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Asides

Thirty Six

I am now solidly entering my late thirties, and fortunately I am in good health, good cheer, and doing one of my favorite things — exploring a part of the world and culture I haven’t experienced before (Maldives and Sri Lanka).

The past year has included a number of professional milestones including a significant amount of fundraising and related activity, bringing in a major new product to the Automattic family, the maturation of Gutenberg in the WordPress ecosystem, launching the Distributed blog and podcast, and a growth in the breadth and depth of the Automattic team.

Partially because of the schedule those milestones required, this ended up being my year with the most travel ever since I started tracking: I flew over 515k miles, to 124 cities in 24 countries. I was able to incorporate a good amount of running in my routine, started picking up musical instruments again, and learning more about sound and its impact on our lives. I found small daily habits, like a little bit of exercise or stretching first thing in the morning, to be sustainable and high-impact.

What suffered in 2019 was my book reading time and making a dent on the top 50 list. I still check tech news every day, but I had to unplug from daily non-tech news because it was just too hectic — I’ve found a lot of value in weekly publications like the Economist to make sense of what’s going on in the world with the benefit of a little distance and time.

Personally my main goals this year are for the health and wellness of my family, incorporating more playing music and photography into my life, and strengthening my meditation practice. If you’re reading this, I hope to run into you online or in person and this year let’s do our best together to leave the world a little better than we found it.

All birthdays: 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 3132, 33, 34, 35.

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Asides

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.

All years: 2017, 2018, 2019.

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Asides

Comments and Collatz Conundrum

Over the summer Terence Tao, a Fields Medal-winning mathematician considered one of the best of his generation, got an anonymous comment on his WordPress blog post from 2011 exploring the Collatz conjecture — one of the most persistent problems in math — suggesting he explore the problem for “almost all” numbers. Terence has been a regular WP.com blogger since 2007 and he and his commenters make extensive use of our LaTeX feature to express and embed equations.

That anonymous comment led him to an important breakthrough on the Collatz Conundrum, as Quanta Magazine reports. If you want great comments, you as the author have to participate in them and Terence is incredibly active in engaging with the commenters on his site.

I’ve always said that comments are the best part of blogging, but this is a particularly cool example. Here’s Terence’s latest post on it, with an excellent comment thread following.

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Asides

Powering Your House

I enjoyed this fun video from xkcd’s Randall Munroe on different ways you could power your home, illustrated. Check out his book How To for more in the same vein.

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Future of Work

Distributed Podcast: Clark Valberg, Lydia X. Z. Brown, Stephen Wolfram, and the Grand Meetup

If y’all haven’t caught up recently with my podcast Distributed, this is a perfect moment to do so—the past several weeks have been full of insights from folks like InVision CEO Clark Valberg, attorney and advocate Lydia X. Z. Brown, Stephen Wolfram, and some of my own Automattic colleagues in-person at our Grand Meetup.

You can subscribe at Apple Podcasts, Google, Overcast, Spotify, or wherever you like to listen. 

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Future of Work Ideas

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.

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WordCamp WordPress

State of the Word 2019

In case you missed it, here’s the first-ever State of the Word… designed completely in Gutenberg:

WordCamp US was a fantastic experience, as always. Thank you again to the hundreds of organizers and volunteers who made it happen, to the thousands who attended, and to the city of St. Louis for hosting us. We’ll be back there again next year.

And special thanks to this next generation of WordPress contributors. So exciting to see KidsCamps continue to expand and thrive:

As you can see, my site is now featuring the new WordPress Twenty Twenty theme. And for more coverage from my State of the Word, check out the recaps from WP Tavern and Post Status. Here’s my full audience Q&A below:

You can see my previous State of the Word keynotes here.

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Asides

New Automattic CFO

As Venturebeat has picked up, Mark Davies will be leaving Vivint and joining the merry band. Automattic is creating the operating system for the web, from websites to ecommerce to social networks. As we zoom past 1,100 employees in over 70 countries, we wanted a financial leader with experience taking businesses from hundreds of millions in revenue to billions (Vivint) and even tens of billions (Alcoa and Dell), as Mark has. I’m excited about working alongside such an experienced leader day-to-day to build what I hope will become one of the defining technology companies of the open web era.

