Taking the plunge

I'm going full-time on The Roots of Progress

October 28, 2019 · 3 min read

Last month I left Flexport and announced that I was a free agent. Today, I have a new announcement: I’m going full-time on my blog, The Roots of Progress, and related projects. You can read the details in my announcement on the Roots of Progress blog.

For me personally, this is a huge leap into the unknown. For something like the last 25 years, I’ve thought of myself as a technical founder. I had multiple businesses as a kid, and even before I graduated from high school, I knew I wanted start a real company someday. I planned my entire career toward that goal.

Several years ago, my big, burning obsession was Fieldbook, the startup I co-founded in 2013. I had been thinking about what has come to be known as low-code/no-code platforms since 2007, and it had hit the point where the idea for a hybrid spreadsheet-database just wouldn’t leave me alone. After I left Groupon, it was clear that I couldn’t really see myself doing anything else.

Fieldbook was the right idea at the right time (I think the success of Airtable, Notion, Webflow, etc. show that), but I had the wrong product approach and dramatically underestimated the resources we would need. After spending five years on it, we shut it down and acquihired the team to Flexport.

When I left Flexport, however, I didn’t have another burning tech startup idea. Instead, I found myself oddly obsessed with the questions I’d been reading and blogging about as a side project for a couple of years: How did mankind come out of the caves and build the modern world? Why did it take so many millenia for progress to really take off? And how can we keep it going—or even accelerate it?

When I started the blog, it wasn’t much more than my research notes, and I didn’t care how many people read it or who they were. Even as late as this July, it only had a couple hundred Twitter followers and about 50 email subscribers. But then a few things happened, all in the span of about a month:

First, my post on the history of the bicycle hit #1 on Hacker News and went viral from there. At that point, my audience started to take off. Then, just a couple weeks later, Tyler Cowen and Patrick Collison published their article in The Atlantic, “We Need a New Science of Progress”, calling for a new interdisciplinary field of “progress studies”. This article galvanized a small movement. Suddenly there was a name for what I was doing, and a community of people interested in it. We had all been interested in it for a while, we just didn’t know about each other, because there wasn’t a banner for us to rally under.

And then I decided to leave my job. I ran a job search (my first in twelve years!), and talked to many exciting startups—I knew there were a lot of ambitious projects going on, but it becomes very real to you when you’re meeting so many of them at once and thinking seriously about joining.

But as I went through the process, it became clear to me that my heart was in progress studies. It was what I was passionate about, what I couldn’t stop thinking about, what I was always eager to talk about—and most importantly, what I had a vision for. It was what I felt uniquely positioned to contribute to the world. And I had started to see that, just maybe, the world was interested in what I had to offer.

Coming to this was at the same time exceedingly strange to me, and also the most natural thing in the world. I had always assumed that if Fieldbook didn’t work out, I would just find another tech startup idea to run with. I’ve spent my entire life studying software, business, and management. Without working in tech, I barely know who I am.

But at the same time, I’ve always had a deep interest in ideas, in philosophy, in how the world works, in how we can make it better. I’ve always been powerfully motivated by what I see as the most fundamental forces shaping society and human history. And this is just the latest evolution of that drive in me.

In doing this, I’m facing more fog and uncertainty than ever—more than when I moved to San Francisco without a job or a place to live, more than either of my experiences as tech co-founder. I may have to develop an entirely new set of skills, work habits, professional network, career plan, and life goals. In a way, I feel that I’m revising my very identity, redefining myself.

It’s exciting and frightening at the same time. It feels completely insane and simultaneously inexorable. And that’s kind of how I know I’m doing the right thing.

I may still blog here occasionally, but most of my effort will now go to The Roots of Progress. Follow my new adventure there.