Before I left town to travel the world, I went for coffee with an acquaintance I knew through my work facilitating writing workshops in prisons. He was starting a company to facilitate student connection, and wanted to know if I'd be available to offer some suggestions.

A month later, as I was heading off across the world, I joined him at BuddyUp as their CTO and co-founder. We had a proof-of-concept desktop app that had been built by students in their spare time, and some funding.

Together, the CEO and I were able to grow the team to six, close contracts with multiple schools, and create a full, ionic-based iOS app, android app, and mobile web-experience.

The app supported 1,000s of concurrent users in real-time, large chat rooms, as well as real-time notifications, camera integration, and a clever threading implementation that kept our interface fast.

But more than the technical achievements, I was most proud of the culture we were able to build where people brought their full selves to the office, and we supported employees' personal and professional development in meaningful ways. We created a working remote culture with open lines of communication, and successfully navigated the challenges of time-zone splits and a diverse team.

BuddyUp ended up running out of money, after failing to land enough big deals - the market was more difficult than anticipated, and though we gave it our best, it simply wasn't enough.

Shortly after GreenKahuna closed up, my life-long dog passed away of old age, and I found myself with a window of opportunity. I took it — founding Ink and Feet, selling everything I owned, and setting out to live across the world.

Ink and Feet was a radical reinvention of my career, based on me primarily working as a writer, and secondarily as an app developer. It's continued ever since, and I've been lucky to live across the planet, experiencing a vast array of cultures and beliefs, learning languages, and making a few things of genuine value.

Alongside that work as a writer, I've also been lucky to get to mentor and coach some amazing people, working on powerful social change missions. From ecosystem conservation to legal access for low-income families, it's been deeply rewarding work to contribute to in a meaningful way. I'm especially proud that every one of my coaching clients has built up their skills and personal toolboxes in a way that means they don't need me by the end!

This was a fascinating and deeply rewarding job, deep in the bowels of a demolitions company. In essence, I was given a team of very green developers, a pie-in-the-sky vision of the platform they wanted to create, and a very solid budget.

I'm proud that we were able to build the backbone of a platform and the first of several products - but moreso about the talent I was able to develop and nuture in my role there. More than any of the products we made for GreenKahuna, or our open source releases (Will being the most signficant), the developers who grew and blossomed in their time with GK are making an impact on the world, continuing to do brilliant things and shape and improve the communities around them.

The biggest challenges were communicating how to make a successful web product with a team of very non-technical executives. In retrospect, I wish I'd spent more time engaging with those relationships, and attempting to bridge that gap. It may not have been possible to bridge, but those divisions are what eventually led to the company's shutdown

Joined Building Energy as a senior, full-stack developer. I was lucky to get to join a team still in the heart of doing architectural design, and worked to help create an innovative, event-based (and language independent) architecture for processing the immense time-series datasets we hosted for our clients.

This is also the role that I was able to contribute to a tools-based devops culture in a big way, and found how much I loved the work. While at BE, I created Flint and Yeti. Flint was a CLI tool for our dev team that handled codebase and machine configuration, builds, commits, merges, and data installs. Yeti was a web-based system that managed branches, tracked goals, securely shared team access, ran tests, and managed our deploy pipeline. Unfortunately, management was against open-source, and so neither tool survived when the company eventually folded.

In my last month there, working together with an astoundingly good designer, we were able to start and ship one big product in just a month - a generic, mapped data import tool - that landed the company a government contract, and kept it afloat.

Joined W+K as a creative technical lead. This work was an entirely new industry for me - the top tier of the advertising world - and was surrounded by brilliant, passionate, fast-moving folks.

There was a fair bit of organizational churn, and the tension between W+K's traditional TV-and-print work and the new, more dynamic digital campaigns was present every day.

But through the struggle, we did make some great work together, and I learned an amazing amount about both ad industry as well as team dynamics in larger organizations. I'm proud that a weekly series I started, Tech Breakfasts was able to inspire and catalyze new thinking about ways to use technology to support our client's goals.

I'm also thrilled that with the help of my boss, we were also able to release open-source projects for the first time in W+K's history.

Co-founded Goodcloud with Tom Noble. Our goal was to deliver a quality CRM and donation management software specifically tailored for small, growing non-profits.

The company grew, turned a profit, and I'm proud to say that we helped a few organizations grow (and outgrow) our software. Ultimately though, we were five years too early to market - marketing and sales weren't problems that could be approached with scale in our market, and three years later, we made the tough call to shut the company down.

Joined a small, nimble development team in Portland working on a natural foods wholesaler's operations software and ecommerce system.I was lucky to work with some brilliant developers, and on some really interesting interfaces - including design and UX for warehouse workers who had never used computers, who were flying around the warehouse with laptops strapped to carts, on rollerblades.

Co-founded Sixlinks.org with fellow Cornell Alum Jeff Gunther. We created a platform and social network centered around the six biggest areas of need in sustainability.

Though the project was let down by our failures to properly monetize or market, I'm proud that we created a deep pool of well-grounded research, and quality guides to sustainable living that are still useful today.

Started as a junior developer, and a year later was leading a team of five super-talented developers tackling difficult medical informatics and patient care problems.

We worked quickly, and were lucky to operate in essentially a blue-sky environment. Many of the tools we got to develop were the first of their kind in the world, and it was an immense privilege to get to tackle these problems with such smart peers. This was the place I learned firsthand how valuable it is to never be the smartest person in the room.

Founded Quantum Imagery, a small consulting company specializing in Actionscript, Javascript, web development, and design. Over the next ten years, I had the opportunity to work on projects ranging from big, global companies to small community non-profits.

I'm most proud that the company was sustainable and successful with no advertising - we did quality work, and our clients were our best advocates. Over the years, I also released a number of open-source packages under Quantum Imagery's umbrella.