Category Archives: Essays

Thirty-Three

I’m taking it easy this week, nothing too crazy — just sharing good meals and wine with friends. Which is probably a good example of my goals for the year: putting family and loved ones first, slowing down (to go further), and deliciousness. (Single Thread Farms blew me away.)

2016 was a year of incredible contrasts: it was the saddest and most challenged I’ve ever been with the passing of my father, and while that overshadowed everything there were also bright moments of coming closer to family, deepening friendships, and growing professionally with incredible progress from both WordPress and Automattic. That momentum on the professional side is carrying through and right now I’m the most optimistic I can recall, and thrilled to wake up and get to work every day with the people I do.

I talked about trying to spend longer stretches of time in fewer places, and that definitely happened. I flew 162k fewer miles than the year before, and visited 35 fewer cities. My blogging decreased a lot too — from 252 posts in 2015 to 76 posts in 2016, but the posts I did write were at least 50% longer. I made it to 9 more of the Top 50 restaurants and stand currently at 50% of the list. I finished 22 books, including a lot more fiction including my first few graphic novels like Ex Machina, Y: The Last Man, and Watchmen. I watched 35 movies, 9 of which were from the Marvel universe on a single flight from Cape Town to Dubai.

Last year I said, “it’s exciting to make the most of the opportunity that the volatility, love, loss, glory, failure, inspirations, and setbacks that 2016 will bring.” I didn’t know how right I would be, and wish I hadn’t been.

This year doesn’t start with new plans, but rather three intentions continued from a few months ago. I revealed one yesterday, and promised I would expand today on the others, so here they are:

  1. Symmetry — Balance in all things, including my body which is stronger on my right side and much tighter on my left side. We also need symmetry in WordPress between the .org and .com products which differ too much.
  2. Stillness — In echoes of Pico Iyer, so much of my life in my 20s was about movement, and “going places to be moved.” In my 30s I’m looking inward. As Saint Augustine said in Book X, chapter 8 of Confessions: “Men go forth to wonder at the heights of mountains, the huge waves of the sea, the broad flow of the rivers, the vast compass of the ocean, the courses of the stars, and they pass by themselves without wondering.”
  3. Yellow Arrows — The idea that there are clear indications of where to go next at every fork in the road, and if not you should paint them. I wrote more on this  yesterday.

Previously: 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, and 32.

Rebirth and Yellow Arrows

My friend Kamal Ravikant has a new book out, Rebirth, which I highly recommend. I had the good fortune to read it a few months ago and the story of the Camino de Santiago touched and inspired me.

Because of the impact of the book, I ended up adopting a few New Year’s intentions long before January 1st — things to ruminate on and keep in mind as the year wound down. The outlook of the world seemed uncertain, and I’m learning to navigate the world without my father.

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Yellow Arrows

The Camino de Santiago is a pilgrimage path in Spain that people have walked since the 9th century AD. The 500 mile path winds through mountains, fields, and sometimes cities, and many pilgrims take a month or more on it. In some ways it is similar to the Kumano Kodo walk I did with Dan and Craig last year.

There are places where the path isn’t exactly clear, either because the trail isn’t strong, there’s been growth, or you might be in a crowded urban area like a city. Over the years pilgrims and people who live on the trail have marked it with yellow arrows pointing the way. If someone gets lost or confused, it’s an opportunity for an additional sign to bring them back on track.

When you know the path, is it clear where someone else walking it should go next? It’s an interesting concept that applies across life. In your relationships, does your friend, loved one, or partner know what to expect, and where you’re headed together? Even in WordPress I feel like there are too many places where we bring someone to a fork in the road and there is no clear indication which way they should take.

Give some thought to the yellow arrows in your life, and I’ll write more about the other two things I’ve been thinking about tomorrow. Also don’t forget to pick up a copy of Kamal’s book. I loved it and I think it will be one I’m recommending to many friends.

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(Image from Camino Travel Center.)

