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Welcome

Hi. I’ve had this blog since 2005. Here are some of my more popular posts from over the years:

Five Reasons Why Your Company Should Be Distributed: A pitch for why distributed, or remote, teams are great.

The Perfect Startup: Can a large company be as fun as a startup?

When A Company Grows But The Office Shrinks: The story of how Automattic decided to shutter its San Francisco headquarters.

In Praise Of Continuous Deployment: A new way of making software (from the early days of WordPress.com).

A New CEO For Automattic: Notes on my transition from CEO to team lead at Automattic.

8 Tips For A Great Company Meetup: Best practices learned from organizing 9 company meetups.

Open Source vs Open APIs: How “openness” impacts both software development and business development.

On The Future Of Work: Another version of why distributed/remote teams make a lot of sense.

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Are your remote team members goofing off?

I worked for a distributed company with hundreds of remote workers around the world for 10 years. The question I was consistently asked the most from people outside the company, especially in the beginning: “How do you make sure people are working instead of goofing off at home?” The question was misaligned with my actual experience. The team wasn’t goofing off – they were working. Remote team members are always at “work” due to the nature of most remote work environments and, if anything, have to be encouraged to set boundaries and take time off. In my opinion, what people were really asking about boils down to this: trust. 

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Making the internet weird again

Some of these quarantine home videos are delightful and remind me of the early days of the internet when people didn’t care so much about looking professional or monetizing their content:

 

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Bose Frames

It’s been a while since I’ve gotten excited by a gadget, but I’m really enjoying these Bose Frames I got a few days ago.

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They look and feel like regular sunglasses, same weight, nice enough materials, and the feeling of using headphones by simply slipping glasses on and off is surprisingly fun. I find it nicer than dealing with putting headphones in and out of my ears, carrying them in my pockets, etc. The audio quality is good even though nothing touches your ears and the microphones are OK. Plus it’s nice to be listening to something while also being able to hear the world around you and having conversations without any awkward headphone fumbling. I’ve not found any apps yet that support the AR features (orientation sensors) so those might be a cool bonus.

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The Perfect Startup

People in startups often talk about how much fun it was during the early days, when everyone was on the same page and things moved quickly. Can the speed and simplicity of that early, perfect-startup moment be retained as companies grow?

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Early days at Automattic

During those early days, a startup team is usually around a dozen people in size. Most team members are engineers and designers, at work on the first product. There are usually also one or two generalists, taking care of early marketing and operational needs. It’s when startups grow beyond that stage that they often hit one or more of these growing pains:

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Magical streets in San Francisco

I was recently asked for neighborhood tips by someone who is moving to SF. Here are some of my favorite spots – beautiful, livable streets near parks and good restaurants:

Cole Valley, Belvedere St:

Cole Valley

Telegraph Hill, Filbert Steps:

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When a company grows, but the office shrinks

Automattic, a distributed company with over 500 people, is moving out of our San Francisco offices. Why?

The story begins in late 2011. Automattic had about 100 employees with 15 of us in the San Francisco Bay Area and the rest spread around the world. We had a small office in San Francisco’s Pier 38 that we used for Bay Area employees, various visitors, and WordPress events. Then we, along with dozens of other startups, got evicted by the San Francisco Port Authority and started looking for a new space. Since 15% of our company was Bay Area based and we were planning to grow to 500+ people over the next 5 years, we decided we needed space for about 75-100 people. We ended up leasing a 14k square foot warehouse in the SOMA area of San Francisco and renovated it into a fantastic space for both co-working and events.

Then something unexpected happened.

Automattic did indeed grow to over 500 employees, but the number of Bay Area based employees never got above the 20-30 range. The company scaled beautifully, yet we never needed all that new headquarter office space. We did use it for many events, including a week long all-company get-together in 2013, but in terms of co-working we never came close to growing into it. So when the time came to renew our lease, we opted out and will move out soon. We might try a co-working space next or find a much smaller office, more like our old Pier 38 space.

