One of the most memorable questions we tackled in this episode was about times we’d been surprised by the kindness of customers or strangers. When I look back over the years, it’s these small moments that seem to have the biggest impact. Kim shared a story from her “Dairy Queen days,” pre-social media, pre-internet, when a customer was so thrilled with the cake she’d decorated, she insisted on snapping Kim’s photo and returning with a copy for display. It was a genuine gesture, and it left Kim feeling like her work mattered.

Tom, meanwhile, pointed out the pride he felt when parents or grandparents took the time to thank us for giving their kids a job and a chance to learn some discipline. His favorite “rewards” weren’t about profit or recognition, but the acknowledgment that we’d given young people an opportunity.

I also recalled the surprising generosity we encountered while closing the grocery store. As we began selling off equipment, multiple customers paid ahead, sometimes for items they wouldn’t collect for weeks or even months. That trust and goodwill became a lifeline during a tough transition, reminding me that business is always a two-way street.

Surprises in Starting (and Managing) Family Businesses

Nobody goes into a family business with the full picture, every venture comes with its own set of surprises. During the episode, we talked about how reality never quite matches your expectations. Shirley admitted that, with years of experience, many surprises have faded into the background, but one story stood out: she moved her cash register to the front of an ice cream parlor, reasoning that being visible and smiling might just attract passersby. And she was right! Even neighboring businesses started copying the move.

Tom joked about all the “crazy ideas” we’ve tried, car washes, flipping houses, storage units. The real surprise, he said, is looking back and realizing that most of it actually worked. Our grocery store, started in 1978, turned out to be our biggest asset, but everything we did together, successes and failures, built foundation for what we have today.

Kim brought up the wild ride of moving from independent entrepreneurship to the world of franchises, specifically the challenges of dealing with corporate bureaucracy and the joy of finding “doers” who will go the extra mile to make things happen. Her advice? Befriend the doers, they’re the ones who show up when you need it most.

Challenges, Setbacks, and Learning Curves

Of course, not everything is sunshine and butterflies. We dug into the hardest challenges, and several common threads emerged: managing people (and their personalities), bouncing back from failure, and pacing yourself. Kim reflected on her early management days’ naivety, thinking she could simply make a list and everyone would follow suit. Turns out, leading people requires understanding what makes each person tick and what motivates them, and just when you have it figured out, the team changes again.

One of our greatest setbacks was trying and failing in Waverly, Iowa, a blow that caught Tom completely off guard. His wisdom for others: don’t obsess over water under the bridge, get up, and get moving again. Resilience is everything.

We also talked about the importance of taking breaks, one day a week, no exceptions. Burnout doesn’t serve anyone, and pacing yourself is crucial to building something that lasts.

Our Advice

As we wrapped up, everyone shared their advice for fellow family business owners. Kim said: Prepare for sleepless nights, and keep a notebook handy for those 2am epiphanies. Tom urged: If you’re not enjoying what you do, get out. Shirley reminded us: Stay positive, work together, and always try. And I added: Make it fun, pace yourself, and take real time off.

In the end, mixing family and business isn’t always easy, but if you have an idea, a strong work ethic, and the will to adapt and persevere, you’ll find those surprises, challenges, and rewards are all part of the adventure. What kind of surprises or challenges have you discovered. Email me at brian@mixingfamilyandbusiness.com and let me know. Thanks for tuning in to our story.

Make sure to listen to all of episode 69 and check out our other content here!