Category Archives: Interview

Conversations, Q&As, and podcast appearances.

Bending Spoons

The story of what Bending Spoons has built is very impressive, and I’m a customer of theirs through Evernote, WordPress uses Meetup a ton. I think Automattic’s Noho office used to belong to Meetup. They’ve built an incredible engineering and product culture that can terraform technology stacks into something much more efficient. I think their acquisitions of Vimeo and AOL are brilliant. This interview with Luca Ferrari on Invest Like The Best goes into their story and unique culture. I also always love a good Matrix reference. 🙂

Conversation with John Borthwick

I’m often on the other side, but it’s such a delight to be an interviewer, I really enjoy it and put a lot of work into coming up with questions and shaping a conversation I think will draw out something novel from the person. Besides the Distributed Podcast, I’ve had a chance at events to interview great minds such as Steve Jurvetson, Patrick Collison, Dries Buytaert, and now John Borthwick.

We discussed his early investments in Airbnb and Tumblr, what made the NYC tech scene so special back then, and how it has evolved since. We also touched on the recent mayoral race, where Betaworks fits into the city’s tech ecosystem, and delved into one of my favorite topics: the comparison between open-source and proprietary models in AI.

Telegram and Weird Al

I have two interesting interviews to share with you today, the first is Lex Fridman interviewing Pavel Durov, the founder of Telegram. I started using and advocating for Telegram back in 2015, and Audrey Capital was part of their aborted fundraise in 2018. As a software craftsperson, I’ve always had tremendous respect for the team and the rate at which they shipped truly novel design and UI. I’m amazed by the speed at which they ship major features across multiple platforms. The network also has incredibly resiliency, which they get into on the podcast. As I’m often in poor connectivity situations in planes or remote locations, Telegram has been one of the networks that works most reliably.

I’ve met Pavel only briefly about a decade ago, but have followed his story as he’s a unique character with an ascetic lifestyle, target of many intelligence agencies, sperm donor father of 100+ children, and many other unique characteristics. I use Telegram like I use X/Twitter, I put things I consider semi-public on it and I think of it like a social network and development platform, and since 2022 I’ve cross-posted my blog to a Telegram channel using a Jetpack bot. It’s probably my favorite community platform. The four hour interview between Lex and Pavel covers a lot of ground, but product builders will probably appreciate most the middle part around the 2-hour mark where they go into their engineering and design philosophies. (BTW I usually watch/listen to these at 2x speed.)

If you’re looking for something a little lighter on a Sunday I recommend this heart-warming conversation between John Mayer and Weird Al Yankovic.

I know this seems like an unusual pairing, but both Pavel and Weird Al are hackers in the sense that they examined the rules of the system and decided to create a new game.

Saturday Shares

A few links for you:

Fun fact: this post has the ID of “150,000” in my wp_posts table.

Weekend YouTubes

One of my favorite YouTubers is Charles Cornell (WordPress-powered!), who creates great videos that break down the music theory of various things you’ve heard, such as this adorable one featuring SNES soundtracks or The Legend of Zelda: Breath of the Wild. I first came across him reacting to Jacob Collier in 2020. Once I got super-into Severance, his breakdown of the spooky music is great. It’s also interesting to see that the YouTube community is going through its own version of fair use and copyright, trademark, etc., enforcement, which he discusses here.

Sam Altman is always interesting to follow, and it’s interesting to contrast this great interview he did with David Perell on writing with this very direct and awkward one with Tucker Carlson. I have immense respect for anyone who enters the arena and engages directly with journalists or critics, rather than hiding behind PR agents or lawyers. Given the current blood feud, it’s fun to go back eight years and see Sam Altman interview Elon Musk, long before any of the AI stuff blew up they were both terribly prescient.

Ray Dalio is always a gem and he went on Diary of a CEO. Theo Browne has a good take on what it means to vibe code. Kishan Bagaria discusses how Beeper is going to reach 100 million users. The story of how Atlassian took a non-traditional enterprise path with Jay Simons is great. Not a YouTube, but don’t miss Bret Taylor on The Verge. Check out Adam D’Angelo at South Park Commons.

And finally, I’ll say that YouTube Premium, which turns off all the ads, is probably one of the highest value subscriptions you can have. Many of these are essentially like podcasts, and from a product perspective, I think we need to figure out how to sync and allow seamless movement between watching, listening, or reading transcripts in Pocket Casts (Automattic’s open-source podcasting app). We support video podcasts, but there’s no good way yet to have a Whispersync-like experience between video, audio, and a transcript.

Automattic Operating System

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.

On with Theo / T3.gg

On Thursday, a prominent developer, YouTuber, Twitch streamer, and journalist posted a video titled This might be the end of WordPress. It was very harsh. In that video you’ll hear him say about me, “he’s a chronic hater” (7:55), “seems like he’s been a pretty petty bastard for a long time now” (10:22), “I hate this shit, I hate when people are assholes and they get away with it because I’m doing it for the greater good, the fake nice guy shit. I’ll take an asshole over a fake nice guy any day, people whose whole aesthetic is being nice, I hated it.” (11:25), “Honestly I’d rather the license just be explicit about it than this weird reality of ‘If you get popular enough you can still use it but the guy who made WordPress is going to be an asshole to you.’ That seems much worse than most open source models.” (14:39)… it goes on.

Ouch!

However, one of my colleagues Batuhan is a follower of Theo’s and suggested I engage with him. It turns out we were both in San Francisco, and he was game for a livestreamed, no-conditions interview at his studio. I believe discussion is the best way to resolve conflict, that’s why my door is open to Lee Wittlinger, Heather Brunner, Brian Gardner, or any WP Engine or Silver Lake representative who wants to talk to resolve things.

Saturday afternoon I went to Theo’s studio, we had a vigorous two hour debate and discussion with some real-time chat polling that also changed my mind on a few things, and his, too. I left feeling like I had a new friend. ️And met some awesome cats. Check out the video.

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!