If you’re obsessed with Sonos like I am, a nice MacOS utility is the Menu Bar Controller. Hat tip to Mike Tatum, who happened to be the gentleman who convinced my parents it was okay for me to drop out of college and move to San Francisco to take a job at CNET. Mike’s now at Sonos and in October arranged for some top execs at Automattic to go to Santa Barbara to meet with their peers at Sonos, and Patrick Spence and I did a joint CEO town hall that was broadcast to both of our companies. It was I think fascinating for both sides because of a shared passion for craft, design, culture, and execution, but our companies are in no way competitive, so it allowed for a lot of transparency. I learned a ton, and I think that kind of sharing is what increases the mimetic evolutionary speed of companies.
Atoms are hard! I think I’ll stick mostly to bits.
To give our current take with regards to iMessage: Right now we run on desktop only, basically automating Apple’s first-party app. This obviously won’t work on iOS or Android. With every network we support we want to have a good, non-adversarial relationship that puts the user first, with the utmost standards for privacy and security, and understanding the principles and values each network is trying to uphold. We’re watching this space unfold very closely, and trying to help where we can. Check out the episode here:
It got a little buried, though, because on Thursday Apple said it was going to support the RCS standard, which Google and others had been lobbying hard for. However, it’s doing the bare minimum: RCS isn’t actually encrypted, and Apple’s not doing the Google proprietary thing to encrypt it, and so non-Apple people still get green bubbles. (More on that later.)
iMessage on Android (and Windows!) is on the roadmap for Texts, the all-in-one messaging platform Automattic acquired last month. The Texts team is obsessed with security, and that’s part of why the platform is desktop-only right now—to keep everything 100% client-side and fully encrypted in a way that could never be accessed by the team, or have any compromise in the middle, they’ve been taking their time to get the engineering right on the mobile versions. So they poked around the Sunbird app that Nothing partnered with, and it wasn’t pretty. Here’s Texts founder Kishan Bagaria:
texts team took a quick look at the tech behind nothing chats and found out it's extremely insecure
it's not even using HTTPS, credentials are sent over plaintext HTTP
backend is running an instance of BlueBubbles, which doesn't support end-to-end encryption yet pic.twitter.com/IcWyIbKE86
The BlueBubbles thing might be a mistake, but seeing the unencrypted data on the wire definitely wasn’t. Sunbird replied and doubled down on Twitter, citing some ISO standard and claiming it was “encrypted.”
Nothing (the company) still makes amazing hardware that you should absolutely check out and use. It’s my favorite Android experience. I think the company got bamboozled by Sunbird, and unfortunately this went mainstream on MKBHD.
Sunbird appears either not to understand security or to lie about it, and probably misled Nothing. I would recommend double-checking what that team claims in the future.
Who should we actually be upset with?
Apple.
You shouldn’t need to jump through all these hoops to have a blue bubble on iMessage. Design can create great things; it can also harm. Apple’s design decisions to “magically” upgrade SMS or texts or RCS into iMessage, which is better and more secure, creates a green-bubble ghetto that’s also a terrible user experience for anyone not on an Apple-made device.
I’ve heard stories of teenagers being ostracized because they couldn’t afford an iPhone, of group chats rejecting people who turn the chat from blue to green. I know that sounds petty, but do you remember middle school? It’s about status, and Apple knows that. Everything they make bleeds status and signaling. They’re the best in the world at it, and I should know—I’m typing this post from a M3 Max black MacBook with 128GB of RAM. But while status signaling with amazing hardware and design touches is harmless, in software and social settings in can be harmful.
Regardless of how it started, today the green bubble indicates cheaper, lower-status, less secure. Apple’s half-hearted support of RCS just continues this. Sunbird (and others) shouldn’t need to jump through so many hoops around this stuff by reverse engineering. Apple should open up iMessage APIs so it can be natively supported just like every other 100M+ messaging platform is: Telegram, Signal, WhatsApp, et al. Teens who can’t afford or don’t want an iPhone should be able to have an app that lets them connect with their friends as peers, securely and with all the features that are easy to support in messaging.
