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:


Top Posts

Hi. I’ve had this blog since 2005. Here are some of my more popular posts from over the years:
The Perfect Startup: Can a large company be as fun as a startup?
Five Reasons Why Your Company Should Be Distributed: A pitch for why distributed, or remote, teams are great.
8 Tips For A Great Company Meetup: Best practices learned from organizing 9 company meetups.
When A Company Grows But The Office Shrinks: The story of how Automattic decided to shutter its San Francisco headquarters.
A New CEO For Automattic: Notes on my transition from CEO to team lead at Automattic.
In Praise Of Continuous Deployment: A new way of making software (from the early days of
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.


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.


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.


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?

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:


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:

Telegraph Hill.png


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.

Why did this happen? There are a few factors that we failed to take into account:

  1. Even when we hire people in the Bay Area, some will move away from San Francisco, or no longer want to commute even if they worked in San Francisco before, once that commute becomes optional. For example, of the current 32 Bay Area based employees, fewer than half come into the office on a busy day.
  2. International growth has accelerated as the company has grown, with our US versus international mix going from 65/35 five years ago to approaching 50/50 this year (!).
  3. We planned to use the headquarters for a lot of team meetups, but hotels and rentals in San Francisco got so expensive that it was cheaper to hold meetups elsewhere despite having “free” office space in San Francisco.
  4. Employee turn over in San Francisco ended up being higher than elsewhere for us, 9.6% in the Bay Area versus just 4.4% everywhere else. I won’t speculate about the reasons behind that gap, but it has obvious cumulative effects that we didn’t anticipate.

I’m going to miss our awesome space in SOMA, but it’s the right call to go smaller. If you are building a distributed tech company, I’m guessing you might see a similar pattern where your initial employee growth is higher near your headquarters and then gets more and more distributed as you get bigger. A good thing to keep in mind when you do your office space planning!

Related Reading: Why True Ventures doesn’t believe in geographic limitations either on the True Blog.



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


360 Photos

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