Alex Payne is a writer based in Portland, Oregon.

since 2001, has served as his online home.

What I've Been Doing

“So, uh, what exactly do you do these days?”

I hear this question and I smile awkwardly, because I’m still not sure how to answer it concisely.

Distant friends and professional acquaintances have admitted, upon reconnecting, that they’ve sort of lost track of me since I left Simple. I don’t blame them: I’ve been all over the place, geographically and work-wise. It doesn’t help that my periodic hiatuses from Twitter have turned semi-permanent, drying up that steady drip of personal context out to whoever wants it.

I had an enjoyable full-time stint at DOBT for the first half of 2014. At that point the company decided to sharpen their focus down to a single product, and not one I had much to contribute to.

Prior and since, I’ve been doing a lot. About as much as I ever have, really, just not neatly packaged up with a job title and a company name and a business card. This is what’s been keeping me busy over the past couple years:


I’ve consulted on API design, building developer communities, systems architecture, devops, and language design, amongst other things. My clients have included Cover, Brick Alloy, Orchestrate, and a couple of stealth companies.

I recently spent a week on-site at the Consumer Financial Protection Bureau in DC. They have a great team and an incredibly important mission. Getting to know them was a blast.

My next consulting project is overhauling a web-based piece for a notable contemporary artist.


Several friends have come to me with product ideas in need of a proof-of-concept implementation. Working with friends can be tricky, especially when everyone’s juggling other commitments, but I’ve had fun building these.


I did two rotations as a resident at Hacker School in NYC. I’ll be in Denver at Turing the first week in March. In a sea of questionable “code schools”, those two are doing it right, to my mind.

Investing and Advising

I’ve continued to make angel investments in select technology startups. My thesis, such as it is, is a combination of “invest in what you know” and investing for social impact. That’s led to a modest portfolio with concentrations in API-driven products, devops tools, products that facilitate team communication, and health data.

I’ve also made larger-dollar investments outside of tech. Those deals have required learning about unfamiliar and rapidly-evolving industries and markets. I find that kind of research really fun, but it can be a job in and of itself.


Without question, the thing I’ve been enjoying the most is giving people time and money; it’s just the best. Giving smartly, though, can be as time-intensive as researching for-profit investments. Plus, as more non-profits leverage technology, there’s at least as much advisory work to be done in that world as there is for startups. I love it.

Over The Bridge

That’s what I’ve been up to, all while moving, traveling a whole bunch, writing, speaking, organizing a conference, and dealing with family health matters. That doesn’t answer it all, though.

“Are you going to do another startup?”

I get this one a lot, too.

As I’ve written before, I don’t believe in startups for the sake of startups. If there’s something I’m really passionate about, and I have the right people with me, and the problem we want to solve is best attacked in the form of a startup, I’d consider it. But I’m not going to jump back into another startup just because that’s what people with my experience are supposed to do.

I like early-stage projects a lot. I’ve found many ways to support them – for-profit and non-profit alike – in full-time roles and otherwise.

“Workin’ on something big?”

Here’s what I know: I’m happier and healthier than I’ve ever been. I attribute at least some of that to the freedom and flexibility I’ve had over the past couple years. Without creating that stable foundation, I wasn’t ever going to accomplish anything again. Good health, mental and physical, is invaluable. I was striving for it years ago, but actually getting there took more: more time, more energy, more experience, and more patience.

I could see myself continuing to enjoy the mishmash of things that have kept me busy. Not being able to tersely explain what I do is really the only downside. Still, I feel like I have another big project in me. Having made a couple of false starts, I’m getting comfortable with taking my time to find that next thing, or to let it find me.

The other morning, a heavy fog spilled over the hills, enshrouding the city totally. As I drove over a bridge, past and future all but disappeared. I could see two car lengths ahead, two car lengths behind. The top of the bridge and the river below were gone, consumed in water vapor. I turned the radio off and enjoyed the car’s low humming reassurance of forward motion. There was nothing else, and it was enough.

Meditation and Performance

Thoughts On Five Years of Emerging Languages