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Asides

Debating OSS with DHH

The other week I ended up going back and forth in tweets with David Heinemeier Hansson, it wasn’t going anywhere but he graciously invited me to their podcast and we were able to expand the discussion in a way I found really refreshing and mind-opening.

DHH and I have philosophies around work and open source that I believe overlap 95% or more, so that makes where we have differences all that more interesting to mine. Although we would see each other logged into the same server 15 years ago, we haven’t actually spoken directly until this podcast started, but the conversation flowed so naturally you’d think we have been talking since then.

Check out the episode on Open Source and Power on the Rework Podcast, hopefully you enjoy listening as much as we enjoyed recording it.

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Asides

Automattic’s Series D

Today Automattic announced it has closed a new $300 million Series D, with Salesforce Ventures taking the entire round. This puts us at a post-round valuation of $3 billion, three times what it was after our last fundraising round in 2014. It’s a tremendous vote of confidence for Automattic and for the open web.

I met Marc Benioff earlier this year, and it became obvious to both of us that Salesforce and Automattic shared a lot of principles and philosophies. Marc is a mindful leader and his sensibilities and sense of purpose feel well aligned with our own mission to make the web a better place. He also helped open my eyes to the incredible traction WordPress and WP VIP has seen in the enterprise market, and how much potential there still is there. I’ve also loved re-connecting with Bret Taylor who is now Salesforce’s President and Chief Product Officer. Bret’s experience across Google Maps, Friendfeed, Facebook, Quip, and now transforming Salesforce makes him one of the singular product thinkers out there and our discussion of Automattic’s portfolio of services have been very helpful already.

For Automattic, the funding will allow us to accelerate our roadmap (perhaps by double) and scale up our existing products—including WordPress.com, WordPress VIP, WooCommerce, Jetpack, and (in a few days when it closes) Tumblr. It will also allow us to increase investing our time and energy into the future of the open source WordPress and Gutenberg.

The Salesforce funding is also a vote of confidence for the future of work. Automattic has grown to more than 950 employees working from 71 countries, with no central office for several years now. Distributed work is going to reshape how we spread opportunity more equitably around the world. There continue to be new heights shown of what can be achieved in a distributed fashion, with Gitlab announcing a round at $2.75B earlier this week.

Next year Automattic celebrates 15 years as a company! The timing is fortuitous as we’ve all just returned from Automattic’s annual Grand Meetup, where more than 800 of us got together in person to share our experiences, explore new ideas, and have some fun. I am giddy to work alongside these wonderful people for another 15 years and beyond.

If you’re curious my previous posts on our fundraising, here’s our 2006 Series A, 2008 Series B, 2013 secondary, and 2014 Series C. As before, happy to answer questions in the comments here. I also did an exclusive interview with Romain Dillet on (WP-powered) Techcrunch.

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Asides

On Vergecast

If you’d like some more background and context on Tumblr and Automattic coming together I had a chance to have a short but nuanced conversation with Nilay Patel and Julia Alexander on The Verge’s podcast, Vergecast. I love how great journalists are able to really dive into the heart of issues, and I really enjoyed the conversation.

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Asides

Tumblr the Day After

It is not surprising that the news about Automattic buying Tumblr has picked up a lot of coverage. I especially appreciated the notes of support from Tumblr founder David Karp, former CTO Marco Arment, and investor Bijan Sabet. I am beyond excited to see what the Tumblr team creates next, and I will definitely be connecting with alumni to hear their perspective.

There has also been a lot of speculation on the purchase price, which I think is missing the real story. I would like to take this opportunity to express my respect for Verizon and how they approached this entire process. They inherited Tumblr through an acquisition of a merger, a few steps removed from its initial sale; it’s probably not a company they would have bought on its own, but they nonetheless recognized that there is a very special community and team behind the product. It’s also worth noting at this point that Verizon is a company that will do over $130B in revenue this year and has over 139,000 employees.

First, they chose to find a new home for Tumblr instead of shutting it down. Second, they considered not just how much cash they would get on day one, but also — and especially — what would happen to the team afterward, and how the product and the team would be invested in going forward. Third, they thought about the sort of steward of the community the new owner would be. They didn’t have to do any of that, and I commend them for making all three points a priority.

