The Five Layers of Sharing Thoughts and Ideas

WordPress

I’ve been thinking a lot about mimetic formation, how a thought becomes an idea, and how that idea gestates and evolves as it’s progressively shared in wider and wider circles.

During a recent product review of Day One, I was struck by how central the app is to my perspective on humans, relationships, and what we share. There are several layers to it, ranging from your innermost thoughts to what you share with the world. Each layer has its own context, challenges, and possibilities, and Automattic offers technology and products tailored to each.

1. Layer one is your internal thoughts. Your consciousness, what exists only in your mind, or what I like to call meatspace. This space is yours and yours alone. This generative space is at the core of human creativity and existence.

2. Layer two is triggered as soon as you put something into a medium, like writing it down. It’s everything that leaves your head, but is just reserved for you. In the past, we only had physical journals. Today, we have Day One as our strongest product in this space, but many people also have a private WordPress installation just for themselves. There are so many tools out there that help you create! Colors, brushes, canvases. Harper, for example, helps you write better — think of it as an open-source Grammarly, right now just in a few limited contexts, but in the future everywhere you write. 

3. Layer three is you and someone else. This is everything you share with one other person, which is an incredibly sacred act. Shared journals on Day One, messaging on Beeper, DMs, private blogs with your best friend. A shared Google doc. This is its own special space. It has an intimacy and privacy that is core to the human experience. This is also phase 3 of Gutenberg, which is all about real-time co-editing and collaboration. This layer is the one I’m most excited about expanding in 2025 and 2026.

4. Layer four is sharing within a finite group. N+1. It’s a space of collaboration and brainstorming with families, tribes, and teams. P2, Linear, Github, group chats, and cozy communities. You lose some of the intimacy of layer three but gain more group intelligence.

5. Finally, we have the fifth layer. This is the public layer, where I have spent a lot of my time at Automattic. It is an extremely competitive space of social media and blogs: WordPress, WordPress.com, and Tumblr. Once you publish publicly, you open yourself up to the beauty and chaos of the wider world. The best reason to blog is comments, the people who find you and add to your thoughts, who you never would have imagined. This is a crucible, but makes your own writing and thinking so much better, it’s worth the mishegoss. 🙂

This has been kicking around in my head and at layer four for a while. Thanks to Kelly Hoffman for helping me get this to layer five.

P.S. Happy 22nd birthday to WordPress! Very excited about the new AI team on .org.

It’s a busy speaking season! I just spoke at the Intelligent Change summit, and will be at SaaStock in Austin on May 14, SXSW London, on June 4, Brilliant Minds in Stockholm, and WordCamp EU in Basel, Switzerland, on June 7.

Remember Gravatar?

Automattic

Gravatar has always been about giving people control over their identity online. One avatar, one profile, synced across the web, verified connections, with a fully open API.

Gravatar is a true open identity layer for the internet, and now for AI. 

For developers, we’ve rolled out mobile SDKs and a revamped REST API that lets you fetch avatars and profile data with just an email hash. Whether you’re building a blog, a community, or an AI agent that needs to understand who it’s talking to, Gravatar provides the infrastructure to make identity seamless and user-centric. 

It’s free, open, and built with developers in mind. We believe identity should belong to the individual, not be locked behind proprietary platforms. Gravatar is our contribution to that vision.​

If you haven’t checked it out lately, now’s a great time to explore what Gravatar can do for your app or your online presence. And think about how your apps can drive more Gravatar signups.

Berkshire Hathaway Meeting

Automattic

I’ve checked off a bucket list item: I’m attending a Berkshire Hathaway shareholder meeting. It’s really an event! Thousands flock to Omaha, Nebraska, for the legendary Q&A sessions with Warren Buffett and shareholder deals. They’ve made it quite the circus, with every Berkshire Hathaway company having a booth of some sort, and typically selling their goods at a discount or with exclusive items you can only buy there, like Warren Buffett and Charlie Munger Squishmallows (which of course I got, to complement my bronze busts).

It’s strange to have a Dairy Queen booth selling $1 ice cream (cash only!) next to NetJets, but those juxtapositions are part of the Berkshire vibe—it’s very high/low, like Costco (a big Berkshire holding). There’s also an element of WordCamps or a Salesforce Trailblazer event in that you can tell there’s a “type” of person that’s easy to spot who’s a Berkshire enthusiast. A lot of Berkshire brands are also WordPress users: Duracell, GEICO, Acme Brick, Berxi, MiTek. I think there is a lot of mimetic overlap between the values of open source and the values of building a Berkshire company.