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Why I think “Marketplaces” are not just software, but a human opportunity

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Many people are worried that software automates human jobs out of existence. But not all software is like that. There are software businesses that have created many thousands of new jobs, and not just jobs at software companies, but new, independent jobs for people all over the world. These businesses use software to create marketplaces, and on those marketplaces sellers of goods and services can thrive: Hundreds of thousands of small businesses who sell on eBay or Etsy, tens of thousands of bands who sell music and merchandise on Bandcamp, tens of thousands of designers who sell web site designs on WordPress, to name a few. This is software used for a great purpose, to attract a large group of buyers and then open up that aggregated buying power to third party vendors instead of keeping it all to yourself. It’s the digital equivalent of using the town center to open a farmers market instead of a box store.

Let me dig into WordPress as an example because I know it well. WordPress helps people create and run web sites and currently powers over 27% of all sites on the internet. The design, building, and hosting of all those millions of sites has created tens of thousands of jobs for WordPress consultants and businesses – good jobs that pay well and can be held anywhere. Those jobs exist because WordPress is an open platform designed to let anyone participate and offer their services. The software itself is not that different from other web site tools – Blogger, Wix, Squarespace, they all offer features similar to WordPress – but none of them have created so many jobs. Some have tried. Blogger gives site owners a cut when showing Google Ads. Wix has some third party plugins. But those are not true marketplaces, they are just add-ons designed to boost the host’s core revenues – a digital share cropping arrangement that does not lead to independent jobs and businesses.

There is nothing inherent in all software that automates and kills jobs, it’s the business model that we choose to sell that software that dictates how the money flows and which services get valued and paid for. In my capacity as an investor at True Ventures, I love meeting entrepreneurs who want to pursue building marketplace businesses. If you have a seed stage startup with an open, marketplace-based business model, I’d love to talk to you to learn more about it.

Photo credit: CC by SMcGarnigle

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360 Photos

Now that WordPress.com supports VR content, I can show you some of the 360 snapshots I’ve taken with my Ricoh Theta camera:




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Comparing the Vive to the Rift

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I’m a big Virtual Reality fan and have had the opportunity to try out many VR systems, including the two best ones currently on the market, the HTC Vive and the Oculus Rift. Here’s my review:

tl;dr: They’re both great and deliver a compelling experience far ahead of everyone else. Graphics are strong on both devices, the Rift has better sound and ergonomics, the Vive has better tracking and controllers. In the end, the Vive is slightly more exciting because tracking your body’s motion is the key to VR, but you can’t go wrong with either device.

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Tinker in Seattle

Joen made a fun Mesh of the Tinker meetup in Seattle:

https://me.sh/19vdob3v

Update: Marcus made one too!

https://me.sh/x3m9vd6

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To my Sophie

Today was a big day. My daughter Sophie is all grown up and has moved out of our home and on to great new adventures in London and NYC. Sophie – it was so hard to see you leave through that airport gate, so many memories of your childhood and of becoming a parent came rushing in, yet I’m also so very proud and excited to see what you do next! Love always, Dad.

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.blog is happening

Big news today from Automattic: .blog domains will soon be available to the world. This project has been years in the making – congratulations to the whole team behind it! More background info on WordPress.com News.

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Real time 3D audio is back

It’s been exciting to see/hear new 3D audio technologies as part of the surge of interest on VR. This one sounds great and for me brings back great memories – I got to work on similar systems early in my career:

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A major relaunch of WordPress.com

A big congratulations to the entire team at Automattic for launching a brand new version of WordPress.com today. It’s the culmination of 18 months of work, built on a completely new tech stack, and an example of how big of a job it is to reinvent yourself when you’re in the middle of running a service for millions of people.

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The first version of WordPress.com did an amazing job for the last 10 years, growing from its humble beginnings to an incredible scale of serving billions of page views a month. Over the last decade, we’ve seen the rise of many new technologies, including smart phones, tablets, JavaScript, Github, and API driven architectures. The new WordPress.com is designed to take advantage of all of them and serve WordPress users for many years to come.

Update: Om has a great post with further details.

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Office optional

The idea of organizing a company so that employees can be distributed and work from anywhere in the world is clearly gaining steam. When a company is distributed, functions that are traditionally office centric, like meetings, job interviews, or all hands, get reinvented to happen online and offices become optional in the process. Geographic limitations fall away and teams can collaborate in new ways that fully embrace a global talent pool. Automattic is now around 400 distributed employees strong and continues to help blaze the trail for this new way of working together. Here’s a collection of articles that dive into various aspects of running a company like Automattic: