Mar 21, 2022 · 1h 17m · how-i-built-this
WordPress & Automattic: Matt Mullenweg
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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 episode of 'How I Built This,' Matt Mullenweg recounts how an open-source side project created in his teenage years grew into WordPress and Automattic, a multi-billion-dollar distributed company powering over 40% of the internet.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 32.7% of the talking time here. How this is scored →
Guy as informed peer 3.7 Guest teaching 1.9 Guest disagreement 0.2 Guy pushing back 0.1
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:04:00 Matt on competitor grudges and Wix dispute
Matt directly addresses intense rivalries like Wix stealing proprietary code, explaining the legal brinksmanship before quoting Buddhist philosophy to explain letting go of grudges.
Hardest push from Guy ▶ 1:03:50 Guy challenging founder claims of ignoring competitorsGuy pushes back against tech founders claiming they ignore competitors, pointing out that in 25 years of interviewing he knows everyone watches their competition closely.
Biggest teaching moment ▶ 11:16 Matt breaking down true quotation typography vs prime marksMatt educates Guy on web typography mechanics, explaining that standard keyboard quotation keys are single prime marks for measurement rather than actual apostrophes.
Guy holds their own ▶ 1:11:00 Guy comparing corporate culture policy to CoinbaseGuy brings up his interview with Brian Armstrong to drill into how Automattic managed explosive political discourse across its internal channels.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Early Life, Music, and Building Computers | 4 | 1 | 0 | 0 | Guy Raz establishes rapport by asking about Matt's performing arts high school background and connection to famous alumni like Beyonce and Solange. Matt elaborates on his early days playing saxophone and building PC computers at home. | |
| First Online Communities and Web Publishing | 3 | 2 | 0 | 0 | Guy asks how Matt learned web development in the early 2000s without modern tooling. Matt explains early internet chat protocols like IRC, basic website building, and launching Photomat. | |
| Discovering Open Source and b2/cafelog | 4 | 3 | 0 | 0 | Guy mentions the challenge of typography on the early web, such as curly quotes. Matt details the exact HTML entities and explains the difference between single prime marks and apostrophes before talking about b2/cafelog. | |
| The Dilemma and Forking b2 | 3 | 2 | 0 | 0 | Matt explains his famous blog post 'The Blogging Software Dilemma' after Michel Valdrighi disappeared, leading Mike Little to suggest forking b2 together. Guy prompts Matt on the low financial costs and the open-source collaboration model. | |
| Naming and Launching WordPress | 3 | 1 | 0 | 0 | Guy asks about naming WordPress and the hobbyist dynamic between Matt and Mike Little. Matt shares how Christine Tremoulet came up with the name WordPress and recounts Michel Valdrighi blessing WordPress upon his return. | |
| Early Adoption and Server Expenses | 3 | 1 | 0 | 0 | Guy compares early WordPress to Wikipedia's collaborative model. Matt explains how consolidating different forks led to fast community growth and high server expenses relative to his modest living costs. | |
| Tech Company Interest and the CNET Offer | 4 | 2 | 0 | 0 | Guy inquires about the sudden surge in tech giant interest and Matt's decision to pick CNET. Matt explains his strategic awareness of intellectual property rights inspired by Motown artists. | |
| Moving to San Francisco and CNET Culture | 4 | 1 | 0 | 0 | Guy explores Matt's psychological transition to San Francisco and whether he suffered imposter syndrome. Matt shares how jazz performance and tech support volunteering gave him confidence to embrace being the least experienced person in the room. | |
| Pitching WordPress.com to CNET | 3 | 2 | 1 | 0 | Matt recounts pitching WordPress.com internally to CNET executives and their dismissive reaction to amateur bloggers. He recalls an awkward meeting where WordPress published articles in seconds while CNET's legacy CMS took 20 minutes. | |
| Founding Automattic and Remote Hiring | 3 | 2 | 0 | 0 | Guy asks about incorporating Automattic and making the first remote hire. Matt explains hiring Donncha O Caoimh in Ireland and building a multi-user version of WordPress. | |
| The Spam Link Crisis and De-indexing | 4 | 2 | 0 | 0 | Guy and Matt discuss the accidental creation of invisible spam links on WordPress.org to pay bills. Matt candidly recounts learning about being de-indexed by Google while on vacation in Venice and hunting for Wi-Fi at the airport. | |
| Creating Akismet and the Freemium Model | 3 | 2 | 0 | 0 | Matt details creating Akismet as a machine-learning anti-spam filter to atone for past spam mistakes. He explains his Robin Hood freemium model of keeping it free for individuals while charging commercial entities. | |
| Raising Capital and Hiring CEO Tony Schneider | 4 | 2 | 0 | 0 | Guy asks about raising a formal funding round. Matt explains how Om Malik connected him with investors and Tony Schneider, whom Matt brought in as the CEO adult supervision. | |
| Golden Tickets and Viral Adoption | 3 | 2 | 0 | 0 | Matt discusses creating the Willy Wonka-inspired golden ticket invite system to throttle server load and discovering people reselling tickets on eBay. He also recalls realizing WordPress powered nearly 1% of the internet from a Google report. | |