Tim Cook, Apple, we love you. Trillion-dollar company, and lots of room still to grow. Allowing iMessage/FaceTime to interoperate (like it used to!) might take .01% off your growth rate, but it’s the right thing for humanity. Yes, I know Google is shady too, and they’re locked in this smartphone death match with you. But take person-to-person communication out of the struggle, make it a DMZ, and be content to compete in all the other areas you’re currently crushing: design, silicon, Continuity, security, privacy, customer experience, retail stores, spatial audio, the list goes on.
I have no idea how to get in touch with YouTubers, but Marques, if you see this, I’m happy to chat about the future of technology, open source, freedom, and privacy.
Today is also my 18th anniversary at Automattic! So, an exciting day all around.
Using an all-in-one messaging app is a real game-changer for productivity and keeping up with things. Texts is a paid app, with discounted student pricing, and I think a lot of people will find value in it. It’s quickly become one of the top three apps I spend time using.
This is obviously a tricky area to navigate, as in the past the networks have blocked third-party clients, but I think with the current anti-trust and regulatory environments this is actually something the big networks will appreciate: it maintains the same security as their clients, opens them up in a way consumers will love and is very user-centric, and because we’re committed to supporting all their features it can actually increase engagement and usage of their platforms.
We’re still working out everything for mobile, so if you’re looking for the all-in-one experience on iOS or Android in the meantime, I recommend checking out Beeper. It really is great to have everything together.
If you’re a reverse engineer hacker that is interested in working with a super-small elite team in this space with the fun of a startup and the air cover of Automattic, get in touch with Kishan on Twitter DM or email (kb at texts). Here’s a fun video for Texts. 😄
Twitter/X is testing charging users $1/year with the idea that will keep out bots and spam. It’s an appealing idea, and charging definitely does introduce a “proof of work” that wasn’t there before, but the history of the web shows this is not really a big deterrent. Domains cost money, usually a lot more than a dollar a year, and millions are used for spam or nefarious purposes. The spammers obviously thought their benefit would be more than the cost of the domain, or they use stolen credit cards and identities. Charging may cause a short-term drop in bots while the bad guys update their scripts, but the value of manipulating X/Twitter is so high I imagine there is already millions of dollars being spent on it.
Long term to keep a platform healthy you really have to take a nuanced look at behavior and content, like Automattic does with Akismet, and have a fairly sophisticated trust and safety operation with great engineers. T&S is really important, not an enemy of progress, which would have been my chief edit to the otherwise exciting The Techno-Optimist Manifesto by Marc Andreessen. (If you missed Marc’s Why AI Will Save the World, that’s also an excellent read with dozens of references you can go down a rabbit hole with.)
This month, Automattic had the privilege of working with the Berkman Klein Center for Internet & Society (BKC) to migrate their early 2000s blogging platform over to our Pressable infrastructure. (Pressable is a small host Automattic runs to develop our WP.cloud infrastructure, it gets you all the performance and security of our high-end WP.com plans, but with a more plain-vanilla WP interface.)
The Harvard Blogs network that the Center launched back in 2003 was an important milestone in internet history. It provided a platform for over 1,500 high-impact bloggers—including Harvard students, faculty, fellows, staff, and alumni—to publish and engage in discussion.
We were alerted to BKC’s plans to decommission blogs.harvard.edu by none other than Dave Winer, the pioneering developer behind blogging, RSS, and podcasting, and a Berkman Center fellow from 2003-2004. As BKC shared in their announcement, the network played a formative role for many now-influential bloggers and internet figures. It also contributed to the rise of podcasting and projects like Ushahidi.
When we learned BKC planned to retire the Harvard Blogs platform, we wanted to ensure this valuable archive of early internet culture was preserved. We offered to host the network’s blogs indefinitely so they can remain publicly accessible for years to come.
The Harvard Blogs multisite consisted of around 1,500 blogs. To move it over, we systematically migrated the archive to our servers and then upgraded the network to the latest version of WordPress (we also updated a handful of plugins and themes and tested the updated versions against the original sites hosted by Harvard).
