My first job was detailing cars at my family's shop. I was 13 years old.
I got pretty good at it — maybe too good, because I started noticing things I probably shouldn't have been noticing at 13. I'd look at a car before the owner even walked through the door and I could tell you things about them. Not just their level of success in life. I mean how they looked. What kind of music they probably listened to. What their personality was going to be like when they came to pick it up. I'd seen enough people come and go that I started seeing patterns, and I came to believe something I still think is true: people really do look like their cars a lot of the time.
But I also knew pretty quickly that detailing wasn't my future. The shop was still new back then, and the industry can attract a rough crowd when you're just getting going. The guys we'd hired weren't exactly the kind of people a teenager needed to be spending his time around. So I started to think maybe the automotive world just wasn't for me.
Then I turned 18, and I had an idea.
It was 2008. Facebook was new, and I was deep into marketing classes and completely fired up about what the internet was going to do for businesses. I went to my parents with a pitch: let me get Gateway Auto on Facebook. They would have been the first automotive shop in Omaha on the platform — probably one of the first in the country.
My parents looked at me the way parents look at a reckless teenager with a half-baked idea. They didn't know what Facebook was. They didn't want to take the risk. They thought I was their son who was 18 years old doing a bunch of stupid things they didn't agree with.
They told me to kick rocks.
And that was it. I decided I was done with the family business.
I went headfirst into tech. I'd always been a geeky kid — video games, computers, constantly curious about how things worked. I knew the industry was rising and I wanted to be part of wherever it was going, even if I couldn't have told you exactly what that looked like yet. After college, my parents essentially said good luck, you're on your own, go figure it out. So I moved to Colorado and did exactly that.
A few years in, I got invited to become a senior-level consultant overseeing some of the biggest products at Google. I'm talking about:
That last one became one of my deepest areas of focus, and it turned out to be more relevant to everything that came later than I ever could have planned.
After about a year and a half, I left Google. Not because of Google specifically, but because I'd become genuinely concerned about where the internet was heading — data privacy, algorithmic manipulation, platforms built to extract attention rather than create value. I wrote a book about it. I started speaking about it around the world. And somewhere along the way I ended up in a documentary that became the most-watched technology documentary in Netflix history: The Social Dilemma.
I was keynoting stages across the world about how to make the internet safer while simultaneously watching my inbox for the next flight.
That's when my parents decided I was finally qualified enough to help us. Which, I'll admit, was a reasonable conclusion to draw. So while I was still traveling and speaking, I started quietly helping with marketing and operations at Gateway Auto on the side. The problem was I was always on a plane. I couldn't be there day to day.
About a year in, I went to speak at a marketing class at the University of Nebraska. Afterward, a student came up to me — sharp, ambitious, loved cars, already doing digital transformation work for Berkshire Hathaway but clearly wanting to build something of his own. I found out later he'd been in the same fraternity I was in years earlier.
I told him I couldn't make him an entrepreneur, but I could help him become an intrapreneur. That was the beginning of me and my then co-founder Alex working together.
The arrangement was unconventional, but it worked. Alex was at the shop every day, on the ground, building relationships with the team. I was remote, mentoring and providing structure — teaching him how to:
Wisdom and vision from 30,000 feet. Execution on the ground.
What we walked into was not pretty.
When Alex first joined, our website had a logo that — if you clicked on it — called the front desk. We had a server room in the back of the shop running everything, slowly dying under a layer of shop dust because no one had maintained it. The computers were so old that software companies had stopped pushing security updates to them. Everything was held together with digital duct tape.
I used to say it was like putting a V8 engine on a go-kart. The ambition was there. The infrastructure wasn't.
That's why it took me three years before I even wanted to get more personally involved. You don't modernize a business like that overnight — you have to bring the people with you, or it doesn't stick.
But that transformation? That's the story I want to tell next.
Next: From Frankenstein to Frankenstein — what it actually took to drag Gateway Auto into the digital era, and what we learned building it.
