Squarespace Direct Listing

Asides

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.

CC Search to join WordPress.org

Asides,

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.

Wix and Their Dirty Tricks

Open Source

Wix, the website builder company you may remember from stealing WordPress code and lying about it, has now decided the best way to gain relevance is attacking the open source WordPress community in a bizarre set of ads. They can’t even come up with original concepts for attack ads, and have tried to rip-off of Apple’s Mac vs PC ads, but tastelessly personify the WordPress community as an absent, drunken father in a therapy session. 🤔

I have a lot of empathy for whoever was forced to work on these ads, including the actors, it must have felt bad working on something that’s like Encyclopedia Britannica attacking Wikipedia. WordPress is a global movement of hundreds of thousands of volunteers and community members, coming together to make the web a better place. The code, and everything you put into it, belongs to you, and its open source license ensures that you’re in complete control, now and forever. WordPress is free, and also gives you freedom.

Wix is a for-profit company with a valuation that peaked at around 20 billion dollars, and whose business model is getting customers to pay more and more every year and making it difficult to leave or get a refund. (Don’t take my word for it, look at their investor presentations.) They are so insecure that they are also the only website creator I’m aware of that doesn’t allow you to export your content, so they’re like a roach motel where you can check in but never check out. Once you buy into their proprietary stack you’re locked in, which even their support documentation admits:

So if we’re comparing website builders to abusive relationships, Wix is one that locks you in the basement and doesn’t let you leave. I’m surprised consumer protection agencies haven’t gone after them.

Philosophically, I believe in open source, and if WordPress isn’t a good fit for you there are other great open source communities like Drupal, Joomla, Jekyll, and Typo3. We also have a great relationship with some of our proprietary competitors, and I have huge respect for the teams at Shopify and Squarespace, and even though we compete I’ve always seen them operate with integrity and I’d recommend them without hesitation.

I have to believe that users will care about that in the long run, and maybe that’s why Squarespace just passed up Wix in market share. They natively support exporting into WordPress’ format and don’t have to resort to dirty tricks to be successful. I expect Squarespace’s upcoming IPO will be a great one.

Wix, though, continues to show their true colors. Regardless of their product, I hope people consider the behavior of companies in the world they support with their dollars. Wix really wants you to see their new campaign though, so let’s take the bait and watch the creepy, misleading way they are trying to represent themselves.

Invest Like the Best and Building Worlds

Asides

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.

Parse.ly & Automattic

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.]

Compounding Ice

Asides

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.

New WhiteHouse.gov

WordPress

After you’ve watched the amazing poem from Amanda Gorman, check out the new WhiteHouse.gov that re-launched today using WordPress & Gutenberg with a number of cool features including dark mode, text zoom, a totally responsive layout, and a Spanish version of the site. The site is clean, fast, and accessible. It’s exciting and an honor that the online home for the Executive branch is on Open Source software, and I’m proud WordPress can carry the torch that Drupal lit in 2009.

Besides Gutenberg, poking around I noticed a HTTP header and HTML comment encouraging people to join USDS, and this great #46 easter egg in the theme file:

Anyone notice any other plugins? I haven’t spoken to him directly but I’d be shocked if Nacin wasn’t involved with this one. I’m also curious if any of the WP agencies were involved, it has touches of 10up but I don’t see any mention of it on their site or Twitter. Hoefler&Co credits Wide Eye Creative with the design.

I noticed a few people happy that some previous pages and files on the old site were returning 404 errors, like the controversial 1776 report, but on this I think the webmasters of the United States of America should demand better, since Cool URIs Don’t Change. Previous websites are all saved by the National Archives, but there doesn’t appear to be any sort of norm for automatically redirecting links that went to any subdirectories or addresses under WhiteHouse.gov.

There are WP plugins that could help, like Redirection, but also perhaps the root domain itself could always redirect to a subdomain, like 46.whitehouse.gov, so we’d have a consistent domain and permalinks for everything, and then each new administration would get a new subdomain.

More coverage on WP Tavern.

Thirty-seven

Birthday

I turn 37 today. I look around and I feel incredibly lucky to be writing this after a topsy-turvy year. I have health. I have friends whom I love. These are all good reasons to feel optimistic about the future. A few unconnected thoughts today:

My father had me when he was exactly 13,300 days old, and this year I passed that number of rotations of the Earth.