Much like our recent unveiling of the 100 Year Plan for WordPress.com, the preservation of the Harvard Blogs archive demonstrates Automattic’s commitment to protect vital pieces of internet history and culture for generations to come. By preserving these blogs, we hope to inspire future generations of online voices.
There was something really nice about the neighborhood of blogs the Harvard blog network provided that I hope they or another university tries again sometime. Harvard is now 387 years old, I hope these blogs last at least that much longer (that would be 2,410 AD!).
I woke up this morning to a lot of people sending me the link to today’s Axios story reporting that Vox Media (which includes The Verge, New York Magazine, Polygon, and many other outlets) is moving from its proprietary CMS, Chorus, to WordPress VIP, Automattic’s open source solution for large publishers.
This is very exciting—not just for the obvious reasons, but because I’ve been a fan and reader of Vox since they started. As a tool-maker, one of the greatest honors is when fantastic people choose your tools to practice their craft. I’m also sure their feedback will make WordPress better! Vox Media folks, if there were any Chorus features you loved, drop them in the comments and we’ll make sure they can become a plugin or get baked into WP core. And if anyone has built amazing features in other CMSes you’d like to see in WordPress, we’re hiring!
As I said in my recent conversation with Dries Buytaert and Mike Little celebrating WordPress’ 20th anniversary, and with a hat tip to Fight Club, I believe that on a long enough timeline, the survival rate of proprietary software drops to zero. I don’t fault anyone for starting a CMS—I’ve been guilty of that myself a half-dozen times, not counting WordPress—but while something custom-built may seem better for your needs in the beginning, that never lasts. Unless you invest heavily in engineering (like tens of millions per year), the steady improvement of a healthy open source community, like the tens of thousands of developers working on WordPress every day, will eventually catch and surpass any proprietary system.
Not all open source projects achieve the famed positive flywheel; it takes decades, and most will fail in the process. The ones that reach exit velocity, though, become part of the fabric of civilization. At that point, it makes more sense to build on top of them rather than recreate the wheel. You’ll still get where you’re going, it’ll just be a smoother, faster ride.
(Midjourney prompt: A chorus of people using WordPress.)
Whoop is an excellent biometrics bracelet I’ve been wearing for a few months since my friend Jaime Waydo joined as their CTO. After many years of being very in the Garmin 945 camp, I now do an Apple Ultra for all the smart stuff, and Whoop for all the great sleep, HRV, and recovery information that I use to be aware of my energy levels throughout the day, complemented by the Rise sleep and energy tracker app. This has been my ideal combo.
The founder and CEO of Whoop, Will Ahmed, interviewed me for their podcast, which we covered for a more mainstream audience my passion for open source and creating an open ecosystem for a web, how I got started as an entrepreneur, how Automattic hires, growth mindset and mental clarity, working with Joe Hudson as an executive coach, and day-to-day routine (or lack thereof, sometimes).
Apple almost never fails to wow, and they had a lot of cool announcements at WWDC yesterday. Apple’s previously favorite (app of the year!) journaling app was Day One, one of Automattic’s products, but they announced their own Journal app. One nice thing about competing with Apple is they only really interoperate with their own devices, and they’re usually not good at social. Day One is launching Shared Journals soon, a social feature so you can have fully end-to-end encrypted shared private journals with friends and family. It’s been the thing I’ve been most excited about since we bought the app. (Paul can attest how much I ask him about it!)
That complements another advantage Day One has, which is being cross-platform. If you have a family member on Android, you don’t want to ostracize them from your Shared Journal. Apple doesn’t care, their priority is getting everyone on the Apple ecosystem. You care, and Day One/Automattic does too, that’s why it works great on all Apple devices, Android devices, and the web itself.
The last year of my thirties! WordPress turns twenty this year. Automattic is now ~2,000 people across 98 countries. There’s so much that has happened in the past decade yet it feels very much like we’re on the cusp of something even more exciting.
This morning started well; I pulled the hammock out of the garage (it had been hiding from the rain) and read for a bit, trying to get my 5-10 minutes of sun in the first 30 minutes like Huberman suggests.
