With You Every Step, Episode 006
Take the High Road:
Josh Habre of Shoe Mill on Partnership, Culture, and Being Somebody’s Shoe Person
For the first time, With You Every Step looks beyond the Brown’s Shoe Fit family for its guest. Hosts Adam Smith and Craig Jarrard sit down with Josh Habre, third-generation CEO of Shoe Mill, the family-owned shoe retailer serving the Portland, Oregon area.
Josh and Adam first crossed paths through the National Shoe Retailers Association (NSRA) and clicked right away — and it’s easy to hear why. Recorded at the Apex Waukee School Podcast Studio, the conversation covers what great vendor partnerships really look like, why culture matters more than any policy manual, and why the future of brick-and-mortar retail belongs to the people on the sales floor.
What makes Josh’s perspective rare is that he sees the shoe business from both sides of the counter. Shoe Mill buys footwear as a retailer, and it also serves as the U.S. distributor for the Ziera and Django & Juliet brands. That dual role shaped nearly every part of this conversation.
Every Job in the Family Business
Josh’s path into the family business started with a reality check. By his junior year of high school, he’d accepted that a basketball career wasn’t in the cards — so he went to work for Shoe Mill instead. His first role was delivery driver, moving inventory between four stores in the same minivan he drove to school. (He’s quick to admit it wasn’t a great look.)
From there, he worked his way through nearly every role the company had: sales floor, assistant manager, store manager, multi-store supervisor, buyer, and vice president. As his father began stepping back, Josh became president and, later, CEO.
His leadership was tested almost immediately. Just weeks before the pandemic shut everything down, Shoe Mill had purchased its largest, highest-volume store in Eugene. A strong online business kept the company moving, and leadership made a deliberate choice to keep managers and office staff on payroll — so that when the doors reopened, a ready team would be waiting behind them.
Breaking Out of the Echo Chamber
Josh credits NSRA’s NextGen program, which took shape while his father served as NSRA chairman, with showing him he wasn’t navigating a family business alone. The peers he met there — people his own age facing the same pressures — went from industry contacts to some of his closest friends.
Just as valuable was the outside perspective. Inside your own stores, Josh explains, it’s easy to drift into an echo chamber where everyone loves the same brands and reinforces the same assumptions. Stepping into a room full of other retailers breaks that cycle.
Craig shared that Brown’s Shoe Fit has been an NSRA member for decades — possibly one of the organization’s oldest members — but has historically kept to itself. Part of the reason is that Brown’s 73 owners already share an unusual level of camaraderie, including monthly visibility into one another’s financials. With the company’s president, Cammie McKenzie, now serving on NSRA’s board, Brown’s is leaning further into learning alongside the wider independent retail community.
Seeing Both Sides of the Counter
Shoe Mill’s move into distribution began with what Josh calls a bit of “warehouse hacking.” The company had carried Ziera for years, but fill-in orders were shipping all the way from New Zealand. So Shoe Mill offered to warehouse the brand’s inventory and fulfill orders locally. It worked so well that Ziera asked Shoe Mill to become its distributor — right before the brand went into bankruptcy.
The opportunity looked finished until MFG, a family-owned company based in Melbourne, acquired Ziera and reached out. Josh and his brother flew to Australia, signed the deal in January 2020, and today Shoe Mill distributes both Ziera and Django & Juliet.
What Retailers Don’t Always See
Working as a distributor gave Josh a new appreciation for the vendor side of the relationship. Brands commit money months before shoes ever reach a store, frequently wait 60 to 90 days after delivery to get paid, and operate on thinner margins than retailers do. Seen in that light, direct-to-consumer (DTC) selling isn’t about undercutting stores — it’s how vendors keep cash flowing and inventory in stock.
His advice to fellow retailers: don’t judge a brand by what its MAP pricing policy says on paper. Judge it by how well it actually executes DTC. Adam and Craig added a silver lining from the retail side — when a vendor’s own website proves demand for a product, stores can buy it on futures with much more confidence.
Hard on Numbers, Soft on People
Josh’s favorite cultural mantra is a familiar one: culture eats policy for breakfast. At Shoe Mill, that translates into being hard on numbers — realistic ones — and soft on people. The team praises in public and handles everything else in private, and Shoe Mill has built a reputation as a place where people can build long careers, as long as they live by the company’s core values.