In Memoriam: Chuck Mullenweg

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My father, Chuck Mullenweg, passed one week ago today. After over a month in ICU he had just been transferred to long-term acute care in a different hospital and we were looking forward to a tough but steady road to being back home when he took an unexpected and sudden turn. I’ve started and stopped writing this dozens of times since then and words continue to fail me.

Here’s the rememberance that ran in the paper a few days ago:

IMG_6024.JPGIt is impossible to overstate the influence my father has had on every part of my life: Why did I play saxophone? Dad did. Computers and programming? Dad did. Travel? He was frequently stationed overseas and even when we didn’t visit he would always bring back a cool gift for myself and my sister. He drove me to the HAL-PC office (local non-profit) every weekend where I’d learn so much fixing people’s broken computers and being exposed to open source for the first time. His O’Reilly “camel book” on Perl was the first scripting I learned, and he pointed me toward Mastering Regular Expressions which became the basis of my first contribution to b2, texturize.

We were in a father / son bowling league. I remember admiring his work ethic so much: he’d get up before dawn every morning and put on a suit, grab his briefcase, and go to work. He often went in on weekends and I loved to go with him because they had “fast” internet at the office and I could read Dilbert and about Babylon 5. He was a voracious reader and learner, and loved tinkering whether it was cars or networking. In the other room I can hear a bitcoin mining rig he set up a few years ago. He was independent minded and unafraid to question the status quo.

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There’s a photo somewhere of my dad mowing the lawn and me following behind him with a toy lawnmower, which is a perfect metaphor for how I’ve always followed in his footsteps.

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I’m at a loss.

Parents are there literally the day you’re born, and it’s hard to imagine a life without them. Most people reading this will outlive their parents, and deal with their mortality and often difficult and painful final days as those who brought us into this world exit it. I’ve been reading and reading all the writing I can find on this topic, but nothing really prepares you for it, and nothing makes it better to go through. It’s terrible.

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He wasn’t someone to tell you what the right way to live was, in fact he was incredibly open minded. He didn’t tell you, he showed you how he lived his life from a place of integrity and trust, how he was in his relationship with my mom, how he was in business. He wasn’t flashy and seldom talked about his accomplishments or all the people he had helped out along the way. Many of the stories of appreciation coming in I’m hearing for the first time. In getting his books and taxes together this past week I was humbled by how simply he lived this season of his life, not into material things but cherishing relationships and his quiet life in the suburbs with my mother.

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My biggest blessing has been my family. Every one is the most supportive you can imagine. So inspiring… much of what I’ve done in the world was in the context of making my parents proud, and their relationship to each other and the amazing man my dad was has set a bar I hope to approach in my lifetime. The last few years he got much better about showing his pride in my sister and I, and even more importantly saying “I love you,” the three words that are among the best gift we can give each other. Don’t forget to use them, even if it feels cheesy or embarrassing, and for those of you with parents still around please give them some extra time and a hug for me. This was unexpected, we really believed he was on an upward trajectory. You never know when the words you share with someone might be the last.

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I made a page you can see his official obituary, information about his memorial service in Katy, and leave any memories you have of him at ma.tt/chuck.

 

Chicken and Eggs

mometablues.jpegI’ve been reading Questlove’s Mo’ Meta Blues, and it’s an incredible education. The book is helping me appreciate an era of music that inspired the era that inspires me — the music that drove the Roots, J Dilla, Fugees, D’Angelo, Common, Erykah Badu, Kendrick Lamar, and so many more to create what they have.

Chronologically, I’m in a chapter covering mid-90s hip-hop, which is full of conflict. There’s a tension alluded to in the book of the musicians that made it and those that didn’t: does increased radio play make songs popular? There’s some science that suggests yes. Or is there something intrinsic to the record that puts it in that virtous loop of requests and airplay, the equivalent of usage and virality in a web product?

There’s a great ancedote in the book that I think is useful when thinking about products. All of the links are my addition, not in the original text.

