When we started tracking it, we were at .8.”
Mullenweg: WordPress launched a 100-year hosting subscription plan
“One thing that we launched last year was a 100 year plan. Yeah. So you could subscribe to a hundred year hosting plan.”
Lemkin: Majority of questions and answers on Quora are AI-driven
“I would say the majority of answers and the majority of questions are all AI driven. They're AI prompt driven. And then AIs are answering all these questions.”
Mullenweg: Web will fill with AI spam, but high-quality content survives
“There is a version of AI that the web gets filled with spam and, you know, everything. I think that will happen and it doesn't matter because ultimately what we're looking for is that discernment, that quality.”
Mullenweg: Automattic will migrate Tumblr to run on WordPress
“Tumblr is not running on WordPress yet, but it will. So we're going to switch Tumblr to be powered by WordPress.”
Mullenweg: WooCommerce is Automattic's largest business
“We went into commerce with WooCommerce. Let's democratize commerce. And we have now an open source Shopify, which is our, now our largest business. It's a growing like a weed.”
Mullenweg: The WordPress ecosystem generates about $10 billion annually
“The WordPress ecosystem, I would estimate to be about ten billion dollars per year.”
Mullenweg: Automattic enforces strict neutrality between WordPress.com and third-party hosts
“The rest is that help the host. So they cannot preference part of the rules. They can't reference WordPress.com over any other host in the world. WordPress.com gets access to all the same code APIs, everything that everyone else does.”
Mullenweg: Automattic initially passed on buying WooCommerce over bad code
“And so to be honest, the code was not good. And so like the first couple of times we looked at it, we decided not to buy it because the code was so bad. But at some point, like we're like, they've really figured out something with the users. That's resonating.…”
Lemkin: Klaviyo was the only B2B tech IPO following HashiCorp in 2023
“In B to B after HashiCorp, there was only one IPO, which was Klaviyo in e-commerce last year.”
Mullenweg: Commits to Finding Liquidity for Any Shareholder Wanting Out
“I tell all my shareholders, like, if you ever want to sell a share, I'm your man. I don't know what the price is, but I don't want to lock them up.”
Mullenweg: Automattic's stock is held only by employees and a few dozen investors
“Automatic is a very closely held stock. It's basically our employees and a few dozen of the most sophisticated investors in the world.”
Mullenweg: Automattic Hired 1,200 Remote Workers During COVID and Productivity Suffered
“Our culture suffered. Like we were not as productive during COVID. People thought, oh, this must be, I had other CEOs. This must be great. You just, you're, you must be running at full speed. I'm like, no, I hired 1200 people the past year that have, the past …”