Category Archives: Ideas

Half-baked thoughts, provocations, and things I’m mulling over.

Popping Bottles

With the rise of GLP-1 drugs, there’s a trend that magnums are being ordered at clubs to meet minimums but left unfinished.

I think there’s a space for an ultra-high-end wellness drink at clubs. Imagine Erewhon meets Magic Mind meets Kin,  maybe with some effervescence. An elixir that comes out with sparklers but makes you feel great with nootropics not hungover. Priced at hundreds of dollars retail so thousands at a club. It could even be a cold chain, with the freshest ingredients that need to be preserved.

Let’s do some turmeric-ginger-cayenne shots and get crunk.

On Lenny’s Podcast

One of my must-read newsletters for the past several years has been Lenny’s Newsletter, probably best known for its writing on growth and product management, which really means it covered everything you need to create a great company.

It expanded into a really well-done podcast; Lenny has always had a knack for finding the best guests and asking the best questions, so when he invited me on I was very excited.

He really wanted to address some of the things that people said I wasn’t being asked, so we do touch on the WP Engine / Silver Lake attacks, but we also covered a lot of my philosophy of why open source is important, philanthropy, and why you should build a movement, not just a product.

You can watch it on YouTube, or listen to it on your favorite podcast app like Pocket Casts.

Some others he has done that I really enjoyed are Nan Yu from Linear, Marc Benioff from Salesforce, Katie Dill from Stripe, Mihika Kapoor from Figma, Drew Houston from Dropbox, and of course the famous Founder Mode one with Brian Chesky.

DrupalCon Singapore

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.

Hugo on Vision Pro

Many of my friends are ridiculous overachievers, and Hugo Barra is no exception. In response to my birthday blog post present request he has published a magnus opus of over 10,000+ words on his thoughts on the Apple Vision Pro from his perspective having been present for some foundational moments for Google, Meta, and Xiaomi. This is my dream, to get people writing more. We need more of this stuff on the internet! It’s fun to go down rabbit holes with experts. Cool that it’s on Hugo.blog, too. 🙂

Thoughts on Tech Employment

The Washington Post writes The U.S. economy is booming. So why are tech companies laying off workers? This article has some good data, but I think misses the point with sub-heads like “Shine has come off the tech industry.” Really? How is that reflected in their stock prices?

I think a few things are happening.

First, tech companies are typically best at adopting new technology, which leads to productivity gains.

AI may be an obvious example of this, though for all its hype it hasn’t had a huge impact on most companies yet. I agree with Sam Altman when he says there may someday be a billion-dollar company run by one person who is able to highly leverage future AI agents to automate most traditional roles at a company. That said, I think there are advantages to teams including allowing people to go on vacation or take time off, and provide business continuity and succession, so literally one-person is probably an exaggeration. We don’t need AI to see very small teams being valued highly: Instagram had only 13 employees when it sold for a billion dollars to Facebook, in 2012!

Some of this productivity gains just come from adoption of existing tools like Google Workspace or Office 365, issue trackers and version control with tools like Gitlab, Github, or Jira. At Automattic we don’t use email to work or communicate internally, it’s all Slack and P2. We also leverage our distributed nature to effectively have teams around the world coordinating several shifts of product work per day, and 24/7 coverage for things like systems and customer support without the need for “graveyard shifts.”

The way tech companies operate, the pace and culture, would be unrecognizable to people at many more traditional companies.

At tech companies some roles are highly leveraged, like systems, engineering, and design, and everything else in the company really exists to support these. These leveraged roles can create enormous amounts of value, and that’s why it’s not unusual to hear of machine learning engineers working on ads at Google with salaries in the seven figures. (There’s been a weird accounting thing where companies put a lot of their compensation into equity, but I think that’s going away as investors are learning to better account for dilution and employees appreciate the fungibility of cash.)

Creators are also highly leveraged, which is why Joe Rogan can sign a new $250M deal with Spotify (which smartly puts him back on Youtube) after laying off 1,500 people in December. Some people like Hagen Terschüren try to tie this together and say you should avoid Spotify for it, but there’s nothing wrong with a business becoming more efficient to serve its customers, it’s the whole point of capitalism. Capitalism is, as Nicholas Stern says (via Marc), the best way to take care of people we don’t know. There’s no honor in keeping people employed inefficiently, it’s better for them to find someplace in the market where their talents will be better leveraged for society and themselves.

There was a bubble in hiring because tech had so much money it tried to throw people at problems. But the unlock in technology can come from a single person, a single insight. It’s the mythical man-month. Tech-first companies are going to become leaner and more leveraged. Fewer people are going to create more value for society, in ways that will follow power laws and I think we should investigate things like Universal Basic Income to provide for all living beings. Technological progress creates abundance, where we have more than what we need.

At Automattic last year we did not do layoffs, but allowed performance management and natural attrition (voluntary regrettable was 2.9%, non-regrettable 6.8% for us in 2023) to allow our size to shrink down more naturally, on average two people left for every person we hired last year, from a peak of about 2,064 to 1,936 today.

Great Mental Models book cover

Farnam Street’s Great Mental Models, Presented by Automattic

I’ve been a fan of Shane Parrish and his indispensable Farnam Street for many years now. Shane is a fascinating person — he’s a former cybersecurity expert for the Canadian intelligence agency and occasional blogger who turned his website into a full-time career. Oh and fs.blog is on WordPress, too. 😎

His book, The Great Mental Models: General Thinking Concepts, has been tremendously valuable to me in my work. So valuable, in fact, that Automattic is now sponsoring the next printing of the hardcover edition. You can pre-order it here, then learn more about the mental models outlined in it.