Automattic is still a startup — I’m sure there are deep-pocketed private equity firms that could have outbid us, but the most likely outcome then would have been an “asset” getting chopped up and sold for parts. (This is a caricature and there are PE firms I like, but it’s not a terrible stretch of the imagination.) Instead, Tumblr has a new chance to redefine itself in 2019 and beyond. Its community is joining with WordPress’ 16-year commitment to open source and the open web.

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Asides

Animated WordPress Wallpaper

I didn’t realize this, but apparently macOS has a built-in ability to show really stunning animated wallpapers, like this one created by Folletto that subtly changes colors throughout the day in an incredibly engaging well:

Check out Folletto’s blog for another dynamic wallpaper and some of process behind creating it. This would be awesome to have for iPhones as well.

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Asides

Just Write with David Perell

I had an interesting conversation with David Perell on his North Star Podcast that I recommend checking out. He’s also leading a really interesting program called Write of Passage which is an online course which helps people grow their career by writing and sharing online, which I think is brilliant and a big source of my career growth over the years. I’ve heard he has another coming soon around information organization. David is someone to watch and follow.

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Asides

Vast, Unbroken Slabs

Writing novels is hard, and requires vast, unbroken slabs of time. Four quiet hours is a resource that I can put to good use. Two slabs of time, each two hours long, might add up to the same four hours, but are not nearly as productive as an unbroken four.

Neil Stephenson on Why I’m a Bad Correspondent
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Asides

Diversifying 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.

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Personal

The Houston Doberge Project

Every year for my Mom’s birthday lunch she has a Doberge cake from Gambino’s in New Orleans, but this year there was a Fedex snafu and it arrived spoiled. We found a last-minute replacement, but it piqued my curiosity as to better alternatives and I commissioned this survey of eight bakeries to answer the question: What’s the best Doberge cake in Houston or New Orleans? The article and pictures that follow are from food critic, travel journalist, and medical science writer Alice Levitt. I hope you enjoy the history, reviews, and surprise winner.

1885, Budapest. Franz Josef I and his wife, Elizabeth, rulers of Austro-Hungary, are attending the National General Exhibition of Budapest. There is much to see, but the emperor’s sweet tooth is pulling him toward one particular display. He simply must taste this new cake he’s been hearing about. He must find the Dobos torte.

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Asides

Prospress joining Automattic

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.

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Podcast

Introducing the Distributed Podcast

Distributed podcast

I’ve been meeting with some brilliant people for Distributed, my new podcast dedicated to exploring the future of work. The first episode is a conversation with Stephane Kasriel, CEO of Upwork, about how they built a distributed culture, and how flexible work will shape the future of the global economy.

Unlike Automattic, Upwork does have an office in Silicon Valley (albeit one with a remote receptionist!). It was interesting to hear how Stephane’s teams balance in-person culture with inclusiveness for all employees, no matter where they live. Read more about Stephane’s work at Distributed.blog, and subscribe at Apple Podcasts, or wherever you listen to podcasts.

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Automattic Future of Work

Happy Tools, for the Future of Work

Distributed work is becoming a reality for more companies. Automattic has been operating in a distributed-first fashion for more than 13 years now — we’re now up to more than 850 employees in 68 countries. But even in companies with physical offices, more employees are distributed around the globe and working together. Google just shared some fascinating stats about its work culture, with 100,000 employees working across 150 cities. Two out of five work groups have employees working from more than one location:

We’re a more connected world, so it makes sense that global business wouldn’t be confined to just one physical space. I often use Google as an example because I’ve been in meetings there where people were one building away from each other but still using video chat because of the time required to walk between meetings on their campus.

With that in mind, the team at Automattic has decided to start sharing our expertise and the technology that makes it all work. Introducing Happy Tools:

Our first product is Happy Schedule, which helps teams manage flexible schedules across time zones. Right now we’re rolling it out in a consultative way with just a few early customers to make sure the team can be totally responsive to their needs. We’re excited about this and other upcoming tools, because we believe that this is the future of work. We’re excited to have other companies give it a try.

Keep an eye on this space: There’s an entire suite of tools that make up the operating system of what has helped Automattic scale so effectively over the years. I’ve always believed it’s important to invest in your internal tools, and I’m excited to release more of them. If there’s something better in the market, we won’t release a tool for it—I’d rather use something external than have to build things ourselves—but where the industry still has a gap after such a long time, we’ll throw our hat into the ring.