From Chaos to Connection: Lessons on Family, Business, and Growing Up Together

Childhood Dynamics: Sibling Bonds and Lessons Learned

Kicking things off, I asked everyone what their family dynamics were like growing up—and how those relationships shifted as we all got older. The stories were as varied as our upbringings. Shirley, who grew up in a big family, recalled a childhood filled with laughter, sibling spats, and Sunday picnics that often included neighbors and whoever else wanted to tag along. She described being fiercely protected by her older sister Doris, even as some “epic battles” among the other siblings occasionally rattled the house. What stood out was how disagreements were handled: no therapy, no timeouts, just working things out or letting them slide—followed by a family meal where you ate what was cooked (unless you had the rare favor of a tomato soup swap for fish).

Tom echoed many of those themes, growing up as the youngest of three before a much younger brother came into the mix. He reminded us that in farm families, chores and hard work were the center of daily life. Visits to grandparents, Sunday dinners, and Christmas gatherings kept family ties strong. Of course, as siblings married and moved out, new space opened up—literally and figuratively—for the ones left behind.

Kim and I both reflected on the unique bond you develop when you move often as kids. For us, frequent relocations meant having to rely on each other as both support and entertainment. The transformation from siblings to friends, especially as adults working together, required effort and understanding few people experience to the same extent.

Advice for Our 30-Year-Old Selves

It’s funny how, looking back, the things we worried about at 30 seem so different from what actually mattered. When I asked everyone what advice they'd give themselves at that age, we collectively circled around a few key pieces of wisdom.

Tom and Shirley both wished they’d thought about retirement earlier, but they also acknowledged the importance of enjoying the present—traveling, investing in experiences, and not getting too hung up on long-term planning. Kim got specific with some candid advice for her younger self: enjoy your kids more, stand your ground, and don’t be a doormat in business or life.

For me, the big one was wishing I’d worked a little less and spent a little more time with family. Business took over so much of my life in those years. While the kids seemed to feel pretty good about our presence, I know now that I could have been there more—for them and for myself.

What We’d Do Differently in Business

When it comes to business, trial and error was our main teacher. Kim and I both admitted that if we’d known at 30 what we know now, our strategy would have been radically different. The biggest lesson? Seek advice from those who have already succeeded where you want to go. Find mentors, hire people smarter than yourself, and invest in continual learning—whether that’s formal education, business classes, or real-world experience.

We also learned not to get too invested in ventures that don’t have real potential, and to be quicker to cut losses. And while starting small is essential for anyone, as your business grows, you need to think bigger and not limit yourself to “safe” opportunities.

The Surprising Gifts We’re Glad We Didn’t Know

One final question I asked was, “What’s one surprising thing you’re glad you didn’t know at 30?” For me, it’s realizing there’s no finish line—no perfect moment when you’ve “arrived.” That’s not discouraging; in fact, it makes life more interesting. Kim reflected on the unpredictability of where her career would go, and Tom shared just how fast time flies as you get older. The consensus was clear: if we’d known all the challenges and the pace of change, we might have been too intimidated to even try. Sometimes, ignorance isn’t just bliss—it’s what keeps you moving forward.

Keep Learning, Keep Dreaming

After all our years in family business, if there’s one thing we’d encourage anyone (at any age) to do, it’s never stop learning and never pack away your bucket list. Growth—whether personal or professional—is an ongoing journey. As Kim said, “Once you stop having goals, life isn’t as much fun anymore.” So here’s to the next chapter, with all its messiness, lessons, and connections—still mixing family and business, one day at a time.

Make sure to listen to the full episode here!