David and Molly Jackson

Sarasota, Florida

Molly's - A Chic & Unique Boutique
Fleet Feet Sarasota
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David and Molly Jackson, Owners of Molly’s - A Chic & Unique Boutique, as well as two New Balance stores and a Fleet Feet store, first met while attending college at Western Carolina University. After college, Molly spent several years in a retail banking program with First Union Bank, now Wells Fargo. They lived in North Carolina and Atlanta, GA, before an employment opportunity for David brought them to Sarasota. That opportunity – a sales representative position with New Balance – opened the doors and laid the foundation for an entrepreneurial journey spanning three decades.

“While working at the bank, David and I owned and operated a small gift store and started doing some real estate investing,” Molly said. “However, David’s involvement with New Balance is definitely where this whole retail journey started.”

Molly continued, “As an independent sales rep, David worked with other owners and saw stores opening across the country. We both kept looking at the possibility of owning our own store and came to the conclusion that it was too good to pass up. In February 2002, we found out we were awarded our own location. The arrangement is a licensing agreement that gives us the exclusive rights to market and sell the New Balance brand.”

In 2006, Molly went back to corporate America to help diversify their income sources. She accepted a Sale Consulting position with Vera Bradley and spent three years in this role, covering a territory from Bradenton to Marco Island.

Just as the economy took a nosedive, Molly and David opened their second New Balance store in May 2008. They were grateful that Molly had a steady and thriving position However, In 2009, with an unexpected surprise on the way, she was inspired, once again, to drive her own ship.

“We had a bonus baby at 40,” Molly said with a laugh. “After that, I got the inspiration bug to go into a different direction to be able to be home more often with our four children. That’s when we decided to open the first Molly’s. From my experience with Vera Bradley, I saw an opportunity to offer a unique store in our community. As a consultant, I worked with many boutique owners. I’d help them manage their businesses and got to see what worked and what didn’t.”

Molly continued, “When we launched Molly’s, our focus was initially on shoes. However, after a few weeks of being open, it felt kind of boring. I wasn’t that inspired by our merchandising assortment, so I decided to do something about it. I grabbed many friends of different ages and family dynamics and went to the Atlanta Gift Market. I gave them all a budget and a brand category to buy with and let them loose. When we reconvened and they showed me what they purchased for the boutique, suddenly we had this amazingly diverse and eclectic offering of gifts and unique items to sell at Molly’s. From that point on, the business was much more than just a shoe store and has even earned us several awards for being Sarasota’s best gift store.”

A year after Molly and David opened Molly’s Boutique, they opened their fourth retail store – Fleet Feet Sarasota. They’d seen the model years before but didn’t act on it at the time.

“We were hearing positive feedback in the athletic specialty retail industry about Fleet Feet franchises and how they were adding new ones quickly,” Molly said. “We got the prospectus and sat on it for a while. When someone else opened the Sarasota store, we were pretty bummed. However, after a few years, we were fortunate enough to be in a position to buy it.”

A little over a year ago, Molly and David added their fifth retail store and second Molly’s. Attached to their Fleet Feet store was an open space they used for training programs, yoga and various community events. According to Molly, using that space for a second Molly’s made a lot of sense.

“We wanted to maximize the use of that real estate,” she said. “Also, we had plenty of inventory on hand from operating the original Molly’s and we knew the building generated traffic. We painted it and made it a great little boutique in downtown Sarasota.”

Over the years, Molly and David have worked through a handful of challenges including staffing and managing a business during a recession and a pandemic. Between their five stores, they employ 45 people and have become well-known in the Sarasota community. They’ve done business with over 300 vendors and continue to use cross marketing strategies to grow their impressive stable of retail stores. Last year, they were named Retailer of the Year by the National Shoe Retailers Association, an organization comprised of 3,000 independent shoe store owners across the United States.

Looking ahead, Molly shared their future goals and how the quarantine measures associated with COVID-19 have caused them to look closely at where and how they want to do business.

“Through the New Balance family, there have been opportunities to open or acquire additional stores throughout the years, However, with our experience with COVID-19, we realize that what we have is really good. We like doing business in our community and can’t imagine having to deal with stores in different states and not being able to see our team members. If and when we grow, it will be locally focused. I also think we’ll always have a traditional brick and mortar, but connecting with people in unique ways is where we’ll invest financially.”

What advice does Molly have for aspiring entrepreneurs? “Build an army around you,” she said. “Build a team that has the same vision and passion and then seek out advice from that army of people and advisors. We’ve been blessed with the partnerships we’ve had and gained over the years, such as with the members of the National Shoe Retailers Association. Networking with those other business owners and being a part of that organization’s leadership team, as the first female to serve on the executive board, has contributed to some of our success. Also, hire professionals for things like lease negotiations. Ten days after opening our first New Balance store, the AC went out. It wasn’t covered under our lease and we ended up having to spend $8,000 on a new unit. Don’t let that happen to you.”


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