To announce and celebrate the incredible engineering achievement of the Beeper team launching local bridges and their premium model we hosted a fun event in Automattic’s space in NYC. The app side of Automattic does some amazing work, and the applications themselves are pretty well known and reviewed, but many don’t know they’re part of Automattic, so it was a good opportunity to tell that side of our story a bit. Here’s the video from the event:

And if you’ve ever wanted to get better control over your instant messages, regardless of what network they may be on, definitely check out Beeper. I find it especially useful on desktop, like a Superhuman for messaging.

Happy to announce that the amazing Clay.earth product and team is joining Automattic. If you haven’t tried the app out yet, here’s a quick video to give you a taste.

TechCrunch has covered the broader strategy pretty well: One of the top requests we’ve heard from Beeper beta testers is they want to tie in more context, like a personal CRM, and some even requested Clay by name. We’ll keep the apps separate, as Clay also has some interesting team uses, but they will complement and integrate with each other as part of our all-in-one messaging strategy.

We share a vision to integrate Clay’s technology, which manages over 140 million relationships, as a layer across many of our products and experiences at Automattic. I’m excited to work with the founders, Matt and Zach, to bring this vision to life. I’ve always felt the missing primitive in WordPress’ content management data architecture was a scalable concept of a Person and Relationships outside of our user table.

Here’s the beautiful announcement on the Clay site and on Automattic’s.

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.

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.

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.

This week, DrupalCon Singapore is bringing together an incredible community of Drupal platform creators, developers, and supporters. 

Last year, I had the chance to share the stage with Dries Buytaert, the founder of Drupal, and the conversation stuck with me. It highlighted the profound impact we can have when communities like ours come together to push the boundaries of Open Source and shape the future of the web.

At Automattic, we believe that Open Source is more than a license—it’s a philosophy that drives innovation and makes publishing accessible to all, and we want to support fellow open source communities. Our team is at DrupalCon to share some of the tools we’ve built, including Akismet (check out the Drupal extension here), The Atavist Magazine, Beeper, Day One, Longreads, and Pocket Casts. These products, much like the web itself, thrive on connection and collaboration. (Basically all our non-WP stuff.)

I’ve loved hearing about how people are engaging with our booth—whether exploring our tools, grabbing a local snack, or taking a moment to recharge. For those of you at the event, I encourage you to swing by the Automattic booth, meet our team, and share your thoughts. Together, we can continue to create an open web that’s full of possibilities.

As announced by Automattic and covered by TechCrunch, I want to take a moment to welcome Elijah Potter and Harper to join Automattic. Harper is a super-fast (way faster than LanguageTool and Grammarly), local English grammar checker. The technology is nascent, but I’m very excited to embed this throughout all of Automattic’s products, and then expanding it to other languages, all in an open source way that can be embedded everywhere. I’m a huge fan of Grammarly and use it every day, but I think we’re doing too much in the cloud right now and there is so much compute and potential at the edge, and I’m excited to drive that forward with projects like Harper, Gutenberg, and Playground.

Last Friday we said goodbye to 159 colleagues as part of our alignment offer. It was a tough day, there are a lot of close relationships within Automattic, and goodbyes are always hard.

On Monday, I got to be Oprah for a few minutes. We had scheduled a town hall for leaders around the company to speak to everyone, and our Woo team had ~350 people in person at a meetup in Tulum. I had five minutes to talk, and over the weekend, I had been brainstorming with finance and HR for something nice we could do for everyone who stayed. We couldn’t give them all a six-month bonus, which would have cost ~$126M, but we did take how much we spent on severance for the 159 people, rounded up a bit, and granted everyone at Automattic 200 shares of A12 stock, so about a $12M bonus for the employees.

What’s A12 stock? This is probably the first time you’re hearing about it, we haven’t had a chance to talk about this publicly much before.

Usually, options or common stock in a private company is fairly illiquid, with rare opportunities to sell or lots of restrictions like what Uber had; it’s not an efficient or predictable market. Options are “nice” because they can defer taxes, but you still have to exercise them, and they can go underwater. Also, as a fully distributed company, we have people in 91 countries, so security and tax laws around options make them not worth it in most places outside of the US.