Building a New Web, and a New Workplace

The Importance of Meeting In-Person

I recently returned from Orlando where Automattic hosted its annual Grand Meetup where nearly all of our 800 employees from around the world, spend a week together in the same place. (And yes, we’re hiring.)

Despite being a fully distributed company, I believe it’s still important to meet face-to-face — just not every day, in the same office. The Grand Meetup is our chance to get to know the people behind the Slack avatars and build relationships that can carry us through other 51 weeks of the year, when we’re working from more than 65 countries. It’s so much easier to hear the nuance in someone’s chat messages or p2 posts if you’ve hung out with them at Harry Potter World, or learned about their family, pets, and hobbies during a flash talk.

Some team, and behind-the-scenes photos after the company photo.

The week can be mentally exhausting, given that you’re often meeting many people for the first time. But we urge people to take it at their own pace, and the results are well worth the effort. Our data team actually studied the impact of the Grand Meetup on our work relationships — the connections established between coworkers using our “Meetamattician” tool were demonstrably closer after the meetup:

Before the Grand Meetup.
After the Grand Meetup.

This year we were proud to welcome some incredible keynote speakers: Wild author Cheryl Strayed talking about creativity and writing; Automattic board member Gen. Ann Dunwoody, the first woman in U.S. Army history to achieve the four-star officer rank; Ari Meisel on delegating and automating your life; and Dan Harris, author of 10% Happier, on the panic attack that led him to embrace meditation and mindfulness.

Photo by Leif Singer
Grand Meetup
Grand Meetup
Photo by jessicacg

Post-Verbal Language

James Beshara has a really interesting read on how communication will change and evolve in a post-verbal world, namely one where human/brain interfaces like Neuralink can more directly transmit thought between people than the medium of language allows today.

After reading the essay I wonder if people's thoughts or the neural pathways they activate, if they could be directly transmitted into another brain, would actually make any sense to someone else with a unique internal set of pathways and framework for parsing and understanding the world. The essay assumes we'd understand and have more empathy with each other, but that seems like a leap. It seems likely the neural link would need it own set of abstractions, perhaps even unique per person, similar to how Google Translate AI invented its own meta-language.

Today idea-viruses that cause outrage (outrageous?) in today's discourse  have been weaponized by algorithms optimizing for engagement, and directly brain-transmitted memes seem especially risky for appealing to our base natures or causing amygdala hijack. But perhaps a feature of these neural interface devices could counteract that, with a command like "tell me this piece of news but suppress my confirmation bias and tribal emotional reactions while I'm taking it in."

Amid the wreckage of fallen startups, Longreads is increasing the original reporting it funds:

Longreads has raised about $250,000 from “thousands of members” since it added memberships in 2012. The suggested monthly amount is now $5 a month or $50 a year, though readers can choose to donate any amount, and Armstrong said that the company’s gotten some thousand-dollar donations. All of that money now goes to pay authors, and WordPress.com matches every $1 from a reader with an additional $3, which clearly makes it a lot easier for Longreads to do what it wants to do.

Rebirth and Yellow Arrows

My friend Kamal Ravikant has a new book out, Rebirth, which I highly recommend. I had the good fortune to read it a few months ago and the story of the Camino de Santiago touched and inspired me.

Because of the impact of the book, I ended up adopting a few New Year’s intentions long before January 1st — things to ruminate on and keep in mind as the year wound down. The outlook of the world seemed uncertain, and I’m learning to navigate the world without my father.

yellow-arrow-3

Yellow Arrows

The Camino de Santiago is a pilgrimage path in Spain that people have walked since the 9th century AD. The 500 mile path winds through mountains, fields, and sometimes cities, and many pilgrims take a month or more on it. In some ways it is similar to the Kumano Kodo walk I did with Dan and Craig last year.

There are places where the path isn’t exactly clear, either because the trail isn’t strong, there’s been growth, or you might be in a crowded urban area like a city. Over the years pilgrims and people who live on the trail have marked it with yellow arrows pointing the way. If someone gets lost or confused, it’s an opportunity for an additional sign to bring them back on track.

When you know the path, is it clear where someone else walking it should go next? It’s an interesting concept that applies across life. In your relationships, does your friend, loved one, or partner know what to expect, and where you’re headed together? Even in WordPress I feel like there are too many places where we bring someone to a fork in the road and there is no clear indication which way they should take.

Give some thought to the yellow arrows in your life, and I’ll write more about the other two things I’ve been thinking about tomorrow. Also don’t forget to pick up a copy of Kamal’s book. I loved it and I think it will be one I’m recommending to many friends.

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(Image from Camino Travel Center.)

I later incorporated this into my thirty-third birthday post.

From Elie Wiesel’s Nobel Peace Price acceptance speech in 1986:

And then I explained to him how naive we were, that the world did know and remain silent. And that is why I swore never to be silent whenever and wherever human beings endure suffering and humiliation. We must always take sides. Neutrality helps the oppressor, never the victim. Silence encourages the tormentor, never the tormented. Sometimes we must interfere. When human lives are endangered, when human dignity is in jeopardy, national borders and sensitivities become irrelevant. Wherever men or women are persecuted because of their race, religion, or political views, that place must – at that moment – become the center of the universe.

Mortgaging your site to a closed-standards vendor gives them, not you, the economic power.

Another Matt from Alley ruminates on Medium’s uncertain future for publishers. I agree that these first couple of publishers probably got a good deal: better than free, they’re guaranteed money regardless of whether Medium makes money or not.

In making the decision to hitch their horse to Medium’s wagon while fording a river, they’re probably betting on Medium not going out of business, which I agree there’s only like a 10% chance of happening. However I think there is a 97% chance that Medium’s business model will change in the future because the path they’re on and these publishers are dependent on will not sustain their current costs or the investment they’ve raised.