Article by Maria Weidich

Photos by Mackenzie Scheie Photography 

In the summer of 2024, a postcard from Time Out Sports showed up in Tyler Gannett’s mailbox. On the back were four words: “Are you still interested?” For years, Tyler had occasionally, and somewhat playfully, asked owner Cindy Thompson whether she might sell him the Billings shoe store. Now she was asking him. 

When Tyler shared the news with his wife, Kari, she seemed to know exactly where it was headed. “So we’re buying a shoe store, huh?” she joked. 

Today, under Tyler and Kari’s ownership, the longtime store is stepping into a new chapter while holding tight to what Tyler believes has kept it going for more than three decades: knowledgeable people, personal service, and a real desire to help customers find the right fit. In an era when a new pair of running shoes can arrive on your doorstep with a few clicks, that is what still brings people through the door. 

Tyler might be the new owner, but he’s hardly a stranger to Time Out Sports. His first “real” job as a teenager was at the store, back when it was housed at 1010 Grand Avenue. “I’ve just always been a shoe guy,” he says with a laugh.  

When Cindy bought the store from its original owner in 1990, Time Out Sports moved to its current location in West Park Promenade, then an enclosed mall. Tyler was Cindy’s first “and obviously best” employee, he jokes. He stayed for more than a decade, learning the trade, before leaving to build a career in the electrical industry. But the shoe store never entirely left him, he says, and he kept in close touch with Cindy over the years. 

Coming back felt natural, Tyler says. “But I had been away for a long time so there was a lot to learn.” He also knew there was plenty he didn’t want to change. “It’s peculiar when someone buys a long-term business and they make a bunch of changes and move away from the exact things that kept that business going.” While he updated the store’s website, digitized the logo, and modernized some behind-the-scenes operations, much of what makes Time Out Sports familiar has stayed the same. 

That includes the people. Store manager Matt Roberts has been a fixture at Time Out Sports since 1994, working alongside Cindy and Tyler in the early years. “Matt is tremendous,” Tyler says. “His customer service is top notch and he’s genuinely here to help.” 

Finding the Right Fit 

In more than three decades of fitting feet, Matt has watched the shoe industry change dramatically. In the ’90s, he remembers, the market was filled with monochromatic shoes designed for specific purposes: football cleats, tennis shoes, basketball and racquetball shoes. Cross-trainers were just beginning to emerge. 

What hasn’t changed? People wearing shoes that are too small or too narrow. “That has not changed over the years,” Matt says. “Especially in adults; they just don’t know the last time they had their feet measured, then they continue to wear the same size.” 

Some customers are hesitant to go up a size, even if it means a more comfortable fit. Matt is happy to make the case. “Nobody cares, but people are resistant. I can promise you I don’t get paid by the size, I’m just trying to fit you correctly,” he says with a laugh. 

The fitting starts the moment a customer walks in. Matt watches how they walk, what shoes they’re wearing, how those shoes have worn down and, perhaps most importantly, what the next pair needs to do. It’s a puzzle he has spent decades learning to solve, and one he still enjoys. The team is confident that within the first two or three pairs they bring out, one will be a winner. 

At times, Matt believes the internet has given customers a false sense of confidence about fit. “The information is coming from people who don’t know anything about you. And I’m over here holding your foot,” he says. 

“We’re gonna pick out what is best for you,” Tyler adds. “We’ll let you try on whatever you want, but we’re gonna have you pretty dialed in, and that’s something Amazon doesn’t offer. If you want to get it done in five minutes, we’ll get it done in five minutes. If you want to spend an hour, we’ll spend an hour.” They will even talk themselves out of a sale, Tyler says, to make sure a customer leaves with the right shoe. “We’ve got a bunch of shoe geeks in here that just really like to sell shoes.” 

Not Just For Runners 

Despite the rows of running shoes lining the walls, most customers at Time Out Sports aren’t runners. Tyler estimates runners make up only about a third of the store’s business. “The other 65% are just everyday people,” he says. 

That includes walkers, people who spend long hours on their feet at work, and anyone who simply wants a more comfortable shoe. Many arrive on referral from a podiatrist or physical therapist, looking for help with overpronation or underpronation, or searching for the right insole. 

“I think there’s a myth that running shoes are just for running,” Tyler says. “While that’s inherently what they’re designed for, they really are the most comfortable, most technically fit you can get.” 

Tyler is grateful the running community has embraced Time Out Sports as its local shoe store, but he hopes the message reaches further. “We definitely want the rest of Yellowstone County to know us, too.” 

More Than Just Shoes 

After fitting thousands of customers, the work has become about more than matching a foot to a shoe. For people who have struggled with foot pain, the right fit can make everyday movement a little easier, and that isn’t lost on Tyler. “It’s pretty satisfying,” he says. “Especially when they’ve never had anybody help them get fitted in a pair of shoes. You kind of make a new friend in that moment.” 

Often, those new friends come back. “Matt’s been here so long, half the time people will walk in the store and he just heads for the backroom and shows up back on the floor with the shoes they wear,” Tyler says. “It doesn’t feel like a job and it’s very gratifying that Time Out Sports has been a big part of the Billings running and fitness community for decades.” 

Ask Tyler and Matt what makes Time Out Sports what it is, and both arrive at the same answer. “The coolest part of our store is the people,” Tyler says. “The people, the staff, the customers,” Matt agrees. Matt’s son, Braxton, now works alongside him, Tyler, and Kari. “It’s a fun place,” Matt adds. “We take what we do seriously, but it’s not a serious atmosphere.” 

For Tyler, carrying that culture forward starts with appreciation for the people who built it. “More than anything, I feel gratitude,” he says. “We’re trying to keep the experience the same, but the world is also changing so fast. Back in the old days, we didn’t have to fight off the internet, we fought off mail-order catalogs,” he adds with a laugh. 

In a world where you can buy almost anything online, Time Out Sports has lasted because what it really sells can’t be shipped in a box: knowledge, relationships, and people who want to help. “Anyone can buy these products anywhere and the internet can turn everybody into an expert in ten minutes,” Tyler says. “We try to make sure we’re accurate with the information we share and we hope people learn a little bit and have some fun, too.” 

As for what comes next, Tyler hopes the shop keeps doing what it has done for decades: adapting with the times without losing what makes it Time Out Sports. If that keeps the store “cranking” for another 30 or 40 years, he’ll be glad to have played a part. “I just hope we helped to push it forward.”  

Originally printed in the November 2026 issue of Simply Local Magazine

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