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What Failure REALLY Teaches You (and Why It’s a Good Thing)

May 13, 20253 min read

Let’s Start at the Beginning: Where Grit is Built

You don’t grow up in a family business without learning a thing or two about picking yourself up. Looking back, our after-school days weren’t packed with scheduled activities or screen time—unless you count reruns of Bonanza and The Lone Ranger as “screen time.” We had chores, bikes, siblings playing tricks (hello, mouse-in-the-shirt), and more than a few skinned knees.

Those everyday moments taught us something we’ve needed our whole lives: you just do what needs doing, and you don’t let a little setback slow you down for long.

When Businesses Bomb: Our Funny (and Painful) Stories

Here’s the truth: For every business that works, at least a couple just flat out don’t.

Take my experience with Hans Market—our foray into organic and natural foods. Wrong location, wrong time, not enough marketing knowledge… let’s just say it ended in a “Thanks for trying!” moment instead of a victory lap. Kim had her share, too. That “limited brazier” at the mall? A disaster from day one. Steak a Skater? Awesome sandwiches, no customers. And don’t get me started on the cost of bailing out of a mall lease!

The list goes on: car washes, shoe shine stands, cookie businesses, house flips—small towns, big mistakes, and a lineup of lessons more valuable than anything we sold.

What You REALLY Learn When Things Go South

Every flop forced us to get clearer about a few things. Tom reminded us that simpler is sometimes better—go with what you know, and don’t bite off more than you can chew.

Kim nailed it: Timing is everything. Sometimes you’re just too early (like selling espresso in the ‘90s) or way too late (jumping in after the crowds move on). And hey, maybe we didn’t know more than Burger King, no matter how many burgers we’d eaten.

Mostly, we all learned it’s not about never screwing up—it’s about how fast you get back up. Sometimes you call it quits, take your lumps, and move on without letting pride drive you further into the hole.

Words for Anyone Feeling the Pain: When to Duck Out

This might be the most important thing: It’s okay to let go. Kim said it best on the show—sometimes, you just need to step back and honestly ask, “Is it time to move on?” Don’t quit too soon, don’t hang on too long, but don’t be ashamed to call it. That next business might be just around the corner. And trust me, after a little time, even your biggest wipeouts will become funny stories over a beer.

The Real Win: Making Every Setback Count

It isn’t easy admitting things went sideways. But honestly? Every failure made us better, more resilient, and—believe it or not—closer as a family. If you’re out there struggling with a business or even just a dream you’re scared might not work, know that you’re not alone. Dust yourself off, take the lessons, and jump back in when you’re ready.

And hey, if you enjoyed these stories (or have your own business “flops” to share!), shoot us an email at [email protected]. Listen to the episode and like and subscribe on your favorite platform so you never miss an episode! Keep following along for more real talk from the front lines of family business.

You’ve got this. The next step might just be your game-changer. Let’s keep moving forward together.


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