“I realized I don’t have to be afraid. I have to say what’s on my mind and what I feel.”

Lessons in success from Stephen Applebaum, president and CEO of Sherson Group

After the death of his business partner and mentor, Stephen Applebaum dug in his heels to become president and CEO of Toronto-based Sherson Group. As one of Canada’s leading footwear and accessories distributors, the company’s impressive portfolio features Nine West, Bandolino, Enzo Angiolini, Rachel Roy, AK Anne Klein, Easy Spirit, Nine and Co., and Mootsies Tootsies. In 1999, Applebaum took another bold step into the retail market and purchased five Nine West stores. Today the Sherson Group oversees 43 retail locations—31 Nine Wests, 9 outlets, and 3 Madison multibrands—and a staff of almost 500 associates. Applebaum recently talked to Advantage about forging his path in the footwear industry.

Advantage: How did you get your start in footwear?

Stephen Applebaum: My mother loved shoes, and since I was the youngest, she was always dragging me to shoe stores. When I was 16, I needed a part-time job, and she knew the manager of a local Town Shoes store—and I was hired. I discovered I had a real talent for selling and seemed to be drawn to the concept of success in sales. After high school, I attended the Schulich School of Business and graduated in 1981. Harvey Routbard, who was the president of Town Shoes, suggested I join their management-training program.

What was it like going back to the company?

I was happy to get the job because I grew up there. I became an assistant buyer, worked temporarily in stores, experienced New York shoe shows, went to Europe with [the company], and through that I met my mentor and friend, Harry Sherman. He taught me the wholesale side of the business. Three years later, I left Town Shoes and went to work with Harry.

How did you become president and CEO of Sherson?

In 1984, Harry and I started a company called Sherson Marketing. We developed and grew the business for three years, and our sales went from $1 million to $18 million. I was in charge of sales management, and Harry was in charge of sourcing and production. In 1990, he passed away. I was a young guy, 33, left with this business of which I owned a minority share, and his estate owned the balance. Fortunately, I had relationships with our suppliers and told them it was going to continue. The industry up here was skeptical—Harry was such a presence in the shoe business. As it turned out, I found a way to buy the rest of the company from his estate, and I was determined more than anything to make it happen, and I did.

Can you describe your day-to-day overseeing Sherson Group?

I’m a hands-on owner and president. I involve myself in all aspects. I attend all of the trade shows in Canada and the United States. I’m involved in the buying end, the wholesale, and the retail.

How did Sherson Group transition into the retail market? 

Nine West chose Sherson to be the distributor of Nine West, Easy Spirit, Calico, and Enzo Angiolini, and then our relationship grew even stronger. Nine West had retail stores all over Canada and all over the world. They wanted to license the retail stores, and came to me in 1998 and asked me if I would be interested. I looked at the list of stores they had, and I was able to convince them that what they had were five or six good ones. We took over those, and since then we’re up to 43. That was my foray into retail, and at the same time we were able to manage our wholesale.

Do you have a business philosophy that guides your decisions?

I do. It’s two words: honesty and integrity. Every decision I make is honest, and for every decision I make, there’s integrity in it.

What do you think planted the seed for this business philosophy?

There was a time in my early years—I was working with one of Canada’s major department stores, and the buyer with one of the brands we had gave me an order that was huge. I was extremely uncomfortable because I felt she had bought too much; it did not sit right with me. I phoned her and told her, “I think you bought too much; you better buy less. As much as I appreciate it, it’s a new thing.” She said, “I can’t believe you’re telling me this—no one’s ever done that before.” She was so appreciative that I was honest and straightforward, and from that day on, I realized I don’t have to be afraid. I have to say what’s on my mind and what I feel. And for the record, I’m still very good friends with that buyer. That was a defining moment for me. I’m not a hit-and-run guy. There’s always the next season.