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Oak Street Bootmakers – Reinventing the Family Trade

By June 23, 2014July 12th, 2023Succession Planning2 min read

Years after working in his father’s shoe repair shop, George Vlagos has returned to his roots and is carrying on the family business with his own shoe-making business, Oak Street Bootmakers.

John Vlagos, George’s father, has owned and operated a shoe repair shop in Chicago for over 30 years. Growing up, George would spend Saturdays at the shop polishing piles of shoes while watching his father carefully repair leather soles as though they were his own.

Although George went to college and taught high school English for several years, he had fond memories of working at his father’s business and never lost his appreciation for a well-made shoe.

“One day I was out shopping for a very specific type of boot,” said George. “I wanted a simple, well-made brown leather boot, and couldn’t find it anywhere. So instead, I made the shoes myself, using the skills I learned at my father’s shop. And almost immediately I realized that others would want this too.”

George launched Oak Street Bootmakers in August 2010. The business boasts its old-fashioned standards for American-made boots with 100% genuine Horween leather and Goodyear welted construction. A fashion blogger wrote about the boots the day of the launch and the business spread like wildfire. Musicians such as the Avett Brothers, Justin Townes Earle and Usher have all sung the company’s praises. And no one could be more proud of George’s success than his father.

“I’m very proud,” said John. “In the beginning he sold maybe one to two pairs of shoes a day, and now I see the trucks come and pick up shipments for Japan and international places. These are nice, high quality, American-made shoes.”

At ReGENERATION Partners, we’ve seen that when family-owned businesses begin succession planning, it can often lead to pressuring younger generations to take over. This is one of the reasons only a third of family businesses survive into the second generation. John Vlagos understood that he could give his son the tools to continue the family trade, but he had to allow George to discover the passion on his own.

Succession doesn’t necessarily have to exist within the same company. Although George didn’t take over the shoe repair shop, he was inspired by the work of his father to reinvent the family trade with his own store.

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