Hailey Coleman


Hailey Coleman, 23
CEO, Damn Heels

When people were lining up for confidence, Coleman came back for seconds. The Great Recession was in full swing when she was studying commerce at Ryerson University, so she created her own job. Recalling how she hobbled home barefoot from a London salsa club during a European vacation, she saw an opportunity in saving women from stiletto sunsets. In 2009, the two-time world’s bronze medalist in synchronized skating launched Toronto-based Damn Heels. Today, her company’s stylish folding ballerina flats, which come tucked away in small expandable bags, are sold through more than 40 retailers internationally. Dr. Scholl’s entered the market with its Fast Flats line last summer, but Coleman insists, “Competition is a good thing. It validates the product and grows the market. We now have people saying they have seen our commercials when they’ve actually seen Dr. Scholl’s advertising. That’s fabulous.” In 2010, Coleman won two business plan competitions, netting $32,000. She also struck a deal on Dragons’ Den last year, but then turned it down when she grew uncomfortable with losing control over marketing.

Coleman, who once wanted to be a hairdresser, caught the entrepreneurial bug while working in a family-run salon. Now she wants an empire, aiming to expand the “Damn” brand beyond footwear to other products and even services. Recently, she got some fresh inspiration when her firm sponsored a Virgin Unite event in Montreal, and she met Richard Branson. “It was amazing, completely surreal,” she gushes. “If I have a business hero, it’s him.” Like Branson, she believes in play, not just work. “If it is not fun, why bother?” she says. “That’s my management philosophy.”

On failing: “You never really fail as an entrepreneur because you are always learning.”


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