Women own and operate more than 100 Chestnut Hill-area businesses. While they focus on financial success -- building brands and developing entrepreneurial skills -- giving back to the community is also a priority.

“It’s a lot. It must be a thing in Chestnut Hill,” said Kate O’Neill, director of operations for the Chestnut Hill Business District. “They all work very well. They’re very cooperative with each other. They talk about things. They meet regularly about things. They support each other. It’s really a good group of women, a good group of retailers.”

The Local interviewed four of the women who’ve made the Hill their business home.

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Debra Jansen opened booked. in September 2021, when coping with COVID-19 was still part of daily life. The experience made building a business that much more interesting, she said.

“Most of the customers that I met were behind the mask, so it was an amazing thing to kind of suddenly see them about a year later, to see their faces,” she said.

Jansen had always had a passion for books, and always knew a bookstore would be a dream come true for her. She had been teaching for 20 years and when the pandemic came along, she figured, “If not now, then when? I was very fortunate to have a fabulous support system in my family and my husband, and decided to take the leap. And it was a big leap.”

After Borders closed at the top of the Hill, Jansen believed the community needed another bookstore. She calls Chestnut Hill a “literary hamlet” because there are now four bookshops in the neighborhood, a development she describes as “fantastic.”

“We are all so very different,” Jansen said. “I feel like we offer the community so many opportunities for reading.

“ I wanted to be in charge because, I guess I wanted to make it feel as important to anyone who walks through that door as it is for me,” she said. “There was never a doubt in my mind that this was going to open and people were going to be happy when they walked through the door.”

Windfall Gallery

Located in Chestnut Hill for 42 years, Windfall Gallery is owned and managed by Cynthia Fillmore. She inherited the business from the previous owner and visionary, Kaye Baluarte, in 2014. For Fillmore, becoming a business owner was an unanticipated shift from her previous career in television production.

“I was on a break,” she said. “I have three girls, and I think I just had my second daughter, and I was kind of contemplating whether I want to go back or not. And one of my editors, his wife, worked at Windfall. He said to me, ‘Cynthia, you would totally love this place, go in, they are looking for a part-time worker.’”

She and Baluarte “hit it off right away and I loved her and the place.” Fillmore worked for Baluarte for seven years prior to her retirement.

“Working for her was kind of like a quasi apprenticeship where I learned how the business was run,” Fillmore said. “We really got into the nitty gritty where I met all the artists she worked with, the sales reps, and we built a relationship.”

Fillmore said she felt there was nothing to change fundamentally about the business once she took over, with the exception of expanding Windfall’s audience reach.

“For me, if it ain’t broke, don’t fix it. I tried to keep it as much the same as possible, but I did try to bring it into the 21st century a little bit,” reaching out to her audience on Instagram, Facebook and TikTok. She also moved the business from 7944 Germantown Ave. to 8419 Germantown Ave.

“I was a production manager in TV. I was kind of like mission control. And it’s kind of like running a small business. You have all of these plates spinning in the air, and you just have to be sure not to drop any of them, because it’s a constant. There’s always something different. It’s not a bad thing. It’s an exciting thing; no two days are ever alike. That’s kind of what I love about it,” Fillmore said about running her business.

Between Friends Boutique

The store, owned by mother-daughter team Claudia Averette and Atiya Smith, started as a pop-up shop. After hearing from customers, they looked for a permanent location and found one at 7833 Germantown Ave.

“As mother and daughter, we were already girlfriends,” Averette said. “We had already spent a lot of time together, but now ... we talk business quite a bit. The relationship as mother and daughter has grown tremendously out of respect. We learn to listen more to each other, because we believe that everybody brings something valuable to the table.”

A passion for business runs in the family, as Averette’s father operated a few different markets. But the mother and daughter have always had a passion for clothing and dressing women.

“We always say shopping is better when done with a girlfriend, either that you come in with, or that you leave with,” she said.

Threadwell

Molly Ellis has owned and operated Threadwell in Chestnut Hill for 15 years. Ellis’ background is in marketing and merchandising, and after leaving New York and coming to Philadelphia, she decided to pursue entrepreneurship.

Threadwell is an in-house embroidery production business. Everything purchased from the store includes a monogram.

“We design it based on what is going on the item,” Ellis said. “If it’s a name or a word or initials or a monogram, everything is custom.

“I have more control over my time, and I can use my time the way that it fits for my life,” she added. “It is difficult; it’s a hard way to make a living. But it is very rewarding, and it’s a cool environment, and we’re very creative here, and it’s just nice to be creative all the time.”