I’m a big believer that you need in-person time with colleagues, but certainly, most workers don’t need to be in the office every single hour, every single day. So given the current pandemic forcing many of us to work from home, I went looking for this post.  And I feel like post-pandemic this might be the right model.  So here goes – my thoughts from over five years ago, with the caveat that things have obviously evolved but most of these ideas I still think are relevant to think about:

January 2015:
Great discussion happening right now about the benefits and downsides to working in an office VS being part of a distributed workforce (aka “remote working”).

The conversation started off with Paul Grahm’s post, and Matt Mullenweg’s response post, plus a ton of chatter on Hacker News.

I actually see arguments for both camps as being pretty solid and think every company needs to decide for itself what works best. My $.02 is that engineering-centric organizations that are very comfortable with async and text-heavy communication tools, will likely have more immediate success than sales heavy organizations. And ultimately it’s an HR challenge, in that distributed workforces need to employ highly independent, motivated, and entrepreneurial folks who don’t need a ton of guidance, and don’t need to be mentored a ton.

But I’d like to make a suggestion for companies who are thinking about this topic. There is no need to be purely distributed, or purely stuck in one office. Go Hybrid!

By Hybrid I mean the following – assume you’ll be in-person for maybe 3 days a week, and the rest of the time your colleagues will work from wherever.  For some that will mean a home office, for others a co-working space or a coffee shop.

Specifically: 

• Have an office near a big city (and/or a good airport) where people will naturally gravitate to, and you’ll be near your customers and partners.
• For large companies, have multiple offices.  I don’t see the need for mega campuses.  You can do meetups for workers that need to collaborate in-person occasionally.
• Stop being so rigid on office culture in terms of when people work. Move to being output driven.
• For meertings/video/audio calls and the like – try and keep them between reasonable hours that don’t force early morning or late night commutes.  ex: only have meetings between 10am and 3pm.. Consider no meetings on Monday and Friday which are heavy traffic / long commute days, and encourage Mon and Fri to be deep project days, where people can grab 2+ hour long chunks of time to go deep on work.  If people only commute 3/week and don’t fight rush our, they may actually get more comfortable living a bit further away in a more affordable housing situation.
• Use the best tools that highly distributed teams use — Slack, Skype, etc – even when you are in the office.
• Document everything!  Every meeting should be summarized (Square has been doing this for years), every discussion, every bit of financial and product metrics should be available to all employees.
• Work on a handbook to get new employees ramped up quickly. Automattic did an amazing job with this effort.
• Invest in internal tools.  You need a team ideally dedicated to making “work from anywhere” efficient.  You need a search tool, you need a way to understand the big goals, the OKRs, and so much more.  The more you make your resources self-serve, the better you’ll do in not needing to be in the office every single moment and a huge secondary effect of this is making new hires more efficient and have quicker ramp=ups.

The days of an expensive office, in a big city, where your employees struggle to find nearby affordable housing just doesn’t feel that viable long-term.  But the idea of only being distributed with no in-person interactions also feels challenging and deprives us of the energy we need to create and be happy & productive.

I remember in the mid to late 90s that there was a whole community that wanted them to work on VR and multi-player worlds, and it just strikes that it’s a near perfect hollywood script that they would end up together again ushering in this next wave of VR.

I’ve personally been interested in VR, starting with VRML (pronounced “vermal” – and maybe the worst pronounced acronym ever), the HTML of VR – and been super excited to watch Oculus and other entrants make their debut.

When people ask me why I’m excited about VR, the way I answer it is the following: The first time I tried the Oculus it was like using a TI/99 (or Apple IIe) for the first time. In that it wasn’t perfect, and had some very clunky aspects to it, but you could instantly imagine what version 5 or 6 would be like, and how mind blowing it would be. As importantly, Oculus was the first VR device that convincingly “tricked my mind” into accepting that what I was seeing was “real”. When I did a racing demo, I tried to crash into a wall, and as hard as I tired, I couldn’t help but flinch and really felt a visceral reaction. It’s hard to explain, but I encourage anyone who hasn’t tried it yet to find a demo, or even better yet, head to a local VR meetup to see a whole bunch of demos and meet the people who are working on this cutting edge stuff.

Last week Abrash gave a talk at F8 on Virtual Reality, and I think it’s a must-watch to understand just why this time around VR might become a very big deal:

As someone who has managed to play once or twice a year for 20 years and remain terrible but hopelessly optimistic that one day the game will get easier, I can understand the frustration.

The biggest gap that jumps out to me with golf is that there is no natural place to practice. The idea of going to the driving range seems tough to pull off. When you play soccer, baseball, basketball, etc with your kids or friends — it’s either in the backyard or down the street at the park.

I think for golf to take off, the industry needs to figure out a way get the game into the backyard and parks so when people actually get to the courses, the game will be easier. Maybe technology will play a role with lower costs simulators, backyard nets, 3D swing analyzers, and other gadgets. Will be an interesting space to watch.

But as one of my editorial colleague back at TIME would frequently remind the team — stop burying the lead. So I’ll take that advice and jump into the TL;DR: After seven incredible, fun, and rewarding years at Automattic, I’m wrapping up in a couple of weeks, and joining Mike Hirshland at Resolute Ventures as a General Partner. Resolute is focused on early stage seed investing, and already has fantastic companies in the portfolio.

