Kenneth Cole reveals to Jay Shetty how he rose to the top of the fashion industry with nothing but good shoes and the right questions.

Kenneth Cole’s success in life and business has catapulted him to the top of the fashion industry. His 35-year-old brand is a household name and a staple in the world of luxury clothing and accessories.

While some in his position would be content to sit on their laurels and reap the benefits of decades of hard work, Cole is not. He has committed to use his success for more than just personal gain.

Jay Shetty recently interviewed this remarkable role model on his podcast, On Purpose with Jay Shetty. Here are his takeaways on Cole’s unique perspective on work, life, and community.

Thriving at Work, at Home, and in the Community

Kenneth Cole has a commitment to thrive in more than just one area of his life. His steadfast dedication to his work, his family, and his community is an example for the world to follow.

“I think that being successful in anything that we set out to do is all consuming and it requires making significant life compromises, which is not easy for anybody in and of itself,” Cole shared with Jay Shetty. So how does he stay committed and engaged in the most important three areas of his life?

Cole purposefully intertwined them. He looked for ways to bring elements of each area of his life together to create personal, professional, and social engagement at every intersection. It worked.

From Law to Luxury Fashion

As a young adult, Kenneth Cole studied law. He didn’t love it, but he wanted the larger opportunities it could eventually bring him. He’s always been a rebel at heart though, like Jay Shetty, and his focus shifted to fashion design after working in his father’s shoe factory one summer.

The shoe business at the time was fascinating to me,” Cole said. “There were essentially no boundaries. You'd take this shoe, this object, and you can transform it in so many different ways. Sometimes even the most subtle ways make the greatest change and impact.”

Cole wasn’t only interested in making shoes. When he created his own brand, he didn’t become a typical business owner looking for profit. Instead, he shaped his company around a mission of helping others and making the most impact he can.

Success is Born Out of Passion and Necessity

Kenneth Cole has always gravitated towards creativity and design. It was no surprise then when he followed his father’s footsteps into the shoe making business. He shared how he went from law school to high fashion shoe design with Jay Shetty.

“I worked with my father one summer and I kept navigating to the pattern room and design room,” explained Cole to Jay Shetty. “I was fascinated because that's where it all happened. And if the product was distinctive, business would reflect it.”

A few years later, Cole took a leap and branched out to create his own brand. A new business with no money seemed like an unlucky combination. Cole proved solutions are available for those willing to ask the right questions, not just the conventional ones.

Like Jay Shetty, Cole went searching for success outside his home area. He went overseas searching for success and found himself working in Italian shoe factories to bring his dreams to reality. It was the change in trajectory he needed.

As his design skills strengthened, so did his creativity and willingness to take risks. Creating and designing allowed him to come up with his own rules, and it paid off.

“You write your rules and in fashion and design specifically, the further those rules are from anything written before you, the more likely it is you'll be successful,” Cole said.This resonated with Jay Shetty, who didn’t take a traditional path in his life either. Shetty had to follow his own path, just like Cole did. It paid off for both of them.

Problem Solve Outside the Box

After setting up business in Italy, Kenneth Cole was ready to take on the American market. He shared with Jay Shetty that he knew he was going to need the American market if his business was going to survive long-term.

Breaking into the American market presented its own set of unique challenges. How could he get noticed in such a crowded market? The New York Shoe Show was his big chance, but he had to stand out among thousands of designers. Renting a booth among the other designers was not going to cut it.

He quickly phoned a friend and asked if he could borrow his 40-foot trailer. Then he called the mayor’s office and asked how he could park the trailer on the street outside the hotel where the shoe show was held. They told him the only permits granted for streetside parking were for utility crews and feature films.

Like Jay Shetty, Cole liked the idea of film better. In an instant, ye became a movie producer and applied for a permit to film, “The Birth of a Shoe.” Cole parked the trailer outside the doors of the largest shoe show in America and invited every important buyer who walked by to be a part of it.

This grabbed the attention of buyers and put him a step ahead of the 1,000+ other companies inside. Two days later, he had sold 40,000 pairs of shoes and was on his way to fame.

