Steve Madden is a global footwear powerhouse, but not many people know about the company’s humble beginnings and the story of the man behind the shoe box — Steve Madden. The new documentary “MADDMAN: The Steve Madden Story,” available now on iTunes, tells the incredible story of the small shoe company-turned-household name, helmed by a college dropout and former addict who took the industry by surprise. Post Studios watched the documentary and uncovered the five most unbelievable and interesting facts about Steve’s life and his company. From selling shoes out of the trunk of his car to serving two-and-a-half years in prison, this is Steve Madden.

He started his company with a $1,100 initial investment; it’s now worth more than $2 billion

“I wanted to sell shoes. I just made my way up there, I didn’t ask.”

After almost a decade working in every aspect of the shoe industry — sales, design, and shipping — Steve quit his job to go out on his own, starting his company with an initial investment of just $1,100. Constantly looking for new inspiration, he was known to buy the shoes right off a woman’s feet. To this day, he still stops pedestrians to take photos of their footwear. The Steve Madden brand is now valued at more than $2 billion.

Some of his very first employees are still with the company

“One of the great things is picking people to help you with the journey.”

Steve’s first employee, David Cristobal, was the night shift doorman at his former apartment building in Manhattan. Steve hired David to be his driver, and they sold shoes out of the trunk of his little red car. Today, David serves as the Steve Madden warehouse manager. Arvind Dharia, the company’s chief financial officer, was brought in to handle financials so that Steve could focus on the shoes, an arrangement that remains intact today.

 

He once woke up naked in his apartment building hallway after a Quaalude trip

“When you’re miserable enough, perhaps you can change.”

 A stoner in college, Steve’s drug and alcohol dependence got so out of hand that one night he woke up in the hallway of his apartment building completely naked after a Quaalude high. After years of struggling, five DUIs, losing his license, and passing out frequently, Steve knew he had to get sober, and once he did, that’s when things really took off.

 

He went to prison after Jordan Belfort’s firm took his company public

 

“I went from an eviction notice to a private jet in like 200 days.”

 Famously portrayed in the film “The Wolf of Wall Street” — which Steve said offers a fairly accurate depiction of reality — Jordan Belfort’s firm Stratton Oakmont gave Steve Madden the lift-off it needed to become successful by taking the company public. Steve unknowingly became part of Belfort’s scheme and eventually faced multiple charges of conspiracy, securities fraud and money laundering. He surrendered to authorities and served two-and-a-half years of a 41-month sentence in federal prison. His greatest had been going to prison, and his greatest fear was realized.

He had hidden messages placed in ads while he was in jail

“You can’t run a business from prison. People can talk to you about business … so I thought, well, let’s give them something to talk about.”

The Madden advertising team was told that Steve wanted discreet messages hidden within Steve Madden print ads while he was incarcerated. From his jail cell number scribbled on a rock, to “Free Steve” emblazoned on a water bottle or a turtle’s shell, he had messages and shout-outs placed wherever he could. In one carnival-themed ad, the different attractions were named for the various inmates he befriended behind bars.

“You know they call me a shoe mogul so it’s funny … it’s kind of an illusion the whole thing, and it’s just like, This is what I have. I didn’t set out to do this, and to this day I struggle with that, you know, I think, What am I? Am I just a great hustler? An entrepreneur? Am I a great businessman? Am I a designer? Am I an artist? I still don’t know.”