Category Archives: Essays

What I Miss and Don’t Miss About San Francisco

A few months ago I was chatting with John Borthwick, who had just returned from a trip to San Francisco. I asked him how the city was doing as if he were a traveler who had visited someplace exotic — “How is it over there?” (As an investor he probably sees the crazier side of the city, since part of his job is looking at hundreds of companies, the vast majority of which will fail, and trying to pick a few winners.)

Despite getting near-daily meeting requests, I don’t currently have any plans to visit San Francisco. I was there in June for a few days for Foo Camp and for drinks with the artist Tom Marioni. I returned for WordCamp San Francisco in October, and again a few weeks ago for Scoble’s 50th birthday party and a board meeting. But the couple-times-a-year rhythm seems to be enough for me. I’m enjoying the distance a bit, in fact.

There has been plenty written about the bubble culture in SF right now, including on the antitech movement that never really took offIt’s a topic I already blogged about in 2013. But I was curious to unpack my own thoughts about being away from it all.

What I don’t miss:

  • Too many meetings — every possible company is there, and everyone wants to meet.
  • High prices for everything, from groceries to cocktails. Not even going to talk about the real estate market and rentals.
  • It takes forever to get across the city, even though it’s only 7 miles.
  • The public transit, while workable, pales in comparison to other places like NYC.
  • The weather isn’t bad, until you drive to Palo Alto or Marin and notice how much nicer it is there. (Or take a one-hour flight to Los Angeles or San Diego.)
  • This is anecdotal, but I feel like cell phone service is terrible, especially for making calls. Calls are unintelligible and drop frequently. I think this is why everyone texts.

I don’t have any problem with the social scene; SF might be tech-heavy, but it’s fairly easy to get out of the tech bubble. Many forget that San Francisco is home to a ton of people working for non-profits, in fashion, finance, bio-tech, art, and music.

What I miss, deeply: the people. Some of my favorite people, professionally and personally, are in the Bay Area, and that’s the thing that will draw me back someday. I’m lucky that I can catch up with folks when they travel, like Jane or Tony in New York or Om in Italy. Of course the Automattic headquarters is there, along with some great colleagues, but I can also catch up with them at meetups.

I miss how much technology permeates the culture there, from billboards to services like Uber or Postmates (or Munchery or Spoonrocket) that today seem like conveniences, but will be the basis of something very meaningful down the line. You can feel like you’re living in the future there. Internet speeds seem to be getting better, too —  local ISPs like Webpass and Monkeybrains are leading the way, but even my Comcast account there delivers 120mbps.

I miss being able to run along the water, and the close proximity to lots of beautiful nature areas (granted I didn’t take much advantage of those when I was still around). The quality of light is really nice — when you can see it. Restaurants, though tending toward pricey, offer great ingredients and quality.

Finally, you can’t deny it’s a city of hustlers. This tweet has since been deleted, but you get the idea:

Advice and Fallacies

One of the toughest things in business is when you get well-meaning advice from advisors, investors, or friends of the company who are valuable but might hold some ideas or ways of approaching problems that just aren’t applicable to your particular company or situation. They might be right most of the time, and it might have worked for them in the past to build a huge success, but it doesn’t mean it’s right for you, right now.

This is especially a struggle for Automattic because so much of what we do is deliberately different from companies that have come before us. The below is a sensitive-info-scrubbed version of a comment I made on an internal P2 in response to someone who had met with a close friend of the company who had said we should “hire more business people, and more people like so-and-so, who have a background in and passion for data analysis and structure. He also shared his ideas about what the additional business hires could be responsible for, such as P&L responsibilities for specific products.” The person he had talked to was asking why we weren’t following that advice.

The first part was easy, because so-and-so was actually leading hiring for a position around data and the early results were going well. The rest I ended up writing more about, which follows. It was only meant for internal consumption, so read it as such, but I got enough requests to share the comment publicly that I wanted to clean it up and release it for y’all.

On the “more biz people + P&L” side, it’s an area we disagree.

We’ve had more “business people” in the past, and found it just didn’t move the needle in the same way that investing on the support, engineering, and design side did. They also tended to generate more meetings and work for other people than was commensurate for their contributions.

