"Undermining my electoral viability since 2001."

In Which I Feel That I Have "Arrived"

Last weekend I had the distinct pleasure of meeting up with an old cast-mate and girlfriend from my days in the Experimental Theater Wing at NYU. It was a cup of tea and the kind of life checkin you can only get from people with whom you share real history, but also have some distance. Hello perspective! This plus the events of the past couple weeks has led me to try and summarize what it is I do with myself these days. Turns out it's not so easy.

When people ask me what I do for a living, over the past five years I've said something general like "oh yeah I make websites for people." This is easy for people to understand, relatively humble, and not all that inaccurate. But it's a much bigger and stranger story than that.

Back in '06 when I decided to stay in California rather than roll back into what was undeniably a pretty amazing life in Brooklyn, I started a company with two other comrades. Up at my digs in Humboldt county, we made a nerdy little video for ourselves:

Last week I went to Chicago with 3,000 other people who do the same thing as me (more or less) to attend a professional conference, complete with a trade floor, technical presentations, and a fashion show. What seemed like a long-shot open-source dream back in '06 has turned into a massive success story. Needless to say, the fun promo videos have leveled-up a few times:

While at said conference, my partners and I announced what we've been doing for the past six months: building something to take this whole scene to the next level, and convincing some pretty smart/successful people to invest in the idea.

When there's a killer hip-hop remix, venture funding, mad science and a fashion show, I'd say something is for real.

So what would you say you do here?

"Drew-pull" (say it fast, like "stumble") is a Content Management System, software you install on a server that lets you deliver webpages (or other internet things) from a database, and allows non-coders to make updates and additions. It is also one of the largest open-source projects in the world right now. There are literally tens of thousands of active contributors creating code for it. As my internet idol Clay Shirky says, "people you don't know, making your life better, for free."

It's also, as I said, a raging success story. Drupal powers high-visibility sites from the White House to Justin Bieber. It drives online collaboration tools for Oxfam International and the World Bank. It also powers this old blog. Drupal is free as in speech and as in beer, but you can engage companies in million-dollar projects around it if you need. I started one fo those companies — Chapter Three — and now have started a sort of meta-company Pantheon designed to help solve the big problems that Drupal is addressing.

Our vision is that the plucky, fun-loving, deeply quirky and amazingly human open-source community can continue flourishing, and that the kick-ass tools that we're creating can help more and more people do wonderful things with the internet. Things are changing as the space gets more professional — I've felt the squeeze and I know many of my peers who run businesses have as well — but I believe that the layer-cake can continue growing and improving. We've got a billion more people coming online this decade. It's gonna be rad.

How I got here is really strange and authentic, but it's hard to tell the story without sounding like some kind of douchebag. Nevertheless, here are the bullet points:

  • After the war begin in 2003, I decided the thing to do was take over the government. Found a website called "hack4dean.org" and didn't look back. Close, but no cigar.
  • However, I discovered Drupal in that process; literally Zack asked in #php what CMS to build on, and we took the advice. It was a decision which had legs beyond the campaign.
  • In the middle of that, also helped bootstrap a non-profit called Music For America that got funded by one of the genius types who made it big in The Valley. Flew on a private jet. Ran through the guts of the '04 election cycle. Made amazing connections and slept under a desk on more than a few nights. Still lost in the end.
  • After recovering from epic burnout, I started working at one of these newfangled Drupal consultancies and enjoyed an idyllic return to Brooklyn.
  • But per that first video, my ambitions let me back West to found my own shop with aforementioned Zack and the legendary Matthew Michael Lippold Cheney, starting with an original website design by my mom and photos by Zack's mom.
  • For the first six months in Humboldt I spent almost every Sunday morning making live online videos about how I did what I did and answering questions for a while, after which I would break and have Norwegian pancakes with my housemates. Got a little cult following going, helped spread the buzz.
  • Turns out a Drupal consultancy works. We gradually accumulated employees, then office space in San Francisco, then an outpost in Humboldt (where I continued living), and eventually a Bicycle Company. Because why the heck not?
  • In late 2008 the primary developer of the Apache webserver (powering more than half the web, yo) had my partners and the cool kids from Four Kitchens together in his living room to try and make a website to power the Obama Transition (change.gov).
  • Turned out we got sandbagged on that bid — old Dean peeps had the hammerlock — but the connections made there were good. I worked with David Strauss again on a project for The Economist, and started getting more serious about the Drupals in general. Started speaking at conferences. Started getting excited about "the cloud."
  • Things picked up speed in 2010. We helped host a huge conference in San Francisco, and coming out of that decided that the existential moment was here and we'd start a new business — partnering with David — to try and level it all up again.
  • Getting serious about that meant moving to SF full time, raising money, starting to develop independent leadership at Chapter Three, and launching a new company.

That pretty much brings us up to now. There are a ton of stories in the middle of course. Love made and lost, vision quests, savage journeys into the heart of America; dark nights, full moons and Red Dawns aplenty. But sticking to the professional stuff, that's the arc. It's happening. New business launched, and almost everything Chapter Three's done this year (e.g. the gorgeous redesign, the training division) happened without my direct or day-to-day involvement. Amazing. Only in America, baby.

It started with an ambition that was literally as big as taking over the government, and that's still there. From both the business and social-good standpoints, I'm making an infrastructure play. The bet: more positive human outcomes will emerge from me working to realize the potential of a free, open and awesome global information network than any other gambit I can realistically see out there right now. It's also a good place to be an entrepreneur. I really believe we're creating thick value, and among the various things I've done so far in life, "making sure 30-some-odd people get a steady paycheck and health insurance" is probably one of my proudest achievements.

So, really, I'm a businessman, but also a self-taught engineer and a kind of natural nerd-politician within this burgeoning global community of makers. I start and run companies. I write code and documentation. I try and convince people that certain ideas are good and they should start companies and write code or documentation to further them.

That's what I do, sixty or seventy hours a week. Weird, right?

I count my blessings every day.