Committing to a System
The biggest catalyst for Shoe Mill’s growth was EOS, the Entrepreneurial Operating System laid out in the book Traction. When Josh became president, he handed a copy to every family member in the business and asked each one to decide whether they were in. With six family members involved, the answer was growth — and EOS gave them the framework to pursue it, built on realistic 90-day priorities and relentless accountability.
The result was significant growth in stores, revenue, and profit through one of the toughest stretches retail has seen. Josh is clear that it wasn’t because anyone was a genius. It was because they committed to a system and stuck with it. Craig, who has explored EOS at the store level, noted that the Brown’s Shoe Fit model functions almost like an operating system in its own right.
Josh’s Reading & Listening List
Recommendation |
Why It Came Up |
|---|---|
Traction (EOS) |
The operating system behind Shoe Mill’s growth — 90-day priorities and accountability |
The 5 Languages of Appreciation in the Workplace |
Understanding how different team members prefer to be recognized |
Driven to Delight by Joseph Michelli |
Building customer experience into every part of a business |
Acquired podcast |
Long-form deep dives into companies like Costco and Rolex that keep landing on the same lesson: it’s always about the customer |
Be Somebody’s Shoe Person
When it comes to hiring, Josh looks for two things above all: high emotional intelligence and authenticity. Selling and fitting can be taught. Personality can’t.
He illustrated the point with his family’s favorite coffee shop. They own just about every coffee maker you can imagine, yet they keep going back to see one barista, Shelby, because of how she makes them feel. The exact same coffee from someone who’s checked out feels like an entirely different experience.
That’s the challenge Josh gives his team: become somebody’s shoe person. Try it a handful of times a day, and before long, regulars start walking in and asking for you by name. The hosts connected the idea to Napoleon Hill, who wrote about buying shoes from his own trusted “shoe guy” back in 1938 — proof that this kind of relationship has always been at the heart of the business. Craig reflected on the human connections, right down to swapping stories about grandkids, that have kept retail joyful for him across 36 years.
Stop Fighting Your Customers
Is brick-and-mortar retail dead? Not even close, according to Josh. Comfort used to be what set an independent shoe store apart. Today, it’s simply what customers expect. The new advantage is people — fitters who can customize the fit for each customer, the same way people customize their phones and playlists.
A store’s website still plays an important role, Josh says, especially for selling “the red after you’ve bought the black.” That supporting role mirrors how Brown’s Shoe Fit approaches brownsshoefitco.com — as a tool that works alongside the in-store experience, not in place of it.
Winning the in-store moment, though, means removing friction — and that starts with returns. Shoe Mill even accepts worn shoes, because customers who know a problem will be handled without a hassle have no reason to shop anywhere else. Josh cautioned against writing policy around the exception rather than the rule. Craig put it plainly for any young owner listening: if a customer is standing in your store and you can’t win them over, the product usually isn’t the problem — how they were treated is. The goal, as the hosts summed it up, is to win the customer, not just the sale.
Take the High Road — Every Time
For his closing advice, Josh returned to a lesson championed by Howard, a longtime mentor to his father: take the high road, always.
Someone can always beat you on price, Josh explains, so push your price points and bring customers the best. He recalled a couple of seasons when Shoe Mill chased lower price points out of fear of losing entry-level shoppers — and how long it took to recover. Now, when a customer says something costs too much, the response is simple and respectful: we understand, and we just thought you deserved the best.
He also warned against selling out of your own wallet — prejudging what a customer can afford based on your own budget or their appearance. The hosts agreed, pointing out that plenty of great customers walk in wearing overalls and work boots. With customers, vendors, and team members alike, Josh says taking the high road is something he has never regretted.
“Take the high road, always… Whenever you take the high road, you don’t lose.”
— Josh Habre, CEO, Shoe Mill
It’s a philosophy that lines up naturally with the people-first values Brown’s Shoe Fit has been built on for 115 years.
What’s Coming Next
The series continues with more conversations featuring store owners, business leaders, and friends of Brown’s Shoe Fit, each episode closing on one guest’s most actionable piece of advice. Josh’s visit is a reminder that some of the best ideas in independent retail come from comparing notes — and there are plenty more conversations on the way.
Thinking About Ownership?
Josh’s story is a reminder that great stores are built by people who care about the customer in front of them — and that the best leaders never stop learning. If that sounds like the kind of business you’d like to build, learn more about the Brown’s Shoe Fit ownership opportunity at brownsshoefitco.com or find your nearest Brown’s Shoe Fit location.
Catch the full conversation with Josh Habre on the With You Every Step podcast, hosted by Adam Smith and Craig Jarrard. #WithYouEveryStep
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