As with any big gathering, the side events are also great, and I was honored to have a fireside chat with a friend and Buffett protégé, Tracy Britt Cool. To an audience of about 60+ CEOs in the Kanbrick community, we talked about Automattic’s history and some of the latest happenings in tech; AI was definitely on people’s minds in the Q&A. They had questions for me, but I also feel like I have a ton to learn from this group that has built founder or family-owned businesses with an average of 80-100M of revenue, the kind of thing that is the engine of the American economy.

It makes me pine for the day when we can have more shareholders in Automattic; I think it would be an amazing cohort of folks that believe in open source and the open web, invested together and learning from each other, and I could imagine an event very much like these shareholder meetings. It’s so much more powerful when you build a business where your customers are also a community.

Update: I knew this would be a special one because it was Warren’s 60th, but he really went above and beyond by announcing his intention for Greg Abel to take over as CEO at the end of the year. The standing ovation was a special moment, 60 years of 19.9% compounding returns! I think the future of Berkshire is very bright because he’s shared so much of his worldview that there are others that have made it their own.

Reflecting

Personal, WordPress

I know there’s been a lot of frustration directed at me specifically. Some of it, I believe, is misplaced—but I also understand where it’s coming from.

The passing of Pope Francis has deeply impacted me. While I still disagree with the Church on many issues, he was the Pope who broke the mold in so many ways, inspiring me and drawing me back to the Catholic faith I grew up with, with an emphasis on service, compassion, and humility. His passing on Easter Monday, a holiday about rebirth, feels historic. Moments like that invite reflection—not just on personal choices, but on the broader systems we’re a part of.

My life, which was primarily about generative creative work that was free for everyone to use, has been subsumed by legal battles. From the start, I’ve said this: after many rounds of negotiation that I approached in good faith, WPE chose to sue. In hindsight, those conversations weren’t held in the same spirit, and that’s unfortunate.

But we can’t rewrite the past. What we can do is decide how we move forward.

The maker-taker problem, at the heart of what we’ve been wrestling with, doesn’t disappear by avoiding it. If we’re serious about contributing to the future of open source, and about preserving the legacy of what we’ve built together, we need space to reset. That can’t happen under the weight of ongoing litigation. The cards are in WPE hands, a fight they’ve started and refuse to end.

So I’m asking for a moment of reflection for us all as stewards of a shared ecosystem. Let’s not lose sight of that.

Greatest Hits

Meta

I’ve been blogging now for approximately 8,465 days since my first post on Movable Type. My colleague Dan Luu helped me compile some of the “greatest hits” from the archives of ma.tt, perhaps some posts will stir some memories for you as well:

Where Did WordCamps Come From? (2023)

A look back at how Foo Camp and Bar Camp inspired WordCamps.

Getting Real Feedback as a CEO (2018)

How do you make sure you get good information when you’re CEO? Something we’ve been trying that’s been working is having an anonymous internal forum. Like Blind, but internal to the company, and really anonymous, without anything linking a user ID to a comment.

Wix and the GPL (2016)

That time Wix built their closed-source mobile app on GPL code.

What I Miss and Don’t Miss About San Francisco (2015)

Self explanatory 🙂

Advice About Advice (2015)

Why you need to think things through from first principles and not just blindly follow advice.

Why the Web Still Matters (2014)

A guest post by Ben Thompson of Stratechery on why “the web is dead” comments were wrong in 2014. Still true today!

The Four Freedoms (2014)

A discussion of Stallman’s four open source freedoms. Our open source Bill of Rights, if you will.

The Intrinsic Value of Blogging (2014)

On ignoring vanity metrics and blogging for intrinsic reasons

What’s in My Bag 2014, 2016, 2017, 2018, 2020, 2023, 2025

What I’ve been carrying in my travel bag 

Why Your Company Should Have a Creed (2011)

I’m really jazzed that dozens of companies have adopted this or similar ideas since then.

1.0 is the Loneliest Number (2010)

On the importance of releasing quickly and getting feedback.

The Twitter API (2010)

A discussion on the Twitter API missing the boat on, as Jack Dorsey put it, becoming a protocol.

I Miss School (2010)

Just like they say, youth is wasted on the young, I think I squandered school when I was in it.

What Startup Idea Would I suggest? Start a Bank (2009)

There’s been a lot of action in the payments space since 2009. For new companies, we have Square (2009), Stripe (2010), and Wealthsimple (2014), among others. Ally Bank (rebranded from GMAC in 2010) has also been trying to provide a modern customer-focused experience.

