Owner Tammy Behm stands amidst crates overflowing with verdant foliage within the greenhouse. (Sritha Rathikindi)

803 Marshall Ave, Webster Groves, MO 63119

Inside Maypop resides a realm of enchantment, where the heady aroma of plants blend seamlessly with the comforting smell of coffee. Beyond a café and plant shop, Maypop is a sanctuary for connection.

Owner Tammy Behm’s journey to Maypop was not a straight path. It was a collection of moments, conversations and inspirations that led her to realize her dream.

“Career-wise, I hit a point, a ceiling. There wasn’t anything else that could happen. But I knew I had something to contribute [to] the world,” Behm said. “In my previous industry [at the Botanical Gardens], I had the privilege of sitting in [on] committees and conversations. I started making a pinboard in my brain of good ideas—things that stuck with me.”

Behm used these ideas to fuel her business, but breaking into the business world was challenging, especially as a woman.

“Men assume I care [for] the plants, that my husband takes care of the business,” Behm said. “My husband is brilliant. He’s a chemist, an educator and an amazing supporter of our family, but business isn’t his thing. It’s a continuing hurdle; people still make that assumption.”

However, Behm persevered because she wanted to defy stereotypes and pave the way for others like her. She made it her mission to uplift women in her community, collaborating with local woman-owned businesses and prioritizing women’s voices in decision-making.

“Men have been coaching each other [to] succeed and raising each other for millennia. But a lot of times, women were left out of that,” Behm said. “Any chance [Maypop] gets, we want to help raise women’s voice, exposure, experience and success in our community. Our marketing firms and marketplace are all women-owned and women-led.”

Behm’s efforts did not go unnoticed. As she immersed herself in the vibrant network of women entrepreneurs in St. Louis, she witnessed firsthand the power of solidarity and support.

“Women in St. Louis are one of the greatest strengths in this city,” Behm said. “I [researched] the number of startup entrepreneurs in St. Louis, and we are almost double the national average. 45.2% of startups in St. Louis are women compared to 24.5% of the national average. There are a lot of women’s business support groups out there. If you don’t have the answer to a question, some other woman entrepreneur has faced the same challenge and is happy to help you.”

Amidst the triumphs, moments of connection truly define Maypop.

“You can buy [coffee, tea, snacks, flowers] anywhere, so we like to think we’re selling connections and experience,” Behm said. “Have you ever eaten a strawberry that’s just come off the plant? It makes you smile because that creates an experience. We want to give people experiences. That is what we sell: the beginning of a dialogue and communication.”

Owner Alyson Garland stands outside her store, Dot Dot Dash, showcasing her clothing collection. Photo courtesy of Dot Dot Dash.

736 DeMun Ave, Clayton, MO 63105

In the heart of Clayton, Dot Dot Dash is a boutique that has transformed from a haven for stylish toddlers into a thriving hub for fashion-forward mothers. As the boutique prepares to move to a new location, its innovation and community collaboration shine brighter than ever.

Dot Dot Dash started as a venture born out of owner Alyson Garland’s desire to merge her passion for fashion with her role as a parent.

“I used to be a stay-at-home mom with two children. But I was missing that side of me that was intellectually challenged by my retail career in the shoe business,” Garland said. “I wanted to start a business that was fashion-based but more directed towards kids [to] tie into the phase of life I was in.”

Garland sought to create a line of comfortable and stylish clothing for toddlers that incorporated language learning. This idea blossomed into a collection of soft, casual garments adorned with French, Spanish or German phrases, stimulating young minds while keeping them cozy.

“Over time, the feedback I kept getting was, ‘The baby clothes are so cute and comfortable. Can you find stuff for the moms?’ So I came up with a mix-and-match clothing situation for the moms. It consisted of some comfy drawstring yoga pants with different-colored tank tops and wraps. I brought it all into that first store in DeMun,” Garland said.

However, as the business evolved, the real market lay in catering to mothers’ needs, who sought both practicality and fashion.

“It was funny because I had this big section filled with baby clothes, and the rest of it had the mom mix-and-match [pieces],” Garland said. “After a while, women would come in and pretend they wanted to shop for their kids because they felt guilty—but then they would go right to the women’s section. As much as I enjoyed designing all the baby clothes, I realized the real business was with the mom clothes.”

As Dot Dot Dash prepares to relocate to a new location adjacent to other local woman-owned businesses, Garland embraces the opportunity for collaboration and collective marketing efforts.

