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Day One at Automattic

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.

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WCEU Open Thread

I just wrapped up a fun session with Matías and Brian, and though we covered a lot of ground we weren’t able to get to all the questions from the audience. Starting at 2:58:

So this is an open thread, if you have any question from the talk please drop it in the comments here, and myself or someone in the community will respond! We’ll keep this open for a day or so.

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WordPress 18

Today marks eighteen years since the very first release of WordPress. I consider myself so lucky to have co-founded the project alongside Mike Little. Who could have imagined that our nights and weekends hacking on blogging software, a fork of b2/cafelog, could turn into something powering over 40% of the web? Or that nearly twenty years in, it would be getting better faster than it ever has been?

I blogged these anniversaries when WordPress was five, ten, fifteen, and last year at seventeen, but as the project reaches an age that, if it were a child, it would be heading off to college, I’m uncharacteristically at a loss for words.

The overwhelming feeling is one of gratitude, so I want to say thank you to every person who has ever been involved with making WordPress as a contributor, a community organizer, or as an end-user of the software. It’s amazing what we can accomplish when we work together.

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Squarespace Direct Listing

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.

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CC Search to join WordPress.org

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.

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Doctorow on IP

It’s not every day you see noted writer Cory Doctorow refer to a column as “the piece I’m most proud of,” and his essay in Locus Magazine on IP doesn’t disappoint, connecting the free software movement and the evolution of the term “author’s monopolies” to “intellectual property.”

The essay on DRM and Apple, available on his WP-powered blog, or Twitter, is also worth reading.

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Invest Like the Best and Building Worlds

On a Founder’s Field Guide episode with Patrick O’Shaughnessy we had an interesting conversation that covered a lot new ground, including an idea I’ve been playing around with on, as Patrick put it:

The idea from @photomatt that the best companies are those that build intricate worlds (in the same way that J. R. R. Tolkien came up with the elvish language) will always stick with me.

We also covered the pendulum of centralization and decentralization, current challenges facing the internet, and being a connoisseur of things overlooked. You can check out the episode on Apple, Google, Spotify, Overcast, and Pocket Casts.

I’ve been impressed by the audience of this podcast, a lot of people I admire reached out after this episode.

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Parse.ly & Automattic

Excited to welcome Parse.ly to the Automattic family, in an acquisition that’s closing today. They’ll be joining our enterprise group, WPVIP. The deal has been nicely covered in the Wall Street Journal and Axios. As a bonus, here’s Parse.ly co-founder Andrew Montalenti’s first comment on this blog, in 2012.

Great article, Matt. I wrote about this on my blog — Fully Distributed Teams: Are They Viable?

http://www.pixelmonkey.org/2012/05/14/distributed-teams

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.]

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Compounding Ice

I learned something novel about how the ice age happened from this Freakishly Strong Base post by Morgan Housel:

The prevailing idea before [Wladimir] Köppen was that ice ages occur when the earth’s tilt supercharges the wrath of cold winters. Köppen showed that wasn’t the case. Instead, moderately cool summers are the culprit.

It begins when a summer never gets warm enough to melt the previous winter’s snow. The leftover ice base makes it easier for snow to accumulate the following winter, which increases the odds of snow sticking around in the following summer, which attracts even more accumulation the following winter. Perpetual snow reflects more of the sun’s rays, which exacerbates cooling, which brings more snowfall, and on and on.

You start with a thin layer of snow left over from a cool summer that no one pays much attention to, and after a few tens of thousands of years the entire earth is covered in miles-thick ice.

Fascinating! The blog goes on to apply the idea to that strong base, accumulating a bit at a time, to investing and business. The power of compounding seems appropriate to share on the day Jeff Bezos announced his retirement.

I’ll leave you with one of my favorite quotes from Charlie Munger, which is also how the article ends:

‘The first rule of compounding: never interrupt it unnecessarily.’

Charlie Munger

The iceberg photo is one I took near Svalbard in 2011.

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Iceland Film

I wanted to share with you all a short film I made with the help of Stephen Bollinger, with videos I made a few years ago on a photography trip to Iceland with Om and Mark. I hope it provides five minutes of serenity in your day.

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Autonomous and Beautiful Home Devices

Of all the smart home upgrades I’ve made, replacing all my regular smoke detectors with Nest Protects (Google’s smoke detector) has been the one that I regret the most.

