Categories
Automattic

Funding, Buyback, and Hiring

In February of this year, Automattic closed a new primary funding round of $288M, bringing in some great new partners including BlackRock, Wellington, Schonfeld, and Alta Park. Existing investors ICONIQ and Aglaé (Bernard Arnault) also participated. This round was common stock, and like all funding since 2011, included a proxy assigning me the right to vote the shares

Automattic was very busy during this time frame, as we were working on what would become the Parse.ly, Day One, and Pocket Casts acquisitions, our investments in Element and Titan, plus more acquisitions and partnerships we haven’t announced yet, so we haven’t mentioned the February funding round until now. And while we are a bit surprised the fundraise did not leak to the press, it’s now been an awkwardly long time since February and I’m pleased to formally announce it now.

And since then, Automattic has continued to grow at a rapid pace and we recently took the opportunity to do a $250M share buyback at a $7.5B valuation that just closed last week. The buyback was primarily targeted at current and former employees. 

We’ve grown and increased our valuation at a rate higher than most other alternate investments available to investors. However, some of Automattic’s employees and former employee shareholders have been part of our journey for a very long time. Selling a bit of their equity holdings could have a significant impact on their lives. 

Automattic was founded 16 years ago and is still private, so it’s important for us to try to provide liquidity to any shareholder who wants it. We do the same with our internal A12 stock plan where we let our employees buy our shares and also offer an opportunity for all holders to sell them back to Automattic, every quarter. (I need to do a longer post on that.)

One interesting thing we’ve been doing in these buybacks is holding the shares as treasury stock within the company instead of canceling the shares at purchase. This allows us to buy shares that come onto the market, and then when an investor comes and wants to put a larger quantum of capital into the company, we can re-sell the treasury shares that the company bought earlier. In effect, we are providing both a sell-side and buy-side for Automattic stock, serving previous and new investors and making money on these trades since we bought and took the risk earlier. We’ve established a logical valuation methodology, which is based on a simple multiple of the last twelve month’s revenue, so shareholders can track and anticipate performance.

All of this has been a lot of fun and we’ve seen a great amount of success, but it’s not all smooth sailing; we still have our share of challenges, probably the biggest being hiring. We have significantly scaled up our ability to find and hire great folks, with 371 accepted offers already in 2021 and it’s only August. However, with the growth of WooCommerce (hiring a Head of Payments) and our enterprise business, WPVIP, in particular, we need to move faster to keep up with the opportunity. For me and many other of the most-tenured Automatticians within the company hiring is the top priority. To that end, I’m also looking for someone to partner with me and our top executive group (which we call Bridge) in Creative Talent Development, an executive recruiter to help craft the highest performing teams of executives for each of our businesses. 

We have a multi-decade opportunity ahead of us to create the best solutions for the open web platform of WordPress, and WooCommerce is doing the same thing for commerce; growing together over the long-term with people passionate about the same mission is my favorite part of my job.

Categories
Open Source

Open Insulin

One of my big themes is that open source will transform every industry, with key examples being WordPress in web publishing, WooCommerce in online commerce, Wikipedia in reference, and Bitcoin/Ethereum in finance. Medicine, though, has been relatively unscathed so far. Here’s a great video introducing the Open Insulin project, which for the past 6 years has been developing their own method of manufacturing insulin and is going to open source its process to the world for anyone to recreate.

It also reminds me of the What If? article in the Economist a few days ago about mRNA self-biohacking. Hat tip: Riaan Knoetze.

Categories
Asides

Day One at Automattic

I’m not sure when I first came across the critically acclaimed Day One product, which is the best private blogging and journaling app out there, but I began seriously using it daily in 2016 when my father was in the ICU and later passed. Having a private, safe place to write what I was going through kept me sane and helped me process everything.

Writing has always been a salve for me, and I’ve had local or private WordPress installations pretty much since 2003 to capture and archive writing that wasn’t fit for the public web.

Day One not only nails the experience of a local blog (or journal as they call it) in an app, but also has (built) a great technical infrastructure — it works fantastic (when) offline and has a fully encrypted sync mechanism, so the data that’s in the cloud is secured in a way that even someone with access to their database couldn’t decode your entries, it’s only decrypted on your local device. Combining encryption and sync in a truly secure way is tricky, but they’ve done it.

This is a long intro to say, as you can read from Day One’s founder and CEO Paul Mayne, from Eli at WordPress.com, and on Tumblr, that Paul and the team are joining the team at Automattic. For many years I’ve talked to anyone who will listen about my vision of making Automattic the Berkshire Hathaway of the internet, and Paul’s decision to continue to grow his amazing business as part of Automattic is a great validation of the way we’ve been building our culture and long-term orientation in our business. Day One is a beloved product, and bringing it into the fold is a responsibility I take very seriously and comes from a deep respect for what’s been built and a belief that working together we can create something for users better than we could working apart.