We’ve also experimented with giving leads P&L responsibility for products and groups, but ultimately it was awkward because we don’t really want leads or teams focused on the loss or costs of what they’re doing — we just want to grow our core metrics and revenue in a healthy and accelerating way, and let Ops and myself worry about overall profit or loss for the company, costs of people and services, capital requirements, etc. We’re still at a stage where our primary goals are investing in growth and product excellence, I wouldn’t want a P&L concern to be a distraction from that, and that also takes us into the territory of different teams having “headcounts” of people they can hire for the year, or budgets set ahead of time and that they’ll lose if they don’t use, zero-sum accounting between teams and more balkanization you often see in larger organizations. When anyone thinks about P&L at Automattic, I want it to be holistically and with a long-term view, not for a single team or product.

It gets backs to the fallacy we talked about and agreed to avoid at the [ leads] meetup, which is the business equivalent of Great Man Theory: the idea that a deficiency in the business or product will be solved by hiring someone senior to be in charge of that thing. Example: Automattic is bad at marketing, we should hire a CMO. (99% of the time when this is suggested it means an external person, because if anyone internal was good the problem wouldn’t exist.) It’s an easy thing for anyone to fall into, you can see it in [a recent internal thread].

This must work sometimes, because it seems to be a near-universal affliction of VCs on startup boards. It also is a little bit of a bikeshed, because while it can be difficult to understand or feel like you can have an influence on something fundamental to the product, like say the signup flow, most VCs have large professional networks and can have long and vigorous discussions talking about potential people who are executives in a given area and their first or second degree connections to them. Of course, like many of us, VCs are consumers of tech media which tends to ascribe all the success of an organization to a single person (like Sheryl Sandberg for Facebook not falling apart, or Adam Bain for revenue at Twitter). However often the problem has root causes more fundamental than a single person could shift.

I subscribe to a more environment-driven approach, that if you break down a problem into its component parts you can address them individually, often with relatively simple next steps, and build things from the ground up, rather than the top down. If you can’t do that, then it’s best to be candid that the area is not a priority and make sure that’s in line with what you’re focusing on instead. In this process leaders will emerge or if the effort matures to a point where one joins as a new hire he or she will have the resources, groundwork, and environment to succeed.

So in summary: always go back to first principles of decisions. Hires are seldom panaceas. Someone being successful in a role at another company doesn’t mean they actually did the work, or were the cause of the success. If there’s an area you’re weak, try to figure out the root causes of why you’re weak, and where possible try to improve the environment that creates the problem before pinning the turnaround on a “Jesus hire.” When you improve the environment it makes it much more likely a new external hire will do well. The majority of success or failure is a result of the environment, at least as much as the individuals involved.

Five for the Future

On Sunday at WordCamp Europe I got a question about how companies contribute back to WordPress, how they’re doing, and what companies should do more of.

First on the state of things: there are more companies genuinely and altruistically contributing to growing WordPress than ever before. In our ecosystem web hosts definitely make the most revenue and profits, and it’s been great to see them stepping up their game, but also the consultancies and agencies around WordPress have been pretty amazing about their people contributions, as demonstrated most recently by the fact the 4.0 and 4.1 release leads both hail from WP agencies (10up and Code for the People, respectively).

I think a good rule of thumb that will scale with the community as it continues to grow is that organizations that want to grow the WordPress pie (and not just their piece of it) should dedicate 5% of their people to working on something to do with core — be it development, documentation, security, support forums, theme reviews, training, testing, translation or whatever it might be that helps move WordPress mission forward.

Five percent doesn’t sound like much, but it adds up quickly. As of today Automattic is 277 people, which means we should have about 14 people contributing full-time. That’s a lot of people to not have on things that are more direct or obvious drivers of the business, and we’re not quite there today, but I’m working on it and hope Automattic can set a good example for this in the community. I think it’s just as hard for a 20-person organization to peel 1 person off.

It’s a big commitment, but I can’t think of a better long-term investment in the health of WordPress overall. I think it will look incredibly modest in hindsight. This ratio is probably the bare minimum for a sustainable ecosystem, avoiding the tragedy of the commons. I think the 5% rule is one that all open source projects and companies should follow, at least if they want to be vibrant a decade from now.

Further reading: There’s been a number of nice blog follow-ups. Post Status has a nice post on Contribution Culture. Ben Metcalf responded but I disagree with pretty much everything even though I’m glad he wrote it. Tony Perez wrote The Vision of Five and What it Means. Dries Buytaert, the founder of Drupal, pointed out his essay Scaling Open Source Communities which I think is really good.

Why the Web Still Matters for Writing

I wanted to share unique perspective for why the web matters in an app world with a guest post from Stratechery writer Ben Thompson:

This week Twitter was abuzz with the most recent report from Flurry that showed people spending most of their time on mobile using apps, not the browser:

Time Spent in APps

Many were quick to once again declare “The Web is Dead,” but I’m not sure that conclusion makes sense, at least for writing.

