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It’s 1990 and 30-something-year-old Steve Madden has $1,100 (Dh4,040) to his name. He’s hustling on the streets of New York, selling shoes out of the boot of his doorman’s car — which he rents for $60 a day.

Now it’s 2019, and 61-year-old Madden is getting ready to celebrate 30 years of his successful shoe brand. His slick booties and trendy heels are available from hundreds of shops around the world, including multiple Dubai locations.

Recently, as UAE residents struggled against a rare and ferocious downpour, Madden arrived to Dubai Mall dressed inconspicuously in a New York Yankees cap, a grey T-shirt, jeans and a pair of Steve Madden boots.

On first sight, you might not guess he’s the man behind a multimillion fashion empire.

“I worked at a shoe store when I was a kid — that’s all I knew,” said Madden. “I was hired as a salesman [when] I was 22 years old. I remember one day, I snuck into the factory and I started fooling around without knowing anything. You know, ‘put this over here, put this under that.’ I made a few shoes and they were a big success. I couldn’t believe I did that — I never really thought of myself as that artistic, frankly.”

A glimpse into Madden’s early transgressions has been immortalised in the 2013 Martin Scorsese film ‘The Wolf of Wall Street’, and more than a decade ago, he served two-and-a-half years out of a 41 month sentence for stock fraud.

However, Madden doesn’t feel like he’s had many low points in his life.

“Is it lonely being an entrepreneur? Yes, it is — very much so. Because you do some things that only you understand. Your whole purpose is to build this business or project,” said Madden.

In a sit-down interview with Gulf News tabloid!, the shoe-making mogul reflected on his origins, his biggest regrets and the famous faces he’d still like to work with.

You were born in Queens, New York — what was it like growing up there and starting up there?

We had a very American, normal childhood. Very American.

How would you define that? American childhood?

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You know, we were very ambitious and hungry.

You started out by selling shoes out of the trunk of your car. Do you remember what kind of car you were driving?

I had a doorman; I lived in a building and I lost my licence. I gave him, I think it was $60 [Dh220] a day. He was a Peruvian guy. He’s still with the company.

Wow. Longest serving employee?

Yes, there’s nobody longer. He had this beat up and boxy red car. I ran the business out of it. I’d bring it to the factory, I would deliver shoes, I would have samples…

What does he do now for the company?

He runs a warehouse for us. His name is David Cristobal. He’s been with me since day one. He used to be Oscar, which was a fake name because of immigration. His real name was David.

How did people react to you when you were selling out of a car? Were people receptive to it?

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Well, I was very sort of tactile. So, having a car lends itself to that kind of, you know, touching everything and being mobile. It was a lot easier [back] then, too, because we didn’t have as much traffic. I could jump into New York City from Brooklyn, go uptown — the traffic in New York is so bad right now. In 30 years, [it takes] double the time everywhere. It really would be impossible to do the things that I did.

Thirty years [of Steve Madden] next year — how do you wrap your head around that? Does it feel like 30 years or does it feel like they flew by?

When I look back, it seems like a long time ago. It’s been a journey. Every day and year brings a whole new set of challenges, so one doesn’t rest on one’s laurels. I mean, in a way we do, because you’ve acquired some wealth over the years. But then outside of that, there’s the challenge of running a really cool business and having great shoes. And it’s much better for me now, because I don’t really have to worry about the business as much. I just have to worry about the shoes.

You spoke earlier about working with celebrities, and Steve Madden being the star [of those campaigns]. But was there any celebrity that you worked with where [you were star struck]? Or was it never a moment for you?

I’ve never really had a moment, no, no.

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Is there someone you’d still like to work with?

Rihanna is one, because she’s so great — such great style. I’ve always been envious of her. And I like Taylor Swift. But we’ve worked with great artists. It’s been fun. I mean, we’ve had everybody from Katy Perry to Cardi B. We’ve worked with all of them. We worked with Madonna! I know that people forget that. Up until two years ago, we had a line with her for a long time. Never met her, though. We worked with her daughter.

Being in the fashion industry, what’s your personal style motto?

Oh god, no. No, if went by that, it would be the worst shoe company in the world. It’s different for me. I try to keep it simple. I have my little uniform and that’s it.

Really? You consider it a uniform?

Yes, very much so. T-shirts. And I change every three years, I get another a uniform. But I have more than one, because, you know… you get spots on them.

Looking back, would you have done anything differently? Do you have any regrets over anything you’ve done?

Maybe a couple of leases, a couple of real estate things that we re-upped when we shouldn’t have. Not too many, but some. Because the digital platform gets so big, the phone business gets so big, online. So I regret some of that — we maybe stayed a little bit too long with bricks and mortar, you know, some of the leases I regret. That’s it. That’s my biggest business regret, frankly. I don’t regret much.

A lot of people know more about you through ‘The Wolf of Wall Street’. It was a big pop culture moment. Six years later, what are your feelings on the film? Do people still talk to you about it?

Oh, yeah. It had a very big impact. People enjoyed the movie. I really was afraid that it was going to have to a terrible effect, but it was the opposite. It became more of a cult.

So, no regrets about that?

No, I don’t have any regrets about the film. I wish I maybe acted differently in my youth, of course.