Great software takes time, and the Day One team has been at it for about a decade now, I can’t wait to see what they accomplish in the coming decade and beyond. If you haven’t tried out Day One yet, please check it out in the Apple or Google’s app store.

Categories
Asides

WCEU Open Thread

I just wrapped up a fun session with Matías and Brian, and though we covered a lot of ground we weren’t able to get to all the questions from the audience. Starting at 2:58:

So this is an open thread, if you have any question from the talk please drop it in the comments here, and myself or someone in the community will respond! We’ll keep this open for a day or so.

Categories
Asides

WordPress 18

Today marks eighteen years since the very first release of WordPress. I consider myself so lucky to have co-founded the project alongside Mike Little. Who could have imagined that our nights and weekends hacking on blogging software, a fork of b2/cafelog, could turn into something powering over 40% of the web? Or that nearly twenty years in, it would be getting better faster than it ever has been?

I blogged these anniversaries when WordPress was five, ten, fifteen, and last year at seventeen, but as the project reaches an age that, if it were a child, it would be heading off to college, I’m uncharacteristically at a loss for words.

The overwhelming feeling is one of gratitude, so I want to say thank you to every person who has ever been involved with making WordPress as a contributor, a community organizer, or as an end-user of the software. It’s amazing what we can accomplish when we work together.

Categories
Future of Work

2021 Streaming Kit

My streaming setup post last year got an amazing reception — there are similar setups being used by executives across the board, from companies fundraising to several I know of with 100B+ valuations. Since that original setup, I’ve updated my own usage of hardware and software combinations to achieve similar or better results for about a quarter of the cost. So here’s the latest and greatest, and below I’ll talk about why the changes.

Video: Camlink, cable, and tripod are still the same, but the camera goes from an A7R IV and a separate lens to an A7C with a kit lens, which saves about $3,000. You also don’t need the dummy battery because the A7C runs great off USB-C.

Lighting: More is more, so I usually use two Key Light Airs (linked above) instead of one. If I’m on the road I’ll pair two Aputure RGB lights with two Lume Cube monopods.

Audio: My best audio advice is to upgrade to an M1 Macbook Pro so your computer is fast and the fan is never on, and position the laptop out of camera view but close to you so the built-in three-mic array picks up pretty good audio from you with no cables or earpieces. (Here’s a singer recording a song on the pre-M1 16-inch version, and note she has to remove fan noise in post-processing.) For bonus points add Krisp.ai ($60/yr) so you get background noise and room echo magically eliminated in real-time.

Teleprompter: The Glide Gear is much easier to set up and way cheaper than my old recommendation. Instead of an external monitor, I use an iPad and the MacOS Sidecar feature. I still don’t have a great way to reverse the screen; in the comments, I’ll share some of what folks have recommended to me.

The above setup removes 75% of the cost without sacrificing any quality.

I’ve gone through every permutation on audio, including using a MixPre-3, NoiseAssist plugin, and a MKH416 shotgun mic ($2k+ total), but I never use that setup unless I’m recording a fancy audio-only podcast.

Why am I using the Sennheiser SC30 in the above photo? Well it was an unusual situation…I was on the side of the road, next to an RV, with logging trucks rumbling by. Sometimes you don’t always know where you need to do a broadcast. 😄

Behind the scenes! We were recording what became this panel.

Categories
Asides

Squarespace Direct Listing

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.

Categories
Asides

CC Search to join WordPress.org

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.

Categories
Open Source

Wix and Their Dirty Tricks

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.

Categories
Asides

Doctorow on IP

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.

Categories
Asides

Invest Like the Best and Building Worlds

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.

Categories
Automattic

Parse.ly & 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.]

Categories
Asides

Compounding Ice

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.

Categories
Automattic

Revue Joins Twitter

Very excited to share the news that Revue is joining Twitter. I’m a huge fan of the idea of better newsletters and Automattic was the largest investor in Revue. I’m looking forward to seeing what the very talented team will do as part of the Twitter network. Also many thanks to Kevin Kelly and Om for introducing me to Revue early on.

Categories
WordPress

New WhiteHouse.gov

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.

Categories
Asides

Iceland Film

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.

Categories
Birthday

Thirty-seven

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.

Categories
Asides

Autonomous and Beautiful Home Devices

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?

Categories
press

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.

Categories
In My Bag

What’s In My Bag, 2020

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!