One of the things that surprised me most about when my Dad was sick last year was that while he was in the hospital over about 5 weeks he lost any interest in music, TV, movies, anything on a screen. Music was particularly surprising given that he had music on at his desk pretty much […]
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 […]
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 […]
In Memoriam: Chuck Mullenweg
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 […]
Chicken and Eggs
I’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 […]
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 […]
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 […]
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 […]
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 […]
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: Many were quick to […]
WhatsApp Takeaway
For 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 […]
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: Freedom of speech. Freedom of worship. Freedom from want. Freedom from fear. Fast […]
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 […]
The Intrinsic Value of Blogging
Blogging is harder than it used to be. We’ve gotten better at counting and worse at paying attention to what really counts. Every time I press Publish the post is publicized to Facebook, Twitter, LinkedIn, Path, and Google+, each with their own mechanisms for enumerating how much people like it. None of those services except […]
Brands Everywhere
While brushing my teeth this morning, which is usually when my mind wanders, I noticed that just on the counter everything I was looking at had a brand or logo of some sort on it. It’s usually invisible to me but once I noticed it became garish as Times Square. I counted 11 brands on […]
Fifth Estate
Here’s the post I wrote on a dinner I attended while at Davos for their forum blog: Online we can act as a fifth estate. The common thread that kept coming up at a dinner, and discussions centred around the idea of “online power”, was equality of access. Before the widespread rise of the Internet […]
Culture of Distraction
From the Hacker News discussion of my Silicon-Valley-is-destroying-the-world remark I came across a Joe Kraus talk on We’re Creating a Culture of Distraction. (I’m a huge fan of Joe and excited to see he’s on WordPress now.) It’s also important to read Paul Graham’s Acceleration of Addictiveness where he compares addictive technology to alcohol and […]
On the Evolution of Investing
Today Y Combinator announced they are adding two new partners, Garry Tan and Aaron Iba. This announcement is unique because it does not list their academic credentials, their previous investments, the boards of companies or non-profits they have sat on, how many years of experience they have, or any of the usual badges of honor […]
What’s Next for Apple
I have no inside information or insight, but historically Apple’s product improvements have strongly broadcasted where they’re going in the future. Here are six things I think are inevitable for Apple to do over the next decade, from most to least obvious: maps, iCloud, payments, TVs, search, and cars. 1. Maps When the iPhone was […]
Why Your Company Should Have a Creed
Does your company have a creed? Twice a year, True Ventures (one of Automattic’s investors) organizes an event called Founders’ Camp, a one-day conference for the founders and CEOs of companies in their portfolio. The latest was held in the Automattic Lounge at Pier 38 in San Francisco (it could be the last). There was an interesting conversation […]