So You Think You’re Ready? What Nobody Warns You About the First Years of Ownership

The Unsung Wins

We kicked things off with the question: “What’s something small you’re proud of that rarely gets talked about?” It made us all stop and think. Kim shared that giving up her old Dairy Queen office, one she designed and spent ages in, felt like a pretty big deal. Funny enough, no one even mentions it anymore. Tom talked about what it was like to leave Iowa and see our old businesses be taken over by other families. Nobody really talks about how weird that feels.

For me, the thing I’m quietly proud of is helping young people land their first jobs. Our stores are where lots of folks start figuring out work (and life), and even though it’s not flashy, it means a lot to see them thrive. It definitely deserves more airtime.

Owning It: The Emotional Rollercoaster

Let me tell you, it’s a whole different ballgame when you actually own the business. Kim admitted it took her nearly five years to really feel like the owner, not just the person running the day-to-day. Those first few times she had to deal directly with the bank or call up Dairy Queen corporate, that ownership stuff got real.

For me, the switch was gradual, your brain keeps telling you you’re just running things, but eventually you realize, “Nope, this is all mine now.” Every decision, every mistake, every big purchase, suddenly it’s your responsibility, and you feel it in your gut.

Surprises You Never Saw Coming

We definitely didn’t see all the bumps coming. I swear, cash flow will always trip you up. We thought we had plenty sitting around, but guess what? We didn’t, and it took a few years to catch up.

We also overestimated customer loyalty. Road construction rerouted people away from our grocery store, and I kept convincing myself they’d come back. They didn’t, until the day we closed the place, and then everyone showed up.

Biggest surprise? Thinking our management team was totally prepared for the new reality. I had to learn the hard way that they needed more guidance than I thought.

Learning (and Messing Up) Builds Confidence

Nothing builds confidence faster than making a decision that actually works, except maybe making a mistake and learning from it. The first time I had to figure out if we should repair or replace a pricey piece of equipment, I dove in head-first and learned real quick how much financial stuff I still needed to learn.

Kim found out interviewing wasn’t her thing (she’ll tell you herself), and I learned that hiring for fit is just as important as hiring for skills. Bad hires hurt, but figuring out where you went wrong makes you sharper for next time.

The Stuff Nobody Can Teach You

You don’t know what you don’t know until you’ve lived it. Owning a business is like getting married or becoming a parent, you have to experience it to really understand. You’ll make mistakes, fix things you thought you’d never have to mess with, and face situations you didn’t see coming. But after a while, things that used to throw you for a loop are just another Tuesday.

Tom reminded us: have confidence, but don’t get cocky. Every challenge is a lesson, and if you’ve worked in the business, you’re more ready than you think.

Ready to Jump In?

If you’re thinking about taking over a family business (or already have), take the leap. It won’t always be smooth, but you’ll learn, grow, and find some hidden victories along the way. And if you ever need advice or just want to swap stories, reach out.

Got questions or a wild transition story of your own? Email me at [email protected]. I’d love to hear from you and maybe even feature you on the podcast!

Make sure to listen to the full episode (82!) right here! And check out our other blogs for more mixing family and business insights.