I don’t really need a smart smoke detector. It doesn’t need to talk, connect to wifi, and cost hundreds of dollars. I don’t need it integrated with my Google account which is impossible to share, so I need to be personally involved to replace one.

But other smoke detectors are just so unsightly, and the Nest is light years ahead of the competition from a design standpoint.

There’s such an opportunity for something that looks as good as the Nest, but doesn’t require two-factor authentication to replace. I didn’t want to call it dumb but beautiful, so let’s say “autonomous and beautiful” appliances and home devices. I still want it to be smart, but if you’re going to have the risk profile of a device that connects to the internet, it needs to be worth it, like Brilliant, Sonos, smart TVs, or connected cameras.

I’m becoming more wary of any hardware that requires an app, just because of the natural decay of non-SaaS and non-open source software. Van Moof bikes are beautiful, but will they still connect well when iOS 24 is out and Bluetooth has been removed from iPhones for security reasons?

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Second-Order Effects

Derek Thompson’s writing for the Atlantic has been some of the most interesting this year. His latest, The Workforce Is About to Change Dramatically, is worth a close read. He gives good arguments for and against how remote working will change real estate, entrepreneurship, and something I’ve been meaning to write about but he did a much better job, how the great migration happening away from superstar cities could reshape politics.

I sincerely hope that all the people moving to new places are registering to vote in their new home, as I did when I moved from San Francisco back to Houston in 2011. The following year was 2012 and in Harris County (Houston) with 4.263 million people, Obama won by 585 votes. I was one of those votes.

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Combating Epidemics With Internet

In 2006 David Eagleman, who wrote one of my favorite books, Sum, wrote a letter published in Nature:

Kathleen Morrison, in News & Views (“Failure and how to avoid it” Nature 440, 752–754; 2006), notes that societies have often prevented collapse by adopting new technological strategies. In today’s world, where one of the most-talked about prospects for collapse is an epidemic of infectious disease, it is worth remembering that perhaps we already have the technological strategy to avoid it — the Internet.

Remote working, made possible by the Internet (‘telepresence’), is already a key component of national and business pandemic plans. Telepresence can inhibit viral transmission by reducing human-to-human contact. Prepared organizations can leverage telepresence to allow continued productivity and functioning of supply chains during an outbreak.

He explores these ideas as well in his Long Now talk in April 2010, in which he talked about Six Easy Steps to Avert the Collapse of Civilization. Here’s an excerpt from that talk covering telepresence and telemedicine. Both videos have had under a thousand views so far. When you watch this remember that it was April, 2010!

This is the topic of his new book, The Safety Net: Surviving Pandemics and Other Disasters.

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Follow-up Questions from WCEU

Matias and I just finished up the discussion and Q&A for the online WordCamp Europe that is going on right now, which was originally happening in Porto.

There were more good questions than we had time to get to, so at the end I suggested that we continue the conversation here, in the comments section! Comments are the best part of blogging.

So if you have a question we didn’t get to, please drop it below. If you don’t have a Gravatar yet now’s a good time to make one.

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Tulsa Remote Worker Experiment

Sarah Holder at Citylab has an interesting article on a program that paid people $10,000, a year of co-working, and a subsidized apartment to move to Tulsa, Oklahoma.

Traditionally, cities looking to spur their economies may offer incentives to attract businesses. But at a time when Americans are moving less frequently than they have in more than half a century, and the anticlimactic race to host an Amazon HQ2 soured some governments on corporate tax breaks, Tulsa is one of several locales testing out a new premise:  Pay people instead.

I love this idea, and hope that after the permanent step-up in remote work from the virus we see much more internal mobility between cities in the United States.

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Physical Distancing

I’ve really had enough of this term “social distancing.” That is not at all what we are looking for, is it? It should be “physical distancing.” In these times of rampant loneliness (especially for seniors), disconnection, and lack of empathy and compassion, we need the opposite — social connecting. And we need it under these circumstances more than ever. Let’s be creative in finding new ways to come together.

Adam Gazzaley, M. D., Ph. D, University of California, San Francisco

Update: On March 20th, the World Health Organization has officially updated it’s recommendation to “physical distancing.”

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Business as Usual in The Information

The Information wrote Business as Usual — Remotely, which includes “85% of its 900 employees working from their homes” Hashicorp, which just raised $175M at a $5.1B valuation today. (I have to get them on Distributed.) Here’s my part:

A survey of American workers by the polling firm Gallup found that in 2016 43% of employees worked remotely at least some of the time, up from 39% in 2012. Of those remote workers, almost a third spent 80% or more of their time working remotely in 2016, compared to 24% in 2012. In computer-related professions, 57% did some remote work in 2016, according to Gallup. 

