Thanks Automattic, Hello Resolute Ventures

In many ways, the number seven holds special value. It’s a lucky number in various cultures, the number of days in a week, plays a role in agriculture and crop rotation, and it’s said that your allergies reset and change after seven years. So changing things up after seven years just feels right.

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 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.

Engineering Recruiting and Early Days Quotes from True University

Some great ones like this:

“There is a secret to closing [a hire] when the person you’re hiring already works at a big company. You say, ‘Out of the 12,000 people there, only 200 people do all the coding and create the product. All the others are there to tell you why you can’t do what you want to do. None of those guys work for us.’”—Amit Kumar,


“A startup is a temporary organization whose purpose is to search for a repeatable and scalable business model. There is no such thing as a 15-year-old startup. There’s a three-year-old startup attached to a 12-year-old failure.”—Steve Blank, author and retired serial entrepreneur

Full post here – thanks to Wade Roush of Xconomy for the write up.


We co-hosted a party Tuesday night in NYC along with The New York Times, Sphere, Hearst Interactive, GigaOM and True Ventures.

The idea was to bring together lots of various media companies, both traditional and new — and talk about tech, web2.0, publishing, and all the great activity happening in our space.

The venue was a perfect symbol of the blending on traditional and new, the recently redesigned Hearst building on 57th & 8th ave, with one of the best views I’ve seen in New York – an unobstructed view of central park.

Big thanks to everyone involved especially Shea Di Donna who as always makes it all happen like magic !

It was great to see lots of familiar face including Jason Schaeffer of CNNMoney, Lindsay Campbell of, Jamie Thingelstad of Dow Jones, Adam Embick of Sphere, Kelly Leach of Dow Jones, Jon Friedman of MarketWatch, Andrew Madden of Google, Josh Macht of HBR, Karen Saltser of Real Simple, Scott Kurnit, Jeff Misenti of Fox News, Ken Marcus of CondeNet, Tim Morrison of, and Christine Mohan of Dow Jones & allthingsD.

Jason Calcanis was also there and captured some video via his mobile hookup, and Jamie Thingelstad and Josh Guttman of Sphere also captured a few photos.

Great event and always fun to be back in New York.