| Turning Down the $200 Million Buyout | 4 | 1 | 0 | 0 | Guy presses on Matt's decision to turn down a $200 million acquisition offer at age 23. Matt explains that after calculating what he would actually spend money on, he realized he already had his dream job. | |
| Secondary Sale and Navigating the 2008 Crisis | 4 | 2 | 0 | 0 | Matt explains the secondary sale structure orchestrated by investors to take money off the table. Guy asks about weathering the 2008 financial crash, and Matt describes how advertising drops and the Great Firewall in China hit the business. | |
| Becoming a Full CMS and Distributed Culture | 4 | 2 | 0 | 0 | Guy asks how Automattic maintained culture without centralized offices. Matt describes transitioning from blogging tool to full CMS and pioneering fully distributed, remote work decades ahead of the tech industry. | |
| Enterprise Growth, Open Source Licenses, and Wix | 5 | 3 | 2 | 1 | Guy asks about open-source vulnerabilities to copycats, citing the conflict with Wix. Matt clarifies the exact GPL licensing requirements regarding downstream redistribution and explains moving past grudges against competitors. | |
| Stepping into the CEO Role | 4 | 2 | 0 | 0 | Guy and Matt discuss Matt taking over as CEO in 2014 and Tony Schneider seamlessly moving to R&D. Matt speaks movingly about dealing with grief after the loss of his father in 2016. | |
| Navigating the Pandemic and Global Perspectives | 4 | 3 | 1 | 0 | Guy references Brian Armstrong's political speech ban at Coinbase and asks how Automattic handled internal discourse during the pandemic and 2020 social unrest. Matt explains how having staff across 93 countries provided global perspective beyond US-centric debates. | |
| Automattic's Scale, Vision, and Hard Work vs. Luck | 4 | 2 | 1 | 0 | Guy asks whether Automattic will pursue an IPO and asks Matt to reflect on skill versus luck. Matt notes that public offerings aren't necessary given modern secondary liquidity, while acknowledging both immense hard work and fortunate breaks. |
Statements from this episode (36)
Mullenweg's early paid project was a $500 website for his saxophone teacher
“He paid me, you know, 500 bucks, and I made him a website. But then, for no good reason, actually, I put forum software on his website, so there was, like, this forum where people could post, and you could ask him questions, but really, it just became, like, a…”
Mullenweg built a pre-Flickr photo website using open-source PHP script Gallery
“Well, I used some open source software called Gallery, and it was a PHP script that would allow pre-Flickr, pre-Facebook, pre-anything to post photos and have galleries online.”
Mullenweg and Mike Little forked abandoned b2/cafelog code to create WordPress
“And so that's what Mike and I ended up doing, was we took the code from B two cafe log, kind of this abandoned code, and we did what an open source is called, we forked it, F-O-R-K. And start, use that as the base to start creating something new.”
A Houston blogger named Christine coined the name 'WordPress'
“One of the bloggers named Christine thought of this name WordPress, and she called me. She was like, I'm so excited. I'm so excited. There's this name, and the .org is available. You should go for it. And I just fell in love with it. So that's how we chose the…”
Original b2 creator officially crowned WordPress as its successor
“When he came back, he had seen that, like, oh, all these things blossomed out of this thing. And so he looked at all the different forks and very graciously sort of crowned WordPress the official continuation of B-II.”
All b2 forks except one eventually joined the WordPress project
“So all of the forks, except for one, joined up with WordPress.”
WordPress launched with only five or six core developers
“WordPress at the time of launch probably had like five or six main developers, but dozens and dozens of people would make like one small change or one little tweak to it.”
Default backlinks in early WordPress installs boosted developers' search rankings
“Every install of WordPress had links to all the main developers. So because these thousands and thousands of websites were all linking to the word Matt, that would make Google think, oh, these websites, you know, Photomat.net, et cetera, is the number one site…”
CNET pioneered modern content management systems with hundreds of daily authors
“And so they invented a lot of, like, what we call CMS, or content management systems, because they were the first to really have hundreds of authors and thousands and thousands of posts and be publishing every day.”
Mullenweg joined CNET because it allowed him to retain code IP
“And the job I took, which was for CNET, I took it for a few reasons. First, they allowed me to retain the intellectual property to the code I was creating. So normally when you join a company like Google, you sign over the rights to everything you create there…”
Accessible open-source licensing depends fundamentally on respecting copyright law
“I'm a big believer in copyright. I choose to license my copyright in a way that's accessible to everyone, but, The core of that is a respect for copyright.”
Mullenweg: Employee job-hopping is the fault of companies, not workers
“I think that the people joke about, or they criticize that people jump between companies. There's no loyalty anymore. But I think that's the fault of the company, not of the people. It's that they're not treating people like they want them around for 20 years.”
