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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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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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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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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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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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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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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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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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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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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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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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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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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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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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A Meditation on the Open Web

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39 Books in 2018

Here’s what I read in 2018, in chronological order of when I finished it, as promised in my birthday post. I’ve highlighted a few in bold but in general I was pretty satisfied with almost all of my book choices this year. I’ve put a lot more time into the “deciding what to read” phase of things, and have also had some great help from friends there, and have been trying to balance and alternate titles that have stood the test of time and newer au courant books.

  1. Hot Seat: The Startup CEO Guidebook by Dan Shapiro
  2. The Unbearable Lightness of Being by Milan Kundera (audio)
  3. A Higher Standard by Ann E. Dunwoody
  4. Extreme Ownership by Jocko Willink and Leif Babin (audio)
  5. The Boat by Nam Le
  6. Charlotte’s Web by E. B. White
  7. Nonviolent Communication by Marshall B. Rosenberg
  8. How to Say Goodbye by Wendy Macnaughton
  9. When Things Fall Apart by Pema Chödrön
  10. Soul of an Octopus by Sy Montgomery
  11. Poor Charlie’s Almanack by Charlie Munger and Peter Kaufman
  12. Sam the Cat by Matthew Klam
  13. The Prophet by Kahlil Gibran
  14. The Vegetarian by Han Kang
  15. The Paper Menagerie by Ken Liu
  16. After On: A Novel of Silicon Valley by Rob Reid
  17. The Conquest of Happiness by Bertrand Russell
  18. How to Write an Autobiographical Novel by Alexander Chee
  19. Ficciones by Jorge Luis Borges
  20. Black Box Thinking by Matthew Syed
  21. Darkness Visible by William Styron
  22. Tin Man by Sarah Winman
  23. Sapiens by Yuval Noah Harari
  24. Let My People Go Surfing by Yvon Chouinard
  25. Pachinko by Min Jin Lee (Update: On Obama’s 2019 book list.)
  26. Homo Deus by Yuval Noah Harari
  27. The Lessons of History by Will & Ariel Durant
  28. Stories of Your Life and Others by Ted Chiang
  29. So You Want to Talk About Race by Ijeoma Oluo
  30. Three Body Problem by Cixin Liu
  31. How to Fix a Broken Heart by Guy Winch
  32. Sum: Forty Tales from the Afterlives by David Eagleman
  33. Exit West by Mohsin Hamid
  34. Tiny Beautiful Things by Cheryl Strayed
  35. Farsighted: How We Make the Decisions That Matter the Most by Steven Johnson
  36. Severance: A Novel by Ling Ma
  37. On the Shortness of Life by Seneca
  38. It Doesn’t Have to Be Crazy at Work by Jason Fried and David Heinemeier Hansson
  39. Notes of a Native Son by James Baldwin

All years: 2017, 2018, 2019.

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All Your Might

Julie Sugar has a beautiful piece in Lilith Magazine about miscarriage and faith.

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Thirty-Five

What a year.

First, it feels amazing to write this inside of the new Gutenberg block editor in WordPress 5.0. It was a labor of love for so many and the next chapters are going to be even more exciting.

The best part of the last year was growing closer to my friends and loved ones — I don’t know if it’s externally perceptible but my heart feels a lot more open.

I’ve found a good balance with meditation, work, sleep, fasting, eating, and reading that gives me a lot of joy, energy, and feels like a combination I could sustain the rest of my life.

Reading in particular was a highlight as I finished 38 books, which is the most in a year since I started tracking, and so many of them were truly excellent I’m going to do another post just on books. I will give a special call out to The Paper Menagerie by Ken Liu. Leaving my Kindle Oasis at an airport ended up being a blessing in disguise as I started using the Kindle app on my iPhone a lot more and that’s become my new favorite habit. (And the physical Kindle was returned!)

It was a strong travel year, covering 126 cities, 20 countries, and 377k miles. I especially enjoyed visits to Tulum, Iceland, Bodrum, Tonga, Kauai, Lanai, and Courchevel. I finally checked off my bucket list item to become scuba certified and had an amazing opportunity to swim with humpback whales.

I was a few feet from Adam Gazzaley when he took this photo.

I also had lots of opportunities to practice patience, weathered a torrent of personally-directed criticism across every medium, and had a few months that were the hardest I’ve worked in my career. With the benefit of a little distance, though, those things don’t loom as large. I learned a ton — often the hard way but often that’s what it takes — and discovered I had some additional gears that can kick in when needed.

As I pass solidly into my mid-thirties, I don’t have any drastic shifts on the horizon but I am looking forward to continuing to strengthen the habits I’ve been able to develop this past year.

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Democratize Publishing, Revisited

During my State of the Word Q&A I received some blogging homework from Toru Miki, a WordPress contributor based in Tokyo. He asked me to revisit the WordPress mission, “Democratize Publishing,” and reflect on what that mission means to me today. So here you go, Toru:

For many years, my definition of “Democratize Publishing” has been simply to help make the web a more open place. That foundation begins with the software itself, as outlined by the Four Freedoms:

0. The freedom to run the program, for any purpose.

1. The freedom to study how the program works, and change it so it does your computing as you wish.

2. The freedom to redistribute copies so you can help your neighbor.

3. The freedom to distribute copies of your modified versions, giving the community a chance to benefit from your changes.

In 2018, the mission of “Democratize Publishing” to me means that people of all backgrounds, interests, and abilities should be able to access Free-as-in-speech software that empowers them to express themselves on the open web and to own their content.

But as Toru noted in the original question, “Democratize Publishing” has come to mean many things to many people in the WordPress community. That’s one reason I like it. The WordPress mission is not just for one person to define.

So I’d like to ask everyone: What does “Democratize Publishing” mean to you?  

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Sponcon Posts

I found this post by Taylor Lorenz describing how aspiring influencers are posting fake, unpaid sponsored content to raise their status or hoping to nab a real sponsorship is totally bananas.