When thinking about a stock plan for Automatticians, we thought, our most sophisticated investors have nice protections like a 1x liquidation preference, what if we gave that to employees, too? So to summarize, A12 is a special class of stock available only to buy if you’re a current Automattician with these characteristics:

• There are twice-a-year windows to buy. You have to hold for 1 year, but then there are quarterly windows to sell, which is very predictable.
• Automattic maintains the internal market, and provides a backstop so you can always sell the shares at what you paid for them or more, like a 1x liquidation preference.
• Current employees can buy, but former employees are eligible for every selling window, there’s no politics like can happen with tender offers. It’s reliable and predictable.
• Unlike options, A12 stock never expires. Once you own it, you own it.
• Initially we only allowed $25k/year of A12 to be purchased, but as our business has scaled we now allow up to $1M/yr of A12 stock to be purchased. (Remember, the company has to backstop the purchase price.)
• A12 is just economic rights, it doesn’t have any voting rights.
• A12 stock can be transferred to a trust.
• The price is set by an external firm, just like our 409a. Because that process discounts us so much for being private, it’s a pretty good deal compared to what investors would pay for a share.
• We’ve mostly moved away from options, which really only work for already wealthy, sophisticated hires. We pay very generous base salary (which banks love, makes it easier to get a mortgage) and then people can make a personal decision whether the characteristics of A12 fits with their financial planning alongside index funds, stocks, and bonds.

We’ve been running this program since 2016. The main downside risk for A12 holders, which isn’t that different from common stock, is that we go out of business and can’t keep our commitments. But that’s true of any stock investment, and we have a pretty solid track record.

We want everyone to have an owner mentality, so we’ve also now started granting 1 share of A12 stock to every new hire.

Our legal team has their hands full right now with the Silver Lake / WP Engine stuff, but we’d like to open source our docs around this so other companies can offer the same thing easily, I’ll see if we can make time for that in the next few weeks.

We also announced something else cool for employees on Monday around our Grand Meetup in 2025, but to know that secret you have to work with us. We are one of the most open companies, but we can’t publish everything! ☺️

Winston Churchill said, “Never let a good crisis go to waste.” Since I last blogged here, WP Engine filed a meritless lawsuit and Automattic responded, and there’s been a hurricane of public activity and press. Inside of Automattic, there’s been a parallel debate and process.

Silver Lake and WP Engine’s attacks on me and Automattic, while spurious, have been effective. It became clear a good chunk of my Automattic colleagues disagreed with me and our actions.

So we decided to design the most generous buy-out package possible, we called it an Alignment Offer: if you resigned before 20:00 UTC on Thursday, October 3, 2024, you would receive $30,000 or six months of salary, whichever is higher. But you’d lose access to Automattic that evening, and you wouldn’t be eligible to boomerang (what we call re-hires). HR added some extra details to sweeten the deal; we wanted to make it as enticing as possible.

I’ve been asking people to vote with their wallet a lot recently, and this is another example!

159 people took the offer, 8.4% of the company, the other 91.6% gave up $126M of potential severance to stay! 63.5% were male. 53% were in the US. By division it impacted our Ecosystem / WordPress areas the most: 79.2% of the people who took it were in our Ecosystem businesses, compared to 18.2% from Cosmos (our apps like Pocket Casts, Day One, Tumblr, Cloudup). 18 people made over 200k/yr! 1 person started two days before the deadline. 4 people took it then changed their minds.

It was an emotional roller coaster of a week. The day you hire someone you aren’t expecting them to resign or be fired, you’re hoping for a long and mutually beneficial relationship. Every resignation stings a bit.

However now, I feel much lighter. I’m grateful and thankful for all the people who took the offer, and even more excited to work with those who turned down $126M to stay. As the kids say, LFG!

There’s an apocryphal story about Ernest Shackleton putting an ad in the newspaper that read:

Men wanted for hazardous journey. Small wages, bitter cold, long months of complete darkness, constant danger, safe return doubtful. Honour and recognition in case of success.

If you’ve read the book Endurance by Alfred Lansing, you know how that went. Pretty legendary. One of my most treasured possessions is actually a copy of Ernest Shackleton’s Heart of the Antarctic book signed by every member of the shore party and Shackleton.

You may have heard the news that we’re going to migrate Tumblr onto WordPress. Automattic has put up a similar page calling for talented engineers of any gender who want to join the voyage.