2025-04-10 01:14:06
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.
2025-03-22 06:15:05
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.
2025-03-20 07:06:02
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.”
2025-03-16 04:46:22
With the world changing so quickly, it’s hard to find alpha, but the best way is by following the brightest thinkers. This CNBC interview with Ray Dalio and Marc Benioff is good, but it’s way better if you go to the livestream about 25 minutes in and see the full discussion without the editing. You hear what these great thinkers actually think, rather than what an editor thought you’d enjoy. A little bit of friction gets you a lot more information.
2025-03-08 19:07:49
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.)
2025-03-04 22:19:50
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.