Six Steps to Kill Your Community (2009)

Platform and product anti-patterns.

In Defense of the GPL for Open Source Projects (2009)

This was a response to a popular post about how GPL open source projects would lose out to projects under licenses like MIT, BSD, and Apache. I didn’t agree then and I don’t agree now. 

The Way I Work (2009)

Self explanatory 🙂

Infrastructure as Competitive Advantage (2008)

On the importance of performance, reliability, and security. This was a core priority for us and it shows. We dominate the competition on third-party performance comparisons at the platform level and on the default user experience, and our security is top-notch.

The Price of Freedom and Open Source Licenses (2007)

A response to a user who wanted the ability to remove GPL freedoms from WordPress.

The PHP5 Transition (2007)

How PHP5 forced us to divert time and attention away from users to deal with migration costs.

Mitch Kapor vs. Mark Zuckerberg (2007)

At Startup School, Kapor advocated for having team diversity while Zuckerberg advocated for a “young and technical” because the best work comes from young people. Now that Facebook (Meta) has grown up, Zuckerberg is doing what Kapor said companies should do and not what Zuckerberg said companies should do! Zuckerberg’s trusted people aren’t young anymore and aren’t being replaced by the young.

Sun Isn’t Relevant to Startups (2007), and Followup (2007)

A discussion of Sun’s Startup Essentials program and Jonathan Schwartz’s (then CEO of Sun) reply.

The RSS Feed Validator is Dead to Me (2006)

The RSS 2.0 feed validator is old news today but the experience here is a good example of why people didn’t take any of these validators seriously and they’re all old news

There’s No Correlation Between Hours Worked and Work Done (2006)

Self explanatory 🙂

Should We Have Hidden Options? (2005)

A discussion of the hidden cost of hidden options.

We probably missed some, if there’s a post you think should be included leave it in the comments.

6.8

WordPress

WordPress 6.8 Cecil is out, and it’s a great release. It’s unbelievable that it’s already been downloaded over 6 million times as I write this. That feeling never gets old.

It’s a funny time in WordPress because there are a lot of really interesting open questions:

  • Can we iterate faster with canonical plugins?
  • What’s the fun thing we can put in to celebrate 7.0, and when will that be? (I was rooting for real-time co-editing like Notion/Canva/Google Docs.)
  • How can we use AI to automate our manual work around WordPress.org?
  • Can AI help us make 60k+ open source plugins and themes in the directory more secure? (I think so.)
  • What should we do with our 13k issue backlog? (That’s a lot of bug gardening.)
  • How will AI change how people build and update sites?
  • Just like RSS and web standards supercharged WordPress for the podcasting and search revolutions, what standards or APIs can we ship to help 40%+ of the web work with AI agents? (Plus an entire rabbit hole of all the new sloppy crawlers using so many resources.)

Some of these broad changes are mixed. At one point, I used Google to search for things and would visit their top result, which is great for website owners. Nowadays, Google pulls almost everything I need into the results page, so I don’t see as many random sites. But on Perplexity, sometimes I’ll read the answer and then visit 4-5 of the sources it cites to learn more, so I’m visiting 4-5x more random websites, usually powered by WordPress, than I would have even in the early days of Google. We don’t know how this all plays out yet.

These questions are also against the backdrop of some of the brightest minds in WordPress spending more time with legal code than computer code, which could last until 2027 or longer with appeals.

Speaking for myself, I was in my first deposition today. I really appreciated the due process and decorum of the rule of law, and just like code, law has a million little quirks, global variables, loaded libraries, and esoteric terminology. But wow, after a full day of that, I’m mentally exhausted. Hence, I’m posting about 6.8 after it’s had 6 million downloads. I’m more impressed than ever by what smart lawyers do, and the entire thing, though sometimes imperfect and frustrating, is a blessing to our democracy. However, I can’t wait to return to spending the plurality of my days with engineers and designers again. I’m sure many other folks in the WordPress community would agree.

The long-anticipated “Big Sky” AI site builder on WordPress.com went live today. It combines several models and can create logos, site designs, typography, color schemes, and content. It’s an entirely new way to interact with and edit a brand-new or existing WordPress site. This AI agent will make WordPress accessible to an entirely new generation and class of customers, and it will be a power tool for professionals to do things in minutes that used to take them hours.

