The Circle of Chairs

On New Year's Eve 2003 I had my songwriter's epiphany, and 2004 did its best to test it.

I was living in San Francisco, out of technology entirely, working as a leak investigator for Jeff England, a brilliant, meticulous construction project manager I'd met through the Landmark Forum, who'd hired me as his assistant at a generous $75 an hour. I'd also hired a vocal coach, Vernon Bush, who gave me the instruction I've never put down: take every opportunity, and give it everything you have.

The first opportunity was called Activate, a big benefit event at CELL Space, an arts warehouse in the Mission: artists, entertainment, nonprofits, a thousand-person room, the idea being to get people activated. My first public performance ever. I practiced like my life depended on it. And then the person in charge of promoting the event... didn't. The only people who showed up were the performers, the nonprofits, and a few of their friends. I gave everything I had to a nearly empty room.

But here's the thing about empty rooms: you can see who's in them. My friend Aaron Pava was there, and he'd brought a work colleague, Henry Poole, then consulting for Dennis Kucinich's presidential campaign. They were headed to the Democratic National Convention to hustle their nascent company, CivicActions, and they invited me to crash it and see what might happen.

So the broke leak investigator bought a road case for his piano, shipped it to his aunt in Virginia, and got on a train to Boston. One thing led to another (it always does if you show up with a piano), and I played all over the DNC, including the Kucinich campaign's wrap party after he conceded. That week I watched a young state senator named Barack Obama give a speech and thought, plainly: he's going to be President.

I went home lit up and made the "Unamerican" video in Flash (this was 2004, when there was almost no political media on the web), and released it. It went properly viral. By late summer, the Kerry campaign's Faith Outreach Coordinator was on the phone inviting me to Florida to tour churches with Michael Moore and Cindy Sheehan. By November I was the only performer at the Florida Democrats' election watch party, which turned out to be one of the gloomiest rooms in America that night. Later, back home, I played the National Anthem at a downtown San Francisco event and got booed by Code Pink for its pro-war implications: a protest singer, booed by protesters. You can watch it; I kept the tape.

Watch on YouTube

And then the wave passed, and I didn't harness it. Some of that was the era: launching a career as a protest singer in the mid-2000s was rowing upstream. More of it was me: the same reluctance to promote myself that runs through every chapter of this site. Meanwhile my $75 an hour became $50, and then $35, exactly the wrong direction, and I understood Jeff's margins and hated my situation anyway. San Francisco expenses, no plan, broke again.

What I did next sounds like nothing and changed everything. I sat down at my desk and did an exercise I now call replacement tapes: I wrote out every story I told myself about money, all of them, the whole inherited script, and replaced each one with the story I actually wanted to live in. It was cathartic in the way real inner work is: unglamorous, private, no witnesses.

And literally as I was sitting at that desk, the phone rang. Aaron Pava. "We've got a job we think might be perfect for you."

I've had this happen to me twice now (once in Grand Central Station, once at that desk), and I've stopped calling it coincidence. When you do the work you're supposed to do, the Universe rises to meet you. It doesn't promise the fortune. It promises the meeting.

The job was part-time: resource scheduler and "resource advocate" for CivicActions. Talk to the contractors, find out what they needed to be happy, schedule the pooled talent against the PMs' estimates. Unsexy, essential work for a ragtag distributed band of progressive geeks building things for Amnesty International, WITNESS, Save the Children. I built rudimentary process, then real process (documentation, scheduling systems, the connective tissue a company made of scattered humans needs), and became a partner. There were thirteen of us, all-remote, in 2004–2006, sixteen years before the world discovered that this was possible.

Then I made the least career-optimal decision of my life, again: a few years into a floundering music career, I moved to Nashville to make The Record. Three weeks after I arrived in a town where I knew no one, in a tech scene shallower than a puddle in July, CivicActions' managing partner resigned. None of the remaining partners wanted the job. I think Henry waited until the last minute to see if someone would step up that he could mentor; he'd already built a successful services agency and had probably concluded, correctly, that the reins are easier to manage from the mentor's seat than the driver's. I took the job. I learned how to run a company from him. The team part I already knew in my bones: I'm the third-oldest of eleven children. Managing unruly distributed teams was my childhood.

The thing I'm proudest of from those years is a piece of furniture-as-philosophy I called the Circle of Chairs. A flat partnership of thirteen people, every one of them with a vote on everything, sits facing inward, everyone with opinions about everyone else's performance and decisions. We turned the chairs around. Each chair faced outward at its own unique functional area; the functionality matrix made sure every base was covered and everyone knew whose base was whose. Opinions inward, accountability outward. It improved things enormously, and it's still how I think about making remote teams work: fewer meetings about each other, and clearer chairs facing the actual work.

We were early leaders in open source and Drupal for nonprofits, a position that eroded slowly and then quickly as the space filled in, the competition hardened, and the projects shrank. We lost clients and people, all while trying to build a culture of balance, openness, and trust: remote work for geeks-for-good, even if we paid less than the banks. I steered us through the Great Recession. And then the board (Henry and Aaron, the majority shareholders) made the strategically correct call to pivot into government contracting: longer, bigger contracts instead of diminishing bespoke work for nonprofits.

Our first contract was with the Department of Defense. For this antiwar singer, the "Unamerican" guy, the one booed over the Anthem, that was the bridge too far. In Q3 of 2014 I lost my motivation and my father in the same season. While I was attending to Dad's remains and estate, I was written out of the budget, and Henry stepped into the CEO chair.

Here's the honest coda. Henry has since grown CivicActions roughly tenfold, about 140 people now, a leading firm in government digital services, and I don't think I could have done that. The company has been buying back my founding stock month by month for years; I'm down from nearly 7% to about 2%. That buyback has quietly paid my bills for a decade of forests and kindness campaigns and civic tools. It ends this year, which is, if I'm honest, why I'm finally sitting down and writing all of this.