Candidly, the last year was a really challenging one for me personally. There were some beautiful moments, and I consider myself the most lucky in my family, friends, and colleagues, yet among that same group there was a lot of loss, existential health challenges, and that weighed heavily on me. It’s also my last year to get on 40 under 40 lists! 😂
Usually when people ask me what I want for my birthday I don’t have a good answer, but this year I do! As Heather Knight wrote about in the SF Chronicle, the beloved Bay Lights are coming down in March. This has to happen — the vibrations and corrosive environment of the Bay Bridge is taking lights out strand by strand. Fortunately it’s now been a decade since the lights first went up, and there’s much better technology both for the lights and how they’re mounted and attached to the suspension cables. Finally, the lights were not visible from Treasure Island or the East Bay before, but this new version 3.0 will be, which is why the artist behind the lights, Leo Villereal, is calling it Bay Lights 360.
Like the Foundation series, we can’t stop the coming period of darkness from happening, but if we raise $11M we can bring the lights back. If we raise it soon we can shorten the time they’re down to just a few months, so I’m working with the 501c3 non-profit Illuminate to help fundraise. The idea is to find ten people or organizations to put one million each, and raise the final million in a broader crowdfunding campaign, to re-light the Bay Bridge and give an incredible gift to the people from every walk of life that see the bridge, and hopefully have their spirits lifted by the art. I’ve heard 25 million people see the Bay Lights every year.
It’s a lot to raise, but every little bit helps so please donate here, and if you are interested to do a larger gift please get in touch. I’m committing a million dollars to the fundraise, and myself, Illuminate director Ben Davis, and the artist Leo Villereal are happy to personally connect with anyone considering a larger donation.
Because of some family health reasons I’m back in lockdown, so going to try and throw an online party tonight in the “Matterverse.” We’re going to party like it’s late 2020. 🎉
Automattic acquired Pocket Casts last July, and since we’ve been tapping away trying to make the best podcast client for people who love listening to podcasts.
And!
The team has been working really hard to make those clients totally open source and available to the world, and it’s now happened. You can see all the code behind the iOS app and the Android app, and modify it, make it your own, suggest a change, fix a bug, add a feature, fork it and make your own client, anything!
If your code gets merged into core, it’ll go out to users listening to literally millions of hours of podcasts a week. It’s also unusual to be able to peek under the hood of a consumer mobile app that is this widely used and see how it works.
Audio publishing and consumption is a beautiful complement to the web publishing that WordPress is already so good at, and that Automattic tries to nurture an ecosystem around. I love Spotify and Apple, and I hope that Pocket Casts can do for podcast clients what Firefox in the early days and Chromium now does for browsers — push the state of the art, be manically focused on user control, and grow a more decentralized and open web.
I spoke with Guy Raz about the early days of WordPress and Automattic on the latest episode of “How I Built This (listen on Pocket Casts).” We ended up talking for over four hours and the show has skillfully edited this down to just over an hour. We discussed my time at CNET, how I accidentally invented a new way to spam, why we didn’t sell Automattic, my feelings on Wix and competitors like Shopify (sponsor of this episode, hah, in which I speak about how their dashboard looks just like WordPress’s). Guy pivoted the conversation to grief that came with the loss of my father and challenges we faced during the pandemic. He kept the conversation going effortlessly and I had a great time taping the episode. Thanks to Guy and his team for a great experience.
Which brings to mind Betteridge’s law of headlines (née Hinchliffe’s rule), “Any headline that ends in a question mark can be answered by the word no.”
I can’t save the internet. But you know who can? A movement. A community of like-minded individuals, unified by a common philosophy, and working together to create tools of freedom.
It’s a human right to be able to see how that technology works and modify it. It’s as key to freedom as freedom of speech or freedom of religion. So that is what I plan to spend the rest of my life fighting for.
Working together we’ve created something special, unlike anything the internet has seen before, and I’m excited to continue.
Since Frontity launched their open source framework, they have been making the integration between React and WordPress easier. Their proven drive and experience with clean technological solutions will benefit our efforts as we continue to make the block and theme APIs a joy to use and WordPress the best development platform on the web.
