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.

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.

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?

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.

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.

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.

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.

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.

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.

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.

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.