Fresh Out of the Program: Four New Owner-Operators on Mentorship, Small-Town Roots, and Learning to Let Go

With You Every Step — Episode 007

Every long career at Brown’s Shoe Fit Co. starts with a first step. In Episode 7 of With You Every Step, host Adam Smith hands the microphone to four owner-operators who took that step recently: Tori in Marshalltown, Emily in Storm Lake, Carissa in Grinnell, and Kaden in Centerville. All four are fresh out of the trainee program and running Iowa stores of their own.

With Craig away for this episode, Adam leads an honest conversation about what drew each of them to Brown’s, what training really prepared them for, and what it means to be the face of a store in a small town. If you’ve ever wondered what the first months of ownership look like, or whether a career with Brown’s might be right for you, this one is worth a listen.

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Meet the Guests

Their paths couldn’t be more different. One came straight out of college with a business degree, one took a part-time job and never wanted to leave, one skipped college altogether, and one spent nearly seven years with the company before taking the keys. All four ended up in the same place.

Four Paths to the Same Front Door

Tori always wanted to own a business but didn’t know how to get from point A to point B on her own. Brown’s gave her the steps and the tools to get there in a few years, plus something she hadn’t expected to love: the chance to move. After growing up in Southeast Missouri, she has since called Texas and now Iowa home.

Emily never planned on ownership at all. Her brother got her started with a part-time job at the Cedar Falls store, and she stayed for the variety of the work and a kind of mentorship she’d never found anywhere else.

Carissa knew after high school that college wasn’t for her, and neither was sitting at a desk. Working part-time, she discovered she was a natural with people and with the bookwork alike.

Kaden began part-time while attending junior college in McCook, Nebraska, then followed a manager’s advice to transfer to the busier Lincoln store. A month after graduating from the University of Nebraska, Caden knew this was his career for life, because it all comes down to the people.

Adam, who trained in Colorado and ran stores in Illinois before settling in Iowa, sees a pattern in stories like these: the more time people spend around the Brown’s culture, the more of it they want.

A Trainee Program Built on Mentorship

Over the past couple of years, Kelsi Bouray has shaped the Brown’s trainee program into a true apprenticeship. When Adam asks what stood out, the first answer is the mentorship. Trainees learn from at least two different store owners, the work is hands-on, and help is always within reach. As one owner puts it, there’s nobody in this company who doesn’t want to see you succeed.

You also don’t need to walk in knowing how to run a business. Alongside the bookwork, the program teaches professionalism and how to work with people, preparing trainees for life and not just for the store.

That camaraderie lasts long after training ends. A quick call to another store about a special order is rarely a two-minute conversation, because everyone genuinely cares how everyone else is doing. Adam, now 15 years into his career with Brown’s, says this network is what separates a Brown’s owner from someone going it alone. The people who came before you have already faced what you’re facing, and they can fast-track your learning and spare you some heartache along the way.

Proving Yourself in a Smaller Town

Trainees typically learn in larger stores, then begin their ownership journey in a smaller town, where the pace makes it easier to prove yourself and figure things out. Some fall in love with their town and stay; others hone their skills and move on to the next opportunity.

For Emily, the biggest change in Storm Lake has been becoming the face of the store. She attends chamber and Rotary meetings to build as many relationships as she can. Tori leans into the same idea in her marketing, which often features her own photo or her dog, and everyone in Marshalltown knows the dog. In a small town, she explains, you recognize people at the grocery store, they recognize you, and some customers stop in as much to visit as to shop.

Adam ties it back to a theme the podcast keeps returning to. Great product matters, and everybody needs shoes, but Brown’s is in the people business. Being locally owned and operated lets each store carry the right product mix for its community and puts a real face on the business.

Care That People Remember

The owners’ customer stories show what that care looks like in practice.

Some offer house calls for homebound customers who can’t easily get to the store. Others scan and trim custom inserts so that a man who couldn’t find work boots that didn’t hurt now goes to work pain free – and the referrals you get from those interactions turn into good publicity, rave reviews, and sometimes a new business account.

Can care be taught? Tori credits Justice, a mentor from her time in Texas, with a lesson that stuck: give to your staff and your community, and they will give back to you. Kaden adds that care doesn’t stop at the door. In a town of about 5,000, you run into customers at Walmart, and asking how those Birkenstocks are treating them matters too.

A first-day fix in Grinnell

On Carissa’s very first day, a gentleman walked in with a pair of shoes he’d bought more than a year earlier that had never fit. She took care of him, and he later stood up at a Rotary meeting to tell the room how well he’d been treated. That’s the kind of word-of-mouth no ad can buy.