The next step in the growth of this relationship is for Frontity and its team to join Automattic and contribute to core WordPress.org as part of our commitment to Five for the Future.
I believe there’s still a lot that we can learn from decoupled systems and we can incorporate those learnings into WordPress itself as we emphasize performance, flexibility, and ease of development. I look forward to Frontity joining WordPress and channeling their efforts into the WordPress APIs, documentation, and Gutenberg’s full-site editing tools.
In February of this year, Automattic closed a new primary funding round of $288M, bringing in some great new partners including BlackRock, Wellington, Schonfeld, and Alta Park. Existing investors ICONIQ and Aglaé (Bernard Arnault) also participated. This round was common stock, and like all funding since 2011, included a proxy assigning me the right to vote the shares.
Automattic was very busy during this time frame, as we were working on what would become the Parse.ly, Day One, and Pocket Casts acquisitions, our investments in Element and Titan, plus more acquisitions and partnerships we haven’t announced yet, so we haven’t mentioned the February funding round until now. And while we are a bit surprised the fundraise did not leak to the press, it’s now been an awkwardly long time since February and I’m pleased to formally announce it now.
And since then, Automattic has continued to grow at a rapid pace and we recently took the opportunity to do a $250M share buyback at a $7.5B valuation that just closed last week. The buyback was primarily targeted at current and former employees.
We’ve grown and increased our valuation at a rate higher than most other alternate investments available to investors. However, some of Automattic’s employees and former employee shareholders have been part of our journey for a very long time. Selling a bit of their equity holdings could have a significant impact on their lives.
Automattic was founded 16 years ago and is still private, so it’s important for us to try to provide liquidity to any shareholder who wants it. We do the same with our internal A12 stock plan where we let our employees buy our shares and also offer an opportunity for all holders to sell them back to Automattic, every quarter. (I need to do a longer post on that.)
One interesting thing we’ve been doing in these buybacks is holding the shares as treasury stock within the company instead of canceling the shares at purchase. This allows us to buy shares that come onto the market, and then when an investor comes and wants to put a larger quantum of capital into the company, we can re-sell the treasury shares that the company bought earlier. In effect, we are providing both a sell-side and buy-side for Automattic stock, serving previous and new investors and making money on these trades since we bought and took the risk earlier. We’ve established a logical valuation methodology, which is based on a simple multiple of the last twelve month’s revenue, so shareholders can track and anticipate performance.
All of this has been a lot of fun and we’ve seen a great amount of success, but it’s not all smooth sailing; we still have our share of challenges, probably the biggest being hiring. We have significantly scaled up our ability to find and hire great folks, with 371 accepted offers already in 2021 and it’s only August. However, with the growth of WooCommerce (hiring a Head of Payments) and our enterprise business, WPVIP, in particular, we need to move faster to keep up with the opportunity. For me and many other of the most-tenured Automatticians within the company hiring is the top priority. To that end, I’m also looking for someone to partner with me and our top executive group (which we call Bridge) in Creative Talent Development, an executive recruiter to help craft the highest performing teams of executives for each of our businesses.
We have a multi-decade opportunity ahead of us to create the best solutions for the open web platform of WordPress, and WooCommerce is doing the same thing for commerce; growing together over the long-term with people passionate about the same mission is my favorite part of my job.
I’m not sure when I first came across the critically acclaimed Day One product, which is the best private blogging and journaling app out there, but I began seriously using it daily in 2016 when my father was in the ICU and later passed. Having a private, safe place to write what I was going through kept me sane and helped me process everything.
Writing has always been a salve for me, and I’ve had local or private WordPress installations pretty much since 2003 to capture and archive writing that wasn’t fit for the public web.
Day One not only nails the experience of a local blog (or journal as they call it) in an app, but also has (built) a great technical infrastructure — it works fantastic (when) offline and has a fully encrypted sync mechanism, so the data that’s in the cloud is secured in a way that even someone with access to their database couldn’t decode your entries, it’s only decrypted on your local device. Combining encryption and sync in a truly secure way is tricky, but they’ve done it.