Automattic Operating System

Automattic

I was interviewed by Inc magazine for almost two hours where we covered a lot of great topics for entrepreneurs but almost none of it made it into the weird hit piece they published, however since both the journalist and I had recording of the interview I’ve decided to adapt some parts of it into a series of blog posts, think of it as the Inc Article That Could Have Been. This bit talks about some of the meta-work that myself and the Bridge team at Automattic do.

At Automattic, the most important product I work on is the company itself. I’ve started referring to it as the “Automattic Operating System.” Not in the technical sense like Linux, but the meta layer the company runs on. The company isn’t WordPress.com or Beeper or Pocket Casts or any one thing. I’m responsible for the culture of the people who build those things, building the things that build those things. It’s our hiring, our HR processes, our expenses, the onboarding docs; it’s all of the details that make up the employee experience — all the stuff that shapes every employee’s day-to-day experience.

Take expense reports. If you’ve got to spend two hours taking pictures of receipts and something like that, that’s a waste of time. You’re not helping a customer there. We switched to a system where everyone just gets a credit card. It does all the reporting and accounting stuff automatically. You just swipe the card and it just automatically files an expense report. Sometimes there’s an exception and you have to work with the accounting rules, but it just works and automates the whole process most of the time.

Another commonly overlooked detail is the offer letter. We think so much about the design of our websites and our products. We have designers work on that and we put a lot of care and thought into it. But I realized we didn’t have the same attention to detail on our offer letter. When you think about it, getting an offer letter from a company and deciding to take it is a major life decision, something you only do a handful of times in your life.  This is one of the things that determines your life path. Our offer letter was just made by attorneys and HR. No designer had looked at it right. We hadn’t really thought about it from a product experience point of view. And so it was just this, generic document with bad typography and not great design. But it’s important, so one of the things we did was redesign it. Now it has a nice letterhead, great typography, and it’s designed for the end user.

I realized that the salary and stuff was buried in paragraph two. It was just a small thing in the document! Well, what’s key when you’re deciding whether to take a job? Start date, salary, you know, that sort of thing, so we put the important parts at the very top.

And then there’s the legal language. All the legal stuff, which is different in every country. We have people in 90 countries, so there’s all the legal stuff that goes in there. And then it has this nudge inspired by the behavioral economics book, Predictably Irrational.

There’s the story about how, if you have an ethics statement above where you sign the test or something, people cheat less. So I thought, well, what’s our equivalent of that? We have the Automattic Creed. It’s an important part of our culture. So we put the creed in, it says

I will never stop learning. I won’t just work on things that are assigned to me. I know there’s no such thing as a status quo. I will build our business sustainably through passionate and loyal customers. I will never pass up an opportunity to help out a colleague, and I’ll remember the days before I knew everything. I am more motivated by impact than money, and I know that Open Source is one of the most powerful ideas of our generation. I will communicate as much as possible, because it’s the oxygen of a distributed company. I am in a marathon, not a sprint, and no matter how far away the goal is, the only way to get there is by putting one foot in front of another every day. Given time, there is no problem that’s insurmountable.

It’s not legally binding, but it’s written in the first person, you read it and you kind of identify with it and then you sign below that. We want people who work at the company who identify with our core values and our core values really are in the creed.

These sorts of things are key to our culture. And they’re universal. Again, we have people from over 90 countries. These are very different cultures, yes, and very different historical backgrounds and cultural makeups. But what’s universal? We have our philosophies that we apply every day regardless of where you were born or where you work.

It’s so funny that my random re-engagement with Radiohead re-emergence coincides with them doing a new entity that might mean something. I did a poll on Twitter and people preferred OK Computer to Kid A 78%!

Grok told me: “The band has recently registered a new limited liability partnership (LLP) named RHEUK25, which includes all five members—Thom Yorke, Jonny Greenwood, Colin Greenwood, Ed O’Brien, and Philip Selway. This move is notable because Radiohead has historically created similar business entities before announcing new albums, tours, or reissues.”

Real WordPress Security

WordPress

One thing you’ll see on every host that offers WordPress is claims about how secure they are, however they don’t put their money where their mouth is. When you dig deeper, if your site actually gets hacked they’ll hit you with remediation fees that can go from hundreds to thousands of dollars.

They may try to sell you a security plan that for example at Godaddy goes from $300 to $700 a year on top of your hosting. (Don’t be fooled by the low entry price, look at renewal.) It’s heartbreaking to hear stories of non-technical people forced into these high fees to fix something their host should have prevented in the first place.

When a host is powered by WP.cloud, it doesn’t need to do this because hacks are so incredibly rare. (That’s why it may appear more expensive, but the total cost of ownership or being a WP.cloud-powered host is much lower when you factor in human time.)