It’s hard to plan when so much is changing, so resolutions this year haven’t felt the same. But in times like these it’s even more important to plan for the long-term. A look back, once a year, is enough to remind of what remains.

I’m so thankful for the internet. It’s where I learned and practiced my trade. It’s where I connect every day with the most interesting and eclectic group of people I could imagine, a modern day Florence during the Renaissance. I hope to make a lot more internet and enable others to do the same.

Many years ago I said “Technology is best when it brings people together.” This quote has taken on a life of its own on motivational posters and images. When I first said it I think I had in mind WordCamps and meetups and other physical gatherings; this year it transformed for me seeing how technology brought together those separated by the pandemic. This year has appeared divisive, so it’s easy to overlook how many times people came together. It’s like the old saying, it’s not how many times you fall, it’s how many times you get up. Fall thirty-six times, get up thirty-seven.

All birthday posts: 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40.

Autonomous and Beautiful Home Devices

Asides

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?

Farnam Street and Postlight

I recorded two interviews very far apart from each other, but which have surprisingly both come out today. The first is for one of my favorite sites on the web, Farnam Street. I was honored to be episode 100 on their Knowledge Project podcast. Knowledge Project is probably one of the podcasts I’ve listened to the most since it started. Please check out their other guests as well, they really do have the most interesting conversations with the most interesting folks.

Shane and I cover turnarounds, how environment affects performance, pros and cons of distributed work, uncovering your lacuna, mental models, and patterns of decision making.

On a completely different vein, I did a deep geek-out on technology and content management systems with Gina Trapani and Paul Ford, two of my favorite technologists, on the Postlight podcast. We covered a lot of tech history, my thoughts on Chromium and Mozilla’s Gecko engine, structured data, Gutenberg, and a lot more. If you’re a developer or a long-time WordPress community member you’ll enjoy this one, but it might be esoteric or technical if you’re not immersed in this world. Here’s a Spotify embed of the episode:

In both we do touch on my idea that, on a long enough timeline, the survival rate for all proprietary software drops to zero. (Hat tip to Fight Club.) Proprietary software is an evolutionary dead end. You can think of open source packages like genetic alleles that have a higher fitness function, and eventually become the fittest organism. The longer I spend watching mega-trends in technology, the more I see that pattern everywhere, from encyclopedias to cryptocurrencies.

What’s In My Bag, 2020

In My Bag

Instead of sharing what’s in my backpack this year, I want to share the apps and pandemic purchases that were meaningful to me, along with a few words on each. Something I haven’t shared with you yet on this blog is… I went down a #vanlife rabbit hole and ended up camping and working remotely a decent chunk of the year. I learned a ton and feel much more resilient. So this is a phoneful and truckful update of my year.

First I’ll start with apps, these all link to Apple’s app store but almost all have Android equivalents that I also use:

  • Calm and Waking Up — Very different but both incredibly valuable meditation apps. I had an 82-day streak with Calm this year! I wouldn’t have survived without these.
  • Fitbod — You tell the app what equipment you have, how much time you have, and it gives you a workout like a trainer would, rotating muscle groups.
  • Streaks — An app for starting and tracking habits. This is a funny one because I actually stopped using it because it worked. The things I was tracking on Streaks became daily habits and I stopped using the app every day. The same thing happened for me with Zero, my daily fast became part of my routine so I’d only use Zero if I was doing a longer one.
  • Tumblr — It was so nice to have a social network centered around creativity and humor.
  • Asana — Getting organized helped lessen anxiety.
  • Pocket Casts — I switched to this because it syncs between devices, and I used my Android device a lot especially while driving.
  • AllTrails — I spent more time in nature this year than almost any previous, and AllTrails was an amazing way to find great hikes.
  • The Economist — The most insightful news, and the weekly cadence helped me avoid the wild variance of the daily news cycle. My favorite news app.
  • YouTube — Wow, there’s a lot of stuff on here. This was the year I started to “get” why people spend so much time on YouTube. Some favorite finds were Jacob Collier and Mark Rober.
  • Walmart — Surprisingly good on road trips for curbside pickup orders scheduled a few hours ahead. Yes, I have now joined 95% of the US population.
  • Blueground and Avantstay — Good for longer stays in places. I found both through Airbnb, which is still the king.
  • Food apps in order of usage: DoorDash, Uber Eats, Tock, Toast TakeOut.
  • Camping apps in order of usage: AllTrails, Chimani, Recreation.gov, iOverlander, Boondocking, FreeRoam, Harvest Hosts.
  • App I deleted and re-added the most: Twitter. I love the things I learn from using it, but hate feeling like I’m wasting time.