“We are moving to 7355 Forsyth in August. It’s going to be so pretty and right next to Crazy Bowls, Wraps and Colleen’s Cookies,” Garland said. “I’m excited to move to this new part of town because Colleen has a great influence there. On a larger scale, we can get together and [leverage] marketing with other woman-owned brands or businesses [to] bring all of us up.”

Owner Colleen Thompson stands inside her bakery. ​“Our business is unique because we specialize in custom-decorated cookies. We can create whatever you want,” Thompson said. “We have all of our bakery, but we also have breakfast and lunch and a full coffee bar, so we have a lot of different elements going on at the same time.” (Sritha Rathikindi)

7337 Forsyth Blvd, Clayton, MO 63105

In Colleen Thompson’s youth, the kitchen served as the bustling heart of her family’s home. Amidst the aroma of simmering sauces and the music of clinking utensils within its walls, Thompson, now the owner of Colleen’s Cookies, nurtured her love for cooking.

“My grandmother did sweets, [and] my mother’s mother did bread, so we were always in the kitchen,” Thompson said. “[Cooking] was embedded in me, [and] to me, that was love. That’s how it all started.”

Encouraged by friends and family who marveled at her culinary creations, Thompson explored the possibility of turning her hobby into a business. During a charity event, she volunteered to bake and decorate cookies, which planted the seeds of her future bakery.

“I decorated cookies, 250 of them. People liked them, [and] the business started to grow so much we had to put in a production kitchen,” Thompson said. “We went into retail and added the bakery [and] coffee bar. [Then,] I started my website in 2000, and we came to this location in 2010.”

However, Thompson encountered skepticism and doubt from some quarters and faced subtle biases and stereotypes. Yet, she refused to be deterred, drawing strength from her conviction and the unwavering support of her community.

“When you first start a business, it’s the unknown [that is challenging]. You don’t know how well you will be received, and the clientele is always different. As a woman, it’s more challenging because we’re perceived differently,” Thompson said. “You have to be calm and strong. If you make mistakes, you have to just roll out of it. If you’re not calm, you become emotional or rational, [which] can be perceived as weak. You have to stand your ground [in public and] be emotional in the back where no one sees you.”

As word of Colleen’s Cookies spread, so did her influence within the community, especially during the COVID-19 pandemic. 

“When COVID hit, we were the only place [around here] to stay open. I talked to my managers, and they said, ‘Let’s carry [it] out.’ Everyone around here was closed except for us. We got a lot of growth from that time [and] became a part of the community from a tragedy,” Thompson said.

She became a role model for aspiring entrepreneurs, particularly women, who look to her as a beacon of inspiration and empowerment. With her fellow business owners, Thompson hopes to foster a more significant presence of woman-owned businesses in Clayton, paving the way for a more inclusive and diverse entrepreneurial landscape. Throughout struggle and numerous moments of accomplishment, Thompson shares a moment that stands out. 

“As silly as this sounds, [I feel] accomplishment every single day. When I walk in the front door and see the shop, and when I get to work with so many amazing people, it makes me proud,” Thompson said. “I had a customer last week say, ‘Thank you [for bringing] our community together.’ And that’s what I hope to do. Community involvement was and is a goal of mine. We have lots of regulars, and [when] I get to know them, I love it.”

Inside Cakewish, visitors encounter an array of pastel frilly attire. (Sritha Rathikindi)

9218 Clayton Rd, St. Louis, MO 63124

For Brooke Ray, co-owner of Cakewish, starting a new business marked the beginning of a challenging journey, especially when it involved convincing national brands to partner without prior sales data.

“We had to show these companies our vision and sell it to them [so that they would] trust us with their brands,” Ray said. “We went to New York and Los Angeles to meet with brands in person and build relationships from the ground up.”

After effectively presenting their business concept to prospective partners, Cakewish emerged—a refined boutique inspired by Ray’s personal encounters specializing in apparel and gifts tailored for tweens and teens.

“[Tween and teen fashion] is an underserved market. When my oldest daughter was going to her first dance in sixth grade, I looked everywhere for a dress and came up empty-handed,” Ray said. “I took my girls on a trip to Chicago, and we had the best experience shopping in person at a tween-centric store. It gave the girls autonomy to pick their clothes, plus everything they bought they wore because they had a hand in choosing each item. I thought, ‘Why not bring this concept to St. Louis?’”

Collaboration, particularly with neighboring woman-owned businesses, is central to Cakewish’s ethos. By partnering with Clayton and St. Louis mothers through Cheree Berry Paper and Amie Corley Interiors, Cakewish champions local excellence while amplifying its reach.

