Interview with Town Shoes founder Leonard Simpson

Author: Yvonne Palkowski
via: UofT


The man behind this Canadian Retail Success Story

Success comes by putting one stylish foot in front of the other

Leonard Simpson is an insightful business man with his heart in the right place. And like many retail mavericks, he’s got allot to say about what it took to get here and more importantly, what it takes to remain at the top.

Enjoy this interview.

How did you turn Town Shoes into the largest footwear retailer in Canada?

My father was in the wholesale shoe business, he owned three stores. He wanted me to go into his business after I graduated but I didn’t want to, so he asked me to at least look at the stores and make suggestions. I advised him to get out of those stores because they were losing so much money and they were terribly run. Then he asked me to sell the stores, which I did. I sold two stores in a week. I was only 22 years old.

As for the third store, I was running it while looking for a buyer when my good friend Avie Bennett (1950 UC) said his parents were opening a shopping centre. I asked him what a shopping centre was—this is 1952. He said it was a strip mall called Sunnybrook Plaza, with 14 stores and a small parking lot. I thought it was a very, very good idea. You have to understand, it was the very first concept of that nature in the entire country. I went to my dad and asked to use the proceeds from the sale of the third store to open a retail store at Sunnybrook Plaza, at the northeast corner of Eglinton and Bayview in Toronto. It turned out to be reasonably successful.

Then Avie said they were opening up another shopping centre, a bigger one at Lawrence and Bathurst called Lawrence Plaza. To make a long story short, I sold the first store to finance the opening of the second store, which turned out to be a bonanza. I did a huge amount of business, and the cash flow from that was the beginning of the rest of the stores. I never borrowed a nickel after that from anybody (except for the usual financing from the bank to turn over inventory). That’s how it started.

Author: Yvonne Palkowski


An interesting person.


Town Shoes is the largest footwear retailer in Canada


No half-stepping.


We love working with Canadian Success stories like Town Shoes. Who knows? Maybe something will rub off on us. : )