What We Learned Mixing Family and Business: Real Stories, Real Lessons
Childhood Holidays: More Chaos Than Champagne
We kicked off the episode reminiscing about New Year's Eve and New Year's Day traditions when we were kids. For many of us, those nights were spent at family gatherings—adults around the card tables late into the night, while us kids often found entertainment driving around town, sneaking the occasional taste of something we weren't quite old enough for.
For Tom, New Year's Eve was always a big event in town. As he put it: “There was a little party down at the sports club, a band, dancing, and always lots of drinking.” When we were in colder climates, there was ice skating for miles down the lake, snowmobiling, and sometimes simply huddling together, seven people to one bathroom in a tiny cabin—one of those memories that seems far more charming with age.
Ultimately, New Year's Day was quieter—a time to recover, reflect, and, for Shirley, even celebrate Christmas with family. It was those early days that, in looking back, probably shaped the resilience and flexibility that's so critical in family-run businesses.
Getting Businesses Off the Ground: It’s Never as Simple as You Think
When we transitioned to talk about our first businesses, the stories were as varied as our holiday recollections. Tom recalled taking the plunge with a car wash—"our first real, by ourselves investment"—and all the lessons that came with financing, trust, and the goodwill of bankers who believed in us. Beth reflected on pulling off tricky deals: "We wanted to do some remodeling at the Dairy Queen, and the bank didn't want to work with us. So instead, our warehouse financed it—something totally unusual."
Our experience made it glaringly clear: most people underestimate just how much is involved in starting, buying, or even taking over a business. Shirley shared her first shock buying the Dairy Queen: “We only have one warehouse we buy 90% of our stuff from. I thought, this won’t be a big deal… until I realized you actually have to call the electric company, garbage, internet, pop contracts, cash register vendors—suddenly, it’s 25 people, not just five.”
What You Think You Need vs. What Actually Matters
It was eye-opening discussing what we thought we needed to succeed versus what actually mattered. We all had our lists: logos, branded materials, the “perfect” business plan. But what truly made the difference? Customers.
I remembered my digital marketing agency launch vividly. My coach nudged me: “Why don’t you try selling something first?” That lesson stuck. You don’t have a business until someone hands you money—no matter how great your idea or product seems on paper. Tom agreed: “Once you start, you need to actually service the customer. It’s about having the ability to deliver consistently, grow with demand, and yes, wait for those checks to arrive in the mail.”
Beth hammered home the importance of cash flow. Selling a few thousand dollars’ worth of product is great, but waiting 30, 60 days or more for payment can make for sleepless nights.
The Real Challenges: People, Change, and Unexpected Surprises
We learned (the hard way) that when you buy a business, the existing team may not be trained the way you expect, even in a franchise like Dairy Queen! As Shirley put it, “We thought there’d be no changes. But people do things their way—and retraining is a challenge. It took months for some to adapt.”
And then there’s equipment. Buy from a “handy” owner, and expect broken machines and hidden costs straight out of the gate.
Our Advice for Families Stepping Into Business
So what’s our best advice? Tom said it plainly: Do your research, be realistic about demand, and don’t underestimate the family dynamic. “The whole place has to go in. If you want to stay married, talk it all through.”
Beth added: “It isn’t easy. You’ll miss out on events, but stick together. Support each other.”
Adaptation, as we all agreed, is vital. Plans will change, markets will shift, and what you start with won’t be what you end with. “Have an open mind, because something’s going to come out of left field—no matter how much you prepare,” Shirley wisely reminded us.
Mixing family with business isn’t for the faint-hearted—but with clear eyes, an open mind, and a little humor about one-bathroom cabins, we’ve found the rewards worth the risks. And if you’re dreaming of a big idea, just remember—prove someone will pull out their checkbook before you bet the farm.
Make sure to listen to the full episode here!
Now, we’d love to hear from you! Have your own stories, insights, or questions about mixing business with family? Don’t hesitate to reach out. Email me at [email protected] with your thoughts, topic suggestions, or experiences. And if this episode sparked something for you, please share this blog and our podcast with others who might need a little encouragement on their own family business journey. Let’s keep the conversation going!
