This week I spoke with TechCrunch about one facet of distributed work that differs from physical offices — the idea of “office politics.” I can’t claim that distributed work will solve everyone’s personal differences, but I do think it relieves some of the pressures that might come from forced cohabitation and environments that are prone to interruption. They also have some great points from Jason Fried and and Wade Foster.

Prospress joining Automattic

Automattic, Marketing

As you may have read on the WooCommerce blog, Prospress blog, WP Tavern, Post Status, or Techcrunch, the team at Prospress is joining forces with WooCommerce at Automattic to help accelerate the adoption and democratization of ecommerce across the web. Whew that’s a lot of links! Prospress was best known for their extension that allowed many types of Subscriptions on top of WooCommerce, but also has some cool marketing automation and automated testing tools as well. I love that Prospress was already a Five for the Future company, which aligns really well with Automattic’s long-term goals and contributions to the wider community.

Diversifying WordPress

Automattic, WordPress

WordPress is about democratizing publishing, removing barriers to getting your words on the web. There’s a cool effort underway right now to remove some barriers that people from groups underrepresented in tech might face when becoming a WordCamp speaker. Automattic is supporting this by sponsoring Jill Binder’s work on the WordPress Diverse Speakers Training Group.

I would love to see the WordPress contributor base become more diverse, and training people from marginalized communities to speak at WordCamps is a great way to help that along. Check out that effort if you’d like to get involved.

Squarespace Direct Listing

Automattic

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.

Sunbird Security Isn’t Nothing

Apple, Audrey, Automattic

This might get lost in the OpenAI earthquake happening, but it’s important so I wanted to post about it. (And gosh! A Starship launch, which is amazing. We live in interesting times.) On Tuesday, Nothing, who makes the cleanest and most interesting Android phones (and whose earbuds sound great), announced via my favorite tech video channel, MKBHD, that the phones would support iMessage on Android, so you can be a blue bubble with your friends. This got a lot of pickup!

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:

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.”

Okay! Now you’re caught up to Friday. Texts says Sunbird isn’t secure, Sunbird says it is. He said, she said, right? Not quite—there are receipts. This blog post lays out even more than Kishan tweeted originally and shares code so you can confirm this yourself. tl; dr: Sunbird puts all your iMessages and attachments into Firebase.

What should you take away from this?

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.

Update: As I was writing this, the Nothing Chats app has been pulled from the Play store.

Update 2: From my colleague Batuhan:

Proprietary software is like creating art which no-one can see. Open Source elevates software engineering to a collaborative art form. Code is poetry.

— Tom Willmot

Some choice words from Tom Willmot, who was watching Kirby Fergusen’s Everything is a Remix, which I’ll check out now.

On StellarWP Podcast

I’m still doing some podcasts as sabbatical-Matt, especially with the WordPress community which for me isn’t really work, it’s building relationships in our community of practice. If you know me, I can wax poetic about WordPress for hours! It’s what I do for fun. Here’s my first post-sabbatical interview with Michelle Frechette. Another unusual thing about this interview is I was quarantining with Covid!

Illuminate has crossed the funding threshold it needed to actually kick off the project of bringing the Bay Lights back to San Francisco, as Heather Knight writes for the New York Times. The upgraded lights will be visible not just from San Francisco but also in Oakland, Treasure Island, Berkeley… all across the Bay. It’s felt like the lights have been the lumen-physical embodiment of San Francisco’s struggles: sparkling and inspiring at the start, then facing troubles, a trough of darkness, and now hope for something better sparked and on the horizon.

I’d love to get as many citizens and addresses in San Francisco as donors, however small, to round out the last bit of the funding, so that as many people as possible can feel the ownership and pride of making the city better. Back in January when I promoted this last it was on a terrible platform, it’s now been re-done by the GiveWP team to be totally native WordPress and a slick donation experience, easy to do on mobile and with Apple Pay. (Major kudos to Devin Walker there!) Please share the link to your friends, especially ones that see the bridge from their home, for $10 it’s the cheapest pro-social dopamine boost you can have every time you look at the bridge.

We no longer need companies, institutions, or government to organize us. We now have the tools to organize ourselves. We can find each other and coalesce around political causes or bad companies or talent or business or ideas. We can share and sort our knowledge and behavior. We can communicate and come together in an instant. We also have new ethics and attitudes that spring from this new organization and change society in ways we cannot yet see, with openness, generosity, collaboration, efficiency. We are using the internet’s connective tissue to leap over borders—whether they surround countries or companies or demographics. We are reorganizing society. This is Google’s—and Facebook’s and craigslist’s—new world order.

— Jeff Jarvis in the book What Would Google Do? Published 2009.

Interesting to revisit as they float trial balloons on breaking Google up (terrible idea) or other antitrust enforcement.

Timex Datalink

Review, Video

I had a huge nostalgia blast today with this video from Lazy Game Reviews showing and setting up a Timex Datalink watch, which was a “smart” watch that would show data that you transmitted to it by holding it in front of your CRT monitor and it flashing a bunch of lines.

It’s hard to describe how much my Ironman Triathlon Datalink watch was my entire world when I was a little kid, I was totally obsessed with it. I filled up every bit of its memory with numbers and notes. And the Indiglo!

UH Magazine, Revisiting My Alma Mater

My father attended University of Houston, and it’s where I went to college to study political science, I started WordPress when there, and then dropped out after two years to move to San Francisco. It was fun seeing UH Magazine feature an article about my journey from a University of Houston student to co-founding WordPress and leading Automattic. I was surprised they put me on the cover of the physical edition! I wish my Dad were still around to see it.

The piece explores my commitment to open-source, my vision for democratizing online publishing, and the values of creativity and adaptability that have shaped my path. It’s an honor to reflect on these experiences with my alma mater.