Walking again in Centerville

Kaden helped a customer who arrived limping from plantar fasciitis, taking her through the full three-step fitting process: scanning and measuring her feet, evaluating what she needed, and fitting her in the right shoe and insole. Three months later she came back close to tears. She could go on walks with her husband again, and she had already sent five people in.

Learning to Let Go

The trainee program prepares owners for a lot, but all four admit the first months still bring surprises. One describes the delicate work of stepping into a store with a well-established staff: figuring out what the team already knows without being overbearing, and retraining respectfully where adjustments are needed. Another sums up the group’s experience with a laugh. They left training sure they had it figured out, then arrived and realized they were still learning.

For several of them, the biggest personal lesson is learning to let go. Used to doing everything themselves to make sure it got done right, they now have to teach, step back, and let their teams make mistakes, just as they once did. Emily shares advice from a manager she trained under in Cedar Falls: most mistakes can be fixed, so they aren’t worth getting worked up over. Take the time to rework the problem and explain it so it doesn’t happen again.

Making the Store Your Own

Each of these owners inherited an established Brown’s Shoe Fit store, so Adam asks what ownership means to them. For one, it’s the freedom of having everything fall on their own shoulders: they control their future, put in as much as they want, and can see how far they’ve come. For another, it’s the chance to try new ideas and pivot with the town, setting their own standards instead of fitting into a big-box company’s.

The key in a new community, the group agrees, is simply being yourself. As self-described people people, they joke that they’re chameleons. Kaden, who grew up in a town of about 300, says that background made it easier to understand how a close-knit community like Centerville works.

When it comes to the in-store experience, their answers sound alike: greet regulars like old friends, remember faces and the shoe someone tried 10 months ago, and make the store feel like home, a place where anyone can sit down with a glass of water and stay awhile.

A Vision Built on Trust

Asked where they want their stores to be in the next few years, all four come back to one word: trust.

Adam also outlines the three pillars every Brown’s store shares: the guest experience, the right inventory, and marketing that brings new people through the door. Each community puts its own spin on them.

At the time of recording in June, Tori was preparing her team and inventory for a huge week in Marshalltown, with RAGBRAI rolling through midweek and Ridiculous Days downtown that Saturday. In Centerville, Kaden rallied several of the larger businesses on the square, including a neighboring men’s clothing store, to stretch the town’s Crazy Days from two days to three. Adam invites businesses in any of these communities to reach out to their local Brown’s Shoe Fit about partnering through Local Loop.

It’s Okay to Mess Up

The episode closes with a round of advice built on one shared truth: you don’t have to be perfect to get started. You just have to keep moving forward.

Tori reminds listeners that everyone messes up; what matters is what you do next. Treat it as constructive feedback, learn from it, and keep moving in the right direction. Adam agrees that perfection isn’t possible, but pursuing excellence is. Emily’s advice for anyone considering Brown’s is simple: don’t be afraid to step out of your comfort zone.

Adam shares his own leap. With a one-year-old at home, he wanted a career rather than a job, and a company that genuinely cared. Training under Jason Wetzel in Longmont, Colorado, showed him that care firsthand, and any early sense that the opportunity seemed too good to be true faded the more he saw. Today he keeps a reminder by his office light switch: today is a good day for a good day.

Carissa has learned that the way you decide your day will go is how it goes, and she starts every morning with a mantra from her training under Ashley in Pella:

“You are Carissa Rozenboom, and you can do hard things.”

— Carissa Rozenboom, Owner-Operator, Brown’s Shoe Fit Grinnell

Kaden closes the round by admitting to trying hard to be perfect as a trainee in Enid and in the early months in Centerville, and to learning from mentors and peers that it’s fine to mess up and just take a breath.

What’s Coming Next

Episode 8 continues the series’ conversations with store owners, business leaders, and friends of Brown’s Shoe Fit, with each episode closing on one guest’s most actionable piece of advice. Hearing from four owners at the very start of their journeys is a reminder that there are plenty more stories to come.

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Interested in Owning a Brown’s Shoe Fit Store?

Tori, Emily, Carissa, and Kaden took four very different routes to ownership, but they all found the same thing waiting for them: mentors who wanted to see them succeed and a company built on caring for people. With 73 locally owned and operated locations and a history dating back to 1911, Brown’s Shoe Fit Co. offers a hands-on trainee program that prepares future owners for the business and for life. To learn more about the Brown’s Shoe Fit opportunity, visit brownsshoefitco.com or stop by a store near you and talk with the owner.