“We love to collaborate with other local woman-owned businesses—it’s important to us and mutually beneficial. We cross-promote one another [and are] able to reach a wider audience that way,” Ray said. “Supporting local businesses and collaborating is one of our favorite aspects of the business. By working together, we can grow market reach and learn from one another.”

Beyond commerce, Cakewish has given back to the community.

“[We] donate $10,000 back to local teen and tween-focused organizations around St. Louis. That’s important to me,” Ray said. “We want to give back to our community because it’s through the support of everybody that we’re successful. Also, [a] lot of our staff is from Clayton, [and] we have several models from Clayton schools.”

Moreover, Cakewish is committed to nurturing the next generation of female entrepreneurs through programs like the Cakewish Crew.

“[Our] program, the Cakewish Crew, caters to [middle and high school girls] and helps them learn more about the business industry,” Ray said. “Sometimes it’s modeling, marketing [or] branding; we work with them to give them a little industry experience. Women especially don’t get that opportunity—they go to college and haven’t had exposure to different careers.”

Reflecting on her journey, Ray shares her biggest takeaway: resilience amidst rejection.

“If someone you want to work with or collaborate with tells you ‘no,’ that just means you need to change your approach,” Ray said. “You can turn any “no” into a “yes”—just think of it as a challenge and keep working towards your goal.”

Owner Katy Morris stands beside her shop. Clad in a colorful top that mirrors the lively atmosphere of her establishment, Morris embodies the spirit of How Sweet Is This. (Sritha Rathikindi)

804 De Mun Ave, Clayton, MO 63105

As children skip along the sidewalk, their noses press against the glass of a candy shop, tracing the colorful rows of candies displayed inside. Katy Morris’ candy shop, How Sweet Is This, pulsates with life, just down the street from Captain Elementary School in a bustling neighborhood.

“When I found the shop, it was [the] right place and time. I had been in my previous career, mortgages, for over 15 years. I was burned out and needed to do something different. I didn’t have that work-life balance and it was wearing on me, so I quit,” Morris said. 

As fate would have it, through her former boss, the candy shop found her a few weeks later. 

“One look inside the shop, and I knew that’s where I belonged. All the stars aligned. Even the color of the walls [was] perfect. I [had] painted [the] rooms of my house the [same] colors of the walls. It was all so perfect,” Morris said.

Wanting to provide candy for everyone, Morris has a wide selection of sweets from which to choose. 

“We’ve got different chocolate-covered items, individually wrapped candies and gummy sours. We also have a selection of vegan candies, kosher candies and all-natural stuff. We also have drinks and shaved ice in the summer,” Morris said.

Working in different versions of customer service her whole life, Morris’ passion stems from her love for people. 

“My favorite part of the candy shop [is] being able to brighten people’s day. Community involvement is our bread and butter because this is such a tight neighborhood,” Morris said. “We try to hire from local neighborhood kids to keep that community feel. This candy shop is such a big part of this neighborhood.”

Visiting Morris’ shop has been a common activity among children in Clayton, where they often purchase sweets. Records indicate a consistent flow of young customers using their own money for these treats, underscoring the shop’s role in the community’s traditions.

“We have teachers that bring their class down from Captain Elementry to do math projects. The kids have to use math to figure [out] what they can buy with their money,” Morris said. “It can be scary for kids to talk to adults. I see kids come in [for the first time] very timid and nervous and by the end of summer, I can’t get rid of them.”

While most people go to the candy shop for a sweet treat, some kids find themselves strolling in through the bright pink doors for more.

“The shop isn’t just a place for people to come in and get their candy. They socialize as well,” Morris said. “I have kids that come in the summer because they’re stressed. We have a mini therapy session, sit together and talk it through.”

Morris’ strong relationships with younger customers carry on through their high school years.

“I love watching kids I’ve seen as babies grow up and become more confident in the shop. I love it so much to the point where when [kids] grow up and graduate from high school, I’m literally in tears,” Morris said.

STL Today, Feast Magazine, Sauce Magazine and Riverfront Times have recognized Morris’s passion locally.

“My favorite feature was when Food Network magazine named us one of the top 50 candy shops in the US. They picked out their favorite candy shop from each state, and they picked us,” Morris said.

Being in the candy business for over 11 years, Morris has words of advice for aspiring business owners. 

“Find what you love—what makes you happy—and find a way to make money doing it. Life is too short to be miserable, so find your joy,” Morris said. “There’s always going to be people that question you, that doubt you, but you can’t listen to that.”