How a Rickety U-Haul Kickstarted My Digital Career

In hindsight, picking up everything and relocating from Cincinnati to Minneapolis might have looked reckless and wayward. But I needed a job — and the company offering me one was right in the sweet spot of everything my friends and I had been trying to build. So we did what any ambitious twenty-somethings would do: we piled everything we owned into a U-Haul and headed northwest.

Rick drove the truck. I followed in my copper Dodge Lancer — burgundy red interior, very trendy at the time — and tried to keep up.

No cell phones in the 90s, so staying close to the U-Haul was Plan A. Good plan, except the U-Haul had other ideas. That thing broke down constantly. We’d limp into a rest stop, find a pay phone, and dial U-Haul support. “Sorry sir, we can’t get a replacement vehicle to your location for about 8 hours.” The thought of unloading and reloading everything was unbearable, so we did what any reasonable person would do: ignored the blinking engine lights, ignored the sounds no engine should make, and kept going.

For most of the trip, Rick couldn’t push past 50 miles per hour. Through sheer grit — and maybe a little stupid stubbornness — we finally rolled into our apartment complex in Eden Prairie. Snow-covered fields stretched out in every direction. We were exhausted, but we were there.

A few days later, we started at Internet Broadcasting System — IBS. The company’s mission aligned almost perfectly with what we’d been building: a community-first approach to bringing local news and information to every major market in the country. Rick moved into sales and business development. I landed in content, marketing, and operations. And theAntenna — our scrappy little marketing tool we’d built to win new clients — was now in the fold at IBS. My job was to build a better mousetrap.

The first big test came quickly. IBS was gearing up for broadcasting’s Super Bowl: the National Association of Broadcasters conference in Las Vegas. Sony, CBS, NBC, Cumulus, Clear Channel — all the major players, all in one place, all navigating an industry in the middle of massive upheaval. We overhauled theAntenna down to the screws for the show — new logo, new branding, new website, new publishing schedule. That conference also gave me my first taste of the exhausted-but-wired feeling you only get after working a trade show for three days straight.

After leading theAntenna for a while, I shifted into a new role: Publisher of Channel 4000, which at the time was the nation’s first profitable TV station website (WCCO-TV). Big opportunity. The editorial team — all veterans of the Twin Cities journalism scene — already had an incredible rhythm and a deep feel for the market. Honestly, my best move was getting out of their way and letting them work.

The dynamic at WCCO wasn’t unlike what I’d experienced earlier in my career — pockets of real advocacy for the web sitting right next to pockets of real resistance. And remember: no smartphones, no apps. People were still getting comfortable with email. So a big part of my job was selling the value of an organic, ever-changing web presence — over and over, in news meetings, in sales meetings, wherever I could get a seat. Minneapolis made me stronger and wiser. It’s a serious journalism town with high-caliber TV stations and two strong metro papers — the Star Tribune and the St. Paul Pioneer Press. The bar was high, and that’s exactly what I needed.

IBS was also where I learned to experiment. Testing messaging, subject lines, and value propositions — then watching what moved the needle on open rates, click-through, conversions, shares — was exciting and eye-opening. The lightbulb moment for me came when I realized that any idea I had could get exponentially better if I just made it public with my teammates. Collaboration was a force multiplier.

As IBS grew, so did its footprint — Portland, Madison, Los Angeles. Working across offices and time zones was new learning for me, and it taught me volumes about negotiating, delegating, listening, and knowing when to fight for what you believe in. This was early internet, remember — no Zoom, no Slack, no modern project management tools. We were wrestling with Microsoft Project and watching it buckle under the pace of digital publishing. We figured it out anyway.

The lessons from IBS — about ownership, leadership, collaboration, and what it means to build something together — set the table for a lot of what was next. I’m grateful for the ride, and appreciative of the people who made the journey fun and meaningful.

Until next time,

Dan Naden