“Resourcefulness and problem solving are so important. The best solution is rarely the most expensive one,” he explained, “It's almost always the most creative.”

Get Involved in Something Bigger

With his newfound success, it would have been easy for Cole to focus on growing his brand and his bank account. Then events around the world began to catch his eye. Cole found himself asking the hard questions, and he encouraged Jay Shetty’s listeners to do the same by asking:How do we make an impact in the world?

How do we make a meaningful impact on people's lives?

How do we make what we do worthwhile and purposeful?One issue that plagued him was the HIV/AIDS epidemic. It bothered him that no one was talking about its effects, so he stepped up to the plate. He didn’t let being a small company with a very limited budget stop him.

Instead, he did what he always does - he got creative. Cole rallied his people and did a photo shoot campaign. The funds raised went to research and education for HIV/AIDS. It was a catalyst in his life and in his work.

“It changed me,” he said, “It changed the man and changed the brand and the company in a very profound way. I had to admit that until then what I was doing was fulfilling but it wasn't meaningful.”

Put the Brand Behind the Mission

Although he’s a household name, Kenneth Cole humbly admits he sells luxury. His products aren’t necessities. That insight, paired with his passion for advocacy and change, has transformed the face of his business.

“We need to be realistic and understand that we create something that people want, not need,” he explained. “If we attach it to something that connects with them in a meaningful way, then what we do becomes more meaningful.”

Cole started by launching campaigns that focus on AIDS epidemic awareness and education. Bringing a face to the problem helps his customers see the AIDS epidemic as a global issue. Doing this makes things personal, which is why Cole’s campaigns have deeply touched Jay Shetty.

In the 1980s, homelessness in New York City reached record levels. Cole offered a 20% discount to anyone who brought in a gently used pair of shoes. Millions of pairs of shoes were handed out to homeless people in desperate need, Cole’s business gained customers, and customers got a discount.

Cole also makes sure his company responds to serve in the aftermath of natural disasters, most recently the 2010 earthquake in Haiti. Cole used money that was raised through one of his campaigns to equip a Haitian hospital with much needed medical equipment. “I've been able to do what I love, and serving adds so much more meaning to what I love,” he explained. “We have those opportunities to continue to grow, not to get bigger, but to get more meaningful.”

Always Look Forward, Never Sit Down

Don’t ask Kenneth Cole to look through a portfolio of his accomplishments or successes over the years. He doesn’t keep one. While others in his position might be tempted to slow down and pat themselves on the back, Cole has never taken that road.

“Success in what was successful yesterday only defines new boundaries for tomorrow,” Cole said. He continues to look forward. There are more fashion boundaries to discover, he says, and more importantly more lives to impact.The example Cole sets inspires Jay Shetty as he looks for new ways to create more wisdom-driven impact.

Stay Timeless Yet Relevant

Like Jay Shetty, Kenneth Cole - the brand and the person - isn’t going anywhere. Part of the appeal of his creations is they stand the test of the ages. People buy pieces knowing they are making an investment in quality. More importantly, the relentless pursuit of deeper meaning for his brand gives people a chance to invest and know they’re making a difference through their purchase.

He’s still asking the right questions and wrestling with finding a way to bring people together to find a cure by 2030. Jay Shetty firmly believes if there is one man to stand at the helm of that ship and navigate it towards that goal, it is Kenneth Cole.

A Message from Jay Shetty

Jay Shetty is passionate about supporting brands that do good. When you purchase a piece of Kenneth Cole clothing, you are helping change the world. It may seem like a small thing, but Cole believes that every small bit helps.

“I can't change the world alone, but I can be an accessory,” he said.What started as a passion for design has evolved into a brand that’s committed to more than just impeccable quality. The Kenneth Cole brand is a movement that offers deep and meaningful support to of some of the most vulnerable populations of the world. Jay Shetty desires that his brand follow in Kenneth Cole’s footsteps.

Listen to the entire On Purpose with Jay Shetty podcast episode with Kenneth Cole now in the iTunes store or on Spotify. For more inspirational stories and messages like Kenneth’s, check out his website at

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