One problem we’ve had on WordPress.com is we do all these amazing things and don’t tell anyone about it, something we’re trying to change with our focus this year on developers and developer tooling. One great example is we’re so confident about our security, if your site gets hacked we’ll fix it for free! We’ve actually been doing this for the better part of a decade, just never mentioned it anywhere.

Pressable (which is WP.cloud-powered) does a better job talking about these things and has a nice landing page on malware cleaning and hack recovery that says essentially the same thing.

WordPress has done a ton over the years to move the hosting industry around upgrading PHP and MySQL, PHP extensions, free SSL, and in general using our clout to advocate for user rights and freedoms from even the largest hosting companies, and I’m proud to say there are a good number, for example the ones you see at WordCamps, that have not just embraced these values but actually been more commercially successful as they’ve done so. I hope security and auto-upgrades not just for core but for plugins and themes becomes the next standard. (Jetpack does this for free, some hosts charge $100/yr per site.)

On Lenny’s Podcast

Press

One of my must-read newsletters for the past several years has been Lenny’s Newsletter, probably best known for its writing on growth and product management, which really means it covered everything you need to create a great company.

It expanded into a really well-done podcast; Lenny has always had a knack for finding the best guests and asking the best questions, so when he invited me on I was very excited.

He really wanted to address some of the things that people said I wasn’t being asked, so we do touch on the WP Engine / Silver Lake attacks, but we also covered a lot of my philosophy of why open source is important, philanthropy, and why you should build a movement, not just a product.

You can watch it on YouTube, or listen to it on your favorite podcast app like Pocket Casts.

Some others he has done that I really enjoyed are Nan Yu from Linear, Marc Benioff from Salesforce, Katie Dill from Stripe, Mihika Kapoor from Figma, Drew Houston from Dropbox, and of course the famous Founder Mode one with Brian Chesky.

WordCamp Asia and Maha Kumbh Mela

Asides

It’s been fantastic being in the Philippines for this year’s WordCamp Asia. We have attendees from 71 countries, over 1,800 tickets sold, and contributor day had over 700 people! It’s an interesting contrast to US and EU WordCamps as well in that the audience is definitely a lot younger, and there’s very little interest in “wpdrama” du jour, in fact I’ve had tons of amazing conversations of support and talking about the strength and growth of the community.

Some of the earliest international WordCamps I went to were in Manila and Davao, back in 2008. (I’m going to share some pictures at the start of my talk.) Between that and spending lots of time in Daly City when I moved to San Francisco when I was 20 I have developed a fondness for the cuisine, creativity, family orientation, and warmth of the culture here.

After this I’ll be taking a bit of time off for a trip to the big Hindu religious pilgrimage in India, the Maha Kumbh Mela, which is currently on a 144 cycle. It’s the largest human gathering in the world, with some days measured with tens of millions of people visiting. I’ll be returning to my Photomatt roots as well and bringing my big camera rig, right now a Nikon Z 7II, and two lenses: 24-70 2.8 and 70-200 2.8.

In high school when 5% of your class doesn’t like you it’s like 3-5 people.

Running a company of 1,700+ when 5% doesn’t like you, that’s 85 people! That fills a room.

150k followers and 5% don’t like you now you have a small stadium of 7,500 people.

It’s still 5%.

Ed Catmull on Change

WordPress

I’ve been really enjoying the book Creativity Inc by Ed Catmull of Pixar, it was recommended to me by my colleague Dave Martin a while back and I finally got around to it. There’s an interesting story in it where George Lucas had asked him to develop a film editing system that was digital.

While George wanted this new video-editing system in place, the film editors at Lucasfilm did not. They were perfectly happy with the system they had already mastered, which involved actually cutting film into snippets with razor blades and then pasting them back together. They couldn’t have been less interested in making changes that would slow them down in the short term. They took comfort in their familiar ways, and change meant being uncomfortable. […] If left up to the editors, no new tool would ever be designed and no improvements would be possible.

This made me think a lot about the early days of Gutenberg and the huge resistance it had in the community, including causing the fork of ClassicPress. Now that we’re much further along there’s a pretty widespread acceptance of Gutenberg, and it’s responsible for the vast majority of all WP posts and pages made, however if we had taken a vote for whether it should happen or not, it probably wouldn’t have ever gotten off the ground.

What’s funny is if you go back even further, using a visual WYSIWYG editor in the first place was very controversial, and many people didn’t want the classic editor brought into WordPress.