Matt Mullenweg

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.

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.

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.

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.

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.

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.