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

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

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
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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.

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:
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Fort Funston
Snapshots from walking the dogs at Fort Funston – a place that makes me grateful that we live in San Francisco.
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Founder Camp snapshot
Once a year, True brings together the entrepreneurs in its portfolio for a day of intimate learning and sharing. This year we held the event in Carmel – here I am with Chris and Jason from Renovo, in what looks to be some kind of serious conversation, or maybe Jason is describing which two cocktails he’s about to try at the closing party 🙂






