Trailheads

Amy Becker, owner of Becker’s Best Shoes in Mount Dora, FL, has over 30 years of experience in retail, as well as a decade of experience teaching special needs children.

During Switchback Spring 2025 in Nashville, TN, Trailheads talked with Becker, who detailed how her teaching career impacted her retail business.

As a former athlete, Becker was greatly affected by seeing the day-to-day struggles of kids dealing with physical challenges, learning disabilities, and difficult social situations. Becker says the film “When the Chips are Down” made her realize that people don’t face equal circumstances in their lives. While the kid with two parents and a happy home arrives at school with a full belly and many other advantages—represented by a bowl full of poker chips—the disadvantaged student arrives hungry and humiliated from being teased on the bus.

“By the time he gets to school, his bowl of chips is already empty, and his day is shattered,” says Becker.

The film inspired her to challenge students to compete against themselves and strive for their personal best rather than trying to outdo their classmates. She would track the improvement of kids over the year and hand out Becker’s Best Awards.

As she established her shoe store in 2015, she considered how retail customers have diverse abilities and goals, just like children. “They don’t all come in with the same mindset. You really have to listen to them and try to be available,” she says, explaining that she wants to help each customer achieve their personal goals.

And that’s why she named the shop Becker’s Best Shoes.

Keeping Customers Comfortable

Located approximately 30 miles northwest of Orlando, Mount Dora is situated in a tranquil part of Florida. However, Becker’s attracts people from cities as far away as Gainesville and Jacksonville, and the shop’s customer database includes more than 40,000 individuals. According to Becker, her nearest true competitor is 45 minutes away, so her store attracts a diverse range of people, from athletes to casual consumers.

Her product mix includes several of the companies typically found in outdoor specialty stores and running specialty shops, such as On, Birkenstock, Keen, and Teva. While the store attracts numerous active enthusiasts, it primarily caters to casual consumers and offers a wide range of brands that prioritize comfort.

Becker says it’s essential that the store offer an easygoing environment because many of her customers shy away from hardcore athletic stores, which can be intimidating.

“We call some of our customers’ pineapple customers’ because buying shoes can be stressful, and they come in a little rigid and prickly,” she says. “But I know there’s a sweet spot in there. So, we try to find the sweet spot by simply talking and making them feel comfortable. We have couches in our store, and it’s very welcoming.”

Becker says that the key to retail success is paying close attention to customers and being aware of their needs. “Honing in on what the customer needs is just kind of natural to me,” she says. While she developed that skill as a teacher, she also employed it when she co-owned a business selling swimwear to professional athletes. She noticed that most competitive swimmers arrived at meets wearing pajama pants. So, she created a line of custom-made swim pants, which helped triple their sales. At one point, the business was one of the top five swimwear dealers in the country.

Facing Challenges

As a shoe retailer, Becker is also enjoying success. When she established Becker’s Best Shoes in 2015, she replaced a retail shoe store that had been open since 1999. In her first year, she tripled the sales of the previous business, and her sales are now 10 times higher than those of the store she replaced. “We had a little hiccup during COVID, but we moved to a bigger space and doubled our sales the next year,” she says, noting that her shop is now 3,400 square feet.

While the store is thriving, Becker says retailers face growing challenges these days. One reason she attended Switchback Spring was to speak directly with brand leaders and express her concerns about MAP (Minimum Advertised Price) pricing. During an educational session on the first day, she and other dealers pointed out that many companies are going “off-MAP,” discounting products at different times, which prevents stores from having a single large storewide sale at a particular time. As a result, customers perceive that the store is constantly offering discounts on its merchandise.

“I can’t keep up with everyone’s MAP and off-MAP,” says Becker.

In addition, retailers face shrinking margins, says Becker. She shared an experience where one brand she carries switched rep groups, and within 30 days, the company raised the wholesale cost of a particular shoe by $4, which reduced her margin. Compounding the financial strain, she and many other retailers are paying more for rent and wages while also facing the prospect of higher wholesale prices due to tariffs. At Switchback Spring, Becker could express these concerns to company leaders and bypass reps who don’t always pass along a retailer’s frustrations.

Becker has also faced roadblocks while trying to acquire certain brands. “I’ve always had to deal with brands saying, well, you can’t carry our brand because you’re not a running store,” she says, adding that some companies won’t take on a shop that caters to casual customers. She says conferences like Switchback provide good opportunities to meet with companies and address their objections.

For Becker, a highlight of Switchback Spring was a presentation by Kelly Davis of the

“It was so good to hear her say what I’ve been saying for years,” says Becker.

Sowing Seeds of Happiness

Despite all of the challenges she faces, Becker remains optimistic about her business and focuses on bringing positivity to people’s lives, just as she did while teaching kids with special needs.

On the store’s checkout counter sit Seeds of Happiness, small clay figures of smiling faces with attached cards that encourage people to either keep the figure or pass it on to someone else who deserves encouragement.

“If I get moved by a customer or they tell me something that I think is quite interesting, I just say, ‘You need a seed of happiness,’ and I’ll just give them one,” says Becker. “We sell them, but sometimes I’ll just put it on the counter and say, I really think this is for you.”

Whether she’s handing out Seeds of Happiness or steering someone toward the appropriate shoes, Becker’s goal is the same—help people be the best version of themselves.