When I joined Automattic back in 2007, we were a handful of folks distributed around the world running WordPress.com and Akismet and contributing everything we did to the WordPress open source project. When we got together in person, we could fit around one table in the old Pier38, which was True Venture’s SF office, and later we got a space of our own at the very same pier.

About a year in I recall that Google and others had estimated that WordPress powered about one percent of the web (which we were ecstatic about!). I remember thinking, here was a company with still a couple of dozen people, having raised just over a million dollars in funding – and what a big impact already!.

Fast forward to today and WordPress is powering over 22% of the web. Automattic is 250 people in 190 cities and 30 countries, profitable (and now with a war chest), a positive force for the open web, and we are still contributing everything we do back into a huge open source project. As Matt Mullenweg, the founder and CEO of Automattic likes to say, “we open source everything but our password files.” It’s a powerful concept, and one that has held true at Automattic for all these years.

Looking at our growth, I decided to flip through the annual company meetup photos over the past few years. It’s fun to look at these photos as a nice visual on just how much the company grew:

I want to especially thank Matt Mullenweg and Toni Schneider for making this an amazing journey. We sketched out some big ambitious plans (often at Crossroads) all those years ago, and it’s incredible to look at where things are now and see how many of those big ideas became a reality. When we started talking about my transition a while back, Matt & Toni were super supportive and it was fun (and a bit nostalgic) to walk down memory lane and add up all the amazing experiences we’ve had together.

At Automattic, maybe more than any other company I’ve worked at, every single team member made themselves available to help at a moments notice – we were real-time before it was cool!. All it took was a “ping” in IRC and you had the top person in the world in their field ready to help (I’m biased, but the talent level at Automattic is incredible). So a special thank-you to those early team members who welcomed me with open arms and helped me ramp-up. Too many to list, but I’ll try: Barry Abrahamson, Mike Adams, Ryan Boren, Andy Skelton, Joseph Scott,Nikolay Bachiyski, Donncha O Caoimh, Mark Riley, Maya Desai, Lloyd DeWolf, Matt Miklic, Alex Shiels, Demitrious Kelly, and many others. You all were unbelievable colleagues and true friends.

I loved every second at Automattic, and have learned a ton along the way. I loved the way we worked and focused on output, and put engineers at the center of the company. Automattic and WordPress will always be part of my DNA, and I can’t wait to see what the talented team tackles next. In fact, I’ll remain an advisor to Automattic, and you’ll still see me out there championing the cause of democratizing publishing. For anyone looking to work at a fast paced, fun, and big impact type of organization – I can 100% recommend working at Automattic.

I also want to thank Phil Black, Jon Callaghan, Tony Conrad, and the whole team at True Ventures. I’ve known many of them even longer than my colleagues at Automattic, and they are just a tremendous group of people who are the embodiment of integrity and loyalty. I’ve learned so much from them, and in many ways they provided the spark that got me hooked on working with early stage companies.

In terms of Resolute Ventures – this was an opportunity that was tailor made for me. My passion is working right in the intersection of technology and entrepreneurship. I’ve always been both a tech entrepreneur who is passionate about building businesses and working on product, and a business guy who thinks the more technical you are, the closer you are to the truth.

I love working with founders and helping early stage companies navigate and make sense of the amazing opportunities and the chaos. I’ve founded companies back in the web 1.0 days, worked at large media companies in NY, and have helped grow Automattic the last few years wearing many different hats — from building up our enterprise VIP business to most recently heading up corp dev and partnerships. The highlights for me at Automattic were definitely helping bring people on board either through hiring or acquisitions — and seeing fantastic people make great contributions has been incredibly rewarding.

Mike Hirshland, the founder of Resolute Ventures, is someone well known here in the Valley, especially for a guy based in Boston. I’ve known him for close to a decade, and he served on our board at Automattic for many years while at Polaris and was part of the original investors in Automattic. Many of you know him from Dogpatch Labs, which he ran, and where Instagram and many other companies got their start. He’s a true advocate for founders, and blends hard work, persistence, and self deprecating humor into something magical.

Part of me is definitely a bit sad to be leaving my family at Automattic, but I’m excited for the next chapter and can’t wait to work with all the fantastic people who are part of Resolute. A special shout-out to my friends who helped me with this transition and were so generous with their time and insights.

So here goes something new — and I’m looking forward to the next seven years and beyond.

Here are the official details from our CEO, Matt Mullenweg:

I’ll start with the big stuff: Automattic is raising $160M, all primary, and it’s the first investment into the company since 2008. This is obviously a lot of money, especially considering everything we’ve done so far has been built on only about $12M of outside capital over the past 8 years.

And a good recap by Liz Gannes and Kara Swisher over on re/code.net.

In February 2013, Google’s senior executives flew in from around the world to meet at the Carneros Inn, a rustic resort in the hilly vineyards of Napa Valley. This was Google’s annual two-day, top-secret retreat for senior executives.

Carneros Inn is a magical place – and is also home to our annual VIP Developer Workshop.

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They need a little bit more to get over the finish line, so if you find this kind of stuff interesting, please consider backing this project now on Kickstarter.

On a related note – finding more and more of my conference calls are now Skype video or Google Hangout video calls. And if it’s audio-only, I’m a big fan of Uber Conference. Great service and has nice little touches like showing you who is speaking, and being able to call-in through your browser.