Prospress joining Automattic

Asides

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.

Jack Dorsey and Running Two Companies

Podcast

I had the pleasure of interviewing Jack Dorsey for the Distributed podcast, a conversation that ended up going a bit deeper and longer than previous episodes.

In preparation for the interview I kept coming across people critical about the fact that Jack is the CEO of two companies simultaneously, Twitter and Square, each having over 5,000 employees.

I think what people miss is that at that scale, running a company is not that different from running a large division of a company. No one asks Jeff Bezos how he’s CEO of both a retail company and a cloud computing one (AWS), or Tim Cook how he’s CEO of a hardware business and a services business, and of course with both of those examples the breadth of what the companies cover is much wider. Also as an added benefit, shareholders can choose to invest in Square and Twitter together or not.

All of that said, I think having a CEO-level seat at two of the most influential technology companies today does allow for accelerated learning, as organizational experiments will naturally happen at each company and then the best practice can be shared to the other. Jack wasn’t aware how much peer executives at each company meet with each other to share learnings, but that seems like an obvious win.

Readers of this blog will especially appreciate how much we talked about open source and cryptocurrencies, and his view on the three things he’s responsible for as CEO. Give it a listen and let me know what you think.

Squarespace Direct Listing

Asides

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.

Tumblr Updates

Asides

Tumblr launched Community Labels yesterday, which allows consistent tagging of addiction, violent, and adult content, and for people to hide, blur, or show that content. It’s gone pretty well so far. We’ve still been getting a lot of questions if it’s going to be free-for-all with adult content again, and the short answer is no, but the longer answer is covered in Why “Go Nuts, Show Nuts” Doesn’t Work in 2022.

If you haven’t tried out Tumblr in a while, check it out. Lots of improvements the past few months, and it can be a refreshing alternative or add-on to your online social life. And get your friends on it too!

Sunbird Security Isn’t Nothing

Apple

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.

Freedom Grants

Audrey

The Audrey Scholars program is still getting started, but I wanted to introduce another opportunity: Freedom grants. As the page says “If you are an open source contributor, and you feel your current political environment is incompatible with open source values, we would like to offer the opportunity for a grant to help you get set up in a new environment. Please state your case below.”

I’m not sure exactly how this will work, but we’ll figure it out together. The offer is out there. This is very much inspired by the work of the Oslo Freedom Forum.

Timex Datalink

Asides

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.