CNET leadership rejected Mullenweg's pitch to build hosted WordPress internally
“I had gone to CNET and said, hey, WordPress is cool, but it's really complicated to set up. If we can make it easy, you just click a few buttons and you get a WordPress, I think that'd be really popular. Let's do that. And that was my pitch to CNET. And I even…”
Early tech blogs outcompeted CNET using faster software and personal writing
“Yeah, and they were moving faster, because the software was faster. They were writing more personally, so it was more interesting and fun to read, often in first person. They didn't know it at the time, but CNET was kind of being out-competed.”
Early WordPress beat enterprise CMS software purely on speed and ease
“And it's true, the software didn't do most of the things their software did. It was worse in so many ways, but it was better in a way that mattered, which was like speed and ease of use.”
Mullenweg incorporated Automattic via LegalZoom, paying early staff $1,000 monthly
“I incorporated Automatic on a website like LegalZoom, like one of these, like you press a few buttons and it becomes a C Corp. So I incorporated the company, and yeah, just started to pay the first few people. You know, not a lot, like a thousand bucks a month…”
Open-source contributors helped WordPress outpace superior competitors through faster iteration
“When WordPress started, it was worse than all the other software out there. It wasn't very good. It didn't have all the same features and everything like that. But because there were literally later hundreds of people working on it from all over the world, it …”
Mullenweg accidentally invented an SEO spam technique using hidden CSS links
“And I unintentionally invented a new way to spam. I basically was able to use some code called CSS to have the code on the website, but if you visited it in a browser, it would be invisible. But if you visited as a bot, like Google, it would look like the word…”
Google de-indexed WordPress.org after discovering hidden CSS spam links
“Then Google came in, and of course, they were pretty mad that this code had outsmarted their search engine. So they actually removed WordPress from Google.”
Spam blocker Akismet was Automattic's first commercial product
“The first commercial product I created Was called a kismet, named by my sister.”
Automattic built a razor-and-blades model with free WordPress and paid add-ons
“Part of the idea was that WordPress would always be free, and that's maybe the razor, but perhaps we could figure out some razor blades we could sell, some add-on services that would be really most useful to people who are using it more seriously, and then bus…”
Early WordPress spread via default 'Powered by WordPress' footer links
“One thing we did at the time was every website running WordPress, by default, in the template, it would say, powered by WordPress. And so, when you visit a website you liked, you would see this link and be like, oh, let me click on that.”
Resold WordPress invites on eBay revealed monetization potential to founders
“And then these tickets started to sell on eBay. So people would get the free ticket, and then they would start to list it or sell it, and tickets were starting to sell for like, 9000 dollars, 120 dollars on eBay. And we were like, huh, maybe people will pay fo…”
A mid-2000s Google survey revealed WordPress powered 0.8% of the web
“Google had done this survey, published a survey of the internet. It was kind of like a statistical analysis of all the websites that were in the Google index and the code they used. And there was this part of the report that said, yeah, and then on .8% of webs…”
Automattic received a $200M buyout offer with only 20 employees
“Because we were only 15, 20 people at the time. I still owned well over half the company. And so this idea that the for-profit company that we'd been building for about two years was gonna be, had this offer. A very serious offer turned a million dollars was r…”
Mullenweg turned down a $200M buyout to keep his dream job
“And when I really thought about it, what I would most want to do. I would want to code every day. I'd want to travel the world and meet WordPress users all over the world. I'd want to make software that people used and do it with people I enjoyed working with.…”
Automattic raised $10M at a $200M valuation for secondary liquidity
“So what they did was they took the two hundred million dollars, and they said, okay, that'll be the valuation of the company. We'll do a new round of investment, but instead of putting in one million dollars, we're going to put in ten million dollars into the …”
China represented up to a third of WordPress before being blocked
“The other thing was about a quarter or a third of our usage at the time was in China. And China decided that the Great Firewall would block WordPress.com.”
Every company acquired by Automattic eventually abandoned its physical office
“Usually what happens is when the company joins, we acquire them, they say, oh, we really need their office. We say, okay, we'll pay the rent, we'll keep it going, we'll keep the lease going. But then once they start to learn our way of working, fewer and fewer…”
Mullenweg: Wix violated copyright by making derived WordPress code proprietary
“What we often go to bat for and fight for, including with this company called Wix, is what they did was they took our code, and then the code they derived from it, so the modifications they met, were, they said were proprietary and secret to Wix. And so what w…”
An extended legal fight with Wix could have bankrupted Automattic
“When Wix did that, they had way more money than us. So a legal battle would have taken years, and even possibly bankrupted automatic, depending on how long it went.”
Automattic currently employs staff distributed across 93 countries
“I have colleagues in 93 countries.”
An Automattic employee was arrested in Belarus for anti-regime blogging
“We had a colleague get arrested in Belarus because he was blogging and speaking out against the dictatorship there and things.”