That includes tech companies like Automattic, which makes WordPress and other software products and has been almost entirely remote since it was founded in 2005. At one point, it opened a large office in San Francisco for employees who preferred a more traditional work environment, but it got rid of that space in 2016 because of how little people used it.  

“We had this 15,000-square-foot place with only five people coming into it,” said Matt Mullenweg, CEO of Automattic, which acquired Tumblr last year. 

Now Automattic rents only one small co-working space in a WeWork suite in New York  and uses another small office in San Francisco exclusively for board meetings. It manages its remote workforce using Slack and Zoom and gives new employees $2,000 so they can purchase home office equipment. 

Employees can also get up to $250 per month for access to a co-working space or for daily coffees at a local coffee shop. But Mullenweg says only about 300 of the company’s 1,200 employees chose to work somewhere other than a home office.

“I hope there can be a silver lining to this crisis, which we all hope is over as soon as possible, that enables people to reexamine how they work and how they interact with things and improve it,” said Mullenweg. “I’m happy to spread the gospel wherever possible for distributed work. I think it’s better for companies, employees, the environment and the world. There are very few downsides.” 

The Information is a worthwhile subscription if you’re in the tech business.

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Sonny Rollins Interview

David Marchese at the NY Times has a beautiful interview with Sonny Rollins up.

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Livestream Tomorrow

About eight of the speakers including myself are going to be doing a livestream tomorrow from 2 to 10 UTC, or what would be 9am to 5pm in Bangkok where the inaugural WordCamp Asia was supposed to happen this weekend.

We’d all much rather be in person, but I do think there is a silver lining in us learning how to do official WordPress livestream events that can be accessible to everyone all over the world, following in the footsteps awesome virtual events like WordSesh.

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29 Books in 2019

As a follow-on to my lists in 2017 and 2018, here are the books I completed this year. I’ve linked all to the Kindle edition except the Great Mental Models, which is so gorgeous in hardcover you should get that one, and the The World is Sound isn’t available as an ebook. Bold are ones I particularly enjoyed or found myself discussing with others a lot.

  1. The Pilgrimage by Paulo Coehlo
  2. 21 Lessons for the 21st Century by Yuval Noah Harari
  3. No Longer at Ease by Chinua Achebe
  4. Imagine it Forward by Beth Comstock
  5. The Great Mental Models Vol. 1 by Shane Parrish
  6. Why Buddhism is True by Robert Wright
  7. There Will Be No Miracles Here by Casey Gerald
  8. Less by Andrew Sean Greer
  9. Bad Blood by John Carreyrou
  10. nejma by Nayyirah Waheed
  11. Trust Exercise by Susan Choi (also on Obama’s book list, and based on the high school I went to, HSPVA)
  12. Genghis Khan and the Making of the Modern World by Jack Weatherford
  13. The Way to Love by Anthony de Mello
  14. The Fifth Agreement by Don Miguel Ruiz, Don Jose Ruiz, and Janet Mills
  15. Empty Planet by Darrell Bricker
  16. Brave New World by Aldous Huxley
  17. How to Talk So Kids Will Listen & Listen So Kids Will Talk by Adele Faber and Elian Mazlish
  18. Make it Scream, Make it Burn by Leslie Jamison
  19. A Short History of Progress by Ronald Wright
  20. Conscious: A Brief Guide to the Fundamental Mystery of the Mind by Annaka Harris
  21. The World Is Sound: Nada Brahma: Music and the Landscape of Consciousness by Joachim-Ernst Berendt
  22. The 15 Commitments of Conscious Leadership by Jim Dethmer and Diana Chapman
  23. Finite and Infinite Games by James P. Carse
  24. Four Soldiers by Hubert Mingarelli
  25. Working by Robert Caro
  26. Attached by Amir Levine and Rachel Heller
  27. Skin in the Game by Nassim Nicholas Taleb
  28. The Devil’s Financial Dictionary by Jason Zweig
  29. How to Do Nothing: Resisting the Attention Economy by Jenny Odell (also on Obama’s book list)

What’s interesting is that if you were to purchase every single one of those books, it would be about $349. You could get them all for nothing from your local library, even on a Kindle. The money I spend on books is by far and away the best investment I make every year — books expand my mind and enrich my life in a way that nothing else does.