My First 30 Years in Tech
I turned 44 recently, which means I’ve now spent exactly half my professional life as an entrepreneur and half as an employee. Fifteen years building and running my own businesses, followed by fifteen years working for others. The symmetry wasn’t planned, but it’s given me a chance to reflect on what I’ve learned about myself along the way.
The Foundation
I fell in love with computers when I was five years old. My dad worked at a Kenworth dealership in Florida, and on one visit to his office I got to play Frogger on their ancient machine—probably pre-8088. I thought it was the most amazing thing I’d ever seen.
When we moved to Michigan, my Uncle John started giving me leftover computer parts from his repair business and swap meets. I’d assemble whatever I could from the scraps. Somewhere around age nine, I entered a home-built PC in the county fair through the 4-H program. I won every award in that category, mostly because I was the only person who had ever entered a computer.
I come from a family of entrepreneurs. My parents had full-time jobs, but they also ran side businesses—my mom did desktop publishing, my dad was a general contractor. I was homeschooled, which meant I learned to teach myself early. I didn’t actually learn to read until I was eight, but once I did, you couldn’t stop me.
By eleven or twelve, I was working part-time for my dad’s construction business. If I finished my schoolwork by lunch, I could go swing a hammer at whatever house he was building or renovating. I learned what hard work looked like, and I learned that you could make your own way.
The Entrepreneur Phase
At fourteen, my best friend Christian Metts and I decided to start a virtual reality arcade. This was 1996. We wrote a business plan, raised $10,000 from family and friends, and set up shop in the Jackson Crossing Mall in Jackson, Michigan—right near the nail salon and pet store.
We had a couple PCs with VFX1 headsets running a game called Descent. It was pretty cool for the time. But that same summer, the Quake demo came out. We spent more time playing Quake than we did selling our service to mall passersby. The business failed by the end of summer. We paid back our investors by working for my dad, swinging hammers and helping build storage units.
That failure didn’t stop me. I’d already been teaching people how to use computers in exchange for things like horseback riding lessons. I started Legend Computer Services and began doing IT consulting for friends, mostly other homeschool families. After high school, I went to work for a local IT shop. The lead technician quit a few days after I started, so I went from filling ink cartridges to repairing PCs almost overnight.
The owner was difficult to work for, so I quit a few times and kept doing my own consulting. But I kept going back because I could make more money there than on my own. Eventually I left for good, taking a chunk of the client base with me.
In 2004, I teamed up with Brad Cochran to buy SabreTech Consulting from a friend who was struggling to make it work. We knew how to make it succeed. A few years later we added Sam Sallows as a partner, and by 2010 we’d grown the business to over a million dollars a year in PC sales and services.
The Pivot
Everything changed in 2006 when Christian Metts—same friend from the VRcade days—introduced me to Ruby on Rails. I went to the first RailsConf in Chicago that year and caught the programming bug. We started building software for SabreTech customers: a billing sync system for a chain of tanning salons, an obituary website called Forever Remember Me, internal tools for our own operations.
In 2007, my wife Natalie and I got married and moved to Elkhart, Indiana. I searched for “ruby south bend” and found a meetup at Notre Dame. That’s where I met John Nunemaker and Steve Smith.
We started hanging out regularly, hacking together at a place called Fiddler’s Hearth in South Bend. One day they were complaining about Slideshare. One of us said, “If it sucks so much, why don’t we build our own?” I pulled out my laptop, figured out how to convert PDFs to images with ImageMagick, and Speaker Deck was born.
Steve and John had started a company called Ordered List. They were building products like Harmony (a CMS) and doing consulting work. In late 2010, they offered me a job.
This was a big decision. I’d been an entrepreneur for fifteen years. The idea of working for someone else felt foreign. But with Natalie’s support, I sold my share of SabreTech to my partners and joined Ordered List in December 2010. Brandon Keepers joined a few weeks later, then Matt Graham a couple months after that.
The GitHub Chapter
Our small team built Gauges (a web analytics tool), maintained Speaker Deck and Harmony, and paid the bills with consulting work—including helping Zynga build Words with Friends for Facebook.
GitHub noticed our products and our work. They made an offer to acquire Ordered List. On December 5th, 2011, all five of us joined GitHub. I became employee #50.
I’d been an early GitHub user—user ID 623, signed up on February 22nd, 2008—back when the platform first launched. Being part of the Ruby community meant you found out about GitHub quickly. Now I was an early employee too, just three years into the company’s life.
The Realization
I’ve now been at GitHub for fourteen years, and an employee for fifteen. The symmetry with my entrepreneur years is complete.
Here’s what I’ve discovered: I love building software more than I love running a business. But it’s more specific than that. I love building teams that solve people’s problems through software.
At GitHub I’ve had the chance to serve our support team, finance team, sales team, product team, and security team by designing, planning, building, and maintaining software. I’ve built and led teams. I’ve found my calling.
But it’s not just the work—it’s where I get to do it. I’ve interviewed at other companies every few years since joining GitHub, and I keep choosing to stay. There’s something special about being at the center of the software universe. I love helping developers—and people who don’t yet know they’re about to become developers—discover and invent a new world. GitHub brings people together. It gives them the opportunity to do meaningful work through collaboration by solving problems together. It’s hard for me to explain the fulfillment I get from contributing to the open source projects and the infrastructure that power everything from research to startups to enterprises—and through protecting that community so it can thrive.
Software development is my calling and GitHub is a huge part of that—and a central part of my identity.
I don’t have grand lessons to share. Just this: reflection matters. I didn’t know what I truly loved until I’d spent fifteen years doing one thing and fifteen years doing another. Sometimes you have to live both paths to understand which one fits.
I hope I get another thirty years doing this work. I want to keep waking up every morning trying to figure out the next cool problem to solve with technology—without necessarily having to worry about all the details of running a business. I want to focus on building teams that help people.
That’s what the first thirty years taught me about myself.