In many ways, The Cobbler is an apt title for the autobiography of a man who began his career as a stock boy in the basement of a shoe store.

Passionate about footwear – particularly women’s – and unwilling to spend all his life selling shoes in someone else’s store, he would, in 1990, invest $1,100 to set up a footwear brand and a company under his own name (after all, what better name than your own).

Barely three decades later, and after some tumultous incidents, Steve Madden today boasts a presence in over 80 countries, including stores in the UAE, and raked in a revenue of $1.7billion in 2019.

That was also the year I first met Steve Madden. The shoe mogul had arrived in Dubai to kick off the 30th anniversary celebrations of Steve Madden, the company, that is. Dressed in his regulation grey tee shirt and denims with a baseball cap and, of course, a pair of his own brand of boots to complete the look, the 5ft-5in, well-built American icon was clearly delighted to note how popular his brand is in the region as he shared stories about himself, the stores and the collections. Addressing the media, he spoke about his pet passions – footwear, shoe designing, the Steve Madden ethos of marketing and sales …

Since he was on a whistle-stop tour at the time, he could not spend more time for an in-depth interview with Friday. That opportunity presented itself recently via an email interview – on the heels of the publication of his autobiography.

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Known for his once flamboyant lifestyle not to mention iconic styles of footwear that he designs and sells, Steve recalls that he was first called The Cobbler by Jordan Belfort, a stockbroker in New York, the man perhaps better known as the Wolf of Wall Street in the Martin Scorsese movie of the same name. While Steve’s relationship with Jordan would, by the shoe czar’s own admission, be "one of the greatest mistakes of my life, one that led to a painful downfall", he admits that he is not unhappy with his nickname.

"A cobbler puts the various pieces of a shoe together… But a real shoe guy knows that shoes are made of more than just raw materials. The inspiration behind the style is just as important and includes references pulled from music, pop culture, and whatever else is going on in the zeitgeist. The result is a shoe that is not just comfortable and well-made but that says something about the person who is wearing it," says Steve, in The Cobbler, co-written with Jodi Lipper.

Steve, clearly, is the real shoe guy. If he perfected the art of crafting the perfect shoe, one that is not just pretty to the eye but is comfortable to the foot as well, he also knows how to craft a book that is not just eminently readable but inspirational to boot.

So, while he does dwell a great deal upon how he first set up his company and where he derived his inspiration from (keenly observing women’s footwear and buying styles whenever and wherever he had the op), he does not gloss over his personal mistakes, including his battles with addiction and the "financial shortcuts" he took that landed him in prison – an incident that nearly wore down his firm.

Sentenced to 41 months in prison for stock manipulation, money laundering and securities fraud, he, however, only served some two and half years and was released in 2005. Returning to his company as creative director, he quickly proved that the time in the pen had not clouded his vision. Righting his ship and setting it once again on course, he saw the company net an increase of nearly $100 million in 2006. The same year, Steven Madden was named ‘Company of the Year’ for the second time at the Footwear News Achievement Awards.

But we are racing ahead. First, a little about the man.

Half Jewish and the youngest of three boys, Steve says it was his father, who was in the textile business, who taught him his single most valuable business lesson. "And that was ‘first things first’," he says in an exclusive interview with Friday. "You have to take care of the fundamentals – like putting food on the table, paying your bills – before anything else."

In fact, when I ask Steve to share five of the best pieces of career advice he ever received, his answer is just one point: "Always pay your bills and on time."

Growing up, young Steve was known for being the class clown – impulsive and fidgety in school and "loud and obnoxious" at home.

Steve says he learned his first important lessons in entrepreneurship from his father, who was in the textile business

Although not the best student, he was an avid reader, particularly biographies of Hollywood producers like Samuel Goldwyn and Louis Mayer, where he found the "intersection of art and commerce" fascinating and intriguing.

Landing a job in a funky shoe store as a stock boy in the basement, Steve was quick on his heels and swiftly climbed up the ladder to being a salesman, but one who had a passion for designing shoes. And even while honing his skills as a shoe designer and salesman, the teenager believed that in many situations, "it was better to seek forgiveness than to ask for permission".

His first job was surely a great learning curve. Here he discovered "the rhythm of retail: how a woman tries on a shoe, what she’s telling you she wants when she twists this way and that in a mirror, whether her mind is made up when she asks to see a certain shoe or you should bring her another colour too. It was sort of like dancing or kissing, an intuitive give and take," he says in his book.

The lessons he picked up here and later at another store – Jildor in New York when he was 20 - would hold him in good stead when he would go on to set up his own label and start making shoes.

If the first shoe he crafted for Steve Madden, his company, was a flat, over-the-knee boot in a style that was popular at the time, he quickly followed it up with some clogs, always adhering to his guiding rules – creating footwear that was affordable, stylish and easy to wear.

Once he began designing and manufacturing shoes, the next step was selling them. Recruiting David, his building’s nightshift doorman who had a car, to be his driver, he would load the vehicle’s boot with his shoes and get Steve Madden’s first staff member to drive him around to stores to make sales.

How did he develop this knack of figuring out the kind of shoes a woman would love to wear?