This is a long intro to say, as you can read from Day One’s founder and CEO Paul Mayne, from Eli at WordPress.com, and on Tumblr, that Paul and the team are joining the team at Automattic. For many years I’ve talked to anyone who will listen about my vision of making Automattic the Berkshire Hathaway of the internet, and Paul’s decision to continue to grow his amazing business as part of Automattic is a great validation of the way we’ve been building our culture and long-term orientation in our business. Day One is a beloved product, and bringing it into the fold is a responsibility I take very seriously and comes from a deep respect for what’s been built and a belief that working together we can create something for users better than we could working apart.
Great software takes time, and the Day One team has been at it for about a decade now, I can’t wait to see what they accomplish in the coming decade and beyond. If you haven’t tried out Day One yet, please check it out in the Apple or Google’s app store.
Squarespace filed their S-1 last month, and went a direct listing route for their stock today under the ticker SQSP, so I’ve been getting lots of questions on my thoughts on their business. It’s easier to share here in a blog than individually.
Squarespace’s CEO Anthony Casalena is a thoughtful, creative leader. It’s amazing what he’s built since 2003, and he obviously has many decades ahead of him. From our conversations I know how seriously he takes the craft not just of designing great products, but designing great organizations that will stand the test of time.
Squarespace is a customer-centric company, that has reliable, well-designed services, great support, and puts their customers first by allowing things like standards-based export. I’ve always observed them to behave and compete with the highest of ethics.
Their products work well, and they’ve been strategic in their acquisitions, including recently Tock which I’m a big fan of.
Their metrics are great, and there’s huge opportunity still. If you add up all the companies (including Automattic) in the independent web space it’s still only tens of millions of subscribers. I truly believe the eventual audience is every business in the world, and a good chunk of the 7 billion individuals, so there is so much room for everyone to grow.
How about the stock? Some of my favorite investing advice comes from Charlie Munger:
“I could improve your ultimate financial welfare by giving you a ticket with only twenty slots in it so that you had twenty punches representing all the investments that you got to make in a lifetime. And once you’d punched through the card, you couldn’t make any more investments at all. Under those rules, you’d really think carefully about what you did and you’d be forced to load up on what you’d really thought about.”
If I had to pick between Squarespace or Wix, I’d pick Squarespace every time. They’re a company you could punch the card with. They’ve built a great brand through their marketing and rightly earned trust with their customers and within the community as a good business, and they have a founder-led path to success for many years to come. I’m wishing them the best in their next chapter as a public company.
The WordPress community has long advocated for a repository with GPL-compatible images, and it’s time to listen to that need. CC Search, a CC0 (Creative Commons Zero) image search engine, is joining the WordPress project with over 500 million openly licensed and public domain images discoverable from over 50 sources, audio and video soon to come.
I am a long-time supporter of Creative Commons and their influential work on open content licenses, and when we heard they were considering shutting down their CC Search engine we immediately started exploring ways we could keep it going. I am eager to give a new home to their open search product on WordPress.org in continued commitment to open source freedoms, and providing this community resource for decades to come. This is an important first step to provide a long-term, sustainable challenger to proprietary libraries like Unsplash.
Automattic has hired key members of the CC Search team and will sponsor their contributions as part of our Five for the Future commitment. I look forward to seeing the project grow and welcome them to the WordPress community! Will share in a few weeks when everything is live and running on the site.
In it, I drew the distinction between “horizontally scaled” teams, in which physical offices are connected to remote workers via satellite (home or commercial) offices, and “fully distributed” teams where, as you said, “the creative center and soul of the organization on the internet, and not in an office.”
At Parse.ly, we’re only a couple years old but have been operating on the distributed team model, with ~13 fully distributed employees, and it’s working well. Always glad to hear stories about how Automattic has scaled it to 10X our size.
And, likewise, we blow some of our office space savings on camaraderie-building retreats; our most recent one was in New York, see [here] and [here.]
Very excited to share the news that Revue is joining Twitter. I’m a huge fan of the idea of better newsletters and Automattic was the largest investor in Revue. I’m looking forward to seeing what the very talented team will do as part of the Twitter network. Also many thanks to Kevin Kelly and Om for introducing me to Revue early on.