First off, Flurry’s numbers don’t account for webviews within mobile apps. On my site, Stratechery, 37% of my iOS traffic comes from webviews (Android doesn’t break out the difference), which on Flurry’s chart would fall mostly in the Twitter slice. More mass market sites likely take up some percentage of Facebook time, as well.

That said, it’s striking how little written content appears on Flurry’s chart; the only category that is primarily about written content is news, and even that includes video. And yet, pageviews on and Jetpack are up 27% year-over-year, new sites ranging from small blogs like Stratechery to huge sites like FiveThirtyEight continue to launch and grow, and multiple startups (and competitors!) continue to find writing something worth investing in.

So is the web dead or not?

I don’t think so, for a few reasons:

  • The total amount of time spent on a computing device (especially mobile), has and continues to grow significantly. This means that many of the activities on our phones, app or not, are additive to what we previously used a computer for. This makes sense: what makes mobile such a big deal is that instead of a computer being a destination device, it’s now a companion that goes with us everywhere. This is how you square the fact that apps seem to dominate usage even as writing on the web continues to grow. When the entire pie is huge and getting bigger, the total size of any particular slice grows as well, even if it becomes relatively thinner.
  • Although apps take up a huge percentage of total time, a significant percentage of app time is dominated by just two categories: games (32%) and social networks and messaging (28%). In fact, the more interesting juxtaposition raised by Flurry’s numbers is not apps versus web, but games and social versus everything else.YouTube and other entertainment apps form a solid percentage of what is left (8%), but the remainder is a mishmash of utilities, productivity, the aforementioned news, and, of course the web, which could be anything and everything.
  • The single most exciting development when it comes to writing on the web is the democratization of publishing. It it now trivial to start a blog, whether on or another provider, and that has led to an explosion of content. As I wrote on Stratechery in FiveThirtyEight and the End of Average:

    Most of what I read is the best there is to read on any given subject. The trash is few and far between, and the average equally rare. This, of course, is made possible by the Internet. No longer are my reading choices constrained by time and especially place.

    Why should I pick up the Wisconsin State Journal – or the Taipei Times – when I can read Nate Silver, Ezra Klein, Bill Simmons, and the myriad other links served up by Twitter? I, and everyone else interested in news, politics, or sports, can read the best with less effort – and cost – than it ever took to read the merely average just a few short years ago.

    While there is still a lot of work to be done on discovery (I mostly use Twitter, but admit the learning curve is steep), I already find the idea of being constrained to any one channel for reading to be laughably old-fashioned. And yet, that’s exactly what an app is: a single channel for one publisher’s content. Contrast this to the web, where any given piece is available instantly by simply clicking a link.

There is no question that apps are here to stay, and are a superior interaction model for some uses. But the web is like water: it fills in all the gaps between things like gaming and social with exactly what any one particular user wants. And while we all might have a use for Facebook – simply because everyone is there – we all have different things that interest us when it comes to reading.

That’s why very few of us devote all of our reading time to a single general interest newspaper these days, and that’s why we at have no intention of pushing anyone to any one particular platform or app. Instead our focus is on enabling and empowering individuals to create new content that is at home in the mobile browser, the app, Facebook or Twitter webviews, or any other channel that makes sense for the reader. Let the water flow to exactly where it’s needed! That’s the power of the web, and now that a computer is with us in so many more places, we need that flexibility more than ever.

You can read more of Ben Thompson’s writing on his excellent WordPress-powered blog Stratechery, one of my favorite sources for the “why” behind the news.

See also: John Gruber on Rethinking What We Mean by ‘Mobile Web.’

WhatsApp Takeaway

whatsappFor better or worse, a great deal of investment in technology is driven by pattern matching. In that world any company (including Automattic) that generally eschews hype, is largely subscription driven, and has a small number of employees relative to its audience should be thrilled at the 19 billion dollar acquisition of WhatsApp. The deal is incredible.

This has kicked off another round of pattern matching and halo effects, which are currently incredibly favorable but will evolve over the coming years based on how things go post-integration, just like the public perceptions of Geocities, Youtube, Doubleclick, Bebo, and Skype wildly shifted based largely on the press coverage over their latest traded value.