"I worked at two shoe stores and learned from the best in the business," he says. "I made sure to work in the stock room and on the sales floor to learn as much as I could. You just have to stay alert and observant. It is fascinating to watch a woman pick out shoes. It became my passion. Moreover, I learned that I was good at it."

Steve cleaning up at the first Steve Madden store in 1993. In the early days of manufacturing his own shoes, Steve would drive around to stores to make sales

He would also be good at spotting a good shoe from even a distance.

There’s an anecdote he narrates in his book where he is in the back seat and David is driving him around town when Steve notices a woman on the sidewalk walking in a lovely pair of shoes. Shouting to his driver to pull over, he steps out and runs up the woman pleading with her, not unlike a creep, to buy the shoes off her. "Please," he begs. "I’ll buy you any pair of shoes if you’ll give me the ones you are wearing."

The plan was to take them back to his little factory, examine them in detail, dismantle them and get an idea of how to tweak the style and make it his own.

When he was not busy observing shoes on women on the streets, he’d spend a lot of time at a major department store observing the kinds of shoes women were buying and their buying styles.

"My pores were always open and I got inspiration from everything around me," he says, in The Cobbler.

What inspires him to create and market shoes?

"We always strive to be the best," says Steve. "I am very competitive, so the want and need for everyone to wear Steve Madden is always top of mind."

In his autobiography, he describes in great detail and with raw honesty how he went about setting up Steve Madden, growing it and making his products one of the most desirable in the world. Even as the book is loaded with tips and pointers for wannabe marketers and entrepreneurs, there are also plenty of insights into the man and how despite being on the slippery slope of addiction, continued to passionately grow his shoe brand.

Making shoes, he says, is a lot like baking a cake. If you don’t use good-quality ingredients the products won’t turn out right. "So how do you make a cake taste great while using less expensive ingredients or in our case how do you craft a shoe that women want to wear for less than a hundred dollars and still turn a profit? […] that’s an art."

Since he has finetuned the art, what does he think makes people happy to slip into a pair of Steve Madden shoes?

"Apart from the comfort, it’s our price point, quality and the trends we hit every season [that] are unmatchable," says Steve. "The team we have in place is incredible and we make sure we are the best of the best, season after season."

The father of three doesn’t hesitate to give all credit to his creative team who "are incredible at staying up to speed with trends".

"You must have smart people who are talented and have different perspectives around you," says the head honcho, to a question on how he creates something the public wants before they know they want it.

Steve with his staff in the factory in 2009. “You must have smart people who are talented and have different perspectives around you.”

Another question about the challenges in maintaining the brand’s legacy, and he points to the team yet again. "The industry is always evolving and changing so you need to make sure you build a team of people who are at the top of their game. It took me a minute to realise I could not do it all. It was an important lesson to learn," he says.

Choosing and nurturing the right team take high priority in Steve’s mix of entrepreneurial success.

"Team building is crucial," he says. Focussing on the team is crucial for a healthy, successful company, he adds.

How important is luck in the scheme of things? I ask.

"Hard work comes first; you cannot have success without that grit and determination. However, you cannot ignore how important luck is; it has definitely played a role in my success," admits the man who once said that he enjoys holding on to a good luck charm of some kind.

Steve Madden – the man and the company – has collaborated with a diverse range of A-list celebrities, from Katy Perry to Taylor Swift, Rihanna to even Madonna, over the years and each of them has left their stamp in some way on the company’s products. "But Cardi B is one that will always stand out in my life," says Steve. "What an incredible career she continues to have. She is a true hustler, something I admire."

While on celebrities, I ask him if he was happy with the way his character was portrayed in The Wolf of Wall Street?

Cardi B stands out among the A-list celebrities Steve has collaborated with. “She is a true hustler, something I admire.”

"When I first heard about the movie, I thought nobody would see it," he says. "But then they announced who was directing it [Martin Scorsese], and who was starring in it [Leonardo DiCaprio], that was kind of like an ‘oh [expletive]’ moment. People are going to see this.

"They actually let me preview the film before they released it in theatres and, like the rest of the world, I think it is a good film. In the end, it was actually good for the company. People all the time shout to me on the streets: ‘STEVEEEEE MADDEENNNN’."

Is his book a confessional?

"It certainly feels that way at this point," says the 62-year-old. "I completed the audio recording for the book in the Fall [of 2019] and it was hard to get through that because I was too honest. Re-reading it became nerve-racking. Like, ‘Why did I say that?’."

The Cobbler, he insists, is extremely personal even in the portions where he talks about the time he served in prison. "I do not think I have ever been so honest about that time in my life."

What are his five pieces of advice to an aspiring entrepreneur.

"I’ll give you three," he says.

"Do what you love; listen to your team, even if you disagree and it kills you; and, brush your teeth every morning and night."

Does he have any regrets personal or otherwise?

"A couple of real estate things maybe," he said in an earlier interview. "Maybe we stayed a little bit too long with brick and mortar, some of the leases. That’s it. That’s my biggest business regrets. I don’t regret too much."

He reiterates the same thoughts in The Cobbler.

"It may sound like an overstatement, but if I could go back, I wouldn’t change a moment, even the time I spent in prison thinking my life was over. Whether it’s a shoe or a life, without each piece carefully stitched together, the final product will never be the same."

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