There was one moment during the recording of Voodoo that really brought this home. We were recording DJ Premier’s scratches for “Devil’s Pie,” and Q-Tip had just let the room to go work on something else, so there were four of us left there: Premier, Dilla, D’Angelo, and myself. During the break, Premier asked if anyone had any new shit to play for the group, and D’Angelo went for a cassette and played a bit of a new song, and the whole room just erupted in hooting. Then Dilla put on some new Slum Village shit and it was the same thing: an explosion of excitement. Then Premier, who had started the whole thing, played an M.O.P. song and some new Gang Starr material that he was working on for The Ownerz.

I was last at bat. All I had on me was a work tape for what would eventually become “Double Trouble” on Things Fall Apart. It didn’t have finished vocals yet, didn’t have Mos Def’s verse. It was just a skeleton. I played it, and I will never forget the feeling that came over the room, including me. It wasn’t that they didn’t hoot and holler like they had for the other songs. They did. But they didn’t mean it. I know the move people resort to when they’re not quite into a song: they keep a straight stare on their face and bob their head a bit, not saying anything, not making eye contact. That’s the sign of death. That’s what they all did to me, and I felt humiliated. I was like Glenn Close in Fatal Attraction: I will not be ignored! I went back into the studio that same night and gave that song a radical, extended facelift. I refused to sleep until I had that thing up and running.

I love the idea of Questlove realizing the song was missing something, and going back to the booth to keep working on it until it resonated with his target audience. A song that doesn’t stand up on its own wouldn’t be any better when bundled as part of an album. (Or Samsung would have the most popular apps on Android.) Fans hear the care and quality of each track, and they become super-fans. The bands that break out weren’t bludgeoned into fan’s ears by radio play, they were pulled by these passionate few into a wider audience.

I love the mixtape culture that so many of today’s successful artists have come up through, and it is amplified online. Drake had three ever-improving mixtapes before his first album. It harkens to a line from PG’s startup canon (in 2009!): Better to make a few users love you than a lot ambivalent.

There’s this tension in everything we produce. Where’s the line to tread between 1.0 is the loneliest and a minimum viable product? Or is it about a minimum lovable product? Are we building a car with no air conditioning or a car with no wheels?

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“Pivot” has become passé, but it’s much worse to assume that distribution will solve something core to your product that isn’t working.

Thirty-Two

My thirty-second birthday has arrived after a whirlwind year, probably my most challenging and rewarding. It went faster than any year I can remember, absolutely flew by. Luckily it was capped at the holidays with a precious few weeks of downtime in Houston. Now I’m back to work in Cape Town and just finished a lovely day of great food, wine, and conversation with colleagues who are here for a meetup starting tomorrow.

Since I started tracking, 2015 was the first year that I traveled fewer miles than the year before, clocking in at 398k, down 27k. (398,553 miles, 111 cities, 20 countries.) In 2016 I’m going to try and get that even lower. It was also one of my best years for blogging on this site, with the most posts (252) I’ve made since 2008, and the most words (24,605) since 2005. (If anyone is curious, I wrote about 60k words over the same time period in Automattic’s internal P2s.) In a weird omission, though, it’s the first year since this site started in 2002 that I didn’t post a single gallery of photos. I’ve developed a mental block around processing and posting the fancier pictures, even as I carry hundreds of gigabytes of them around the planet several times over. Hopefully this is something I can get past in 2016.

I ran 163 miles in 2015, more than I did the year before, and I think that trend will continue. Last year I talked about habits and small actions, and a daily todo list with some small items to nourish the mind, soul, and body has become central to my routine. I dyed my hair (grey) just for fun and also to show the rest of Automattic they could too, how you look doesn’t matter one iota. My restaurant quest has continued, and I’ve now been to 38% of the current top 50 list.

More so than before, I really don’t know what’s around the corner. While there is a lot in motion, there is even more still being defined and started. There’s freedom in the groove, to reference Joshua Redman’s great album, and I’m getting a lot more comfortable with ambiguity and the faster pace of life in general. More than ever, I consider myself incredibly lucky, so it’s exciting to make the most of the opportunity that the volatility, love, loss, glory, failure, inspirations, and setbacks that 2016 will bring.

Previously: 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, and 31.

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 [WordPress.com 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.