I’m thrilled with the outcome for WhatsApp and the manner in which they built their company, their product, and I hope they bring more of that thinking to Facebook, but I don’t think they should become a playbook any more than Instagram should inspire a no-revenue playbook. The pattern we should take away from this story is that there is no pattern. (In Perl, “there’s more than one way to do it” or Tim Toady.) As an entrepreneur making decisions for your company, always go back to your first principles of what’s important to you and why you started in the first place. As a journalist, try not to fit everyone into arcs you’ve seen before or ascribe value to previous coverage (or lack of coverage). As an investor try to evaluate every situation on its unique merits. Should founders be CEOs or not? Well, it depends on the founders, the company, and what it means to be CEO, not what an over-normalized sample of a few hundred companies did before in completely different contexts.

There are also products that succeed with design that seems childish or terrible on the surface (Myspace, eBay, Snapchat). A lot of what it comes down to is have you made something people want, and are they finding out about it from their friends. That’s often the realm people think of as marketing. The best marketers in the world don’t fit our preconceptions of what that word means because they’re in hoodies instead of suits and create environments and ecosystems rather than the traditional trappings of marketing.

Update: From @dsa, here’s a great follow-up read on Techcrunch: What Games Are: Flappy Bird, Patterns, And Context.

The Four Freedoms

Eleven months before the U.S. declared war on Japan, President Franklin D. Roosevelt said “As men do not live by bread alone, they do not fight by armaments alone.” He articulated four fundamental freedoms that everyone in the world ought to enjoy:

  1. Freedom of speech.
  2. Freedom of worship.
  3. Freedom from want.
  4. Freedom from fear.

Fast forward 72 years: technology has advanced at dizzying rates and permeated every aspect of our lives, from how we are born to how we die and everything in between. In this co-evolution of society and technology, what it means to be truly “free” is no longer about just the country we live in, or even its laws, but is shaped by the products we live on.

As Marc Andreessen says, software is eating the world. It’s a creative gale of destruction that irreversibly changes every industry it touches, and if you don’t control the software, the software controls you. It mediates how and with whom you communicate, what news you see, and what other software you’re able to run. It influences the very way your brain works, as you process the creative gale of distraction that interrupts us all hundreds of times each day. With every ping, software burrows deeper into our lives.

In the early nineties, a prescient hacker named Richard Stallman — working at MIT, where today’s future had already happened — recognized this shift. He proposed a set of four freedoms that were fundamental for software in an enlightened, tech-dependent society.

  1. The freedom to run the program, for any purpose.
  2. The freedom to study how the program works, and change it so it does your computing as you wish.
  3. The freedom to redistribute copies so you can help your neighbor.
  4. The freedom to distribute copies of your modified versions, giving the community a chance to benefit from your changes.

(Aside: I originally thought Stallman started counting with zero instead of one because he’s a geek. He is, but that wasn’t the reason. Freedoms one, two, and three came first, but later he wanted to add something to supercede all of them. So: freedom zero. The geekness is a happy accident.)

This is our Bill of Rights. Stallman called it Free Software. The “free” doesn’t have to do with price, as you’re still free to charge for your software, but with freedom to create. Or as we geeks often say: not free as in beer, free as in speech.

People are scared of free software, and I understand why. You’re taking the most valuable thing you have, your intellectual property, and granting the freedom you enjoy as a creator to anyone who downloads your work. It’s terrifying, actually. It’s releasing your ideas, and letting anyone build on them — in a way that might be better than your own work. It’s releasing your traditional understanding of ownership, and your fear of being out-developed.

The most experienced entrepreneurs can cling to the concept that your idea is something precious that must be protected from the world, and meted out in a controlled way. Lots of us hang on to the assumption that scarcity creates a proprietary advantage. It’s how many non-tech markets work.

Open source abdicates your flexibility as a developer to better serve the people who actually use your products. You can see that as a constraint… or you can see it as a door to iteration, innovation, and constant progress.

I’ve spent a third of my life building software based on Stallman’s four freedoms, and I’ve been astonished by the results. WordPress wouldn’t be here if it weren’t for those freedoms, and it couldn’t have evolved the way it has.

WordPress was based on a program called B2/cafelog that predated it by two years. I was using B2 because it had freedoms 0 and 1: I could use it for whatever I wanted, including my zero-budget personal blog, and the source code was open. It was elegant and easy to understand, and anyone could tweak it.

B2 was ultimately abandoned by its creator. If I’d been using it under a proprietary license, that would have been the end — for me, and all its other users. But because we had freedoms 2 and 3, Mike Little and I were able to use the software as a foundation, giving us a two-year headstart over building something from scratch, and realize our own vision of what blogging could be.

We were just consumers of the software, volunteers in the forums, and occasional contributors to the codebase, but because (of the GPL) we had the freedom to build on B2, we were able to continue development as if it had been our own creation.

