For those who don’t know me all that well, I am both not a creature of habit and very much a creature of habit.
For the last five years, I have driven back and forth to Wisconsin nearly every weekend. My son Jack — known to many of his classmates as “Johny” — lives there with his mom. Door to door, it’s about five hours one way. When I mention that, people usually pause, do the math in their head, and look at me like I’ve just told them I commute to the moon.
But parents understand. The things we do for our kids don’t always make sense on paper. They just make sense.
That, however, isn’t really what this week’s column is about.
It’s about what happens in those five hours.
For a long time, I treated those drives like an extension of my workday. Phone calls. Mental to-do lists. Trying to squeeze productivity out of every mile of asphalt between Mitchell County and Green Bay. Over the last couple of years, as my family and my life have evolved, I’ve made a conscious decision to stop doing that. Focusing on the road — and on my own head — felt more important than trying to steal extra work minutes behind the wheel.
So I did something new for me: I started listening to podcasts.
I’ve always been an avid reader, and I’ve always had a hunger to absorb as much information as I possibly can. Business, entrepreneurship and history have long been my go-to subjects. Podcasts, I discovered, fit perfectly into long stretches of highway where your hands are busy, but your mind is wide open.
One podcast, in particular, stopped me in my tracks.
It’s called “Acquired.”
The premise is simple but incredibly ambitious. Every company has a story. “Acquired,” hosted by Ben Gilbert and David Rosenthal, goes deep behind the scenes of some of the biggest companies, IPOs and acquisitions of all time. And when I say deep, I mean deep.
Episodes regularly run two to four hours. The hosts spend about a month researching, preparing and rehearsing a single company’s story. They’ve tackled Walmart, Costco, Mars, The New York Times Company and, most recently, Coca-Cola. They don’t skim. They don’t rush. They build the story brick by brick.
What surprised me most wasn’t just how much I learned about these companies, but how applicable it all felt. How companies are built. How they scale. Where they stumble. What decisions matter decades later. I’ve found myself listening not just as a consumer, but as an owner — stealing ideas, testing concepts in my head, and seeing how lessons from global giants might translate into my everyday life and businesses.
That’s saying something, because I’ve read no shortage of entrepreneurship books. Sam Walton. Sol Price. Jeff Bezos. Steve Jobs. Plenty of others. Those books are excellent. “Acquired” somehow manages to feel like all of them combined — and then expanded.
One episode I listened to recently focused on the rise of the NFL. I thought I knew that story. I was wrong. Three hours later, my understanding of the league’s inner workings, its early struggles, and how it became what it is today was completely reshaped. It made the modern NFL make more sense in ways I hadn’t expected.
There’s something powerful about learning this way — almost mentor-style — where you’re quietly sitting in on decades of hard-earned lessons while the miles roll by outside your windshield.
So if you’re someone who likes to learn, someone with a curious mind, or someone who just wants something meaningful to listen to while driving, walking or exercising, I can’t recommend “Acquired” enough. Give it a try the next time you’re in the car.
You might arrive at your destination with a few more ideas than you left with — and on a long road, that’s a pretty good companion to have.