Playing with Computers

I did poorly in high school. F’s finally after years of C’s and D’s coming up through junior high. Instead of homework, I spent my nights pushing my 75mhz win95 box further and further online. Geocities and early Bungie games. That phone line screamed moving bits around at 9600 baud. AOL discs piled up as I spent their promised “100 free hours” each to access the proto-internet. HTML and game-modding led to ColdFusion and IIS servers.

At like 16 years old I picked up a gig putting a website together for a friend of the family that wanted to sell his custom sports gear online. That led to a gig making a portal for Kadets at the Air Force Academy to hear about drink specials and other discounts around town. Then a local web dev firm picked me up the summer following my sophomore year. I built sites all summer, now with proper mentors around me: teaching me databases, source control and the like.

Off work, I was competing with my friends to build the hottest web things, building web apps for fun. Who I wanted to be professionally was coming into sharp focus. I wanted to build a thriving software company. The internet was where I’d make my bones. This was all before Unicorns, before Facebook, pre-MySpace. I spent a decade getting better at all these technologies. I fell in with some C# folks and got even more legitimizing technical influence from some dear friends. I took a detour through college in my mid twenties.

A place to run

The month I graduated I also landed a new coding gig with some excited young salesmen that had this idea for an app to help people sell more effectively across the internet. It was video, it was duct-taped together. They’d just had a catastrophic total data loss. They needed someone to be the guy.

I worked there for over thirteen years. It was just the environment I needed. Motivated business partners that knew what they needed from the perspective of their prospects and customers. It soared. For a year it was just me creating. I hired a friend, then another and another. It grew and grew. When we were all firing on all cylinders we sold $1MM in new accounts in a single day.

We exploded onto AWS, mixing all their awesome tools together. For years my life was work queues, and microservices and saying yes to every challenge. Python, PHP, Node, Serverless, Lambda, Jenkins, FFMPEG. We ingested and presented millions of personal video messages, we integrated with dozens of CRMs and other tools. We authored and supported a busy public API.

My engineering team swelled past 45 technical professionals: DevOps folks, Data Science PHDs, folks that went on to Netflix and Google. I got good at making these teams coherent and happy. We had all the personality conflicts, egos, personal dramas and successes and failures of lives lived well. Friends moved on.

It was sublime for a long time.

Green field

I want to get closer to the computers again. The last years became more about teams and roadmaps and challenging strategic decision making. I didn’t get to make the computers dance like I’d used to. I could have. I still can.

I hung a lot of my best coaching that I shared with Engineers that I helped along the way on the idea of Play. Playfulness is rooted in joy and the relationships we can build with one another. Playfulness turns off fear. Playfulness with computers is the core of what led me to teach myself to become a coder, then a software engineer. I’m not sure it’s what propelled me to become a CTO. That was something else, like a turn of responsibility, or of duty earned with age.

Experimentation. Showing off. Surprising people. Using my own hands to create things yielded the best times of my life. Maybe these memories are rose tinted. But I think it was more my style.

I’m going to dig into Rust for a while. I’m going to keep my Python chops warm. I’m going to play with computers a little more and see if I don’t still love it.