Ten years later, those freedoms are still embedded in every copy of WordPress downloaded, including the 9.2 million downloaded in the past month or so since our 3.8 release.

I believe that software, and in fact entire companies, should be run in a way that assumes that the sum of the talent of people outside your walls is greater than the sum of the few you have inside. None of us are as smart as all of us. Given the right environment — one that leverages the marginal cost of distributing software and ideas — independent actors can work toward something that benefits them, while also increasing the capability of the entire community.

This is where open source gets really interesting: it’s not just about the legal wonkery around software licensing, but what effect open sourced software has on people using it. In the proprietary world, those people are typically called “users,” a strange term that connotes dependence and addiction. In the open source world, they’re more rightly called a community.

The core features of WordPress aren’t rocket surgery. A handful of smart people in a room for a year could create a reasonable approximation of the software, and undoubtably improve some things — I see other startups do this three or four times a year.

What they miss is that WordPress isn’t a checklist of features. It’s over 29,000 plugins created by the community, from the in-demand things like SEO to niche features like using your 404 page to help adopt homeless dogs in Sweden. Every WordPress site looks different, because of the thousands of themes available. Instead of one event to outdo, there are more than 70 volunteer-organized WordCamps on six continents (and there’ll be more in 2014).

WordPress marketing has nothing to do with its website or logo, it’s the tens of thousands of people who make a living building WordPress sites and receive so much value from it that they proselytize to anyone that will listen, spreading the flame one site at a time. It works — as of December 2013, 21% of websites are powered by WordPress. One-fifth of the web is built with a tool that anyone can use, change, or improve, whenever and however they want (even more when you count other open source projects, like Drupal).

This approach to building isn’t an abdication of developers’ and designers’ responsibility to build beautiful, functional software. Design and forethought are more important than ever when every change sends millions of independent actors down a new path. Changes to WordPress have consequences today, tomorrow, five years, and ten years down the road, but the passion and talent of the community helps ensure that it always moves forward in a positive way.

The four freedoms don’t limit us as creators — they open possibilities for us as creators and consumers. When you apply them to software, you get Linux, Webkit/Chrome, and WordPress. When you apply them to medicine, you get the Open Genomics Engine, which is accelerating cancer research and bringing us closer to personalized treatment. When you apply them to companies, you get radically geographically distributed, results-based organizations like Automattic. When you apply them to events you get TEDx, Barcamp, and WordCamp. When you apply them to knowledge, you get Wikipedia.

William Gibson is attributed with saying “The future is already here — it’s just not very evenly distributed.” The world is changing faster than any one person or organization can keep up with it. Closed off, proprietary development creates closed off, proprietary products that won’t keep pace in the long run. Open source provides another path — one that’s open to everyone, and can take advantage of the skills and talents of anyone in the world to build software that helps everyone.

As Bill Joy said, “No matter who you are, most of the smartest people work for someone else.” Good ideas aren’t the sole province of groups of people behind high walls, and software shouldn’t be either.

This was adapted from a talk I gave at the Life is Beautiful festival in Downtown Las Vegas. Thanks to Michelle, Ben, Davide, and Paul for help with this.

Matt 3.0

As in WordPress, the X.0 release is just the one that came after (X-1).9 before it, so while it seems more significant, it’s just another iteration in the steady march of progress, a job never done. I’ve now managed to stay alive for three decades, thirty rotations around the sun, and I woke up this morning a little hungover (there’s a lot of tequila in Mexico) but with a huge grin on my face.

In many ways life accumulates complexity as you get older, but the things that are most important are simple and universal: friends and loved ones, health, and working on something you enjoy and has an impact. I’m happier and finding balance more often than at any period I can remember since I was a young child.

This was another year in motion, traveling 345,211 miles to 78 cities in 13 countries. I’m still really enjoying being on the road, and it’s very intrinsic to how Automattic works, so I expect that to continue or even pick up pace.

Every generation feels this way, but it also genuinely seems like we’re at shift in how society works, with technology accelerating change, and navigating and more importantly creating that change is one of the most interesting challenges I can imagine working on.

Finally I’m humbled and amazed by the support for the charity: water campaign, which already is going to bring close to 2,000 people clean water.

Tomorrow I’ll wake up a little sunburnt, but hopefully with that same grin and ready to take on the years of my life that start with 3 and hopefully end with a bigger impact than my 20s had. It was a decade when I failed a lot, tried even more, and most importantly learned how to say yes and how to say no, something that gets easier as you learn about yourself.

My twenties: 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, and 29.