Rooted & Reaching Podcast Interview
I recently sat down with Marty Mechtenberg on the Rooted and Reaching podcast to talk about my entrepreneurial journey, from struggling through my first programming class at Bethel to building multiple SaaS businesses while staying rooted in the South Bend area.
The Early Days: Learning to Code (the Hard Way)
I wasn't a natural programmer. In my sophomore year at Bethel, I was pulling a D in my programming class while my future business partner Steve would walk in, hand in his homework, and leave. I spent hours in office hours, terrified of failure after a lifetime of straight A's. But that struggle taught me something important: once I learned something the hard way, it stuck.
What really hooked me was the internet. The moment I could make something and have my mom see it by typing a URL into her browser, that was magic. That's when programming stopped being abstract loops on a screen and became something I couldn't stop doing.
Ordered List and the Power of Sharing
After Notre Dame, I joined my friend Steve Smith at Ordered List, a small agency. We had a simple philosophy: talk about everything we built. We blogged about our process, spoke at conferences, and contributed to open source. We weren't trying to be clever about marketing, it was just what we knew how to do.
That openness led to opportunities we never expected. Speaking at a Ruby conference in New Orleans, I reconnected with a friend who had started GitHub. One conversation led to another, and eventually GitHub acquired our five-person team in 2011.
The GitHub Years (and Why I Left)
GitHub was an incredible ride—from 45 employees to over a thousand in just four years. But as the company grew, so did the layers between me and any real decision-making power. By 2016-17, I was seven layers deep and itching to get back to building things my own way.
When Microsoft acquired GitHub in 2019, I took my exit. I needed to reclaim my indie spirit.
Building for Flexibility, Not Fortune
Today I run multiple products: Box Out Sports (sports graphics for schools), Flipper (feature flags for developers), and Fireside (podcast hosting). The common thread? I've always optimized for flexibility over maximum revenue.
I watched my dad work 90-hour weeks on the farm. I wanted the freedom to take a seven-week camping trip in the summer.
My advice for aspiring entrepreneurs: work your tail off in your 20s across different environments. Figure out what you actually like. Then optimize for the life you want, not just the biggest paycheck.
Why South Bend?
People ask why I didn't move to San Francisco. The answer is simple: South Bend has everything I need. Good restaurants, Notre Dame athletics, a reasonable cost of living, no brutal traffic. It's big enough to have what matters, small enough to avoid what doesn't.
Plus, there's something special here I didn't expect to find: South Bend had its own watch company in the early 1900s, making precision pocket watches for the railroad industry. I've become obsessed with finding and restoring these watches—physical artifacts I can pass down to my kids, unlike software that rots in three years without constant care.
The AI Era
I'm not worried about AI taking over. I'm obsessed with it. It's made me multilingual as a programmer. I can now contribute to Go projects despite being a Ruby developer for 20 years. The fundamentals I learned the hard way? They translate perfectly to telling Claude or ChatGPT exactly what I need.
The key is knowing what to ask for. Twenty years of programming principles don't disappear, they become the foundation for working with AI effectively.
Hope you enjoy!