When on road trips I found Android Auto running off the Pixel 5 much more reliable than CarPlay, which would frequently freeze up on me. Things have improved with iOS 14, but I still always use the Pixel when I’m on a longer drive.

I also have been living with my Mom since July, including her two cats and new Coton du Tulear puppy. Pets are humbling! It’s been great to learn how to support them best, as I last lived with animals when I was in high school and wasn’t that conscious of the responsibility then.

Amazon says I made over 850 orders this year, more than double from any previous year. Here are the non-tech purchases that ended up having a big impact on me:

Clothing and wearables, like much of the world I trended toward comfort and away from normal shoes and socks:

Electronics:

There you have it. As always, if you’ve tried something here and found an alternative that’s better, let me know in the comments!

Jack Dorsey and Running Two Companies

Podcast

I had the pleasure of interviewing Jack Dorsey for the Distributed podcast, a conversation that ended up going a bit deeper and longer than previous episodes.

In preparation for the interview I kept coming across people critical about the fact that Jack is the CEO of two companies simultaneously, Twitter and Square, each having over 5,000 employees.

I think what people miss is that at that scale, running a company is not that different from running a large division of a company. No one asks Jeff Bezos how he’s CEO of both a retail company and a cloud computing one (AWS), or Tim Cook how he’s CEO of a hardware business and a services business, and of course with both of those examples the breadth of what the companies cover is much wider. Also as an added benefit, shareholders can choose to invest in Square and Twitter together or not.

All of that said, I think having a CEO-level seat at two of the most influential technology companies today does allow for accelerated learning, as organizational experiments will naturally happen at each company and then the best practice can be shared to the other. Jack wasn’t aware how much peer executives at each company meet with each other to share learnings, but that seems like an obvious win.

Readers of this blog will especially appreciate how much we talked about open source and cryptocurrencies, and his view on the three things he’s responsible for as CEO. Give it a listen and let me know what you think.

State of the Word 2020

This tumultuous year, two things really helped me get through it: my colleagues at Automattic and the community of WordPress.

At the end of the year I usually deliver a speech to the WP community we call the State of the Word, that celebrates what we accomplished the previous year and shines a light on what we could focus on in the coming year. There’s always a great energy in the room and I love mixing with the audience before and after the talk. This year we did it online, which meant we could produce the talk a little more, and we made extra time for the Q&A afterward with answers not just from me but folks across the community.

One thing I’ll call out WordPress 5.6 had an all women and non-binary release squad of over 50 people, a first for WordPress and probably any large open source project. Also the market share of WordPress grew more in 2020 than it has in any year since it started being tracked!

If you’re curious about what’s next for WordPress, check it out:

Second-Order Effects

Asides

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.

Corner Office Interview

Future of Work

If you pick up a print edition of the Sunday New York Times today you’ll see the Corner Office interview with David Gelles in the business section.

(Hat tip to Mary Conrad for the picture, I haven’t seen it in person yet.)

A quote that seems to be resonating with people,

This column is called Corner Office, and most people who choose to have offices are usually the bosses. And I’ve been to the offices of billionaire C.E.O.s that have their own private bathroom, beautiful art and couches. But these are all things that you can have in your house. What I love about distributed organizations is every single employee can have a corner office.

Sometimes my corner office has been the corner of an airport floor next to a power outlet! I’ve also heard from colleagues that feel like their office feels like an unsupervised day care center since the quarantine started. The point I want to make is there’s a world of possibility that opens up when you move from the finite space of a shared office, and all the politics of dividing up the scarce resource of desirable space, to the infinite game where people can define their own “office” as the place where they will be most productive, and do so however they like with no penalties or restraints.

If you had the best space in the legacy office, you probably liked it and may even have had motivated reasoning around ineffable things that happened in the office like “culture” that would be impossible without it, but the average experience of an entry-level worker was not as positive. Now there can be a much more even playing field. At Automattic we have a home office allowance people can use to buy equipment they need to make their home work area comfortable and productive, and it’s the same if you’re leading a team of hundreds or if it’s your first job.

If you’d like to hear the entire conversation they’ve posted the original audio and interview that was distilled into the print version.

Combating Epidemics With Internet

Asides

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.

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.